The interaction of boronic acid-substituted viologens with pyranine: The effects of quencher charge on fluorescence quenching and glucose response

被引:70
作者
Cordes, DB [1 ]
Gamsey, S [1 ]
Sharrett, Z [1 ]
Miller, A [1 ]
Thoniyot, P [1 ]
Wessling, RA [1 ]
Singaram, B [1 ]
机构
[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA
关键词
D O I
10.1021/la050219x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The fluorescence sensing of several monosaccharides using boronic acid-substituted viologen quenchers in combination with the fluorescent dye pyranine (HPTS) is reported. In this two-component sensing system, fluorescence quenching by the viologen is modulated by monosaccharides to provide a fluorescence signal. A series of viologen quenchers with different charges were prepared and tested for their ability both to quench the fluorescence of HPTS and to sense changes in glucose concentration in aqueous solution at pH 7.4. Both quenching efficiency and sugar sensing were found to be strongly dependent upon viologen charge. The molar ratio between HPTS and each of the viologen quenchers was varied in order to obtain an optimal ratio that provided a fairly linear fluorescence signal across a physiological glucose concentration range. Both the quenching and sugar sensing results are explained by electrostatic interaction between dye and quencher.
引用
收藏
页码:6540 / 6547
页数:8
相关论文
共 42 条
[1]   High ionic strength glucose-sensing photonic crystal [J].
Alexeev, VL ;
Sharma, AC ;
Goponenko, AV ;
Das, S ;
Lednev, IK ;
Wilcox, CS ;
Finegold, DN ;
Asher, SA .
ANALYTICAL CHEMISTRY, 2003, 75 (10) :2316-2323
[2]  
Argaman D, 2003, DIABETOLOGIA, V46, pA309
[3]   Photonic crystal carbohydrate sensors: Low ionic strength sugar sensing [J].
Asher, SA ;
Alexeev, VL ;
Goponenko, AV ;
Sharma, AC ;
Lednev, IK ;
Wilcox, CS ;
Finegold, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (11) :3322-3329
[4]   Excitation and emission wavelength ratiometric cyanide-sensitive probes for physiological sensing [J].
Badugu, R ;
Lakowicz, JR ;
Geddes, CD .
ANALYTICAL BIOCHEMISTRY, 2004, 327 (01) :82-90
[5]   A fluorescent glucose sensor binding covalently to all five hydroxy groups of α-D-glucofuranose.: A reinvestigation [J].
Bielecki, M ;
Eggert, H ;
Norrild, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (03) :449-455
[6]   Boronic acid substituted viologen based optical sugar sensors: modulated quenching with viologen as a method for monosaccharide detection [J].
Camara, JN ;
Suri, JT ;
Cappuccio, FE ;
Wessling, RA ;
Singaram, B .
TETRAHEDRON LETTERS, 2002, 43 (07) :1139-1141
[7]   Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides [J].
Cao, H ;
McGill, T ;
Heagy, MD .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :2959-2966
[8]   Evaluation of pyranine derivatives in boronic acid based saccharide sensing: Significance of charge interaction between dye and quencher in solution and hydrogel [J].
Cappuccio, FE ;
Suri, JT ;
Cordes, DB ;
Wessling, RA ;
Singaram, B .
JOURNAL OF FLUORESCENCE, 2004, 14 (05) :521-533
[9]   Nanotechnology and biosensors [J].
Chen, JR ;
Miao, YQ ;
He, NY ;
Wu, XH ;
Li, SJ .
BIOTECHNOLOGY ADVANCES, 2004, 22 (07) :505-518
[10]   Highly sensitive biological and chemical sensors based on reversible fluorescence quenching in a conjugated polymer [J].
Chen, LH ;
McBranch, DW ;
Wang, HL ;
Helgeson, R ;
Wudl, F ;
Whitten, DG .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (22) :12287-12292