Novel lipoamino acid- and liposaccharide-based system for peptide delivery: application for oral administration of tumor-selective somatostatin analogues

J Med Chem. 1999 Sep 23;42(19):4010-3. doi: 10.1021/jm9910167.

Abstract

Lipoamino acid and liposaccharide conjugates of somatostatin analogue TT-232 were synthesized to modify the physicochemical properties of the parent peptide. The relative position, the number, and the nature of the lipid and/or saccharide moieties were varied. Experiments in vitro clearly showed that many compounds modified at the N- and/or C-terminus with lipid or sugar moieties retained the biological activity of the parent compound. An interesting construct was synthesized containing lipid and sugar units at opposite ends of the somatostatin analogue, so that the entire molecule could be considered as an amphipathic surfactant.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Antineoplastic Agents / administration & dosage
  • Caco-2 Cells
  • Carbohydrate Sequence
  • Cell Division / drug effects
  • Glycopeptides*
  • Humans
  • Intestinal Absorption / drug effects
  • Lipopolysaccharides*
  • Molecular Sequence Data
  • Oligopeptides*
  • Peptides, Cyclic / administration & dosage
  • Somatostatin / administration & dosage*
  • Somatostatin / analogs & derivatives*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Glycopeptides
  • Lipopolysaccharides
  • Oligopeptides
  • Peptides, Cyclic
  • TT2-32
  • Somatostatin