Document Detail


Modelling, synthesis and biological evaluation of novel glucuronide-based probes of Vibrio cholerae sialidase.
MedLine Citation:
PMID:  16275104     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The development of sialidase inhibitors is an area of continuing interest due to their potential use as therapeutic agents to combat viral and bacterial infections. Herein, we report our studies involving the sialidase from the pathogen Vibrio cholerae, through the modelling, synthesis and biological evaluation of mimetics of 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid (Neu5Ac2en, 1), a naturally occurring sialidase inhibitor. These mimetics are O- and S-glycosides of N-acetyl-D-glucosaminuronic acid in which the aglycone portion effectively replaces the C-6 glycerol side chain of Neu5Ac2en (1). The choice of aglycones was aided by use of the X-ray crystal structure of V. cholerae sialidase complexed with Neu5Ac2en (1). All Neu5Ac2en mimetics tested were found to inhibit V. cholerae sialidase as determined using a standard fluorometric assay.
Authors:
Maretta C Mann; Robin J Thomson; Jeffrey C Dyason; Sarah McAtamney; Mark von Itzstein
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Publication Detail:
Type:  Evaluation Studies; Journal Article; Research Support, Non-U.S. Gov't     Date:  2005-11-04
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  14     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2006 Mar 
Date Detail:
Created Date:  2006-01-23     Completed Date:  2006-05-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  1518-37     Citation Subset:  IM    
Affiliation:
Institute for Glycomics, Griffith University (Gold Coast Campus), Australia.
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MeSH Terms
Descriptor/Qualifier:
Animals
Bacterial Infections / drug therapy
Binding Sites
Crystallography, X-Ray
Enzyme Inhibitors / chemical synthesis*,  pharmacology*
Fluorometry
Glucuronides / chemical synthesis*,  pharmacology
Glycerol / chemistry
Glycosides / chemistry
Humans
Molecular Mimicry
Neuraminidase / antagonists & inhibitors*
Structure-Activity Relationship
Uronic Acids / chemistry
Chemical
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Glucuronides; 0/Glycosides; 0/Uronic Acids; 34047-66-0/N-acetylglucosaminuronic acid; 56-81-5/Glycerol; EC 3.2.1.18/Neuraminidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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