Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells

Bioorg Med Chem. 2006 Feb 1;14(3):622-31. doi: 10.1016/j.bmc.2005.08.036. Epub 2005 Oct 3.

Abstract

(R)- and (S)-Goniothalamin (1) and analogues 2-9 were efficiently prepared in high overall yield and enantiomeric purity, and their cytotoxic activities were evaluated against eight human cancer cell lines. A structure-activity relationship study (SAR) allowed us to establish the relevant structural features for the cytotoxic activity of goniothalamin analogues. In addition, we have identified non-natural form of goniothalamin (S)-1 and analogue 5 as the highest and more selective cytotoxic compounds against kidney cancer cell growth (786-0) with IC50 = 4 and 5 nM, respectively, and compound 8 (IC50 = 4 nM) as the more potent against breast cancer cells with resistance phenotype for adryamycin (NCI.ADR).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Breast Neoplasms / drug therapy
  • Cell Line, Tumor
  • Doxorubicin / pharmacology
  • Drug Resistance, Neoplasm
  • Female
  • Humans
  • Kidney Neoplasms / drug therapy
  • Kidney Neoplasms / pathology
  • Magnetic Resonance Spectroscopy
  • Male
  • Neoplasms / drug therapy*
  • Pyrones / chemistry*
  • Pyrones / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Pyrones
  • goniothalamin
  • Doxorubicin