Mimicking the biological activity of diazobenzo[b]fluorene natural products with electronically tuned diazofluorene analogs

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5148-51. doi: 10.1016/j.bmcl.2006.07.024. Epub 2006 Jul 25.

Abstract

Under appropriate electronic modulation, simple diazofluorene analogs recapitulate the DNA cleavage activity of kinamycin D under thiol-based reducing conditions. Achieving DNA cleavage under these reducing conditions is key to anticancer activity, as the most active compound, 1-methoxydiazofluorene, inhibits the proliferation of HeLa cells.

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

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Carbazoles / pharmacology
  • Cell Proliferation / drug effects
  • DNA Damage / drug effects*
  • Fluorenes / chemical synthesis*
  • Fluorenes / pharmacology
  • HeLa Cells
  • Humans
  • Molecular Mimicry
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Carbazoles
  • Fluorenes
  • kinamycin D