文献类型：期刊文献

英文题名：A phenazine-based near-infrared (NIR) chemodosimeter for cysteine obtained via a carbonyl-assisted cycloaddition process

作者：Qu, Yi[1];Zhang, Xiao[2,3];Wang, Linlin[1];Yang, Huiran[4];Yang, Lin[2,3];Cao, Jian[1];Hua, Jianli[2,3]

机构：[1]Shanghai Univ Engn Sci, Coll Chem & Chem Engn, 333 Longteng Rd, Shanghai 201620, Peoples R China;[2]E China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[4]Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

年份：2016

卷号：6

期号：27

起止页码：22389

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20161002079423);WOS:【SCI-EXPANDED(收录号:WOS:000371716300021)】；

基金：This work was partially supported by the National Basic Research 973 Program (2013CB733700), NSFC/China (21172073, 21372082, 21572062 and 21404068), Dr Qu thanks the talent programs from Shanghai Education Commission (ZZGCD15029) and SUES. We are also grateful to Prof. Fuyou Li of the Fudan University and Prof. A. P. deSilva of Queen's University Belfast for intelligent discussions. The CLSM research is also indebted to Prof. Li's laboratory.

语种：英文

外文关键词：Addition reactions - Fluorescence - Biocompatibility - Infrared devices - Amino acids - Lanthanum compounds - Cell culture

摘要：A phenazine derivative with a succinimide endcap (PHS) was designed and synthesized for cysteine (Cys) with near-infrared (NIR) emission. Upon the addition of Cys, the color of the solution changed clearly from greenish black to orange, which was attributed to the disappeared absorbance at 616 nm. An enhanced NIR emission band at 670 nm was found in the fluorescence spectra and a corresponding excitation peak at 466 nm arose in the excitation spectra. Verified by the dynamic reaction, the cyanoacetic acid moiety should be susceptible to be attacked by the -SH group in a fast rate through Michael addition reaction. Being highly reactive to the amino group (-NH2), the NHS-active carbonyl site could target the amino acid and accelerate the process of nucleophilic attack from the -SH group. This cycloaddition mechanism of the alpha,beta-unsaturated carbonyl NHS-ester was proved by H-1 NMR titration. In addition to its good biocompatibility, PHS was successfully applied to the detection of Cys in Hela cell lines with NIR fluorescence signals.