文献类型：期刊文献

英文题名：Target-Activated Coumarin Phototriggers Specifically Switch on Fluorescence and Photocleavage upon Bonding to Thiol-Bearing Protein

作者：Lin, Qiuning[1];Bao, Chunyan[1];Cheng, Shuiyu[1];Yang, Yunlong[1];Ji, Wei[1];Zhu, Linyong[1]

机构：[1]E China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2012

卷号：134

期号：11

起止页码：5052

外文期刊名：JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

收录：;EI(收录号：20121314897229);WOS:【SCI-EXPANDED(收录号:WOS:000302191900013)】；

基金：This research was supported by NSFC (21173078, 20903039), Shanghai Rising-Star Program (10QA1401600), Shanghai Science and Technology Commission (11JC1403300), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：Proteins - Excited states - Amino acids

摘要：A new concept in which only the molecular target, such as a thiol-bearing protein, can activate the phototrigger has been demonstrated. Such target-activatable phototriggers comprise three parts: a 7-aminocoumarin phototrigger, an electron acceptor (maleimide) that efficiently quenches the coumarin excited state, and a caged leaving group attached to the coumarin. In the absence of mercaptans, photoinduced electron transfer between coumarin and maleimide effectively blocks both the fluorescence and photocleavage pathways. Thiol-bearing molecules, however, readily annihilate the electron acceptor and thus restore the phototrigger for photorelease of the caged cargo (e.g., biotin). Unlike traditional phototriggers, functional-group-activated phototriggers allow easy handling under ambient light, report specific bonding to the target, and enable photocleavage capability selectively at the binding site in situ, thus effectively positioning the photoreleased cargo at the target. Meanwhile, the unique feature of thiol-specific activation of the fluorescence and photocleavage make our new phototrigger a universal tool that can be used to identify accurately protein cysteine S-nitrosylation, a physiologically important posttranslational modification.