Synthesis and biological evaluation of pentacyclic strychnos alkaloids as selective modulators of the ABCC10 (MRP7) efflux pump

J Med Chem. 2014 Dec 26;57(24):10383-90. doi: 10.1021/jm501189p. Epub 2014 Dec 8.

Abstract

The selective modulation of ATP-binding cassette (ABC) efflux pumps overexpressed in multidrug resistant cancers (MDR) and attendant resensitization to chemotherapeutic agents represent a promising strategy for treating cancer. We have synthesized four novel pentacyclic Strychnos alkaloids alstolucines B (2), F (3), and A (5) and N-demethylalstogucine (4), in addition to known Strychnos alkaloid echitamidine (16), and we evaluated compounds 1-5 in biochemical assays with ABCC10 and P-glycoprotein (P-gp). Alstolucines B (2) and F (3) inhibited ABCC10 ATPase activity at 12.5 μM without affecting P-gp function; moreover, they resensitized ABCC10-transfected cell lines to paclitaxel at 10 μM. Altogether, the alstolucines represent promising lead candidates in the development of modulators of ABCC10 for MDR cancers overexpressing this pump.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Adenosine Triphosphatases / antagonists & inhibitors
  • Alkaloids / chemical synthesis*
  • Alkaloids / pharmacology*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Proliferation / drug effects*
  • Drug Resistance, Multiple / drug effects*
  • Drug Resistance, Neoplasm / drug effects*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • HEK293 Cells
  • Humans
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / pharmacology*
  • Multidrug Resistance-Associated Proteins / antagonists & inhibitors*
  • Paclitaxel / pharmacology
  • Strychnos / chemistry*

Substances

  • ABCC10 protein, human
  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Enzyme Inhibitors
  • Indole Alkaloids
  • Multidrug Resistance-Associated Proteins
  • alstolucine B
  • alstolucine F
  • Adenosine Triphosphatases
  • Paclitaxel