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Original Articles

ZEBULARINE: A UNIQUE MOLECULE FOR AN EPIGENETICALLY BASED STRATEGY IN CANCER CHEMOTHERAPY. THE MAGIC OF ITS CHEMISTRY AND BIOLOGY

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Pages 305-318 | Published online: 15 Nov 2011

REFERENCES

  • Suhadolnik , R. J. 1979 . Nucleosides as Biological Probes. , 244 New York, NY : Wiley .
  • Funakoshi , R. , Irie , M. and Ukita , T. 1961 . Synthesis of unnatural pyrimidine nucleosides . Chem. Pharm. Bull. , 9 : 406 – 409 .
  • Oyen , T. B. 1969 . Synthesis and properties of ribosylpyrimidin-2-one . Biochim. Biophys. Acta , 186 : 237 – 243 .
  • Pischel , H. , Holy , A. and Wagner , G. 1972 . Glycosyl derivatives of heterocycles. XLV. Ribosyl derivatives of pyrimidinones . Coll. Czech. Chem. Commun. , 37 : 3475 – 3482 .
  • Wightman , R. H. and Holy , A. 1973 . Nucleic acid components and their analogs. CLIX. Synthesis of some 2-pyrimidinone nucleosides . Coll. Czech. Chem. Commun. , 38 : 1381 – 1386 .
  • Cech , D. and Holy , A. 1977 . Nucleic acid components and their analogs. CXC. Preparation of 2-pyrimidinone nucleosides from uracil nucleosides . Coll. Czech. Chem. Commun. , 42 : 2246 – 2260 .
  • Holy , A. 1977 . Preparation of acyl derivatives of pyrimidine-2-one nucleosides by the silyl variant of the Hilbert-Johnson reaction . Coll. Czech. Chem. Commun. , 42 : 902 – 908 .
  • McCormack , J. J. , Marquez , V. E. , Liu , P. S. , Vistica , D. T. and Driscoll , J. S. 1980 . Inhibition of cytidine deaminase by 2-oxopyrimidine riboside and related compounds . Biochem. Pharmacol. , 29 : 830 – 832 .
  • Driscoll , J. S. , Marquez , V. E. , Plowman , J. , Liu , P. S. , Kelley , J. A. and Barchi , J. J. Jr. 1991 . Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues . J. Med. Chem. , 34 : 3280 – 3284 .
  • Oyen , T. B. , Votruba , I. , Holy , A. and Wightman , R. H. 1973 . Mechanism of inhibition of DNA synthesis in Escherichia coli by pyrimidin-2-one . Biochim. Biophys Acta , 324 : 14 – 23 .
  • Holy , A. , Ludzisa , A. , Votruba , I. , Sediva , K. and Pischel , H. 1985 . Preparation of analogs of cytosine and 2-pyrimidinone nucleosides and their effect on bacterial (Escherichia coli A19) cytidine aminohydrolase . Coll. Czech. Chem. Commun. , 50 : 393 – 417 .
  • Shih , P. and Wolfenden , R. 1996 . Enzyme-substrate complexes of adenosine and cytidine deaminases: absence of accumulation of water adducts . Biochemistry , 35 : 4697 – 4703 .
  • Liu , P. S. , Marquez , V. E. , Driscoll , J. S. and Fuller , R. W. 1981 . Cyclic urea nucleosides. Cytidine deaminase activity as a function of aglycon ring size . J. Med. Chem. , 24 : 662 – 666 .
  • Marquez , V. E. , Rao , K. B.V. , Silverton , J. V. and Kelley , J. A. 1984 . A ring expansion approach to 1,3-diazepin-2-one nucleosides . J. Org. Chem. , 49 : 912 – 919 .
  • Rao , K. B.V. , Marquez , V. E. , Kelley , J. A. and Corcoran , M. T. 1983 . A new synthesis of 3-(β-D-ribofuranosyl)uracil (isouridine) via the intermediacy of an O6,5′-cyclotetrahydropyrimidinone nucleoside . J. Chem. Soc., Perkin Trans 1 , : 127 – 130 .
  • Trehan , S. B. , MacDiarmid , J. E. and Bardos , T. J. 1994 . Synthesis of 5-ethyl-2-pyrimidinone-2′-deoxyriboside as a new potential antiviral agent . Nucleosides Nucleotides , 13 : 235 – 243 .
  • Barchi , J. J. Jr. , Musser , S. and Marquez , V. E. 1992 . The decomposition of 1-(β-D-ribofuranoyl)-1,2-dihydropyrimidin-2-one (zebularine) in alkali: mechanism and products . J. Org. Chem. , 57 : 536 – 541 .
  • Frick , L. , Yang , C. , Marquez , V. E. and Wolfenden , R. 1989 . Binding of pyrimidin-2-one ribonucleoside by cytidine deaminase as the transition-state analogue 3,4-dihydrouridine and the contribution of the 4-hydroxyl group to its binding affinity . Biochemistry , 28 : 9423 – 9430 .
  • Betts , L. , Xiang , S. , Short , S. A. , Wolfenden , R. and Carter , C. W. Jr. 1994 . Cytidine deaminase. The 2.3 A® crystal structure of an enzyme:transition state analogue complex . J. Mol. Biol. , 235 : 635 – 656 .
  • Laliberte , J. , Marquez , V. E. and Momparler , R. L. 1992 . Potent inhibitors for the deamination of cytosine arabinoside and 5-aza-2′-deoxycytidine by human cytidine deaminase . Cancer Chemother. Pharmacol. , 30 : 7 – 11 .
  • Brank , A. S. , Eritja , R. , Garcia-Guimil , R. , Marquez , V. E. and Christman , J. K. 2002 . Inhibition of HhaI DNA (cytosine-C5) methyltransferase by oligodeoxyribonucleotides containing 5-aza-2′-deoxycytidine: examination of the intertwined roes of co-factor, target, transition-state structure and enzyme conformation . J. Mol. Biol. , 323 : 53 – 67 .
  • Beisler , J. A. 1978 . Isolation, characterization, and properties of a labile hydrolysis product of the antitumor nucleoside, 5-azacytidine . J. Med. Chem. , 21 : 204 – 208 .
  • Ivanetich , K. M. and Santi , D. V. 1992 . 5,6-dihydropyrimidine adducts in the reactions and interactions of pyrimidines with proteins . Prog. Nucleic Acid Res. Mol. Biol. , 42 : 127 – 156 .
  • Klimasauskas , S. , Kumar , S. , Roberts , R. J. and Cheng , X. 1994 . Hhal Methyltransferase flips its target base out of the DNA helix . Cell , 76 : 357 – 369 .
  • Zhou , L. , Cheng , X. , Connolly , B. A. , Dickman , M. J. , Hurd , P. J. and Hornby , D. P. 2002 . Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases . J. Mol. Biol. , 321 : 591 – 599 .
  • Marquez , V. E. , Eritja , R. , Kelley , J. A. , VanBemmel , D. and Christman , J. K. 2003 . Potent inhibition of HhaI DNA methylase by the aglycon of 2-(1H)-pyrimidinone riboside (zebularine) at the GCGC recognition domain . Ann. N. Y. Acad. Sci. , 1002 : 154 – 164 .
  • Jones , P. A. and Baylin , S. B. 2002 . The fundamental role of epigenetic events in cancer . Nat. Rev. Genet. , 3 : 415 – 428 .
  • Gonzalez-Zulueta , M. , Bender , C. M. , Yang , A. S. , Nguyen , T. , Beart , R. W. , Van Tornout , J. M. and Jones , P. 1995 . Methylation of the 5′ CpG island of the p16/CDKN2 tumor suppressor gene in normal and transformed human tissues correlates with gene silencing . Cancer Res. , 55 : 4531 – 4535 .
  • Cheng , J. C. , Matsen , C. B. , Gonzales , F. A. , Wei , Y. , Greer , S. , Marquez , V. E. , Jones , P. A. and Selker , E. U. 2003 . Inhibition of DNA methylation and reactivation of silenced genes by zebularine . J. Natl. Cancer Inst. , 95 : 399 – 409 .
  • Cheng , J. C. , Weisenberger , D. J. , Gonzales , F. A. , Liang , G. , Xu , G.-L. , Hu , Y.-G. , Marquez , V. E. and Jones , P. A. 2004 . Continuous zebularine treatment effectively sustains demethylation in human bladder cancer cells . Mol. Cell Biol. , 24 : 1270 – 1278 .
  • Ben-Kasus , T. , Ben-Zvi , Z. , Marquez , V. E. , Kelley , J. A. and Agbaria , R. 2005 . Metabolic activation of zebularine, a novel DNA methylation inhibitor in human bladder carcinoma cells . Biochem. Pharmacol. , 70 : 121 – 133 .
  • Lim , M.-I. , Moyer , J. D. , Cysyk , R. L. and Marquez , V. E. 1984 . Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase . J. Med. Chem. , 27 : 1536 – 1538 .

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