文献类型：期刊文献

英文题名：Colorimetric and fluorimetric detection of cysteine: Unexpected Michael addition-elimination reaction

作者：Qu, Hao-Ran[1];Zhang, Zi-You[1];Wang, Nan[1];Sun, Qian[1];Liu, Shan-Shan[1];Zhang, Wei-Bing[1];Qian, Jun-Hong[1,2]

机构：[1]E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2015

卷号：26

期号：10

起止页码：1249

外文期刊名：CHINESE CHEMICAL LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000364253800012)】；

基金：This work was financially supported by National 973 Program (No. 2011CB910403), Shanghai Municipal Natural Science Foundation (No. 15ZR1409000) and the open fund of Shanghai Key Laboratory of Chemical Biology (No. SKLCB-2013-03).

语种：英文

外文关键词：Michael addition; Sulfur-containing compounds; Cysteine; Fluorescent probe

摘要：The synthesis of three isomers based on Michael addition mechanism for the detection of sulfur-containing species in aqueous solution is described. These compounds are constructed by conjugating an enone to a coumarin fluorophore. A substituted-phenyl (o, in, or p-) was appended at the carbonyl carbon to adjust the reactivity. The experimental results showed that (E)-7-(diethylamino)-3-(3-(3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one (m-QPS) and (E)-7-(diethylamino)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one (p-QPS) barely react with sulfur-containing nucleophiles, while (E)-7-(diethylamino)-3-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one (o-QPS) exhibited a fast response toward sulfite, sulfide and thiols in DMSO/phosphate buffer (2:1). The above results are probably due to the intramolecular H-bonding activated Michael addition. More interestingly, cysteine triggered unusual photophysical responses of o-QPS: the original absorption (488 nm) and emission peaks (573 nm) underwent significant blue shifts initially and then recovered, which might be caused by the Michael addition and elimination reaction, respectively. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.