Comparison of the binding behavior of oxaliplatin, cisplatin and analogues to 5'-GMP in the presence of sulfur-containing molecules by means of capillary electrophoresis and electrospray mass spectrometry

Author(s): Angelika Kueng, Dirk B. Strickmann, Mathea Sophia Galanski, Bernhard Keppler
Abstract: Capillary electrophoresis as well as ESI-MS has been applied for investigating the influence of the sulfur-containing amino acids L-cysteine and L-methionine on the binding behavior of oxaliplatin (trans-R,R-diaminocyclohexane(oxalato)platinum(II)), cisplatin (cis-diamminedichloroplatinum(II)), carboplatin (cis-diammine-1,1-cyclobutanedicarboxylatoplatinum(II)), cis-diammine(malonato)platinum(II) and cis-diammine(2-hydroxymalonato)platinum(II) to 5'-GMP. The presence of L-methionine resulted in a different kind of adduct formation which involves ammine release due to the trans-effect of sulfur. In addition, the time-dependent behavior of the reaction with 5'-GMP changed significantly. Due to the high stability of the diaminocyclohexane (DACH) platinum fragment, oxaliplatin showed a completely different behavior in comparison to diammine platinum complexes. Formation of [Pt(DACH)(L-Met-S,N)]+ inhibits coordination of 5'-GMP. Displacement of L-Met by 5'-GMP does not occur. Differences concerning the mode of action of oxaliplatin are expected. Characterization of the analytes was performed by UV, NMR and mass spectrometry. Œ 2001 Elsevier Science B.V. All rights reserved.
Organisation(s): Department of Inorganic Chemistry
External organisation(s): University of Vienna
Journal: Journal of Inorganic Biochemistry
Volume: 86
Pages: 691-698
No. of pages: 8
ISSN: 0162-0134
DOI: https://doi.org/10.1016/S0162-0134(01)00225-2
Publication date: 2001
Peer reviewed: Yes
Austrian Fields of Science 2012: 1040 Chemistry
Portal url: https://ucrisportal.univie.ac.at/en/publications/3ee9c5b6-eeaf-4797-8954-5e84e6bb317c