| 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: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 0376425 Medline TA: Photochem Photobiol Country: United States |
Other Details:
|
Languages: eng Pagination: 641-8 Citation Subset: IM |
Affiliation:
|
Molecular Biosensor and Imaging Center, Carnegie Mellon University, Pittsburgh, PA 15213, USA. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| 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 |
| 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
Previous Document: Photocatalytic degradation of toluene using a novel flow reactor with Fe-doped TiO2 catalyst on poro...
Next Document: Toward understanding the mechanism of chromophore-assisted laser inactivation--evidence for the prim...