Unique Use of Alkylation for Chemo-Redox Activity by a Pt(IV) Prodrug

Chemistry. 2016 Feb 24;22(9):3029-36. doi: 10.1002/chem.201503866. Epub 2016 Jan 25.

Abstract

Resistance towards chemotherapeutics displayed by cancer cells is a significant stumbling block against fruitful cisplatin-based therapy. A unique dual-acting chemotherapeutic modality, Platin-B, a prodrug of cisplatin and pipobroman-mimicking alkylating agent, was constructed to circumvent tumor resistance. Platin-B exhibited a superior cytotoxicity profile in cisplatin-resistant cancer cells. Enhanced activity and the ability to overcome cancer-induced resistance of Platin-B was related to adduct formation with intracellular glutathione, followed by the activity of Platin-B on the mitochondria of cells, along with its conventional nuclear activity. Alkylating moieties present on Platin-B enhanced its cellular and subcellular concentration and protected it from early drug sequestration by biological thiols.

Keywords: DNA repair; alkylating agent; cancer; cisplatin; glutathione.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cisplatin / chemistry
  • Cisplatin / pharmacology*
  • DNA Repair
  • Glutathione / chemistry*
  • Humans
  • Mitochondria / chemistry*
  • Organoplatinum Compounds / chemistry
  • Organoplatinum Compounds / pharmacology*
  • Organoplatinum Compounds / therapeutic use
  • Oxidation-Reduction
  • Prodrugs / chemistry*
  • Prodrugs / therapeutic use*

Substances

  • Antineoplastic Agents
  • Organoplatinum Compounds
  • Prodrugs
  • platin-B
  • Glutathione
  • Cisplatin