Nocardioazines: a novel bridged diketopiperazine scaffold from a marine-derived bacterium inhibits P-glycoprotein

Org Lett. 2011 May 20;13(10):2770-3. doi: 10.1021/ol200904v. Epub 2011 Apr 22.

Abstract

An Australian marine sediment-derived isolate, Nocardiopsis sp. (CMB-M0232), yielded a new class of prenylated diketopiperazine, indicative of the action of a uniquely regioselective diketopiperazine indole prenyltransferase. The bridged scaffold of nocardioazine A proved to be a noncytotoxic inhibitor of the membrane protein efflux pump P-glycoprotein, reversing doxorubicin resistance in a multidrug resistant colon cancer cell.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / antagonists & inhibitors*
  • Actinomycetales / chemistry*
  • Australia
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification*
  • Diketopiperazines / pharmacology*
  • Dimethylallyltranstransferase / metabolism*
  • Doxorubicin / pharmacology
  • Drug Resistance, Multiple / drug effects
  • Marine Biology
  • Models, Molecular

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Diketopiperazines
  • nocardioazine A
  • nocardioazine B
  • Doxorubicin
  • Dimethylallyltranstransferase