Sugar interaction with biologically active cis-PtCl2(NH3)2 (anticancer) and its inactive trans isomer.
The interaction of D-glucuronic and D-gluconic acids with cis- and trans-PtCl2(NH3)2 (cisplatin and transplatin) has been investigated in aqueous solution and solid complexes of the type cis-[PtL(NH3)2]L.H2O and trans-[PtL2(NH3)2]L.H2O, where L = D-glucuronate or D-gluconate anions, are isolated and characterized by means of Fourier transform-infrared and 1H-NMR spectroscopy, and molar conductivity and X-ray powder diffraction measurements. Spectroscopic and other evidence indicated that the sugar anions bind monodentately in trans-[PtL2(NH3)2].H2O and bidentately in cis-[PtL(NH3)2]L.H2O complexes through the carboxylate oxygen atoms and other sugar donor groups. The strong sugar intermolecular hydrogen-bonding network is altered to that of the sugar-OH...NH3(H2O)...OH-sugar, upon platinum-ammine interaction. The D-glucuronate anion has the beta-anomer configuration both in the free salt and in these platinum-sugar complexes.
Tajmir-Riahi
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Department of Chemistry, University of Laval, Québec, Canada.
D002945:Cisplatin; D005583:Fourier Analysis; D005965:Glucuronates; D020723:Glucuronic Acid; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D014961:X-Ray Diffraction
D005965:Glucuronates; C034697:transplatin; C004940:glucuronolactone; D020723:Glucuronic Acid; D002945:Cisplatin