In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons

Bioorg Med Chem. 2016 Apr 15;24(8):1665-74. doi: 10.1016/j.bmc.2016.02.041. Epub 2016 Mar 2.

Abstract

Cancer chemoprevention involves prevention/delay/reverse of the carcinogenic process through administration of cancer chemopreventive agents (CCA). Compounds which are able to induce detoxification-enzymes, especially monofunctional phase II enzymes, have become in excellent approaches for new CCA. Herein, we report the synthesis of new furoxanyl chalcone-like hybrid compounds as CCA. In vitro studies showed that phenylfuroxanyl derivatives 6 and 9 displayed the best activities being 9 the greatest monofunctional-inducer. Additionally, compounds were non-mutagenic against TA98 Salmonella typhimurium strain (Ames test) and could be used in the prevention of the progression of pre-malignant lesions for their cytotoxic activity against tumoral cells. In vivo proof of concept showed increment on phase II-enzymes activities in liver, colon and mammary gland having derivative 9 the best induction profiles. We probed Nrf2 nuclear translocation is operative for both compounds allowing to exert protective effects via expression of downstream phase-II enzymes.

Keywords: Cancer; Chalcone; Chemoprevention; Furoxan; Phase II enzymes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Chalcone / chemical synthesis
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Cytochrome P-450 Enzyme System / metabolism
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Enzyme Induction / drug effects
  • Female
  • Glutathione Transferase / metabolism*
  • HT29 Cells
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / metabolism*
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Rats
  • Rats, Wistar
  • Salmonella typhimurium / drug effects
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • 1,2,5-oxadiazole 2-oxide
  • Antineoplastic Agents
  • Oxadiazoles
  • Chalcone
  • Cytochrome P-450 Enzyme System
  • NAD(P)H Dehydrogenase (Quinone)
  • Glutathione Transferase