Ion-activated photolabile compounds

Patent metadata

Field	Value
Publication number	US-10407399-B2
Application number	US-201615756788-A
Country	US
Kind code	B2
Filing date	Sep 1, 2016
Priority date	Sep 1, 2015
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

The presently-disclosed subject matter relates to analyte-activated photolabile compounds. The compounds include the formula: wherein Z includes a maskable molecule; L is selected from a bond, C, C(O), O, alkyl, (O)alkyl, and alkoxy; R1 is selected from H, halogen, alkyl, and acyl; each R2 is independently selected from H, alkyl, aryl, and acyl, and is optionally substituted with one or more heteroatoms independently selected from COOH and COO(alkyl); and R3 is selected from H, alkyl, aryl, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, and SO3H, and is optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COO, COOH, COO(alkyl), COO(aryl), C(O)NR2, PO3H2, and/or SO3H. Also provided are methods of detecting calcium and treating a subject with the analyte-activated photolabile compounds.

First claim

What is claimed is:

1. A compound of the formula:

wherein:
Z includes a maskable molecule;
L is selected from a bond, C, C(O), O, alkyl, (O)alkyl, and alkoxy;
R 1 is selected from H, halogen, alkyl, and acyl;
each R 2 is independently selected from H, alkyl, aryl, and acyl, and is optionally substituted with one or more moieties independently selected from COOH and COO(alkyl) or the R 2 groups, taken together with the carbon atom to which they are bound, form a 4-10 membered ring;
each R 4 is independently selected from H, alkyl, and alkenyl; and
X is selected from H, alkyl, aryl, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, CHO, COOH, COO(alkyl), COO(aryl), PO 3 H 2 , pyrrolidine, and SO 3 H, R 3 being optionally substituted with one or more moieties independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO, CHO, COO, COOH, COO(alkyl), COO(aryl), C(O)NR 2 , PO 3 H 2 , and/or SO 3 H.

2. The compound of claim 1 , wherein Z is selected from the group consisting of a fluorophore and an active agent.

3. The compound of claim 2 , wherein the active agent is selected from an enzyme, catalyst, ribozyme, organometallic, protein, glycoprotein, peptide, polyamino acid, antibody, nucleic acid, steroidal molecule, antibiotic, antiviral, antimycotic, anticancer agent, analgesic agent, antirejection agent, immunosuppressant, cytokine, carbohydrate, oleophobic, lipid, pharmaceutical, chemotherapeutic, and combinations thereof.

4. The compound of claim 1 , wherein R 2 is selected from CH 2 COOH and CH 2 COO(alkyl).

5. The compound of claim 1 , wherein X is selected from methoxy and pyrrolidine.

6. The compound of claim 1 , according to the formula:

7. The compound of claim 1 , according to the formula:

8. The compound of claim 1 , according to the formula:

9. The compound of claim 1 , according to the formula:

10. The compound of claim 1 , wherein the R 4 groups, taken together with the carbon atoms to which they are bound, form a 5-6 membered ring.

11. The compound of claim 10 , according to the formula:

12. The compound of claim 10 , according to the formula:

Assignees

• Hughes Howard Med Inst

Inventors

• Lavis Luke D
• Grimm Jonathan B
• Heckman Laurel M
• Schreiter Eric R

Classifications

• G01N33/84

  involving inorganic compounds or pH · CPC title

• G01N33/582

  with fluorescent label · CPC title

• A61N5/06

  using light · CPC title

• C07D311/16 Primary

  substituted in position 7 · CPC title

• A61N5/062

  Photodynamic therapy, i.e. excitation of an agent · CPC title