Photolabile compounds

• US 9,273,032 B2
• Filed: 10/24/2011
• Issued: 03/01/2016
• Est. Priority Date: 12/29/2003
• Status: Active Grant

• Current Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Original Assignee: Trustees Of Columbia University In The City Of New York (Columbia University)
• Inventors: Etchenique, Roberto, Yuste, Rafael, Baraldo, Luis
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US13/279,876
• Publication Number:
  US 20120116287A1
• Time in Patent Office: 1,590 Days
• Field of Search: 546/2, 546/304, 514/188
• US Class Current: 1/1
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07F 15/0046 Ruthenium compounds
• CPC Class Codes: C07F 15/06 Cobalt compounds
• CPC Class Codes: G01N 33/5008 for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics

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.

Claims

1. A compound of Formula IVb:

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′

;