Separation and characterization of products resulting from the reaction of cis-diamminedichloroplatinum(II) with deoxyribonucleosides

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Abstract
The cancer chemotherapeutic drug cis-diamminedichloroplatinum(II) (cis-DDP) was reacted with deoxyribonucleosides; the products were separated by high-pressure liquid chromatography and characterized by 1H-NMR. Monofunctional platination occurred at N(3) of cytidine, N(7) of guanosine, N(1) of adenosine and N(7) of adenosine. Bifunctional platination occurred with guanosine N(7) to N(7), adenosine N(7) to N(7) and adenosine N(1) to N(7). In addition, mixed bifunctional products N(7) of guanosine-N(1) of adenosine and N(7) of guanosine-N(7) of adenosine were obtained. No bifunctional adducts were obtained that contained cytidine, presumably due to steric hindrance, as trans-DDP did cross-link 2 cytidine residues. Similarly, no adenosine N(1) to N(1) was detected with cis-DDP. The only other products detected were obtained at high levels of cis-DDP and probably represented polymeric forms in which P chelates to itself.

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