Caged compound delivery and related compositions, methods and systems

Patent metadata

Field	Value
Publication number	US-9636656-B2
Application number	US-201214362888-A
Country	US
Kind code	B2
Filing date	Dec 7, 2012
Priority date	Dec 7, 2011
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

Methods are described and related devices, compositions, and systems, in which a caged compound is administered to a biological environment, the caged compound being caged with a long wavelength absorber, the long wavelength being a wavelength greater than or equal to 750 nm; and irradiating the biological environment to excite the long wavelength absorber with light at a wavelength in a range from 900-1100 nm, thus decaging the compound.

First claim

The invention claimed is:

1. A method comprising
administering a photoacid compound to a biological environment, wherein the photoacid compound comprises a caged compound and a light absorbing moiety, the caged compound being caged with the light absorbing moiety having an absorption wavelength greater than or equal to 750 nm; and
irradiating the biological environment to excite the light absorbing moiety with light at a wavelength in a range from 900-1100 nm, thus releasing the caged compound wherein the photoacid compound is represented according to formula (I):

wherein: R 4 is the light-absorbing moiety presenting a hydroxyl group for interaction with the carbonyl oxygen of R 3 (CO)O, wherein the light-absorbing moiety is a substituted or unsubstituted polycyclic aromatic hydrocarbon containing 2 to 7 aromatic rings, a substituted or unsubstituted closed chain cyanine, or a substituted or unsubstituted hemicyanine, and wherein the hydroxyl group is covalently bonded to the polycyclic aromatic hydrocarbon or closed chain cyanine or hemicyanine and is ortho to X 1 ; R 3 is the caged compound, wherein the caged compound is substituted or unsubstituted alkyl, aryl, heteroaryl, aminoalkyl, or oxyalkyl moiety; X 1 is independently selected from the group consisting of C and O;
m is between 0 and 3; and R 1 and R 2 are independently C 1 -C 6 alkyl groups, cycloalkyl, or substituted or unsubstituted hydrocarbylene groups wherein when R 1 and R 2 are substituted or unsubstituted hydrocarbyl groups they are linked together to form a cyclic moiety.

2. The method of claim 1 , wherein the light absorbing moiety is able to absorb light at a wavelength of from about 900 nm to about 1100 nm.

3. The method of claim 1 wherein R1 and R2 are methyl groups.

4. The method of claim 1 , wherein the biological environment is a body part of an individual and the administering is performed by systemic or topic administration of the photoacid compound.

5. The method of claim 4 , wherein the biological environment exhibits inflammation or an inflammatory response.

6. The method of claim 1 , wherein the caged compound is a drug or imaging agent.

7. The method of claim 1 , wherein the irradiating is performed by a wearable infrared emitting device suitable to worn around a body part of an individual.

Assignees

• California Inst Of Techn
• Univ Southern California

Inventors

• Dougherty Dennis A
• Grubbs Robert H
• Humayun Mark
• Regan Clinton J
• Emami Azita

Classifications

• A61K9/0085 Primary

  Brain, e.g. brain implants; Spinal cord · CPC title

• C07D209/20

  substituted additionally by nitrogen atoms, e.g. tryptophane · CPC title

• A61K47/48246

  Human Necessities · mapped topic

• A61K41/0042

  Photocleavage of drugs in vivo, e.g. cleavage of photolabile linkers in vivo by UV radiation for releasing the pharmacologically-active agent from the administered agent; photothrombosis or photoocclusion · CPC title

• A61K49/0021

  the fluorescent group being a small organic molecule · CPC title