Non-azo naphthalimide dyes

• US 5,235,045 A
• Filed: 03/19/1992
• Issued: 08/10/1993
• Est. Priority Date: 03/19/1992
• Status: Expired due to Term

• Current Assignee: Alumend LLC
• Original Assignee: Microbiomed Corp.
• Inventors: Lewis, David E., Judy, Millard M., Utecht, Ronald E., Matthews, J. Lester
• Primary Examiner(s): Higel, Floyd D.
• Application Number:
  US07/854,416
• Time in Patent Office: 509 Days
• Field of Search: 546/99, 546/101, 546/98, 546/100, 546/13, 546/22, 546/23, 546/14, 514/296, 514/89, 514/150, 544/333, 544/1, 534/560, 530/350, 535/1.1
• US Class Current: 534/560
• CPC Class Codes: A61L 2/0011 using physical methods
• CPC Class Codes: A61L 2/0082 using chemical substances
• CPC Class Codes: C07D 221/14 Aza-phenalenes, e.g. 1,8-naphthalimide
• CPC Class Codes: C09B 57/08 Naphthalimide dyes; Phthalimide dyes

Abstract

A class of predominantly hydrophobic non-azo N-substituted 1,8-naphthalimide compounds, each bearing, at its 3-position, a nucleofuge and, at its 4-position, a heteroatomic electron-releasing group. The heteroatomic electron-releasing group is being characterized as having a heteroatom directly linked to the 4-position of the ring, and having at least one hydrogen directly attached to the heteroatom. Upon activation by an activating agent in an environment independent of the presence or absence of oxygen, these compounds generate activated species. The activated species initiate chemical changes in lipid bilayer membranes of viruses and other target cells. These changes can eradicate viruses and other target cells. The activated species can also cause structural changes in lipid and any associated proteins and polypeptides at a level beneath the surface of the membrane, leading to polymerization and crosslinking.

Claims

1. A non-azo N-substituted-1,8-naphthalimide compound substituted by, at a 3-position, a nucleofuge and, at a 4-position, a heteroatomic electron-releasing group, aid heteroatomic electron-releasing group being characterized as having a heteroatom directly linked to said 4-position and having at least one hydrogen directly attached to said heteroatom, said non-azo N-substituted-1,8-naphthalimide compound being characterized as predominantly hydrophobic and, after being activated by a sufficient amount of activating agent gives an activated derivative.

2. The compound of claim 1, wherein said nucleofuge is a halogen, a sulfonate ester, or a nitrogen-containing leaving group.

3. The compound of claim 1, wherein said heteroatom is nitrogen or oxygen.

4. The compound of claim 1, wherein said activating agent is light energy, X-ray radiation, or thermalized neutron particles.

5. The compound of claim 1, wherein said activating agent is light energy having a wavelength range of from about 200 nm to about 1000 nm.

6. The compound of claim 5, wherein said light energy has a wavelength range of from about 290 nm to about 750 nm.

7. The compound of claim 5, wherein said light energy has a wavelength range of from about 600 nm to about 750 nm.

8. The compound of claim 5, wherein said light energy has a wavelength range of from about 650 nm to about 700 nm.

9. The compound of claim 1, wherein said activated derivative is characterized as being relatively non-toxic to normal tissues or normal cells at effective dosages yet can undergo photoinduced tautomeric alkylation with a target protein- based nucleophile.

23. A pharmaceutical composition for eradicating a pathogenic biological contaminant from body tissue, which comprises a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof, having been activated by a sufficient amount of an activating agent, as an active ingredient, in combination with a pharmaceutically acceptable carrier for said active ingredient.

24. The composition of claim 23 wherein said body tissue is body fluid, packed red blood cell, packed white blood cell, cryo precipitate from blood plasma, plasma protein, skin or cornea.

25. The composition of claim 24 wherein said body fluid is whole blood, blood plasma, serum, fluid from plasmapheresis, bone marrow or plasma fibrinogen.

26. The composition of claim 24 wherein said body fluid is albumin, gamma globulin or semen.

27. The composition of claim 23 wherein said body tissue is platelet.

28. The composition of claim 23 wherein said pathogenic biological contaminant is virus, tumor cell, bacterium or parasite.

10. A naphthalimide compound having the formula ##STR1## which is a mixture of stereoisomers wherein:

R and R'"'"';

saturated straight-chain or branched-chain alkyl, C_n H_2n+1 (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q+1 (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m+1 (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m+1 (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q+1 (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p+1 Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q+1 Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 00≦

q≦

2m) with saturated or unsaturated sidechains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar and their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m≦

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1<

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule (steroids, phospholipids, mono-, di- or triglycerides, mono- or polysaccharides, nucleosides, and polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

X;

halogen (F, Cl, Br, I);

sulfonate ester (alkanesulfonates, partially or totally fluorinated alkanesulfonates, arenesulfonates, or partially or totally fluorinated arenesulfonates);

or

a nitrogen leaving group (diazonium ion);

or pharmaceutically acceptable salts thereof.

11. A non-azo N-substituted-1,8-naphthalimide compound having at least two 1,8-naphthalimide moieties each substituted by, at a 3-position, a nucleofuge and, at a 4-position, a heteroatomic electron-releasing group, said heteroatomic electron-releasing group being characterized as having a heteroatom directly linked to said 4-position and having at least one hydrogen directly attached to said heteroatom, said non-azo N-substituted-1,8-naphthalimide compound being characterized as predominantly hydrophobic and, after being activated by a sufficient amount of activating agent, gives an activated derivative.

12. The compound of claim 11 wherein said nucleofuge is a halogen, a sulfonate ester, or a nitrogen-containing leaving group.

13. The compound or claim 11, wherein said heteroatom is nitrogen or oxygen.

14. The compound of claim 11, wherein said activating agent is light energy, X-ray radiation, or thermalized neutron particles.

15. The compound of claim 11, wherein said activating agent is light energy having a wavelength range of from about 200 nm to about 1000 nm.

16. The compound of claim 15, wherein said light energy has a wavelength range of from about 290 nm to about 750 nm.

17. The compound of claim 15, wherein said light energy has a wavelength range of from about 600 nm to about 750 nm.

18. The compound of claim 15, wherein said light energy has a wavelength range of from about 650 nm to about 700 nm.

19. The compound of claim 11, wherein said activated derivative is characterized as being relatively non-toxic to normal tissues or normal cells at effective dosages yet can undergo photoinduced tautomeric alkylation with a target protein-based nucleophile.

29. A pharmaceutical composition for eradicating a pathogenic biological contaminant from body tissue, which comprises a therapeutically effective amount of a compound of claim 11, or a pharmaceutically acceptable salt thereof, having been activated by a sufficient amount of an activating agent, as an active ingredient, in combination with a pharmaceutically acceptable carrier for said active ingredient.

30. The composition of claim 29 wherein said body tissue is body fluid, packed red blood cell, packed white blood cell, cryo precipitate from blood plasma, plasma protein, skin or cornea.

31. The composition of claim 30 wherein said body fluid is whole blood, blood plasma, serum, fluid from plasmapheresis, bone marrow or plasma fibrinogen.

32. The composition of claim 30 wherein said body fluid is albumin, gamma globulin or semen.

33. The composition of claim 29 wherein said body tissue is platelet.

34. The composition of claim 29 wherein said pathogenic biological contaminant is virus, tumor cell, bacterium or parasite.

35. A composition for cross-linking protein, which comprises an effective amount of a compound of claim 11, or an acceptable salt thereof, having been activated by a sufficient amount of an activating agent, as an active ingredient, in combination with an acceptable carrier for said active ingredient.

20. A bis-naphthalimide compound having the formula ##STR2## which is a mixture of stereoisomers wherein:

R and R'"'"';

saturated straight-chain or branched-chain alkyl, C_n H_2n+1 (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q+1 (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m+1 (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

m≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m+1 (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q+1 (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p+1 Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q+1 Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p+1 Y_p (n=1-30, 1≦

m<

n, 1≦

c≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule (steroids, phospholipids, mono-, di- or triglycerides, mono- and polysaccharides, nucleosides, or polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

X;

halogen (F, Cl, Br, I);

sulfonate ester (alkanesulfonates, partially or totally fluorinated alkanesulfonates, arenesulfonates, or partially or totally fluorinated arenesulfonates);

or

a nitrogen leaving group (diazonium ion);

saturated straight-chain or branched-chain alkyl, C_n H_2n (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-1, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar and their acyl (including aminoacyl and peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule ( steroids, phospholipids, mono-, di- and triglycerides, mono- and polysaccharides, nucleosides, and polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

or

pharmaceutically acceptable salts thereof.

21. A bis-naphthalimide compound having the formula ##STR3## which is a mixture of stereoisomers wherein:

R and R'"'"';

saturated straight-chain or branched-chain alkyl, C_n H_2n+1 (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q+1 (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m+1 (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m+1 (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q+1 (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p+1 Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q+1 Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, , PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule (steroids, phospholipids, mono-, di- and triglycerides, mono- and polysaccharides, nucleosides, and polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

X;

halogen (F, Cl, Br, I);

sulfonate ester (alkanesulfonates, partially or totally fluorinated alkanesulfonates, arenesulfonates, or partially or totally fluorinated arenesulfonates);

or

a nitrogen leaving group (diazonium ion);

Q;

saturated straight-chain or branched-chain alkyl, C_n H_2n (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m≦

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted and benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule ( steroids, phospholipids, mono-, di- and triglycerides, mono- or polysaccharides, nucleosides, or polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

or

pharmaceutically acceptable salts thereof.

22. A bis-naphthalimide compound having the formula ##STR4## which is a mixture of stereoisomers wherein:

R and R'"'"';

saturated straight-chain or branched-chain alkyl, C_n H_2n+1 (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q+1 (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m+1 (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q+1 (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q+1 (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p+1 Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q+1 Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m+1 (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, or ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q+1 Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar and their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m+1 Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar and their acyl (including aminoacyl or peptide) derivatives, and where R is saturated alkyl (C_n H_2n+1, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q+1, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m+1, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q+1, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule (steroids, phospholipids, mono-, di- and triglycerides, mono- and polysaccharides, nucleosides, and polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

X;

halogen (F, Cl, Br, I);

sulfonate ester (alkanesulfonates, partially or totally fluorinated alkanesulfonates, arenesulfonates, or partially or totally fluorinated arenesulfonates);

or

a nitrogen leaving group (diazonium ion);

Q;

saturated straight-chain or branched-chain alkyl, C_n H_2n (n=1-30);

partially or totally fluorinated saturated straight-chain or branched-chain alkyl, C_n H_q F_2n-q (n=1-30, 0≦

q≦

2n);

unsaturated straight-chain or branched-chain alkyl, C_n H_2m (n=1-30, 1≦

m<

n);

partially or totally fluorinated unsaturated straight-chain or branched-chain alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m);

alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched);

partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-q (n=1-30, 1≦

m<

n, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched);

aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m (n=1-30, 1≦

m≦

n), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-q (n=1-30, 1≦

m≦

n, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

substituted saturated straight-chain or branched-chain alkyl, C_n H_2n-p Y_p (n=1-30, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2n-p-q Y_p (n=1-30, 1≦

p≦

10 0≦

q≦

2n);

substituted unsaturated straight-chain or branched-chain alkyl, C_n H_2m-p Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated straight-chain or branched-chain alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m);

substituted alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_2m (n=1-30, 1≦

m≦

n) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated alicyclic (monocyclic or polycyclic, fused-ring, bridged-ring or spirocyclic) alkyl, C_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m<

n, 1≦

p≦

10, 0≦

q≦

2m) with saturated or unsaturated side-chains (branched or unbranched) where Y is a substituted aryl group (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_2m-p Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

substituted partially or totally fluorinated aryl substituted branched, unbranched or alicyclic, saturated or unsaturated alkyl, ArC_n H_q F_2m-p-q Y_p (n=1-30, 1≦

m≦

n, 1≦

p≦

10, 0≦

q≦

2m), where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus, and where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo);

a straight-chain or branched-chain group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar or their acyl (including aminoacyl and peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

a substituted alicyclic group capable of complexing a metal ion, C_n H_2m Y_q (n=1-30, 1≦

q≦

n/2), where Y is O, S, Se, NH, N-R, N-Ar, PH, P-R and/or P-Ar and their acyl (including aminoacyl and peptide) derivatives, and where R is saturated alkyl (C_n H_2n, n=1-30), fluorinated saturated alkyl (C_n H_q F_2n-q, n=1-30, 0≦

q≦

2n), unsaturated alkyl (C_n H_2m, n=1-30, 1≦

m<

n), fluorinated unsaturated alkyl (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), alicyclic (C_n H_2m, n=1-30, 1≦

m≦

n), fluorinated alicyclic (C_n H_q F_2m-q, n=1-30, 1≦

m<

n, 0≦

q≦

2m), and where Ar is an aromatic moiety (benzene, naphthalene, azulene, phenanthrene, anthracene, pyridine, quinoline, isoquinoline, purine, pyrimidine, pyrrole, indole, carbazole, furan, thiophene, imidazole, isoxazole, thiazole or their substituted or benzo derivatives) located either within the chain of the alkyl group or at a terminus;

or

a modified or unmodified biomolecule (steroids, phospholipids, mono-, di- and triglycerides, mono- and polysaccharides, nucleosides, and polypeptides), where Y is a substituted aryl group (defined above), a charged group (CO₂^-, SO₃^-, PO₃^2-, and ROPO₂^2-), a silicon derivative (SiZ₃, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a boron derivative (BZ₂, where Z is alkyl, aryl, alkoxy, aryloxy, or halo), or a biocompatible oligomer or polymer (polyglycolic acid);

or

pharmaceutically acceptable salts thereof.