Synthesis and in-vitro anticancer evaluation of polyarsenicals related to the marine sponge derived Arsenicin A

Sci Rep. 2017 Sep 14;7(1):11548. doi: 10.1038/s41598-017-11566-6.

Abstract

In the light of the promising bioactivity of the tetraarsenic marine metabolite arsenicin A, the dimethyl analogue 2 and four isomeric methylene homologues (including the natural product itself) were obtained using a one-pot microwave-assisted synthesis, starting from arsenic (III) oxide. Due to the poor diagnostic value of the NMR technique in the structural elucidation of these molecules, they were fully characterized by mass spectrometry and infrared (IR)-spectroscopy, comparing density functional theory (DFT) simulated and experimental spectra. This synthetic procedure provided a fast and efficient access to the cytotoxicity evaluation of organoarsenical leads of the natural hit molecule. From in vitro screening, each tested compound resulted in being more active than the FDA-approved arsenic trioxide, with the most lipophilic molecule in the series showing the best growth inhibition of both leukemia and solid tumor cell lines. These results may open promising perspectives in the development of new more potent and selective arsenical drugs against solid tumors.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Arsenicals / chemical synthesis*
  • Arsenicals / pharmacology*
  • Cell Line, Tumor
  • Drug Evaluation, Preclinical
  • Humans
  • Mass Spectrometry
  • Molecular Structure
  • Spectrophotometry, Infrared

Substances

  • Antineoplastic Agents
  • Arsenicals