Regioselective arylation of ribose in adenosine and guanosine with the antitumor drug N2-methyl-9-hydroxyellipticinium acetate.
The transformation of the antitumor drug N2-methyl-9-hydroxy-ellipticinium by a peroxidase-hydrogen peroxide system, which has been shown to occur in vivo, leads to an electrophilic quinone-imine derivative. This unstable molecule arylates in vitro purine nucleosides and nucleotides, leading to regioselective adducts substituted only at the 2'-O position of the ribose, as shown by mass spectrometry and NMR. It is likely that an important preliminary step in this reaction is a stacking process between the ellipticinium ion and the purine rings, which might explain this regioselectivity.
D000241:Adenosine / Q000031:analogs & derivatives; D000470:Alkaloids; D000970:Antineoplastic Agents; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004611:Ellipticines; D006151:Guanosine / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012265:Ribonucleotides; D013053:Spectrophotometry
D000470:Alkaloids; D000970:Antineoplastic Agents; D004611:Ellipticines; D012265:Ribonucleotides; D006151:Guanosine; C027767:elliptinium; D000241:Adenosine