Matrix-supported sapphyrins

• US 5,808,059 A
• Filed: 08/28/1995
• Issued: 09/15/1998
• Est. Priority Date: 10/21/1992
• Status: Expired due to Fees

• Current Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Original Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Inventors: Sessler, Jonathan L., Iverson, Brent L., Shreder, Kevin, Kral, Vladimir, Thomas, Richard E., Furuta, Hiroyuki
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): Sripada, Pavanaram K.
• Application Number:
  US08/424,288
• Time in Patent Office: 1,114 Days
• Field of Search: 540/474, 540/4, 536/23.1
• US Class Current: 540/474
• CPC Class Codes: A61K 41/0076 PDT with expanded (metallo)porphyrins, i.e. having more than 20 ring atoms, e.g. texaphyrins, sapphyrins, hexaphyrins, pentaphyrins, porphocyanines
• CPC Class Codes: A61K 47/54 the modifying agent being an organic compound
• CPC Class Codes: A61K 47/546 Porphyrines; Porphyrine with an expanded ring system, e.g. texaphyrine
• CPC Class Codes: A61K 47/558 the modifying agent being a chemiluminescent acceptor
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07H 15/26 Acyclic or carbocyclic radicals, substituted by hetero rings
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C12N 15/101 by chromatography, e.g. electrophoresis, ion-exchange, reverse phase

Abstract

The invention relates to the field of polymer- and other matrix-supported sapphyrins. Disclosed are silica gel, glass, resin and other polymer- and matrix-supported sapphyrins and sapphyrin-containing chromatographic and electrophoretic supports.

Claims

1. A sapphyrin-containing composition comprising a sapphyrin or a sapphyrin derivative joined to a polymeric or solid support matrix.

2. The composition of claim 1, wherein the polymeric or solid support matrix is silica gel, silica, Merrifield resin, glass, controlled pore glass, polystyrene, sepharose, agarose, clay, zeolite or polyacrylamide.

3. The composition of claim 1, wherein the sapphyrin or the sapphyrin derivative joined to a polymeric or solid support matrix is formulated into an HPLC column or a capillary electrophoresis tube.

4. The composition of claim 1, further having a long chain alkyl group.

5. The composition of claim 4, wherein the long chain alkyl group is attached to the polymeric or solid support matrix.

6. The composition of claim 4, wherein the long chain alkyl group is attached to the sapphyrin or the sapphyrin derivative.

7. The composition of claim 1, further comprising a nucleobase-containing group.

8. The composition of claim 7, wherein the nucleobase-containing group is attached to the polymeric or solid support matrix.

9. The composition of claim 7, wherein the nucleobase-containing group is attached to the sapphyrin or the sapphyrin derivative.

12. The composition of claim 1 selected from the group consisting of a matrix-supported sapphyrin of structure 31, a matrix-supported sapphyrin of structure 32, a matrix-supported sapphyrin of structure 33, a matrix-supported sapphyrin of structure 34, a matrix-supported sapphyrin of structure 35, a matrix-supported sapphyrin of structure 36, a matrix-supported sapphyrin of structure 37 or a matrix-supported sapphyrin of structure 38 of FIG. 5D.

10. A method for separating a first molecule from a mixture of at least two molecules, the method comprising:

(a) preparing a matrix support with a sapphyrin or a sapphyrin derivative; and

(b) contacting the prepared matrix-supported sapphyrin or sapphyrin derivative with said mixture to separate said first molecule.

11. A method of introducing a selected charged compound into a target cell, which method comprises contacting the cell with a sapphyrin derivative comprising the selected charged compound.

13. A sapphyrin-containing composition comprising a sapphyrin or a sapphyrin derivative joined to a polymeric or solid support matrix, wherein the sapphyrin is a sapphyrin derivative having the structure:

##STR4## wherein, each of R¹ -R¹⁰ is independently H, alkyl, alkene, alkyne, halide, alkyl halide, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, aldehyde, ether, ketone, carboxylic acid, phosphate, phosphonate, sulfate, phosphate substituted alkyl, phosphonate substituted alkyl, or sulfate substituted alkyl, such that the total number of carbon atoms in each substituent R is less than or equal to 10; and

wherein at least one of R¹ R¹⁰ are of the formula (CH₂)_n --A--(CH₂)_m --B, wherein A is CH₂, O, S, NH or NR¹¹, wherein R¹¹ is alkyl, alkene, alkyne, halide, alkyl halide, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, phosphate, phosphonate, sulfate, phosphate substituted alkyl, phosphonate substituted alkyl, sulfate substituted alkyl, COO, CONH, CSNH, CONR¹¹ ;

B is the polymeric or solid support matrix; and

n and m are integers of less than or equal to 10 or zero.

14. The composition of claim 13, wherein the polymeric or solid support matrix is silica gel, silica, Merrifield resin, glass, controlled pore glass, polystyrene, sepharose, agarose, clay, zeolite or polyacrylamide.

15. The composition of claim 13, wherein the sapphyrin or the sapphyrin derivative joined to a, polymeric or solid support matrix is formulated into an HPLC column or a capillary electrophoresis tube.

16. The composition of claim 13, further comprising a long chain alkyl group.

17. The composition of claim 16, wherein the long chain alkyl group is attached to the polymeric or solid support matrix.

18. The composition of claim 16, wherein the long chain alkyl group is attached to the sapphyrin or the sapphyrin derivative.

19. The composition of claim 13, further comprising a nucleobase-containing group.

20. The composition of claim 19, wherein the nucleobase-containing group is attached to the polymeric or solid support matrix.

21. The composition of claim 19, wherein the nucleobase-containing group is attached to the sapphyrin or the sapphyrin derivative.

22. The composition of claim 13, wherein B further comprises an aryl, silyl, siloxy, aminoaryl, amino, amidoaryl or silyloxy group as a linking agent to said polymeric or solid support matrix.

23. A method of cleaving DNA, which method comprises contacting DNA with a sapphyrin derivative under conditions effective to promote cleavage of the DNA.