Oxaliplatin is an anticancer drug that reacts with DNA, RNA, and proteins both in vitro and in vivo. Our research focuses on synthesizing analogs of oxaliplatin and understanding how bulky ligand groups affect reaction with amino acids. (R,R)-N,N’-dimethyl-1,2-diaminocyclohexane platinum(II) oxalate or Pt(Me2dach)(ox) varies from oxaliplatin or Pt(dach)(ox) in that it has one methyl group attached to each platinum coordinated nitrogen. Nuclear Magnetic Resonance (NMR) spectroscopy has shown that the reactions of N-Acetylmethionine (N-AcMet) with Pt(Me2dach)(ox) and Pt(dach)(ox) proceed at similar rates suggesting that the methyl groups of Pt(Me2dach)(ox) have little effect on the initial reaction. Whereas the reaction of Pt(dach)(ox) and N-AcMet can form 1:1 or 1:2 complexes, Pt(Me2dach)(ox) with N-AcMet can form only 1:1 products. Depending on the Pt:N-AcMet ratios, Pt(dach)(ox) has the potential to form either a [Pt(dach)(N-AcMet-S)2] or [Pt(dach)(N-AcMet-S,N)] complex. The bis product is not found in Pt(Me2dach)(ox) reactions because the formation of a [Pt(Me2dach)(N-AcMet-S,O)]+ product hinders the coordination of a second N-AcMet. It has therefore been deduced that the additional methyl groups of Pt(Me2dach)(ox) limit reaction with N-AcMet to a 1:1 molar product.
Advisor(s) or Committee Chair
Dr. Kevin Williams
Hendrie, Jonathan D., "Characterization and Reaction of an Analog of the Anticancer Drug Oxaliplatin" (2013). Honors College Capstone Experience/Thesis Projects. Paper 431.