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. 1984 Mar;81(5):1297–1301. doi: 10.1073/pnas.81.5.1297

Regioselective arylation of ribose in adenosine and guanosine with the antitumor drug N2-methyl-9-hydroxyellipticinium acetate.

J Bernadou, B Meunier, G Meunier, C Auclair, C Paoletti
PMCID: PMC344820  PMID: 6584882

Abstract

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.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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