Pyrenexulfonic acids useful in fluorescent lipid probes

• US 4,844,841 A
• Filed: 09/11/1987
• Issued: 07/04/1989
• Est. Priority Date: 06/13/1986
• Status: Expired due to Fees

• Current Assignee: Ernst Koller, Otto S. Wolfbeis
• Original Assignee: Ernst Koller, Otto S. Wolfbeis
• Inventors: Koller, Ernst, Wolfbeis, Otto S.
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US07/096,043
• Time in Patent Office: 662 Days
• Field of Search: 260/508, 260/509, 260/512 C, 560/14, 558/408, 558/410, 558/413, 546/347
• US Class Current: 562/55
• CPC Class Codes: C07C 2603/50 Pyrenes; Hydrogenated pyrenes
• CPC Class Codes: C07C 309/38 formed by at least three rings
• CPC Class Codes: C07C 309/41 containing singly-bound oxygen atoms bound to the carbon skeleton

Abstract

Compounds of formula ##STR1## wherein X is long-chain alkyloxy, long-chain alkylamino or long-chain dialkylamino,

M is alkali metal, pyridinium or ammonium,

Y is hydroxy or long-chain alkyloxy,

which are especially useful in photometric and fluorimetric investigations of lipids and lipid-water interactions and of cationic biomolecules such as nicotine adenine dinucleotide.

Claims

1. A compound having the formula ##STR6## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

6. The compound of claim 1 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chloro-decyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical and M is sodium.

2. A compound having the formula ##STR7## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

12. The compound of claim 2 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical;

and M is sodium.

3. A compound having the formula ##STR8## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

13. The compound of claim 3 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical;

and M is sodium.

4. A compound having the formula ##STR9## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

14. The compound of claim 4 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical;

and M is sodium.

5. A compound having the formula ##STR10## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

15. The compound of claim 5 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical;

and M is sodium.

7. A compound have the formula ##STR11## wherein R₁ is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyloxy, alkenyloxy, arylalkyloxy, alkylamino, alkenyl-amino, dialkylamino, and dialkenylamino radical which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine, or sulfonato groups;

R₂ is a hydroxy or sulfonato group; and

M is chosen from the group consisting of alkali metal, pyridinium, and ammonium.

8. The compound of claim 7 wherein:

R₁ is chosen from the group consisting of decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, 10-carboxy-decyloxy, 14-carboxy-tetradecyloxy, 10-ethoxycarbonyldecyloxy, 14-methoxycarbonyl-tetradecyloxy, 12-bromododecyloxy, and 14-hydroxy-tetradecyloxy radical; and

M is sodium.

9. The compound of claim 7 wherein:

R₁ is chosen from the group consisting of a decylamino, didecylamino, dodecylamino, didodecylamino, tetradecylamino, ditetradecylamino, hexadecylamino, dihexadecylamino, bis(10-carboxydecyl)amino, and bis(12-carboxydodecyl)amino radical; and

M is sodium.

10. A compound having the formula ##STR12## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, whch can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

16. The compound of claim 10 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14-hydroxy-tetradecyl radical;

and M is sodium.

11. A compound having the formula ##STR13## wherein R is a radical consisting of 4-22 carbon atoms chosen from the group consisting of alkyl, alkenyl and arylalkenyl, which can be substituted by carboxy, alkoxycarbonyl, hydroxy, cyano, chlorine, bromine or sulfonato groups;

and

M is chosen from the group consisting of alkali metal, pyridinum or ammonium.

17. The compound of claim 11 wherein R is chosen from the group consisting of decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, 10-carboxy-decyl, 14-carboxy-tetradecyl, 10-ethoxycarbonyl-decyl, 14-methoxycarbonyl-tetradecyl, 10-chlorodecyl, 12-bromo-dodecyl, 12-hydroxy-dodecyl, 14hydroxy-tetradecyl radical;

and M is a sodium.