Photoremovable protecting groups and uses thereof

Patent metadata

Field	Value
Publication number	US-9957498-B2
Application number	US-201615016467-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Feb 5, 2015
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The invention relates to a method for photoreleasing a moiety G from a compound of the formula A-G. The methods of the present invention comprise irradiating a composition comprising the compound of the formula A-G at a wavelength of >500 nm, so as to photorelease the moiety G from the moiety A; wherein the moiety A comprises a chromophore and the moiety G comprises an organic compound.

First claim

What is claimed is:

1. A method for photoreleasing a moiety G, or a fragment thereof, from a compound of formula A-G comprising:
irradiating a composition comprising the compound of formula A-G at a wavelength of >500 nm, so as to photorelease the moiety G, or a fragment thereof, from the moiety A;
wherein:
the moiety A is a moiety of formula I:

wherein:
the wavy line represents the attachment point of the moiety A to the moiety G or L-G;
R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, halogen, optionally substituted C 1 -C 6 -alkyl, optionally substituted C 2 -C 6 -alkenyl or (C 6 -C 14 -aryl)-(C 2 -C 6 -alkenyl-), wherein the (C 6 -C 14 -aryl)-(C 2 -C 6 -alkenyl-) is optionally substituted on the C 2 -C 6 -alkenyl or the C 6 -C 14 -aryl; and
the moiety G is a protein, an oligopeptide, an amino acid, an oligonucleotide, an ion, or a small molecule.

2. The method of claim 1 , wherein the compound of the formula A-G has a wavelength absorption maximum, λ max , between about 510 nm to about 1000 nm.

3. The method of claim 1 , wherein the compound of the formula A-G has an extinction coefficient measured at the compound A-G λ max , of from about 4.0×10 4 M −1 cm −1 to about 8.0×10 4 M −1 cm −1 .

4. The method of claim 1 , wherein the protein comprised in the moiety G is selected from the group consisting of caspases, phosphatases, cholinesterases, esterases, transferases, restriction endonucleases, and hemoglobin.

5. The method of claim 1 , wherein the small molecule comprised in the moiety G is at least one of a dye, fragrance, nucleoside, nucleotide, neurotransmitter, and pharmaceutical agent.

6. The method of claim 5 , wherein the nucleoside comprised in the moiety G is adenine, thymidine, cytosine, guanosine or uridine.

7. The method of claim 5 , wherein the nucleotide comprised in the moiety G is adenosine triphosphate (ATP) or guanosine triphosphate (GTP).

8. The method of claim 5 , wherein the neurotransmitter comprised in the moiety G is norepinephrine, glutamate, dopamine, gamma-aminobutyric acid, serotonin or an endorphin.

9. The method of claim 1 , wherein R 1 and R 4 are each, independently, an optionally substituted C 1 -C 6 -alkyl.

10. The method of claim 1 , wherein R 1 and R 4 are each methyl.

11. The method of claim 9 , wherein R 3 and R 6 are each, independently, an optionally substituted C 1 -C 6 -alkyl.

12. The method of claim 11 , wherein R 3 and R 6 are each methyl.

13. The method of claim 11 , wherein R 2 and R 5 are each, independently, an optionally substituted C 1 -C 6 -alkyl.

14. The method of claim 13 , wherein R 2 and R 5 are each, independently, methyl or ethyl.

15. The method of claim 13 , wherein R 2 and R 5 are each, independently, halogen.

16. The method of claim 1 , wherein R 1 and R 4 are each, independently, (C 6 -C 14 -aryl)-(C 2 -C 6 -alkenyl-), wherein the (C 6 -C 14 -aryl)-(C 2 -C 6 -alkenyl-) is optionally substituted on the C 2 -C 6 -alkenyl or the C 6 -C 14 -aryl.

17. The method of claim 16 , wherein R 1 and R 4 are each, independently, (C 6 -C 10 -aryl)-(C 2 -C 4 -alkenyl-), wherein the (C 6 -C 10 -aryl)-(C 2 -C 4 -alkenyl-) is optionally substituted on the C 2 -C 4 -alkenyl or the C 6 -C 10 -aryl.

18. The method of claim 1 , wherein the moiety A is a moiety of the formula:

wherein R 11 is H; C 1-6 -alkyl-O—; —N(R 8 ) 2 , wherein each R 8 is hydrogen, alkyl, aryl or alkaryl, or —O—C 1-6 -alkyl-O—C 1-6 -alkyl.

19. The method of claim 18 , wherein R 11 is H; —OCH 3 , —N(CH 3 ) 2 ; or —(OCH 2 CH 2 ) 3 OCH 3 ).

20. The method of claim 18 , wherein the moiety A is a moiety of the formula:

21. The method of claim 1 , wherein the moiety G is a moiety of the formula —O-G′, wherein G′ is at least one of a protein, an oligonucleotide, a polynucleotide, an ion, and a small molecule.

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Winter Arthur Henry
• Beck Christie Lynn
• Mahoney Kaitlyn Marie
• Albright Toshia Renee
• Goswami Pratik Pran

Classifications

• C07K14/805

  Haemoglobins; Myoglobins · CPC title

• C12N13/00 Primary

  Treatment of microorganisms or enzymes with electrical or wave energy, e.g. magnetism, sonic waves · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• C07D209/16

  Tryptamines · CPC title

• C09B11/06

  Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus {and their ethers or esters} · CPC title