The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1,2,5]oxadiazole dyes  

作　　者：Dongyang Li Weijie Chen Sheng Hua Liu Xiaoqiang Chen Jun Yin 

机构地区：[1]Key Laboratory of Pesticide and Chemical Biology.Ministry of Education,Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis,International Joint Research Center for Intelligent Biosensing Technology and Health,College of Chemistry,Central China Normal University,Wuhan 430079,China [2]State Key Laboratory of Materials-Oriented Chemical Engineering,College of Chemical Engineering,Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM),Nanjing Tech University,Nanjing 211816,China

出　　处：《Chinese Chemical Letters》2020年第11期2891-2896,共6页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China(Nos.21676113,21402057,21772054,21472059);Distinguished Young Scholar of Hubei Province(No.2018CFA079);Youth Chen-Guang Project of Wuhan(No.2016070204010098);the 111 Project B17019;the Ministry-Province Jointly Constructed Base for State Key Lab-Shenzhen Key Laboratory of Chemical Biology(Shenzhen),the State Key Laboratory of Materials-Oriented Chemical Engineering(No.KL17-10);Open Project Fund of Key Laboratory of Natural Resources of Changbai Mountain&Functional Molecules(Yanbian University),Ministry of Education(No.NRFM201701);the Foundation of Key Laboratory of Synthetic and Biological Colloids,Ministry of Education,Jiangnan University(No.JDSJ2017-07);the Self-determined Research Funds of CCNU from the Colleges’Basic Research and Operation of MOE(No.CCNU18TS012)。

摘　　要：The different oxidation states of sulphur atom play a significant role on functional materials.In this work,a aryl-thioether and its sulphone substituted benzo[c][1,2,5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino acids.The result of selectivity experiments showed they detected the cysteine and homocysteine under physiological condition with negligible interference from other amino acids.In comparison to the thioether dye,the sulphone-based dye exhibited much faster response time for Cys and Hcy.However,the sulphone restricted its thiol-reactivity and bioimaging performance in living cells.By reducing the oxidation state of sulphur atom,we amazedly found that the sulfoxide-based dye still maintained high selectivity ultrafast response time for Cys/Hcy under physiological condition.It was worth mentioning that it also had high reactivity and good bioimaging performance that sulfone compounds did not have.

关 键 词：Benzo[c][1 2 5]oxadiazole dye SULFOXIDE Sulphone Thiol response 

分 类 号：R318[医药卫生—生物医学工程] O657.3[医药卫生—基础医学]