Methanethiosulfonate derivatives as ligands of the STAT3-SH2 domain

J Enzyme Inhib Med Chem. 2017 Dec;32(1):337-344. doi: 10.1080/14756366.2016.1252757.

Abstract

With the aim to discover new STAT3 direct inhibitors, potentially useful as anticancer agents, a set of methanethiosulfonate drug hybrids were synthesized. The in vitro tests showed that all the thiosulfonic compounds were able to strongly and selectively bind STAT3-SH2 domain, whereas the parent drugs were completely devoid of this ability. In addition, some of them showed a moderate antiproliferative activity on HCT-116 cancer cell line. These results suggest that methanethiosulfonate moiety can be considered a useful scaffold in the preparation of new direct STAT3 inhibitors. Interestingly, an unusual kind of organo-sulfur derivative, endowed with valuable antiproliferative activity, was occasionally isolated. [Formula: see text].

Keywords: Anticancer drug; S3I-201 analogs; SH2 antagonist; STAT3; cytotoxicity.

MeSH terms

  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Humans
  • Ligands
  • Mesylates / chemistry
  • Mesylates / metabolism
  • Mesylates / pharmacology*
  • STAT3 Transcription Factor / metabolism*
  • src Homology Domains

Substances

  • Ligands
  • Mesylates
  • STAT3 Transcription Factor
  • STAT3 protein, human
  • methanethiosulfonate