2. Academic Validation
  3. Synthesis and biological evaluation of a D-ring-contracted analogue of lamellarin D

Synthesis and biological evaluation of a D-ring-contracted analogue of lamellarin D

  • Bioorg Med Chem. 2017 Nov 15;25(22):6137-6148. doi: 10.1016/j.bmc.2017.02.005.
Vanessa Colligs 1,  Steven Peter Hansen 1,  Dennis Imbri 1,  Ean-Jeong Seo 2,  Onat Kadioglu 2,  Thomas Efferth 3,  Till Opatz 4
Affiliations

Affiliations

  • 1 Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
  • 2 Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University, Staudinger Weg 5, 55128 Mainz, Germany.
  • 3 Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University, Staudinger Weg 5, 55128 Mainz, Germany. Electronic address: efferth@uni-mainz.de.
  • 4 Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany. Electronic address: opatz@uni-mainz.de.
PMID: 28233677 DOI: 10.1016/j.bmc.2017.02.005
Abstract

A D-ring contracted analogue of the strongly cytotoxic marine pyrrole alkaloid lamellarin D was synthesized and investigated for its antiproliferative action towards a wild type and a multidrug resistant (MDR) Cancer cell line. The compound was found to inhibit tumor cell growth at submicromolar concentrations and showed a lower relative resistance in the MDR cell line than the antitumor drug camptothecin to which lamellarin D shows cross resistance and with which lamellarin D shares the same binding site.

Keywords

Alkaloid synthesis; Antitumor activity; Molecular docking; Natural product mimetics; Transition metal catalysis.

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