Hybrid molecules based on fullerene C60 and 5Z,9Z-dienoic acids: Synthesis and cytotoxic activity

Bioorg Med Chem Lett. 2020 Aug 15;30(16):127289. doi: 10.1016/j.bmcl.2020.127289. Epub 2020 May 28.

Abstract

The present research project details synthesis of new hybrid methanofullerenes based on acetylene and triazole esters of malonic acid containing 5Z,9Z-dienoic acids and fullerene C60 under Bingel-Hirsch conditions, including study of the cytotoxic activity with respect to Jurkat, K562, U937 and HL60 tumor cell lines. Hybrid methanofullerenes containing acetylenic fragments, unlike triazole substituents, were found to exhibit higher cytotoxicity, but are characterized by lower selectivity of action in relation to healthy cells.

Keywords: 1,2,3-triazole; 5Z,9Z-dienoic acid; Bingel-Hirsch reaction; Cytotoxic activity; Methanofullerene; [60]Fullerene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology*
  • Fullerenes / chemistry
  • Fullerenes / pharmacology*
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • 5,9-eicosadienoic acid
  • Antineoplastic Agents
  • Fatty Acids, Unsaturated
  • Fullerenes
  • fullerene C60