Document Detail

Modelling, synthesis and biological evaluation of novel glucuronide-based probes of Vibrio cholerae sialidase.
MedLine Citation:
PMID:  16275104     Owner:  NLM     Status:  MEDLINE    
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.
Maretta C Mann; Robin J Thomson; Jeffrey C Dyason; Sarah McAtamney; Mark von Itzstein
Related Documents :
6847304 - Sialic acid content of human spermatozoa and seminal plasma in relation to sperm counts.
3924604 - Further characterization of the tracheal receptor for pseudomonas aeruginosa.
9629854 - N-glycolylneuraminic acid-containing gm1 is a new molecule for serum antibody in guilla...
3383434 - The carbohydrate composition of human serum amyloid p component.
10807414 - Interactive roles of endogenous prostaglandin and nitric oxide in regulation of acid se...
7582024 - Uptake of amino acids by the parasitic, flagellated protist trichomonas vaginalis.
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    
Institute for Glycomics, Griffith University (Gold Coast Campus), Australia.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Bacterial Infections / drug therapy
Binding Sites
Crystallography, X-Ray
Enzyme Inhibitors / chemical synthesis*,  pharmacology*
Glucuronides / chemical synthesis*,  pharmacology
Glycerol / chemistry
Glycosides / chemistry
Molecular Mimicry
Neuraminidase / antagonists & inhibitors*
Structure-Activity Relationship
Uronic Acids / chemistry
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Glucuronides; 0/Glycosides; 0/Uronic Acids; 34047-66-0/N-acetylglucosaminuronic acid; 56-81-5/Glycerol; EC

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

Previous Document:  A combined approach of docking and 3D QSAR study of beta-ketoacyl-acyl carrier protein synthase III ...
Next Document:  3D QSAR study of hypolipidemic asarones by comparative molecular surface analysis.