Isolation and Identification of the Novel Tubulin Polymerization Inhibitor Bifidenone

J Nat Prod. 2017 Mar 24;80(3):616-624. doi: 10.1021/acs.jnatprod.6b00893. Epub 2016 Nov 14.

Abstract

The pursuit of structurally novel compounds has led to the isolation of a series of neolignans (2-6), for which the structures have been determined from microgram quantities using microcryoprobe NMR technology. Compounds 2-6 provided some unexpectedly clear structure-activity relationship data, with compound 2 demonstrating significantly more potency in the in vitro cytotoxicity assay than the other analogues. Further screening found that compound 2 induces apoptosis with activation of caspase 3/7. The NCI Compare algorithm suggested that compound 2 acts through the inhibition of tubulin/microtubule dynamics. Compound 2 was confirmed to be a tubulin polymerization inhibitor that binds directly to tubulin.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Caspase 3 / metabolism
  • Drug Screening Assays, Antitumor
  • Humans
  • Lignans / chemistry
  • Lignans / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Structure-Activity Relationship
  • Tubulin / metabolism
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / pharmacology*

Substances

  • 5-methoxybifidenone
  • Antineoplastic Agents
  • Lignans
  • Tubulin
  • Tubulin Modulators
  • Caspase 3