Synthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents

Bioorg Med Chem. 2022 Mar 15:58:116653. doi: 10.1016/j.bmc.2022.116653. Epub 2022 Feb 5.

Abstract

Aminothiophene is a scaffold that is widely present in drugs and biologically active small molecules as chemical probes. In this study, 43 compounds sharing a 2-aminothiophenone-3-carboxylate (ATPC) scaffold, known to activate the ribonuclease L (RNase L), were synthesized and selected ATPCs showed enhancement of thermal stability of RNase L upon binding. Screening of antiproliferation activities against human cancer cell lines revealed that ATPCs represented by compounds 4l and 50 showed potent single-digit micromolar antiproliferation activity against human cancer cell lines. Compounds 4l and 50 exhibited time- and dose-dependent proliferation inhibition, induced cellular apoptosis measured by cleaved PARP and via flow cytometry, inhibited cell migration, and inhibited cell colony formation. Combining the results reported in this work, ATPCs were evaluated as potential anticancer agents mediated by RNase L-binding and apoptosis induction. The work contributes to the study on the polypharmacological properties of aminothiophene-containing small molecules.

Keywords: Aminothiophene; Anticancer; Apoptosis; Ribonuclease L; Small molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Binding Sites
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Endoribonucleases / chemistry*
  • Endoribonucleases / metabolism
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Thiophenes / chemistry
  • Thiophenes / metabolism
  • Thiophenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Thiophenes
  • Endoribonucleases
  • 2-5A-dependent ribonuclease