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
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
收藏
页码:6032 / 6059
页数:28
相关论文
共 135 条
[81]   Homocysteine and cardiovascular disease [J].
Refsum, H ;
Ueland, PM ;
Nygård, O ;
Vollset, SE .
ANNUAL REVIEW OF MEDICINE, 1998, 49 :31-62
[83]   A Mesoporous 3D Hybrid Material with Dual Functionality for Hg2+ Detection and Adsorption [J].
Ros-Lis, Jose V. ;
Casasus, Rosa ;
Comes, Maria ;
Coll, Carmen ;
Marcos, M. Dolores ;
Martinez-Manez, Ramon ;
Sancenon, Felix ;
Soto, Juan ;
Amoros, Pedro ;
El Haskouri, Jamal ;
Garro, Nuria ;
Rurack, Knut .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (27) :8267-8278
[84]   A regenerative chemodosimeter based on metal-induced dye formation for the highly selective and sensitive optical determination of Hg2+ ions [J].
Ros-Lis, JV ;
Marcos, MD ;
Mártinez-Máñez, R ;
Rurack, K ;
Soto, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4405-4407
[85]   Squaraines as fluoro-chromogenic probes for thiol-containing compounds and their application to the detection of biorelevant thiols [J].
Ros-Lis, JV ;
García, B ;
Jiménez, D ;
Martínez-Máñez, R ;
Sancenon, F ;
Soto, J ;
Gonzalvo, F ;
Valldecabres, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4064-4065
[86]   Visual detection of cysteine and homocysteine [J].
Rusin, O ;
St Luce, NN ;
Agbaria, RA ;
Escobedo, JO ;
Jiang, S ;
Warner, IM ;
Dawan, FB ;
Lian, K ;
Strongin, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :438-439
[87]   SENSITIVITY OF SERUM METHYLMALONIC ACID AND TOTAL HOMOCYSTEINE DETERMINATIONS FOR DIAGNOSING COBALAMIN AND FOLATE DEFICIENCIES [J].
SAVAGE, DG ;
LINDENBAUM, J ;
STABLER, SP ;
ALLEN, RH .
AMERICAN JOURNAL OF MEDICINE, 1994, 96 (03) :239-246
[88]   Plasma homocysteine as a risk factor for dementia and Alzheimer's disease. [J].
Seshadri, S ;
Beiser, A ;
Selhub, J ;
Jacques, PF ;
Rosenberg, IH ;
D'Agostino, RB ;
Wilson, PWF ;
Wolf, PA .
NEW ENGLAND JOURNAL OF MEDICINE, 2002, 346 (07) :476-483
[90]   A spiropyran-based ensemble for visual recognition and quantification of cysteine and homocysteine at physiological levels [J].
Shao, Na ;
Jin, Jian Yu ;
Cheung, Sin Man ;
Yang, Rong Hua ;
Chan, Wing Hong ;
Mo, Tian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4944-4948