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Comparison of N-acetylmethionine reactivity between oxaliplatin and an oxaliplatin derivative with chiral (S,S) amine nitrogen atoms.
MedLine Citation:
PMID:  23626375     Owner:  NLM     Status:  Publisher    
We have synthesized an oxaliplatin derivative using N,N'-dimethyl-1,2-diaminocyclohexane (Me2dach) as the diamine ligand. The complex (S,R,R,S)-Pt(Me2dach)(oxalate), where S,R,R,S represents the chiralities at N,C,C,N, respectively, was prepared and characterized by (1)H NMR spectroscopy, COSY, NOESY, and HMQC. Oxaliplatin reacts with N-acetylmethionine (N-AcMet) to form [Pt(dach)(N-AcMet-S)2] and [Pt(dach)(N-AcMet-S,N)], with the former favored at higher molar ratios of N-AcMet. In contrast, Pt(Me2dach)(oxalate) reacts to form [Pt(Me2dach)(N-AcMet-S,O)](+) even in the presence of excess N-AcMet. Molecular mechanics calculations are consistent with significant steric clashes in models of [Pt(Me2dach)(N-AcMet-S)2]. When N-AcMet was reacted with an excess of each platinum complex, the rate of N-AcMet decrease was very similar for both complexes. Thus, the methyl groups at the nitrogen atoms had little to no effect on the addition of the sulfur atom of a single N-acetylmethionine, but they prevented chelation of the amide nitrogen or coordination of a second N-acetylmethionine residue.
Kevin M Williams; Amy D Poynter; Jonathan D Hendrie; Daniel C Jackson; Virginia K Martin
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Publication Detail:
Journal Detail:
Title:  Inorganica chimica acta     Volume:  401     ISSN:  0020-1693     ISO Abbreviation:  Inorganica Chim Acta     Publication Date:  2013 May 
Date Detail:
Created Date:  2013-4-29     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9875013     Medline TA:  Inorganica Chim Acta     Country:  -    
Other Details:
Languages:  ENG     Pagination:  64-69     Citation Subset:  -    
Department of Chemistry, Western Kentucky University, 1906 College Heights Blvd #11079, Bowling Green, KY 42101-1079.
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