Neo-tanshinlactone D-ring modified novel analogues induce apoptosis in human breast cancer cell via DNA damage

Bioorg Med Chem. 2017 Jan 1;25(1):202-212. doi: 10.1016/j.bmc.2016.10.026. Epub 2016 Oct 21.

Abstract

Neo-tanshinlactone (NTL) a natural product is known for its specificity and selectivity towards the breast cancer cells. By NTL D-ring modification approach, 13 new analogues were synthesized (1A-1M). Among them 1J showed the best anticancer activity in MCF-7 (ER+, PR+/-, HER2-), SKBR3 (ER-, PR-, HER2+) and MDA-MB-231 (ER-, PR-, HER2-) cells lines with IC50 value 11.98nM, 23.71nM, and 62.91nM respectively. 1J showed minor grove binding interaction with DNA at AT-rich region and induced DNA double strand breaks (DDSBs). This had triggered several key molecular events involving, activation of ATM, Chk2 and p53, reduction in mitochondrial potential (Δψm) leading to caspase-3 and PARP cleavage mediated apoptosis. These results along with other biochemical studies strongly suggest that novel NTL analogue 1J caused DNA cleavage mediated apoptosis in the breast cancer cells and this may serve as potential lead for future breast cancer treatment.

Keywords: Apoptosis; DNA damage; HDAC; Neotanshinlactone; γH2AX foci.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects*
  • Cell Line, Tumor
  • DNA Breaks, Double-Stranded / drug effects*
  • E2F1 Transcription Factor / metabolism
  • Furans / chemical synthesis
  • Furans / pharmacology*
  • Histone Deacetylases / metabolism
  • Histones / metabolism
  • Humans
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Docking Simulation
  • Molecular Structure
  • Pyrones / chemical synthesis
  • Pyrones / pharmacology*
  • Retinoblastoma Protein / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • E2F1 Transcription Factor
  • E2F1 protein, human
  • Furans
  • H2AX protein, human
  • Histones
  • Pyrones
  • Retinoblastoma Protein
  • neotanshinlactone
  • Histone Deacetylases
  • histone deacetylase 3