Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery

Bioorg Med Chem. 2007 Nov 15;15(22):7012-20. doi: 10.1016/j.bmc.2007.07.048. Epub 2007 Aug 22.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Bacillus subtilis / drug effects
  • Caco-2 Cells
  • Chromatography, Liquid / methods
  • Drug Delivery Systems*
  • Drug Design
  • Enterobacter aerogenes / drug effects
  • Escherichia coli / drug effects
  • Glycolipids* / chemical synthesis
  • Glycolipids* / chemistry
  • Glycolipids* / pharmacology
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Monosaccharides / chemistry
  • Piperacillin* / chemical synthesis
  • Piperacillin* / chemistry
  • Piperacillin* / pharmacology
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Tandem Mass Spectrometry / methods

Substances

  • Amino Acids
  • Glycolipids
  • Monosaccharides
  • Piperacillin