Synthesis of somatostatin analogues containing C-terminal adamantane and their antiproliferative properties

J Med Chem. 2008 Aug 28;51(16):5121-4. doi: 10.1021/jm701599w. Epub 2008 Aug 5.

Abstract

On the basis of the structure of somatostatin analogue TT-232 (1), which exhibited a highly potent antitumor activity, we synthesized small linear peptide derivatives and evaluated their antitumor and apoptotic activity. Of them, Boc-Tyr-D-Trp-1-adamantylamide (5) had the most potent cell antiproliferative activity in SW480 and A431 cell lines, which was supported in A431 cell lines by FACS analysis that demonstrated a major increase in DNA fragmentation in the subG1 fraction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / chemistry*
  • Antineoplastic Agents / chemical synthesis*
  • Apoptosis / drug effects*
  • Cell Proliferation / drug effects
  • Humans
  • Somatostatin / analogs & derivatives*
  • Somatostatin / chemical synthesis
  • Somatostatin / pharmacology
  • Tumor Cells, Cultured / drug effects

Substances

  • Antineoplastic Agents
  • Somatostatin
  • Adamantane