Document Detail


A new class of fluorescent boronic acids that have extraordinarily high affinities for diols in aqueous solution at physiological pH.
MedLine Citation:
PMID:  20938931     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The boronic acid group is an important recognition moiety for sensor design. Herein, we report a series of isoquinolinylboronic acids that have extraordinarily high affinities for diol-containing compounds at physiological pH. In addition, 5- and 8-isoquinolinylboronic acids also showed fairly high binding affinities towards D-glucose (K(a)=42 and 46 M(-1), respectively). For the first time, weak but encouraging binding of cis-cyclohexanediol was found for these boronic acids. Such binding was coupled with significant fluorescence changes. Furthermore, 4- and 6-isoquinolinylboronic acids also showed the ability to complex methyl α-D-glucopyranose (K(a)=3 and 2 M(-1), respectively).
Authors:
Yunfeng Cheng; Nanting Ni; Wenqian Yang; Binghe Wang
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  16     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2010 Dec 
Date Detail:
Created Date:  2010-11-29     Completed Date:  2011-02-16     Revised Date:  2013-07-03    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  13528-38     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4098, USA.
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MeSH Terms
Descriptor/Qualifier:
Alcohols / chemistry*
Boronic Acids / chemical synthesis*,  chemistry,  diagnostic use
Combinatorial Chemistry Techniques
Cyclohexanols / chemistry*
Fluorescence
Fluorescent Dyes / chemical synthesis*,  chemistry,  diagnostic use
Glucose / chemistry
Hydrogen-Ion Concentration
Isoquinolines / chemical synthesis*,  chemistry,  diagnostic use
Molecular Structure
Solubility
Stereoisomerism
Water / chemistry
Grant Support
ID/Acronym/Agency:
GM084933/GM/NIGMS NIH HHS; GM086925/GM/NIGMS NIH HHS; R01 GM084933/GM/NIGMS NIH HHS; R42 GM086925/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/8-isoquinolinylboronic acid; 0/Alcohols; 0/Boronic Acids; 0/Cyclohexanols; 0/Fluorescent Dyes; 0/Isoquinolines; 50-99-7/Glucose; 7732-18-5/Water
Comments/Corrections

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