Theoretical investigations and density functional theory based quantitative structure-activity relationships model for novel cytotoxic platinum(IV) complexes

J Med Chem. 2013 Jan 10;56(1):330-44. doi: 10.1021/jm3016427. Epub 2012 Dec 27.

Abstract

Octahedral platinum(IV) complexes are promising candidates in the fight against cancer. In order to rationalize the further development of this class of compounds, detailed studies on their mechanisms of action, toxicity, and resistance must be provided and structure-activity relationships must be drawn. Herein, we report on theoretical and QSAR investigations of a series of 53 novel bis-, tris-, and tetrakis(carboxylato)platinum(IV) complexes, synthesized and tested for cytotoxicity in our laboratories. The hybrid DFT functional wb97x was used for optimization of the structure geometry and calculation of the descriptors. Reliable and robust QSAR models with good explanatory and predictive properties were obtained for both the cisplatin sensitive cell line CH1 and the intrinsically cisplatin resistant cell line SW480, with a set of four descriptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Carboplatin / chemistry
  • Carboplatin / pharmacology
  • Cell Line, Tumor
  • Cisplatin / analogs & derivatives
  • Cisplatin / chemistry
  • Cisplatin / pharmacology
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Ethylamines / chemistry
  • Ethylamines / pharmacology
  • Ethylenediamines / chemistry
  • Ethylenediamines / pharmacology
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Organoplatinum Compounds / chemistry
  • Organoplatinum Compounds / pharmacology
  • Oxaliplatin
  • Platinum*
  • Quantitative Structure-Activity Relationship*
  • Thermodynamics

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Ethylamines
  • Ethylenediamines
  • Organoplatinum Compounds
  • Oxaliplatin
  • Platinum
  • nedaplatin
  • Carboplatin
  • Cisplatin