Photolabile compounds

Patent metadata

Field	Value
Publication number	US-9273032-B2
Application number	US-201113279876-A
Country	US
Kind code	B2
Filing date	Oct 24, 2011
Priority date	Dec 29, 2003
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

The present invention describes photolabile compounds and 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

What is claimed is:

1. A compound of Formula IVb:

wherein:
L 1 is 4-aminopyridine, whose pyridyl nitrogen atom forms a bond with Ru;
L 2 is (R 2 ) 3 P, wherein each R 2 is 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. 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, wherein the organic molecule is 4-aminopyridine (4-AP).

3. 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, thereby making the organic molecule bioavailable to the subject, wherein the organic molecule is 4-aminopyridine (4-AP).

4. The method of claim 3 , wherein the light is sunlight, photo-optic light, or laser light.

5. The method of claim 3 , wherein the light is visible light or infrared light.

6. The method of claim 3 , wherein the exposing occurs at the site of a tumor, cancer, or neoplasm.

7. The method of claim 3 , wherein the administering occurs intravenously, topically, intradermally, intramuscularly, transdermally, subcutaneously, intranasally, parenterally, intrathecally, vaginally, rectally, colorectally, orally, intracranially, retroorbitally, intrasternally, or by injection.

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

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

10. A method for assaying an organic molecule, comprising exposing a photolabile compound of claim 1 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, wherein the organic molecule is 4-aminopyridine (4-AP).

11. 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 , wherein the organic molecule is 4-aminopyridine, whose pyridyl nitrogen atom forms a bond with Ru.

Assignees

• Etchenique Roberto
• Yuste Rafael
• Baraldo Luis
• Univ Columbia

Inventors

• Etchenique Roberto
• Yuste Rafael
• Baraldo Luis

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• C07F15/0046 Primary

  Ruthenium compounds · CPC title

• G01N33/5008

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

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07F15/06

  Cobalt compounds · CPC title