메뉴 건너뛰기




Volumn 9, Issue 4, 1999, Pages 415-421

Oligonucleotides containing 5,6-dihydro-5-azacytosine at cpg sites can produce potent inhibition of dna cytosine-c5-methyltransferase without covalently binding to the enzyme

Author keywords

[No Author keywords available]

Indexed keywords


EID: 18244408991     PISSN: 10872906     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (1)

References (34)
  • 1
    • 0031014414 scopus 로고    scopus 로고
    • Reversal of loss of imprinting in tumor cells by 5-aza-2′-deoxycytidine
    • BARLETTA, J.M., RAINIER, S., and FEINBERG, A.P. (1997). Reversal of loss of imprinting in tumor cells by 5-aza-2′-deoxycytidine. Cancer Res. 57, 48-50.
    • (1997) Cancer Res. , vol.57 , pp. 48-50
    • Barletta, J.M.1    Rainier, S.2    Feinberg, A.P.3
  • 2
    • 0017801980 scopus 로고
    • Isolation, characterization, and properties of a labile hydrolysis product of the antitumor nucleoside, 5-azacytidine
    • BEISLER, J.A. (1978). Isolation, characterization, and properties of a labile hydrolysis product of the antitumor nucleoside, 5-azacytidine. J. Med. Chem. 21, 204.
    • (1978) J. Med. Chem. , vol.21 , pp. 204
    • Beisler, J.A.1
  • 3
    • 0017704196 scopus 로고
    • Synthesis and antitumor activity of dihydro-5-azacytidine, a hydrolytically stable analogue of 5-azacytidine
    • BEISLER, J.A., ABBASI, M.M., KELLEY, I.A., and DRISCOLL, J.S. (1977). Synthesis and antitumor activity of dihydro-5-azacytidine, a hydrolytically stable analogue of 5-azacytidine. J. Med. Chem. 20, 806-812.
    • (1977) J. Med. Chem. , vol.20 , pp. 806-812
    • Beisler, J.A.1    Abbasi, M.M.2    Kelley, I.A.3    Driscoll, J.S.4
  • 4
    • 0023277806 scopus 로고
    • Fetal hemoglobin gene activation in phase II study of 5.6-dihydro-5-azacytidine for bronchogenic carcinoma
    • CARR, B.I., RAHBAR, S., DOROSHOW, J.H., BLAYNEY, D., GOLDBERG, D., LEONG, J., and ASMERON, Y. (1987). Fetal hemoglobin gene activation in phase II study of 5.6-dihydro-5-azacytidine for bronchogenic carcinoma. Cancer Res. 47, 4199-4201.
    • (1987) Cancer Res. , vol.47 , pp. 4199-4201
    • Carr, B.I.1    Rahbar, S.2    Doroshow, J.H.3    Blayney, D.4    Goldberg, D.5    Leong, J.6    Asmeron, Y.7
  • 5
    • 0026316928 scopus 로고
    • Direct identification of the active-site nucleophile in a DNA (cytosine-5)-methyltransferase
    • CHEN, L., MACMILLAN, A.M., CHANG, W., EZAZ-NIKPAY, K., LANE, W.S., and VERDINE, G.L. (1991). Direct identification of the active-site nucleophile in a DNA (cytosine-5)-methyltransferase. Biochemistry 30, 11018-11025.
    • (1991) Biochemistry , vol.30 , pp. 11018-11025
    • Chen, L.1    Macmillan, A.M.2    Chang, W.3    Ezaz-Nikpay, K.4    Lane, W.S.5    Verdine, G.L.6
  • 6
    • 0029163078 scopus 로고
    • Structure and function of DNA methyltransferases
    • CHENG, X. (1995). Structure and function of DNA methyltransferases. Annu. Rev. Biophys. Biomol. Struct. 24, 293-318.
    • (1995) Annu. Rev. Biophys. Biomol. Struct. , vol.24 , pp. 293-318
    • Cheng, X.1
  • 7
    • 0029127302 scopus 로고
    • 5-Methyl-2′-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation
    • CHRISTMAN, J.K., SHEIKHNEJAD, G., MARASCO, C., and SUFRIN, J.R. (1995). 5-Methyl-2′-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation. Proc. Natl. Acad. Sci. USA 92, 7347-7351.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 7347-7351
    • Christman, J.K.1    Sheikhnejad, G.2    Marasco, C.3    Sufrin, J.R.4
  • 8
    • 0023035969 scopus 로고
    • Difference in DNA damage produced by incorporation of 5-aza-2′-deoxycytidine or 5,6-dihydro-5-azacytidine into DNA of mammalian cells
    • COVEY, J.M., D'INCALCI, M., TILCHEN, E.J., ZAHARKO, D.S., and KOHN, K.W. (1986). Difference in DNA damage produced by incorporation of 5-aza-2′-deoxycytidine or 5,6-dihydro-5-azacytidine into DNA of mammalian cells. Cancer Res. 46, 5511-5517.
    • (1986) Cancer Res. , vol.46 , pp. 5511-5517
    • Covey, J.M.1    D'Incalci, M.2    Tilchen, E.J.3    Zaharko, D.S.4    Kohn, K.W.5
  • 9
    • 0020032366 scopus 로고
    • Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidine and 5-aza-2′-deoxycytidine
    • CREUSOT, F., ACS, G., and CHRISTMAN, J.K. (1982). Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidine and 5-aza-2′-deoxycytidine. J. Biol. Chem. 257, 2041-2048.
    • (1982) J. Biol. Chem. , vol.257 , pp. 2041-2048
    • Creusot, F.1    Acs, G.2    Christman, J.K.3
  • 10
    • 0026763827 scopus 로고
    • Binding of the EcoRII methyltransferase to 5-fluorocytosine-containing DNA: Isolation of a bound protein
    • FRIEDMAN, S., and ANSARI, N. (1992). Binding of the EcoRII methyltransferase to 5-fluorocytosine-containing DNA: Isolation of a bound protein. Nucleic Acids Res. 20, 3241-3248.
    • (1992) Nucleic Acids Res. , vol.20 , pp. 3241-3248
    • Friedman, S.1    Ansari, N.2
  • 11
    • 0023881452 scopus 로고
    • Synthesis of a phosphoramidite of 2′-deoxy-5, 6-dihydro-5-azacytidine. Its potential application in the synthesis of DNA containing dihydro-5-aza- And 5-azacytosine bases
    • GODDARD, A.J., and MARQUEZ, V.E. (1988). Synthesis of a phosphoramidite of 2′-deoxy-5, 6-dihydro-5-azacytidine. Its potential application in the synthesis of DNA containing dihydro-5-aza- and 5-azacytosine bases. Tetrahedron Lett. 29, 1767-1770.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1767-1770
    • Goddard, A.J.1    Marquez, V.E.2
  • 12
    • 0028947749 scopus 로고
    • The effect of 5-azacytidine and 5-azadeoxycytidine on chromosome structure and function: Implications for methylation-associated cellular processes
    • HAAF, T. (1995). The effect of 5-azacytidine and 5-azadeoxycytidine on chromosome structure and function: Implications for methylation-associated cellular processes. Pharmacol. Ther. 65, 19-46.
    • (1995) Pharmacol. Ther. , vol.65 , pp. 19-46
    • Haaf, T.1
  • 13
    • 0029898837 scopus 로고    scopus 로고
    • DNA methylation errors and cancer
    • JONES, P.A. (1996). DNA methylation errors and cancer. Cancer Res. 56, 2463-2467.
    • (1996) Cancer Res. , vol.56 , pp. 2463-2467
    • Jones, P.A.1
  • 14
    • 0018860957 scopus 로고
    • Cellular differentiation, cytidine analogs and DNA methylation
    • JONES, P.A., and TAYLOR, S.M. (1980). Cellular differentiation, cytidine analogs and DNA methylation. Cell 20, 85-93.
    • (1980) Cell , vol.20 , pp. 85-93
    • Jones, P.A.1    Taylor, S.M.2
  • 15
    • 0028151343 scopus 로고
    • Toxicity of 5-aza-2′-deoxycytidine to mammalian cells is mediated primarily by covalent trapping of DNA methyltransferase rather than DNA demethylation
    • JUTTERMANN, R., LI, E., and JAENISCH, R. (1994). Toxicity of 5-aza-2′-deoxycytidine to mammalian cells is mediated primarily by covalent trapping of DNA methyltransferase rather than DNA demethylation. Proc. Natl. Acad. Sci. USA 91, 11797-11801.
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 11797-11801
    • Juttermann, R.1    Li, E.2    Jaenisch, R.3
  • 16
    • 0028010888 scopus 로고
    • Hhal methyltransferase lips its target base out of the DNA helix
    • KLIMASAUSKAS, S., KUMAR, S., ROBERTS, R.J., and CHENG, X. (1994). Hhal methyltransferase lips its target base out of the DNA helix. Cell 76, 357-369.
    • (1994) Cell , vol.76 , pp. 357-369
    • Klimasauskas, S.1    Kumar, S.2    Roberts, R.J.3    Cheng, X.4
  • 17
    • 0019856151 scopus 로고
    • High performance liquid chromatographic analysis and chemical stability of 5-aza-2′-deoxycytidine
    • LIN, KT., MOMPARLER, R.L., and RFVARD, G.E. (1981). High performance liquid chromatographic analysis and chemical stability of 5-aza-2′-deoxycytidine. J. Pharm. Sci. 70, 1228-1232.
    • (1981) J. Pharm. Sci. , vol.70 , pp. 1228-1232
    • Lin, K.T.1    Momparler, R.L.2    Rfvard, G.E.3
  • 18
    • 0018878649 scopus 로고
    • Synthesis of 1, 3-diazepin-2-one nucleosides as transition-state inhibitors of cytidine deaminase
    • MARQUEZ, V.E., LIU, P.S., KELLEY, J.A., DRISCOLL, J.S., and McCORMACK, J.J. (1980). Synthesis of 1, 3-diazepin-2-one nucleosides as transition-state inhibitors of cytidine deaminase. J. Med. Chem. 23, 713-715.
    • (1980) J. Med. Chem. , vol.23 , pp. 713-715
    • Marquez, V.E.1    Liu, P.S.2    Kelley, J.A.3    Driscoll, J.S.4    McCormack, J.J.5
  • 20
    • 0030572656 scopus 로고    scopus 로고
    • Enzymatic C5-cytosine methylation of DNA: Mechanistic implications of new crystal structures for HhaI methyltransferase-DNA-AdoHcy complexes
    • O'GARA, M., KLIMASAUKAS, S., ROBERTS, R.J., and CHENG, X. (1996). Enzymatic C5-cytosine methylation of DNA: Mechanistic implications of new crystal structures for HhaI methyltransferase-DNA-AdoHcy complexes. J. Mol. Biol. 261, 634-645.
    • (1996) J. Mol. Biol. , vol.261 , pp. 634-645
    • O'Gara, M.1    Klimasaukas, S.2    Roberts, R.J.3    Cheng, X.4
  • 21
    • 0024604147 scopus 로고
    • Predictive motifs derived from cytosine methyltransferases
    • POSFAI, J., BHAGWAT, A.S., POSFAI, G., and ROBERTS, R.J. (1989). Predictive motifs derived from cytosine methyltransferases. Nucleic Acids Res. 17, 2421-2433.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 2421-2433
    • Posfai, J.1    Bhagwat, A.S.2    Posfai, G.3    Roberts, R.J.4
  • 22
    • 0031025621 scopus 로고    scopus 로고
    • Inhibition of tumorigenesis by a cytosine-DNA, methyltransferase, antisense oligodeoxynucleotide
    • RAMCHANDANI, S., MACLEOD, R.A., PINARD, M., VON HOFE, E., and SZYF, M. (1997). Inhibition of tumorigenesis by a cytosine-DNA, methyltransferase, antisense oligodeoxynucleotide. Proc Natl. Acad. Sci. USA 94, 684-698.
    • (1997) Proc Natl. Acad. Sci. USA , vol.94 , pp. 684-698
    • Ramchandani, S.1    Macleod, R.A.2    Pinard, M.3    Von Hofe, E.4    Szyf, M.5
  • 23
    • 0029068629 scopus 로고
    • The crystal structure of Haell methyltransferase covalently complexed to DNA: An extrahelical cytosine and rearranged base flipping
    • REINISCH, K.M., CHEN, L., VERDINE, G., and LIPSCOMB, W.N. (1995). The crystal structure of Haell methyltransferase covalently complexed to DNA: An extrahelical cytosine and rearranged base flipping. Cell 82, 143-153.
    • (1995) Cell , vol.82 , pp. 143-153
    • Reinisch, K.M.1    Chen, L.2    Verdine, G.3    Lipscomb, W.N.4
  • 25
    • 0020582853 scopus 로고
    • On the mechanism of inhibition of DNA-cytosine methyltransferases by cytosine analogs
    • SANTI, D.V., GARRETT, C.E., and BARR, P.J. (1983). On the mechanism of inhibition of DNA-cytosine methyltransferases by cytosine analogs. Cell 33, 9-10.
    • (1983) Cell , vol.33 , pp. 9-10
    • Santi, D.V.1    Garrett, C.E.2    Barr, P.J.3
  • 26
    • 2442750985 scopus 로고
    • A new type of protection mode for the guanine residue by using 1,2-diisobutyrylloxyethylene group
    • SEKINE, M., MATSUZAKI, J., and HATA, T. (1982). A new type of protection mode for the guanine residue by using 1,2-diisobutyrylloxyethylene group. Tetrahedron Lett. 23, 5287-5290.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 5287-5290
    • Sekine, M.1    Matsuzaki, J.2    Hata, T.3
  • 28
    • 0026523796 scopus 로고
    • Mechanism of human methyl-directed DNA methyltransferase and the fidelity of cytosine methylation
    • SMITH, S.S., KAPLAN, B.E., SOWERS, L.C., and NEWMAN, E.M. (1992). Mechanism of human methyl-directed DNA methyltransferase and the fidelity of cytosine methylation. Proc. Natl. Acad. Sci. USA 89, 4744-4748.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 4744-4748
    • Smith, S.S.1    Kaplan, B.E.2    Sowers, L.C.3    Newman, E.M.4
  • 29
    • 0031817856 scopus 로고    scopus 로고
    • Targeting DNA methyltransferase in cancer
    • SZYF, M. (1998). Targeting DNA methyltransferase in cancer. Cancer Metastatis Rev. 17, 219-231.
    • (1998) Cancer Metastatis Rev. , vol.17 , pp. 219-231
    • Szyf, M.1
  • 30
    • 0024371483 scopus 로고
    • Rapid appearance of hypomethylated DNA in livers of rats fed cancer-promoting, methyl-deficient diets
    • WAINFAN, E., DIZIK, M., STENDER, M., and CHRISTMAN, J.K. (1989). Rapid appearance of hypomethylated DNA in livers of rats fed cancer-promoting, methyl-deficient diets. Cancer Res. 49, 4094-4097.
    • (1989) Cancer Res. , vol.49 , pp. 4094-4097
    • Wainfan, E.1    Dizik, M.2    Stender, M.3    Christman, J.K.4
  • 31
    • 0016717997 scopus 로고
    • On the interaction of 3, 4, 5, 6-tetrahydrouridine with human liver cytidine deaminase
    • WENTFORD, D.F., and WOLFENDEN, R. (1975). On the interaction of 3, 4, 5, 6-tetrahydrouridine with human liver cytidine deaminase. Biochemistry 14, 5099-5105.
    • (1975) Biochemistry , vol.14 , pp. 5099-5105
    • Wentford, D.F.1    Wolfenden, R.2
  • 32
    • 0002903441 scopus 로고
    • Analog approaches to the structure of the transition-state in enzyme reactions
    • WOLFENDEN, R. (1972). Analog approaches to the structure of the transition-state in enzyme reactions. Ace. Chem. Res. 5, 10-15.
    • (1972) Ace. Chem. Res. , vol.5 , pp. 10-15
    • Wolfenden, R.1
  • 33
    • 0031416750 scopus 로고    scopus 로고
    • Genetic and epigenetic aspects of DNA methylation on genome expression, evolution, mutation and carcinogenesis
    • ZINGG, J.-M., and JONES. P.A. (1997). Genetic and epigenetic aspects of DNA methylation on genome expression, evolution, mutation and carcinogenesis. Carcinogenesis 18, 869-882.
    • (1997) Carcinogenesis , vol.18 , pp. 869-882
    • Zingg, J.-M.1    Jones, P.A.2
  • 34
    • 0031416750 scopus 로고    scopus 로고
    • ZINGG, J.-M., and JONES. P.A. (1997). Genetic and epigenetic aspects of DNA methylation on genome expression, evolution, mutation and carcinogenesis. Carcinogenesis 18, 869-882.
    • ZINGG, J.-M., and JONES. P.A. (1997). Genetic and epigenetic aspects of DNA methylation on genome expression, evolution, mutation and carcinogenesis. Carcinogenesis 18, 869-882.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.