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Potent inhibition of HhaI DNA methylase by the aglycon of 2-(1H)-pyrimidinone riboside (Zebularine) at the G(C)under-barGC recognition domain

  1. Author:
    Marquez, V. E.
    Eritja, R.
    Kelley, J. A.
    Vanbemmel, D.
    Christman, J.

  2. Author Address

    Marquez, VE, NCI, Ctr Canc Res, Med Chem Lab, 376 Boyles St,Bldg 376,Rm 104, Ft Detrick, MD 21702 USA NCI, Ctr Canc Res, Med Chem Lab, Ft Detrick, MD 21702 USA. CSIC, Ctr Invest & Desarrollo, E-08034 Barcelona, Spain. Univ Nebraska, Med Ctr, Dept Biochem & Mol Biol, Omaha, NE 68198 USA. Univ Nebraska, Coll Med, Eppley Canc Ctr, Omaha, NE 68198 USA.
    1. Year: 2003
  2. Book Title: THERAPEUTIC OLIGONUCLEOTIDES
  3. Series Title: ANNALS OF THE NEW YORK ACADEMY OF SCIENCES
    1. 1002
    2. Pages: 154-164
  5. Type of Work: Book Chapter
  1. Abstract:

    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

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