Document Detail

Improving the membrane permeability of sialic acid derivatives.
MedLine Citation:
PMID:  16214357     Owner:  NLM     Status:  MEDLINE    
The potential of boronic acids to improve the bioavailability of carbohydrate derived drugs was investigated through the study of the transport of four sialic acid derivatives through a lipophilic supported liquid membrane at departure phase pH's of 7.4, 8.5 and 10.0. It was found that facilitated transport did occur in most cases, but interestingly, and in contrast to that observed with monosaccharides such as d-fructose, the lipophilic ammonium salt, Aliquat 336, promoted fluxes than those of the boronic acid. The triol side chain of the sialic acid derivatives, combined with the amide at C5, appears to represent a previously unrecognised chloride binding domain which promotes extraction of these compounds into membranes containing Aliquat 336, leading to fluxes greater than those produced by boronic acids.
Timothy M Altamore; Peter J Duggan; Guy Y Krippner
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2005-10-07
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  14     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2006 Feb 
Date Detail:
Created Date:  2006-01-09     Completed Date:  2006-03-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  1126-33     Citation Subset:  IM    
School of Chemistry, Monash University, Clayton, Melbourne, Victoria, Australia.
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MeSH Terms
Boronic Acids / chemistry
Cell Membrane Permeability*
Chlorides / chemistry
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Membranes, Artificial*
Molecular Structure
N-Acetylneuraminic Acid / analogs & derivatives*,  chemistry,  metabolism*
Reg. No./Substance:
0/Boronic Acids; 0/Chlorides; 0/Membranes, Artificial; 0/Octanols; 131-48-6/N-Acetylneuraminic Acid; 7732-18-5/Water

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