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Short Communications

Dimeric bisbenzimidazoles inhibit the DNA methylation catalyzed by the murine Dnmt3a catalytic domain

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Pages 295-300 | Received 11 Feb 2010, Accepted 03 Jun 2010, Published online: 08 Jul 2010

References

  • Lei H, Oh SP, Okano M, Jüttermann R, Goss KA, Jaenisch R, Li E. De novo DNA cytosine methyltransferase activities in mouse embryonic stem cells. Development 1996;122:3195–3205.
  • Okano M, Xie S, Li E. Cloning and characterization of a family of novel mammalian DNA (cytosine-5) methyltransferases. Nat Genet 1998;19:219–20.
  • Chen T, Li E. Structure and function of eukaryotic DNA methyltransferases. Curr Top Dev Biol 2004;60:55–89.
  • Kim GD, Ni J, Kelesoglu N, Roberts RJ, Pradhan S. Co-operation and communication between the human maintenance and de novo DNA (cytosine-5) methyltransferases. Embo J 2002;21:4183–95.
  • Fatemi M, Hermann A, Gowher H, Jeltsch A. Dnmt3a and Dnmt1 functionally cooperate during de novo methylation of DNA. Eur J Biochem 2002;269:4981–84.
  • Métivier R, Gallais R, Tiffoche C, Le Pé,ron C, Jurkowska RZ, Carmouche RP, Ibberson D, Barath P, Demay F, Reid G, Benes V, Jeltsch A, Gannon F, Salbert G. Cyclical DNA methylation of a transcriptionally active promoter. Nature 2008;452:45–50.
  • Jia D, Jurkowska RZ, Zhang X, Jeltsch A, Cheng X. Structure of Dnmt3a bound to Dnmt3L suggests a model for de novo DNA methylation. Nature 2007;449:248–51.
  • Jurkowska RZ, Anspach N, Urbanke C, Jia D, Reinhardt R, Nellen W, Cheng X, Jeltsch A. Formation of nucleoprotein filaments by mammalian DNA methyltransferase Dnmt3a in complex with regulator Dnmt3L. Nucleic Acids Res 2008;36:6656–63.
  • Jones PA, Baylin SB. The fundamental role of epigenetic events in cancer. Nat Rev Genet 2002;3:415–28.
  • Baylin SB, Esteller M, Rountree MR, Bachman KE, Schuebel K, Herman JG. Aberrant patterns of DNA methylation, chromatin formation and gene expression in cancer. Hum Mol Genet 2001;10:687–92.
  • Jones PA, Baylin SB. The epigenomics of cancer. Cell 2007;128:683–92.
  • Gowher H, Jeltsch A. Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy. Cancer Biol Ther 2004;3:1062–8.
  • Kirsanova OV, Cherepanova NA, Gromova ES. Inhibition of C5-cytosine-DNA-methyltransferases. Biochemistry (Mosc) 2009;74:1175–86.
  • Santi DV, Norment A, Garrett CE. Covalent bond formation between a DNA-cytosine methyltransferase and DNA containing 5-azacytosine. Proc Natl Acad Sci USA 1984;81:6993–7.
  • Fang MZ, Wang Y, Ai N, Hou Z, Sun Y, Lu H, Welsh W, Yang CS. Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylation-silenced genes in cancer cell lines. Cancer Res 2003;63:7563–70.
  • Piña IC, Gautschi JT, Wang GY, Sanders ML, Schmitz FJ, France D, Cornell-Kennon S, Sambucetti LC, Remiszewski SW, Perez LB, Bair KW, Crews P. Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase. J Org Chem 2003;68:3866–73.
  • Brueckner B, Garcia Boy R, Siedlecki P, Musch T, Kliem HC, Zielenkiewicz P, Suhai S, Wiessler M, Lyko F. Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases. Cancer Res 2005;65:6305–11.
  • Klimasauskas S, Kumar S, Roberts RJ, Cheng X. HhaI methyltransferase flips its target base out of the DNA helix. Cell 1994;76:357–69.
  • Teng MK, Usman N, Frederick CA, Wang AH. The molecular structure of the complex of Hoechst 33258 and the DNA dodecamer d(CGCGAATTCGCG). Nucleic Acids Res 1988;16:2671–90.
  • Loontiens FG, Regenfuss P, Zechel A, Dumortier L, Clegg RM. Binding characteristics of Hoechst 33258 with calf thymus DNA, poly[d(A-T)], and d(CCGGAATTCCGG): multiple stoichiometries and determination of tight binding with a wide spectrum of site affinities. Biochemistry 1990;29:9029–39.
  • Ivanov AA, Strel’tsov SA, Prikazchikova TA, Gottikh MB, Zhuze AL. Synthesis and properties of a symmetric dimeric bisbenzimidazole, a DNA-specific ligand. Bioorg Khim 2008;34:285–8.
  • Gowher H, Jeltsch A. Molecular enzymology of the catalytic domains of the Dnmt3a and Dnmt3b DNA methyltransferases. J Biol Chem 2002;277:20409–14.
  • Maltseva DV, Baykov AA, Jeltsch A, Gromova ES. Impact of 7,8-dihydro-8-oxoguanine on methylation of the CpG site by Dnmt3a. Biochemistry 2009;48:1361–68.
  • Loewe H, Urbanietz J. Basic-substituted 2,6-bisbenzimidazole derivates, a novel class of substances with chemotherapeutic activity. Arzneimittelforschung 1974;24:1927–33.
  • Fairley TA, Tidwell RR, Donkor I, Naiman NA, Ohemeng KA, Lombardy RJ, Bentley JA, Cory M. Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). J Med Chem 1993;36:1746–53.
  • Streltsov SA, Gromyko AV, Oleinikov VA, Zhuze AL. The Hoechst 33258 covalent dimer covers a total turn of the double-stranded DNA. J Biomol Struct Dyn 2006;24:285–302.
  • Pjura PE, Grzeskowiak K, Dickerson RE. Binding of Hoechst 33258 to the minor groove of B-DNA. J Mol Biol 1987;197:257–71.
  • Streltsov SA, Zhuze AL. Hoechst 33258–poly(dG-dC).poly(dG-dC) complexes of three types. J Biomol Struct Dyn 2008;26:99–114.
  • Subach OM, Baskunov VB, Darii MV, Maltseva DV, Alexandrov DA, Kirsanova OV, Kolbanovskiy A, Kolbanovskiy M, Johnson F, Bonala R, Geacintov NE, Gromova ES. Impact of benzo[a]pyrene-2′-deoxyguanosine lesions on methylation of DNA by SssI and HhaI DNA methyltransferases. Biochemistry 2006;45:6142–59.
  • Subach OM, Maltseva DV, Shastry A, Kolbanovskiy A, Klimasauskas S, Geacintov NE, Gromova ES. The stereochemistry of benzo[a]pyrene-2′-deoxyguanosine adducts affects DNA methylation by SssI and HhaI DNA methyltransferases. FEBS J 2007;274:2121–34.
  • Chen AY, Yu C, Gatto B, Liu LF. DNA minor groove-binding ligands: a different class of mammalian DNA topoisomerase I inhibitors. Proc Natl Acad Sci USA 1993;90:8131–5.
  • Link A, Tempel K. Inhibition of O6-alkylguanine-DNA alkyltransferase and DNase I activities in vitro by some alkylating substances and antineoplastic agents. J Cancer Res Clin Oncol 1991;117:549–55.
  • Selby CP, Sancar A. Noncovalent drug-DNA binding interactions that inhibit and stimulate (A)BC excinuclease. Biochemistry 1991;30:3841–9.
  • Suzuki T, Tanaka R, Hamada S, Nakagawa H, Miyata N. Design, synthesis, inhibitory activity, and binding mode study of novel DNA methyltransferase 1 inhibitors. Bioorg Med Chem Lett 2010;20:1124–7.
  • Popov KV, Egorova EI, Ivanov AA, Gromyko AV, Zhuze AL, Bolsheva NL, Yurkevitch OYu, Muravenko OV, Zelenin AV. Dimeric bisbenzimidazole Hoechst 33258-related dyes as novel AT-specific DNA-binding fluorochromes for human and plant cytogenetics. Biochemistry (Mosc) Ser A: Membr Cell Biol 2008;2:203–9.

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