Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery.
A series of lipoamino acid-based glycolipids were synthesised. Suitably derivatised lipoamino acid derivatives were prepared and conjugated to monosaccharides (including glycosyl azides, isothiocyanates, thiols and sulphones) to yield novel O-, N-, S- and C-linked glycolipids in good yields. Their potential to improve the oral absorption of piperacillin is reported.
Falconer
Robert A
RA
Institute of Cancer Therapeutics, School of Life Sciences, University of Bradford, Bradford BD7 1DP, UK.
Toth
Istvan
I
D000284:Administration, Oral; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001412:Bacillus subtilis / Q000187:drug effects; D018938:Caco-2 Cells; D002853:Chromatography, Liquid / Q000379:methods; D016503:Drug Delivery Systems; D015195:Drug Design; D021902:Enterobacter aerogenes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D010878:Piperacillin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D053719:Tandem Mass Spectrometry / Q000379:methods
D000596:Amino Acids; D006017:Glycolipids; D009005:Monosaccharides; D010878:Piperacillin