A crystalline end product produced by the hydrolytic cleavage of an RNA-like fragment by an organometallointercalator: 1,10-phenanthroline-platinum(II)-ethylenediamine-cytidine 3' monophosphate.

Abstract

1,10-Phenanthroline-platinum(II)-ethylenediamine ( PEPt ) forms a crystalline complex with cytidine-3'-phosphate (3'-CMP) and its structure has been determined by X-ray crystallography. 3'-CMP molecules are hemiprotonated and form hydrogen-bonded pairs that stack above and below the phenanthroline-platinum(II) drug molecule. Sugar residues are in the C2' endo conformation, with glycosidic torsional angles intermediate between the high and low anti forms. The structure is of particular interest since it forms as an end product of the hydrolytic cleavage of the dinucleoside monophosphate, CpG, by the platinum organometallointercalator ( PEPt ). This hydrolytic activity appears to be specific for the RNA dinucleoside monophosphate fragment, since deoxycytidylyl (3'-5')deoxyguanosine (d-CpG) and other deoxyribooligonucleotides are not cleaved under similar conditions.