New cytosine derivatives as inhibitors of DNA methylation

European Journal of Medicinal Chemistry

Volumn 55, Issue , 2012, Pages 243-254

  Plitta, Beata ^a   Adamska, Ewelina ^a   Giel Pietraszuk, Małgorzata ^a   Fedoruk Wyszomirska, Agnieszka ^a   Naskrȩt Barciszewska, Mirosława ^a   Markiewicz, Wojciech T ^a   Barciszewski, Jan ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

4 N Furfurylcytosine; Cancer therapy; Cytosine derivatives; Furfural; Inhibitors of DNA methyltransferase 1

Indexed keywords

4 N (5 HYDROXYMETHYLFURFURYL)CYTOSINE; 4 N ARYLMETHYL 5 METHYL 2' DEOXYCYTIDINE 5 METHYL 4 (1,2,4 TRIAZOL 1 YL) 1 (BETA D 3,5 DI O ACETYL 2 DEOXYRIBOFURANOSYL)PYRIMIDIN 2 (1H)ONE; 4 N BENZYL 5 ACETYLOXYMETHYLCYTOSINE; 4 N BENZYL 5 FORMYLCYTOSINE; 4 N BENZYL 5 HYDROXYMETHYLCYTOSINE; 4 N BENZYL 5,6 DIHYDRO 5 AZACYTOSINE; 4 N BENZYLCYTOSINE; 4 N BENZYLCYTOSINE 5 METHYLSULFONIC ACID SODIUM SALT; 4 N BUTYLCYTOSINE; 4 N BUTYLIDENECYTOSINE ACETATE; 4 N ETHYLCYTOSINE; 4 N ETHYLIDENECYTOSINE ACETATE; 4 N FURFURYL 2' DEOXYCYTIDINE; 4 N FURFURYL 5 (N BUTYLAMINE)METHYLCYTOSINE; 4 N FURFURYL 5 ACETYLOXYMETHYLCYTOSINE; 4 N FURFURYL 5 FORMYLCYTOSINE; 4 N FURFURYL 5 HYDROXYMETHYLCYTOSINE; 4 N FURFURYL 5 METHYL 2' DEOXYCYTIDINE; 4 N FURFURYL 5,6 DIHYDRO 5 AZACYTOSINE; 4 N FURFURYLCYTOSINE; 4 N FURFURYLCYTOSINE 5 METHYL SULFONIC ACID SODIUM SALT; 4 N OMICRON NITROBENZYLOCYTOSINE; 4 N PARA METHYLBENZYLCYTOSINE; 4 N PARA TOLUENESULFONYLCYTOSINE; 4 N PICOLYLCYTOSINE; 4 N PROPYLIDENECYTOSINE ACETATE; CYTOSINE DERIVATIVE; DNA METHYLTRANSFERASE 1; DNA METHYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CANCER THERAPY; COLORIMETRY; DNA METHYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; IN VITRO STUDY; NUCLEOTIDE SEQUENCE;

CHEMISTRY TECHNIQUES, SYNTHETIC; CYTOSINE; DNA METHYLATION; HEK293 CELLS; HELA CELLS; HUMANS;

EID: 84865756359     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.07.024     Document Type: Article

References (46)

1. F. Lyko, and R. Brown DNA methyltransferase inhibitors and the development of epigenetic cancer therapies J. Natl. Cancer Inst. 97 2005 1498 1506
2. H. Gowher, and A. Jeltsch Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy Cancer Biol. Ther. 3 2004 1062 1068
3. B. Brueckner, and F. Lyko DNA methyltransferase inhibitors: old and new drugs for an epigenetic cancer therapy Trends Pharmacol. Sci. 25 2004 551 554
4. P.J. Bastian, S. Yegnasubramanian, G.S. Palapattu, C.G. Rogers, X. Lin, A.M. De Marzo, and W.G. Nelson Molecular biomarker in prostate cancer: the role of CpG island hypermethylation Eur. Urol. 6 2004 698 708
5. P.W. Laird, and R. Jaenisch The role of DNA methylation in cancer genetic and epigenetics Annu. Rev. Genet. 30 1996 441 464
6. C. Mund, B. Brueckner, and F. Lyko Reactivation of epigenetically silenced genes by DNA methyltransferase inhibitors: basic concepts and clinical applications Epigenetics 1 2006 7 13
7. P.A. Jones, and S.B. Baylin The fundamental role of epigenetic events in cancer Nat. Rev. Genet. 6 2002 415 428
8. P.A. Jones Overview of cancer epigenetics Semin. Hematol. 42 Suppl. 2 2005 S3 S8
9. M. Szyf The DNA methylation machinery as a therapeutic target Curr. Drug Targ. 1 2000 101 118
10. C.B. Yoo, and P.A. Jones Epigenetic therapy of cancer: past, present and future Nat. Rev. Drug Discov. 5 2006 37 50
11. V.M. Komashko, and P.J. Farnham 5-Azacytidine treatment recognizes genomic histone modification patterns Epigenetics 5 2010 1 12
12. M.Z. Fang, Y. Ai, N. Wang, Z. Hou, Y. Sun, H. Lu, W. Welsh, and C.S. Yang Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylation-silenced genes in cancer cell lines Cancer Res. 63 2003 7563 7570
13. H. Nakagawa, K. Hasumi, J.T. Woo, K. Nagai, and M. Wachi Generation of hydrogen peroxide primarily contributes to the induction of Fe(II)-dependent apoptosis in Jurkat cells by (-)-epigallocatechin gallate Carcinogenesis 25 2004 1567 1574
14. Z. Liu, Z. Xie, W. Jones, R.E. Pavlovicz, S. Liu, J. Yu, P.K. Li, J. Lin, J.R. Fuchs, G. Marcucci, C. Li, and K.K. Chan Curcumin is a potent DNA hypomethylation agent Bioorg. Med. Chem. Lett. 19 2009 706 709
15. B. Brueckner, R.G. Boy, P. Siedlecki, T. Musch, H.C. Kliem, P. Zielenkiewicz, S. Suhai, M. Wissler, and F. Lyko Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases Cancer Res. 65 2005 6305 6311
16. A. Mai, and L. Altucci Epi-drugs to fight cancer: from chemistry to cancer treatment, the road ahead Int. J. Biochem. Cell Biol. 41 2009 199 213
17. N.O. Reich, and N. Mashhoon Inhibition of EcoRI DNA methylase with cofactor analogs J. Biol. Chem. 265 1990 8966 8970
18. J.M. Zingg, J.C. Shen, A.S. Yang, H. Rapoport, and P.A. Jones Methylation inhibitors can increase the rate of cytosine deamination by (cytosine-5)-DNA methyltransferases Nucleic Acids Res. 16 1996 3267 3275
19. A. Villar-Garea, M.F. Fraga, J. Espada, and M. Esteller Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells Cancer Res. 63 2003 4984 4989
20. B.H. Lee, S. Yegnasubramanian, X. Lin, and W.G. Nelson Procainamide is a specific inhibitor of DNA methyltransferase 1 J. Biol. Chem. 280 2005 40749 40756
21. M. Nieto, E. Samper, M.F. Fraga, G. González de Buitrago, M. Esteller, and M. Serrano The absence of p53 is critical for the induction of apoptosis by 5-aza-2′-deoxycytidine Oncogene 23 2004 735 743
22. J. Barciszewski, G.E. Siboska, B.O. Pedersen, B.F. Clark, and S.I. Rattan Evidence for the presence of kinetin in DNA and cell extracts FEBS Lett. 393 1996 197 200
23. J. Barciszewski, G.E. Siboska, B.O. Pedersen, B.F. Clark, and S.I. Rattan A mechanism for the in vivo formation of N6-furfuryladenine, kinetin, as a secondary oxidative damage product of DNA FEBS Lett. 414 1997 457 460
24. E. Wyszko, M.Z. Barciszewska, M. Markiewicz, M. Szymański, W.T. Markiewicz, B.F. Clark, and J. Barciszewski "Action-at-a distance" of a new DNA oxidative damage product 6-furfuryl-adenine (kinetin) on template properties of modified DNA Biochim. Biophys. Acta 1625 2003 239 245
25. E.R. Garrett, J.K. Seydel, and A.J. Sharpen The acid-catalyzed solvolysis of pyrimidine nucleosides J. Org. Chem. 31 1966 2219 2227
26. W.T. Markiewicz, G. Gröger, R. Rösch, A. Zebrowska, M. Markiewicz, M. Klotz, P. Godzina, and H. Seliger New method of synthesis of fluorescently labelled oligonucleotides and their application in DNA sequencing Nucleic Acid Res. 25 1997 3672 3680
27. S. Dincer Synthesis of some cytosine Schiff bases Indian J. Chem. B Org. 35B 1996 1335 1336
28. Y. Kawai, K. Uchida, and T. Osawa 2′-Deoxycytidine in free nucleosides and double-stranded DNA as the major target of lipid peroxidation products Free Radic. Biol. Med. 36 2004 529 541
29. R.H.E. Hudson, Y. Liu, and F. Wojciechowski Hydrophilic modifications in peptide nucleic acid synthesis and properties of PNA possessing 5-hydroxymethyluracil and 5-hydroxymethylcytosine Can. J. Chem. 85 2007 302 312
30. W.L. Sung Chemical conversion of thymidine into 5-methyl-2′- deoxycytidine J. Chem. Soc. Chem. Commun. 1981 1089
31. T.R. Webb, and M.D. Matteucci Hybridization triggered cross-linking of deoxyoligonucleotides Nucleic Acids Res. 14 1986 7661 7674
32. C. Cristescu, and F. Czobor As-triazine derivatives with potential therapeutic action. XXVI. Syntheses of 5-substituted-6-azauracil acyclonucleosides Nucleosides Nucleotides 17 1998 1319 1324
33. J. Song, O. Rechkoblit, T.H. Bestor, and D.J. Patel Structure of DNMT1-DNA complex reveals a role for autoinhibition in maintenance DNA methylation Science 331 2011 1036 1040
34. J.B. Margot, A.M. Aguirre-Arteta, B.V. Di Giacco, S. Pradhan, R.J. Roberts, M.C. Cardoso, and H. Leonhardt Structure and function of the mouse DNA methyltransferase gene: Dnmt1 shows a Tripartite structure J. Mol. Biol. 297 2000 293 300
35. P. Siedlecki, R.G. Boy, S. Comagic, R. Schirrmacher, M. Wiessler, P. Zielenkiewicz, S. Suhai, and F. Lyko Establishment and functional validation of a structural homology model for human DNA methyltransferase Biochem. Biophys. Res. Commun. 306 2003 558 563
36. E.V. Koudan, J.M. Bujnicki, and E.S. Gromova Homology modeling of the CG-specific DNA methyltransferase SssI and its complexes with DNA and AdoHcy J. Biomol. Struct. Dyn. 22 2004 339 345
37. M. Dixon The determination of enzyme inhibitor constants Biochem. J. 55 1953 170 175
38. A. Cornish-Bowden Statistical considerations in the estimation of enzyme kinetic parameters by the direct linear plot and other methods Biochem. J. 139 1974 721 731
39. J. Yoo, J.H. Kim, K.D. Robertsona, and J.L. Medina-Franco Molecular modeling of human DNA methyltransferase with a crystal structure: discovery of novel DNMT1 inhibitor Adv. Protein Chem. Struct. Biol. 87 2012 219 247
40. M.Z. Barciszewska, A.M. Barciszewska, and S.I.S. Rattan TLC-based detection of methylated cytosine: application to aging epigenetics Biogerontology 8 2007 673 678
41. Y.G. Zheng, J. Wu, Z. Chen, and M. Goodman Chemical regulation of epigenetic modifications: opportunities for new cancer therapy Med. Res. Rev. 28 2008 645 687
42. X. Cheng Structure and function of DNA methyltransferases Annu. Rev. Biophys. Biomol. Struct. 24 1995 293 318
43. J.K. Christman 5-Azacytidine and 5-aza-2′-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy Oncogene 21 2002 5483 5495
44. C.A. Lipinski Drug-like properties and the causes of poor solubility and poor permeability J. Pharmacol. Toxicol. Methods 1 2000 235 249
45. P.B.R. Kumar, M. Soni, B.U. Bhikhalal, I.R. Kakkot, M. Jagadeesh, P. Bommu, and M.I. Nanjan Analysis of physicochemical properties for drugs from nature Med. Chem. Res. 19 2010 984 992
46. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254