Document Detail


Synthesis, photophysical, photochemical and biological properties of caged GABA, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] butanoic acid.
MedLine Citation:
PMID:  15623351     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The photorelease of a caged neurotransmitter can be used to investigate the function of neuronal circuits in tissues. We have designed and synthesized a stable, caged gamma-aminobutyric acid (GABA) derivative, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy)carbonyl]amino] butanoic acid (BC204), that releases the neurotransmitter in physiological medium when irradiated with UV light at 300-400 nm in PBS at pH 7.4. The release of GABA occurs with the formation of the major photoproduct, 7-amino-4-(hydroxymethyl)-2H-1-benzopyran-2-one, via a solvolytic photodegradation mechanism of the coumarin moiety and was confirmed by electrospray mass spectrometry/mass spectrometry (ESI MS/MS). BC204 is chemically stable and shows no intrinsic activity after many hours under physiological dark conditions. These properties suggest that BC204 is an excellent form of caged GABA that is well suited for long-term biological studies.
Authors:
Beate Cürten; Paul H M Kullmann; Mark E Bier; Karl Kandler; Brigitte F Schmidt
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Photochemistry and photobiology     Volume:  81     ISSN:  0031-8655     ISO Abbreviation:  Photochem. Photobiol.     Publication Date:    2005 May-Jun
Date Detail:
Created Date:  2005-06-13     Completed Date:  2005-10-03     Revised Date:  2014-05-09    
Medline Journal Info:
Nlm Unique ID:  0376425     Medline TA:  Photochem Photobiol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  641-8     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Coumarins / chemistry
Drug Stability
Molecular Structure
Neurotransmitter Agents / metabolism*
Photochemistry*
Photolysis*
Spectrometry, Mass, Electrospray Ionization
Time Factors
gamma-Aminobutyric Acid / analogs & derivatives*,  chemical synthesis,  metabolism,  pharmacology
Grant Support
ID/Acronym/Agency:
R01 DC004199/DC/NIDCD NIH HHS
Chemical
Reg. No./Substance:
0/4-(((2H-1-benzopyran-2-one-7-amino-4-methoxy)carbonyl)amino) butanoic acid; 0/Coumarins; 0/Neurotransmitter Agents; 56-12-2/gamma-Aminobutyric Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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