β-Ionone derived apoptosis inducing endoperoxides; Discovery of potent leads for anticancer agents

Eur J Med Chem. 2014 Nov 24:87:228-36. doi: 10.1016/j.ejmech.2014.09.049. Epub 2014 Sep 16.

Abstract

A series of endoperoxides (3a-j) were synthesized and evaluated for cytotoxic activity against four human cancer cell lines by using SRB dye assay. All the compounds displayed moderate to high cytotoxic effect against almost all investigational cancer cells. Particularly, compounds bearing electron withdrawing groups such as nitro substituted compound 3j (IC50 = 0.001 μM) and fluoro substituted compound 3i (IC50 = 0.003 μM) showed comparatively more cytotoxic potential than standard drugs against lung cancer cell line (A549). All synthesized endoperoxides (3a-j) were further evaluated for their apoptotic potential through various parameters such as flow-cytometric analysis of nuclear DNA, flow-cytometric determination of mitochondrial membrane potential (ΔΨm), spectrofluorimetric estimation of intracellular ROS level and caspase-3 & 9 assays in treated lung cancer cells (A549); results reveal that endoperoxides induce apoptosis in cancer cells via mitochondrial pathway.

Keywords: Anticancer activity; Apoptosis; Cytotoxic activity; Endoperoxides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / toxicity
  • Apoptosis / drug effects*
  • CHO Cells
  • Caspase 3 / metabolism
  • Caspase 9 / metabolism
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cricetinae
  • Cricetulus
  • DNA / metabolism
  • Drug Design*
  • Humans
  • Intracellular Space / drug effects
  • Intracellular Space / metabolism
  • L-Lactate Dehydrogenase / metabolism
  • Membrane Potential, Mitochondrial / drug effects
  • Norisoprenoids / chemistry*
  • Norisoprenoids / pharmacology*
  • Norisoprenoids / toxicity
  • Peroxides / chemistry*
  • Reactive Oxygen Species / metabolism

Substances

  • Antineoplastic Agents
  • Norisoprenoids
  • Peroxides
  • Reactive Oxygen Species
  • DNA
  • beta-ionone
  • L-Lactate Dehydrogenase
  • Caspase 3
  • Caspase 9