Boronic acid-appended bis-viologens as a new family of viologen quenchers for glucose sensing

被引:26
作者
Sharrett, Zachary [1 ]
Gamsey, Soya [1 ]
Levine, Paul [1 ]
Cunningham-Bryant, Dan [1 ]
Vilozny, Boaz [1 ]
Schiller, Alexander [1 ]
Wessling, Ritchie A. [1 ]
Singaram, Bakthan [1 ]
机构
[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA
关键词
D O I
10.1016/j.tetlet.2007.11.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new family of boronic acid-appended viologen quenchers has been synthesized containing two viologen subunits in a single quencher moiety. Relative to the single viologen-based quenchers previously developed in our laboratory, the bis-viologen ortho-boronic acid (BoB) compounds, in combination with the fluorescent dye, HPTS, display greatly enhanced Stern-Volmer quenching constants and much greater signal modulation in response to glucose. The superior performance is realized at lower quencher-to-dye ratios than are required for the single-viologen systems. Published by Elsevier Ltd.
引用
收藏
页码:300 / 304
页数:5
相关论文
共 40 条
[1]   Supramolecular analytical chemistry [J].
Anslyn, Eric V. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :687-699
[2]   Supramolecular optical chemosensors for organic analytes [J].
Bell, JW ;
Hext, NM .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :589-598
[3]   ELECTROCHEMISTRY OF THE VIOLOGENS [J].
BIRD, CL ;
KUHN, AT .
CHEMICAL SOCIETY REVIEWS, 1981, 10 (01) :49-82
[4]   Luminescent sensors and switches in the early 21st century [J].
Callan, JF ;
de Silva, AP ;
Magri, DC .
TETRAHEDRON, 2005, 61 (36) :8551-8588
[5]   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
[6]   Fluorescent chemosensors for carbohydrates: A decade's worth of bright spies for saccharides in review [J].
Cao, HS ;
Heagy, MD .
JOURNAL OF FLUORESCENCE, 2004, 14 (05) :569-584
[7]   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
[8]   The interaction of boronic acid-substituted viologens with pyranine: The effects of quencher charge on fluorescence quenching and glucose response [J].
Cordes, DB ;
Gamsey, S ;
Sharrett, Z ;
Miller, A ;
Thoniyot, P ;
Wessling, RA ;
Singaram, B .
LANGMUIR, 2005, 21 (14) :6540-6547
[9]   Optical glucose detection across the visible spectrum using anionic fluorescent dyes and a viologen quencher in a two-component saccharide sensing system [J].
Cordes, DB ;
Miller, A ;
Gamsey, S ;
Sharrett, Z ;
Thoniyot, P ;
Wessling, R ;
Singaram, B .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (09) :1708-1713
[10]  
Czarnik A. W., 1993, FLUORESCENT CHEMOSEN, V538