4β-amidotriazole linked podophyllotoxin congeners: DNA topoisomerase-IIα inhibition and potential anticancer agents for prostate cancer

Eur J Med Chem. 2018 Jan 20:144:595-611. doi: 10.1016/j.ejmech.2017.12.050. Epub 2017 Dec 14.

Abstract

Topoisomerases (topo-I and topo-II) have occupied a significant role in DNA replication, transcription, and are a promising set of antitumor targets. In the present approach, a series of new 4β-amidotriazole linked podophyllotoxin derivatives (10a-i and 11a-k) were designed, synthesized by employing the click chemistry and their biological activities were evaluated. The majority of derivatives showed promising antiproliferative activity with IC50 values ranging from 1 to 10 μM on the six human cancer cell lines; cervical (HeLa), breast (MCF-7), prostate (DU-145), lung (A549), liver (HepG2) and colon (HT-29). Among them, some of the congeners 10b, 10g and 10i have shown remarkable cytotoxicity with IC50 values of, < 1 μM against the tested cancer cell lines and found to be more active than etoposide. Topoisomerase-mediated DNA relaxation assay results showed that the derivatives could efficiently inhibit the activity of topoisomerase-II. In addition, flow cytometry analysis on DU-145 cells revealed that these compounds arrest G2/M phase of cell cycle. Further apoptotic studies were also performed on these DU-145 cells, which showed that this class of compounds could induce apoptosis effectively.

Keywords: Anticancer activity; Apoptosis; Cell cycle; Topo-II inhibition; Triazole.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects
  • DNA Topoisomerases, Type II / metabolism*
  • Dose-Response Relationship, Drug
  • Humans
  • Male
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Docking Simulation
  • Molecular Structure
  • Podophyllotoxin / chemistry
  • Podophyllotoxin / pharmacology*
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / metabolism
  • Prostatic Neoplasms / pathology
  • Reactive Oxygen Species / analysis
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship
  • Topoisomerase II Inhibitors / chemical synthesis
  • Topoisomerase II Inhibitors / chemistry
  • Topoisomerase II Inhibitors / pharmacology*
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Reactive Oxygen Species
  • Topoisomerase II Inhibitors
  • Triazoles
  • DNA Topoisomerases, Type II
  • Podophyllotoxin