Oxaliplatin degradation in the presence of chloride: identification and cytotoxicity of the monochloro monooxalato complex

Pharm Res. 2004 May;21(5):891-4. doi: 10.1023/b:pham.0000026444.67883.83.

Abstract

Purpose: To study the degradation of oxaliplatin in chloride media and evaluate the cytotoxicity of oxaliplatin in normal and chloride-deficient medium.

Methods: The products of the reaction of oxaliplatin with chloride were separated on a Hypercarb S column with a mobile phase containing 40% methanol in 0.05 M ammonia and subjected to electrospray ionization mass spectrometry. The cytotoxicity of oxaliplatin in normal and chloride-deficient medium was evaluated by 30-min incubations on human colon adenocarcinoma cells (HT-29).

Results: We identified a new intermediate degradation product, the monochloro monooxalato complex ([Pt(dach)oxCl]-) and the final product. the dichloro complex (Pt(dach)Cl2), by liquid chromatography-mass spectrometry. [Pt(dach)oxCl]- was found as the negative ion, M-, at m/z 431, and the positive ion, [M+2H]+, m/z 433. Pt(dach)Cl2 was found as the negative ion, [M-H]-, m/z 377, and the positive ion, [M+NH4]+, m/z 396. The fast initial degradation of oxaliplatin can be coupled to the fast formation of [Pt(dach)oxCl]-. In the cytotoxic assay, the cell survival was not affected by the chloride levels.

Conclusions: [Pt(dach)oxCl]-, a new transformation product of oxaliplatin, has been identified. Its in vitro cytotoxic effect does not appear to exceed that of oxaliplatin.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Survival / drug effects
  • Chlorides / chemistry
  • Chromatography, Liquid
  • Culture Media
  • Dose-Response Relationship, Drug
  • HT29 Cells
  • Humans
  • Organoplatinum Compounds / chemistry*
  • Organoplatinum Compounds / pharmacology*
  • Oxaliplatin
  • Spectrometry, Mass, Electrospray Ionization
  • Tumor Stem Cell Assay

Substances

  • Antineoplastic Agents
  • Chlorides
  • Culture Media
  • Organoplatinum Compounds
  • Oxaliplatin