文献类型：期刊文献

英文题名：A highly selective ratiometric near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging

作者：Guo, Zhiqian[1,2,3,4];Nam, SeongWon[1,2];Park, Sungsu[1,2];Yoon, Juyoung[1,2]

机构：[1]Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea;[2]Ewha Womans Univ, Dept Bioinspired Sci WCU, Seoul 120750, South Korea;[3]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[4]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2012

卷号：3

期号：9

起止页码：2760

外文期刊名：CHEMICAL SCIENCE

收录：;EI(收录号：20123215306963);WOS:【SCI-EXPANDED(收录号:WOS:000306931300014)】；

基金：This work was supported by the National Research Foundation of Korea Grant funded by the Korean Government (SRC Program: 2012-0000647), WCU Program (R31-2008-000-10010-0) and by the Converging Research Center Program through the Ministry of Education, Science and Technology (2011K000720). This work was supported by the Ewha Global Top5 Grant 2011 of Ewha Womans University. Z. Q. Guo acknowledges NSFY/China (Grant 61177034). The co-first author, S.-W. Nam was supported by RP-Grant 2011 of Ewha Womans University.

语种：英文

外文关键词：Amino acids - Emission spectroscopy - Cancer cells - Infrared devices - Ketones

摘要：We developed a highly selective ratiometric near-infrared cyanine-based probe CyAC for cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). Upon the addition of Cys to the solution of CyAC, remarkable shifts in the spectra of CyAC can be monitored (from 770 nm to 515 nm in absorption spectra and from 780 nm to 570 nm in emission spectra). For the first time, the novel strategy that reversibly modulates the polymethine pi-electron system by conjugation and removal of the specific trigger moiety was implemented for the generation of a ratiometric cyanine-based sensor. Hydroxy cyanine CyAE was chosen as the flurophore scaffold because the tautomerism (CyAE and CyAK or CyAD) can cause the reversible change in the pi-conjugation system of the dyes with large shifts in the spectra. An acrylate group containing a alpha, beta-unsaturated ketone as a functional trigger moiety was incorporated with CyAK to form the sensor CyAC. This specific response for Cys was based on the differences of the kinetics of intramolecular adduct/cyclizations. Moreover, CyAC was successfully applied for bioimaging Cys in living cancer cells. This paradigm by modulation of the polymethine p-electron system in the cyanine dye provides a promising methodology for the design of ratiometric cyanine-based sensors.