Thiol-addition reactions and their applications in thiol recognition

被引：531

作者：

Yin, Caixia ^{[1
]}

Huo, Fangjun ^{[2
]}

Zhang, Jingjing ^{[1
]}

Martinez-Manez, Ramon ^{[3
,4
]}

Yang, Yutao ^{[1
,2
]}

Lv, Haigang ^{[1
]}

Li, Sidian ^{[1
]}

机构：

[1] Shanxi Univ, Inst Mol Sci, Minist Educ, Key Lab Chem Biol & Mol Engn, Taiyuan 030006, Peoples R China

[2] Shanxi Univ, Res Inst Appl Chem, Taiyuan 030006, Peoples R China

[3] Univ Valencia, Unidad Mixta Univ Politecn Valencia, Ctr Interunive Reconocimiento Mol & Desarrollo Te, E-46003 Valencia, Spain

[4] CIBER Bioingn Biomat & Nanotecnol CIBER BNN, Madrid, Spain

来源：

CHEMICAL SOCIETY REVIEWS | 2013年 / 42卷 / 14期

基金：

中国国家自然科学基金; 山西省青年科学基金;

关键词：

TURN-ON PROBE; INTRAMOLECULAR CHARGE-TRANSFER; PHOTOINDUCED ELECTRON-TRANSFER; SELECTIVE FLUORESCENT-PROBE; CONTAINING AMINO-ACIDS; COLORIMETRIC CHEMOSENSOR; CHEMILUMINESCENCE DETERMINATION; GLUTATHIONE DEFICIENCY; PLASMA HOMOCYSTEINE; METHYLMALONIC ACID;

D O I：

10.1039/c3cs60055f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Because of the biological importance of thiols, the development of probes for thiols has been an active research area in recent years. In this review, we summarize the results of recent exciting reports regarding thiol-addition reactions and their applications in thiol recognition. The examples reported can be classified into four reaction types including 1,1, 1,2, 1,3, 1,4 addition reactions, according to their addition mechanisms, based on different Michael acceptors. In all cases, the reactions are coupled to color and/or emission changes, although some examples dealing with electrochemical recognition have also been included. The use of thiol-addition reactions is a very simple and straightforward procedure for the preparation of thiol-sensing probes.

引用

页码：6032 / 6059

页数：28

共 135 条

[1] A specific HPLC-UV method for the determination of cysteine and related aminothiols in biological samples [J].

Amarnath, K ;

Amarnath, V ;

Amarnath, K ;

Valentine, HL ;

Valentine, WM .

TALANTA, 2003, 60 (06) :1229-1238

[2]

[Anonymous], 1994, DANGEROUS PROPERTIES, V14, P92

[3] A highly selective fluorescent probe for thiol bioimaging [J].

Bouffard, Jean ;

Kim, Youngmi ;

Swager, Timothy M. ;

Weissleder, Ralph ;

Hilderbrand, Scott A. .

ORGANIC LETTERS, 2008, 10 (01) :37-40

[4] Definitive identification of cysteine and glutathione complexes of bismuth by mass spectrometry: assessing the biochemical fate of bismuth pharmaceutical agents [J].

Burford, N ;

Eelman, MD ;

Mahony, DE ;

Morash, M .

CHEMICAL COMMUNICATIONS, 2003, (01) :146-147

[5] Selective phosphorescence chemosensor for homocysteine based on an iridium(III) complex [J].

Chen, Huili ;

Zhao, Qiang ;

Wu, Yanbo ;

Li, Fuyou ;

Yang, Hong ;

Yi, Tao ;

Huang, Chunhui .

INORGANIC CHEMISTRY, 2007, 46 (26) :11075-11081

[6] A ruthenium(II) complex with environment-responsive dual emission and its application in the detection of cysteine/homocysteine [J].

Chen, Huili ;

Li, Xiaokai ;

Wu, Yanbo ;

Gao, Wei ;

Bai, Ruichun .

DALTON TRANSACTIONS, 2012, 41 (43) :13292-13297

[7] Determination of thiols and disulfides via HPLC quantification of 5-thio-2-nitrobenzoic acid [J].

Chen, Wei ;

Zhao, Yong ;

Seefeldt, Teresa ;

Guan, Xiangming .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2008, 48 (05) :1375-1380

[8] Fluorescent and colorimetric probes for detection of thiols [J].

Chen, Xiaoqiang ;

Zhou, Ying ;

Peng, Xiaojun ;

Yoon, Juyoung .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135

[9] A thiol-specific fluorescent probe and its application for bioimaging [J].

Chen, Xiaoqiang ;

Ko, Sung-Kyun ;

Kim, Min Jung ;

Shin, Injae ;

Yoon, Juyoung .

CHEMICAL COMMUNICATIONS, 2010, 46 (16) :2751-2753

[10] A Coumarin-based Fluorescence Sensor for the Reversible Detection of Thiols [J].

Cho, A. Young ;

Choi, Kihang .

CHEMISTRY LETTERS, 2012, 41 (12) :1611-1612

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