A novel class of highly potent multidrug resistance reversal agents: disubstituted adamantyl derivatives

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5376-9. doi: 10.1016/j.bmcl.2009.07.127. Epub 2009 Aug 6.

Abstract

Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism*
  • Adamantane / chemical synthesis
  • Adamantane / chemistry*
  • Adamantane / pharmacology*
  • Cell Line, Tumor
  • Cytochrome P-450 CYP3A / metabolism
  • Drug Resistance, Multiple / drug effects*
  • Drug Resistance, Neoplasm / drug effects
  • Humans
  • Sarcoma / drug therapy
  • Structure-Activity Relationship

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Adamantane