Ncm, a Photolabile Group for Preparation of Caged Molecules: Synthesis and Biological Application

被引：20

作者：

Muralidharan, Sukumaran ^{[1
,2
]}

Dirda, Nathaniel D. A. ^{[1
,2
]}

Katz, Elizabeth J. ^{[3
,4
,6
]}

Tang, Cha-Min ^{[3
,4
]}

Bandyopadhyay, Sharba ^{[5
]}

Kanold, Patrick O. ^{[5
]}

Kao, Joseph P. Y. ^{[1
,2
,3
]}

机构：

[1] Univ Maryland, Sch Med, Ctr Biomed Engn & Technol, Baltimore, MD 21201 USA

[2] Univ Maryland, Sch Med, Dept Physiol, Baltimore, MD 21201 USA

[3] Univ Maryland, Program Neurosci, Baltimore, MD 21201 USA

[4] Univ Maryland, Sch Med, Dept Neurol, Baltimore, MD 21201 USA

[5] Univ Maryland, Dept Biol, College Pk, MD 20742 USA

[6] US FDA, Ctr Devices & Radiol Hlth, Silver Spring, MD USA

来源：

PLOS ONE | 2016年 / 11卷 / 10期

基金：

美国国家卫生研究院;

关键词：

ACID ESTER PRODRUGS; ORTHO-NITROBENZYL ESTERS; IN-VITRO; ARYLNITROSO COMPOUNDS; REDUCED GLUTATHIONE; CHEMICAL-STABILITY; PROTECTING GROUP; AUDITORY-CORTEX; DRUG-DELIVERY; THIOLS;

D O I：

10.1371/journal.pone.0163937

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Ncm, 6-nitrocoumarin-7-ylmethyl, is a photolabile protective group useful for making "caged" molecules. Ncm marries the reliable photochemistry of 2-nitrobenzyl systems with the excellent stability and spectroscopic properties of the coumarin chromophore. From simple, commercially available starting materials, preparation of Ncm and its caged derivatives is both quick and easy. Photorelease of Ncm-caged molecules occurs on the microsecond time scale, with quantum efficiencies of 0.05-0.08. We report the synthesis and physical properties of Ncm and its caged derivatives. The utility of Ncm-caged glutamate for neuronal photostimulation is demonstrated in cultured hippocampal neurons and in brain slice preparations.

引用

页数：22

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