Photolabile compounds

Patent metadata

Field	Value
Publication number	US-9688708-B2
Application number	US-201615056340-A
Country	US
Kind code	B2
Filing date	Feb 29, 2016
Priority date	Dec 29, 2003
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

The present invention describes Photolabile Compounds methods for use of the compounds. The Photolabile Compounds have a photoreleasable ligand, which can be biologically active, and which is photoreleased from the compound upon exposure to light. In one embodiment, the light is visible light, which is not detrimental to the viability of biological samples, such as cells and tissues, in which the released organic molecule is bioactive and can have a therapeutic effect.

First claim

The invention claimed is:

1. A compound of Formula IVa:

wherein:
each L 1 is independently an organic molecule having an amine group whose nitrogen atom forms a bond with Ru, wherein said organic molecule containing an amine group is selected from the group consisting of an amino acid, dopamine, GABA, serotonin, and aminobutyric acid;
L 2 is (R 2 ) 3 P, (R 2 O) 3 P, wherein each R 2 is independently —C 1 -C 18 alkyl, or phenyl, and m is 2;
R 1 to R 8 are independently —H, —C 1 -C 18 alkyl; —NH 2 , —COOH, —(C 1 -C 18 alkyl)-O—(C 1 -C 18 alkyl), or —OC(O)(C 1 -C 18 alkyl); and
X is Cl − , F − , Br − , I − , PF 6 − , CF 3 SO 3 − , (C 1 -C 18 alkyl)-CO 2 − , or (C 1 -C 18 alkyl)-SO 3 − .

2. The compound of claim 1 , wherein the organic molecule is an amino acid.

3. The compound of claim 1 , wherein the organic molecule is dopamine.

4. The compound of claim 1 , wherein the organic molecule is GABA.

5. The compound of claim 1 , wherein the organic molecule is serotonin.

6. The compound of claim 1 , wherein the organic molecule is aminobutyric acid.

7. The compound of claim 1 , wherein the organic molecule is glutamate.

8. The compound of claim 1 , wherein L2 is (R 2 ) 3 P.

9. The compound of claim 1 , wherein L2 is trimethylphosphine.

10. The compound of claim 1 , wherein L2 is triphenylphosphine.

11. A method for releasing an organic molecule from a photolabile compound, comprising:
exposing a compound of claim 1 to light under conditions sufficient to release the organic molecule.

12. The method of claim 11 , wherein the light comprises visible light or infrared light.

13. A method for protecting an organic molecule from an effect of an enzyme, comprising:
allowing the organic molecule and a compound of Formula IVb′:

wherein m is 2; R 1 to R 8 are independently —H, —C 1 -C 18 alkyl; —NH 2 , —COOH, —(C 1 -C 18 alkyl)-O—(C 1 -C 18 alkyl), or —OC(O)(C 1 -C 18 alkyl); and X is Cl − , F − , Br − , I − , PF 6 − , CF 3 SO 3 − , (C 1 -C 18 alkyl)-CO 2 − , or (C 1 -C 18 alkyl)-SO 3 − ,
to react under conditions sufficient to make a compound of claim 1 .

14. A method for making an organic molecule bioavailable to a subject, comprising:
(a) administering a compound of claim 1 to the subject; and
(b) exposing the compound to light under conditions sufficient to release the organic molecule from the compound.

15. The method of claim 14 , wherein the light is sunlight, photo-optic light, or laser light.

16. The method of claim 14 , wherein the light is visible light or infrared light.

17. The method of claim 14 , wherein the exposing occurs at the site of a tumor, cancer, or neoplasm.

18. The method of claim 14 , wherein the administering occurs intravenously, topically, intradermally, intramuscularly, transdermally, subcutaneously, intranasally, parenterally, intrathecally, vaginally, rectally, colorectally, orally, intracranially, retroorbitally, intrasternally, or by injection.

19. A composition comprising a compound of claim 1 and a physiologically acceptable carrier, vehicle, diluent, or excipient.

20. A kit comprising a compound of claim 1 and instructions for use of the compound.

21. A method for assaying an organic molecule, comprising exposing a photolabile compound of claim 1 and a biological sample in vitro to light under conditions sufficient to release the organic molecule from the photolabile compound, and determining an effect of the organic molecule on the biological sample.

Assignees

• Univ Columbia
• Univ Buenos Aires

Inventors

• Etchenique Roberto
• Yuste Rafael
• Baraldo Luis

Classifications

• C07F15/06

  Cobalt compounds · CPC title

• G01N33/5008

  for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07F15/0046 Primary

  Ruthenium compounds · CPC title