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1: Ann N Y Acad Sci. 2003 Dec;1002:154-64.Click here to read Links

Potent inhibition of HhaI DNA methylase by the aglycon of 2-(1H)-pyrimidinone riboside (zebularine) at the GCGC recognition domain.

Marquez VE, Eritja R, Kelley JA, Vanbemmel D, Christman JK.

Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, Maryland 21702, USA. marquezv@dc37a.nci.nih.gov

A short oligodeoxynucleotide (ODN) with 2-(1H)-pyrimidinone at the HhaI DNA methyltransferase target site (GCGC) is shown to induce a level of inhibition of methyl transfer and thermal stability of the complex with the enzyme identical to that achieved with a similar ODN substituted with 5-azacytosine. The drugs responsible for these effects-zebularine and 5-azacytidine/2'-deoxy-5-azacytidine-are contrasted in terms of chemical stability and possible metabolic activation by a brief structure-activity analysis.

PMID: 14751833 [PubMed - indexed for MEDLINE]