Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore

被引:82
作者
Du, Lupei
Li, Minyong
Zheng, Shilong
Wang, Binghe [1 ]
机构
[1] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA
基金
美国国家卫生研究院;
关键词
hydrogen peroxide; reactive oxygen species (ROS); hydroxycoumarin; umbelliferone; fluorescence;
D O I
10.1016/j.tetlet.2008.03.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we report a novel water-soluble umbelliferone-based fluorescent probe for hydrogen peroxide. This probe shows very large increases (up to 100-fold) in fluorescent intensity upon reaction with hydrogen peroxide, and good selectivity over other reactive oxygen species (ROS). (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3045 / 3048
页数:4
相关论文
共 24 条
[1]  
Aaron J J, 1995, J Fluoresc, V5, P337, DOI 10.1007/BF01152560
[2]   A study of the relationship between the chemical structures and the fluorescence quantum yields of coumarins, quinoxalinones and benzoxazinones for the development of sensitive fluorescent derivatization reagents [J].
Azuma, K ;
Suzuki, S ;
Uchiyama, S ;
Kajiro, T ;
Santa, T ;
Imai, K .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2003, 2 (04) :443-449
[3]   A selective, cell-permeable optical probe for hydrogen peroxide in living cells [J].
Chang, MCY ;
Pralle, A ;
Isacoff, EY ;
Chang, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15392-15393
[4]   ROS as signalling molecules:: mechanisms that generate specificity in ROS homeostasis [J].
D'Autreaux, Benoit ;
Toledano, Michel B. .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2007, 8 (10) :813-824
[5]   Hydrogen peroxide: A metabolic by-product or a common mediator of ageing signals? [J].
Giorgio M. ;
Trinei M. ;
Migliaccio E. ;
Pelicci P.G. .
Nature Reviews Molecular Cell Biology, 2007, 8 (9) :722-728
[6]   Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates [J].
Ishiyama, T ;
Itoh, Y ;
Kitano, T ;
Miyaura, N .
TETRAHEDRON LETTERS, 1997, 38 (19) :3447-3450
[7]   Strong emission increase of a dicarboxyterpyridene europium(III) complex in the presence of citrate and hydrogen peroxide [J].
Kozhevnikov, VN ;
Mandl, C ;
Miltschitzky, S ;
Duerkop, A ;
Wolfbeis, OS ;
Koenig, B .
INORGANICA CHIMICA ACTA, 2005, 358 (07) :2445-2448
[8]   ELECTROPHILIC DISPLACEMENT REACTIONS .7. CATALYSIS BY CHELATING AGENTS IN THE REACTION BETWEEN HYDROGEN PEROXIDE AND BENZENEBORONIC ACID [J].
KUIVILA, HG ;
WILES, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (18) :4830-4834
[9]   ELECTROPHILIC DISPLACEMENT REACTIONS .9. EFFECTS OF SUBSTITUENTS ON RATES OF REACTIONS BETWEEN HYDROGEN PEROXIDE AND BENZENEBORONIC ACID [J].
KUIVILA, HG ;
ARMOUR, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (21) :5659-5662
[10]   Role of reactive oxygen species in apoptosis:: implications for cancer therapy [J].
Matés, JM ;
Sánchez-Jiménez, FM .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 2000, 32 (02) :157-170