A glucose-selective fluorescence sensor based on boronic acid-diol recognition

被引:123
作者
Karnati, VV [1 ]
Gao, XM [1 ]
Gao, SH [1 ]
Yang, WQ [1 ]
Ni, WJ [1 ]
Sankar, S [1 ]
Wang, BH [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
关键词
D O I
10.1016/S0960-894X(02)00767-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A glucose selective diphenylboronic acid fluorescent sensor (10a) vith a K-a of 1472 M-1 has been synthesized and evaluated. This sensor shoals a 43- and 49-fold selectivity for glucose over fructose and galactose, respectively. The binding affinity improvement is about 300-fold and the selectivity. improvement for glucose over fructose is about 1400-fold compared vith the monoboronic acid compound. phenylboronic acid. H-1 NMR studies indicate that sensor 10a binds with alpha-D-glucofuranose in a bidentate manner (1:1 ratio). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3373 / 3377
页数:5
相关论文
共 30 条
  • [1] Implantation of a refillable glucose monitoring-telemetry device
    Atanasov, P
    Yang, S
    Salehi, C
    Ghindilis, AL
    Wilkins, E
    Schade, D
    [J]. BIOSENSORS & BIOELECTRONICS, 1997, 12 (07) : 669 - 680
  • [2] A fluorescent glucose sensor binding covalently to all five hydroxy groups of α-D-glucofuranose.: A reinvestigation
    Bielecki, M
    Eggert, H
    Norrild, JC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (03): : 449 - 455
  • [3] Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose
    Cao, HS
    Diaz, DI
    DiCesare, N
    Lakowicz, JR
    Heagy, MD
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1503 - 1505
  • [4] Daniloff G Y, 1999, Diabetes Technol Ther, V1, P261, DOI 10.1089/152091599317170
  • [5] A new glucose-selective fluorescent bisboronic acid.: First report of strong α-furanose complexation in aqueous solution at physiological pH
    Eggert, H
    Frederiksen, J
    Morin, C
    Norrild, JC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) : 3846 - 3852
  • [6] Building fluorescent sensors for carbohydrates using template-directed polymerizations
    Gao, SH
    Wang, W
    Wang, BH
    [J]. BIOORGANIC CHEMISTRY, 2001, 29 (05) : 308 - 320
  • [7] Performance of subcutaneously implanted glucose sensors for continuous monitoring
    Gerritsen, M
    Jansen, JA
    Lutterman, JA
    [J]. NETHERLANDS JOURNAL OF MEDICINE, 1999, 54 (04) : 167 - 179
  • [8] JAMES TD, 1994, ANGEW CHEM INT EDIT, V33, P2207, DOI 10.1002/anie.199422071
  • [9] Saccharide sensing with molecular receptors based on boronic acid
    James, TD
    Sandanayake, KRAS
    Shinkai, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (17) : 1910 - 1922
  • [10] NOVEL SACCHARIDE-PHOTOINDUCED ELECTRON-TRANSFER SENSORS BASED ON THE INTERACTION OF BORONIC ACID AND AMINE
    JAMES, TD
    SANDANAYAKE, KRAS
    IGUCHI, R
    SHINKAI, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) : 8982 - 8987