Synthesis and evaluation of bi-functional 7-hydroxycoumarin platinum(IV) complexes as antitumor agents

Bioorg Med Chem. 2019 May 15;27(10):2112-2121. doi: 10.1016/j.bmc.2019.04.009. Epub 2019 Apr 6.

Abstract

A series of bi-functional 7-hydroxycoumarin platinum(IV) complexes were synthesized, characterized, and evaluated for antitumor activities. The 7-hydroxycoumarin platinum(IV) complexes display moderate to effective antitumor activities toward the tested cell lines and show much potential in overcoming drug resistance of platinum(II) drugs. In reducing microenvironment, the title compounds could be reduced to platinum(II) complex accompanied with two equivalents of coumarin units. By a unique mechanism, the 7-hydroxycoumarin platinum(IV) complex attacks DNA via the released platinum(II) compound, meanwhile it also inhibits the activities of cyclooxygenase by coumarin fragment. This action mechanism might be of much benefit for reducing tumor-related inflammation in the progress of inhibiting tumor proliferation and overcoming cisplatin resistance. The incorporation of 7-hydroxycoumarin leads to significantly enhanced platinum accumulation in both whole tumor cells and DNA. The HSA interaction investigation reveals that the tested coumarin platinum(IV) compound could effectively combine with HSA via van der Waals force and hydrogen bond.

Keywords: Antitumor; Coumarin; Cyclooxygenase inhibition; DNA damage; Platinum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / metabolism
  • Coordination Complexes / pharmacology
  • Cyclooxygenase 2 / chemistry
  • Cyclooxygenase 2 / metabolism
  • DNA Damage / drug effects
  • Humans
  • Platinum / chemistry*
  • Protein Binding
  • Serum Albumin / chemistry
  • Serum Albumin / metabolism
  • Umbelliferones / chemistry*

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Serum Albumin
  • Umbelliferones
  • Platinum
  • 7-hydroxycoumarin
  • Cyclooxygenase 2