Evaluation of platinum-ethacrynic acid conjugates in the treatment of mesothelioma

ChemMedChem. 2011 Dec 9;6(12):2287-93. doi: 10.1002/cmdc.201100426. Epub 2011 Oct 24.

Abstract

Malignant pleural mesothelioma (MPM) cells are characterized by chemoresistance associated with glutathione (GSH) metabolism. Ethacrynic acid (EA) is able to inhibit the detoxifying enzyme glutathione-S-transferase (GST), which catalyzes the conjugation between GSH and Pt-based drugs. With the aim of obtaining active bifunctional drugs, a Pt(II) complex containing two EA moieties as leaving groups, namely cis-diamminobis(ethacrynato)platinum(II), was synthesized, characterized, and tested on four MPM cell lines. The resulting antiproliferative activity was compared with that elicited by the analogue Pt(IV) complex, cis,cis,trans-diamminodichloridobis(ethacrynato)platinum(IV) (ethacraplatin) and by the co-administration of free EA and cisplatin. The Pt(II) and Pt(IV) bifunctional complexes showed poorer performance than the reference drug cisplatin alone or in combination with EA. After treatment, cellular GST activity remained consistently unchanged, while the GSH level increased.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Drug Evaluation, Preclinical
  • Ethacrynic Acid / chemistry*
  • Glutathione / metabolism
  • Glutathione Transferase / antagonists & inhibitors
  • Glutathione Transferase / metabolism
  • Humans
  • Mesothelioma / drug therapy
  • Platinum / chemistry*

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Platinum
  • Glutathione Transferase
  • Glutathione
  • Ethacrynic Acid