Use of Drosophila deoxynucleoside kinase to study mechanism of toxicity and mutagenicity of deoxycytidine analogs in Escherichia coli

DNA Repair

Volumn 9, Issue 2, 2010, Pages 153-160

  Betham, Brittany ^a   Shalhout, Sophia ^a   Marquez, Victor E ^b   Bhagwat, Ashok S ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Anti cancer chemotherapy; Anti metabolite chemotherapy; Decitabine; Zebularine

Indexed keywords

2' DEOXY ZEBULARINE; 5 AZA 2' DEOXYCYTIDINE; AZACITIDINE; CELL DNA; CYTOSINE DERIVATIVE; DEOXYCYTIDINE; DEOXYRIBONUCLEOTIDE; DEOXYRIBONUCLEOTIDE KINASE; DNA BASE; PHOSPHOTRANSFERASE; UNCLASSIFIED DRUG; ZEBULARINE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BACTERIAL STRAIN; CELL DEATH; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; DROSOPHILA; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME SPECIFICITY; ESCHERICHIA COLI; FLUORESCENCE; GENE EXPRESSION; MISMATCH REPAIR; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; AZACITIDINE; CYTIDINE; DEOXYCYTIDINE; DNA; DNA METHYLATION; DNA MISMATCH REPAIR; DROSOPHILA MELANOGASTER; ESCHERICHIA COLI; FLUORESCENCE; MICROBIAL SENSITIVITY TESTS; MUTAGENESIS; PHOSPHORYLATION; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR);

ESCHERICHIA COLI;

EID: 75149147505     PISSN: 15687864     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dnarep.2009.11.006     Document Type: Article

References (41)

1. Pizzorno G., Diasio R.B., and Cheng Y.-C. Pyrimidine and purine antimetabolites. In: Kufe D.W., Holland J.F., and Frei E. (Eds). Cancer Medicine, vol. 6 (2003), BC Decker, Hamilton, Ont.
2. Parker W.B. Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer. Chem. Rev. 109 (2009) 2880-2893
3. Gowher H., and Jeltsch A. Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy. Cancer Biol. Ther. 3 (2004) 1062-1068
4. Kuo H.K., Griffith J.D., and Kreuzer K.N. 5-Azacytidine induced methyltransferase-DNA adducts block DNA replication in vivo. Cancer Res. 67 (2007) 8248-8254
5. Doiron K.M., Lavigne-Nicolas J., and Cupples C.G. Effect of interaction between 5-azacytidine and DNA (cytosine-5) methyltransferase on C-to-G and C-to-T mutations in Escherichia coli. Mutat. Res. 429 (1999) 37-44
6. Lal D., Som S., and Friedman S. Survival and mutagenic effects of 5-azacytidine in Escherichia coli. Mutat. Res. 193 (1988) 229-236
7. Miller J.K., and Barnes W.M. Colony probing as an alternative to standard sequencing as a means of direct analysis of chromosomal DNA to determine the spectrum of single-base changes in regions of known sequence. Proc. Natl. Acad. Sci. U.S.A. 83 (1986) 1026-1030
8. Jackson-Grusby L., Laird P.W., Magge S.N., Moeller B.J., and Jaenisch R. Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 4681-4685
9. Juttermann R., Li E., and Jaenisch R. 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. U.S.A. 91 (1994) 11797-11801
10. Lee G., Wolff E., and Miller J.H. Mutagenicity of the cytidine analog zebularine in Escherichia coli. DNA Repair (Amst.) 3 (2004) 155-161
11. Marquez V.E., Eritja R., Kelley J.A., Vanbemmel D., and Christman J.K. 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 (2003) 154-164
12. Zhou L., Cheng X., Connolly B.A., Dickman M.J., Hurd P.J., and Hornby D.P. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. J. Mol. Biol. 321 (2002) 591-599
13. Schmuck G., Pechan R., Wild D., Schiffmann D., and Henschler D. SOS-dependent mutagenic activity of 5-azacytidine in Salmonella. Mutat. Res. 175 (1986) 205-208
14. Podger D.M. Mutagenicity of 5-azacytidine in Salmonella typhimurium. Mutat. Res. 121 (1983) 1-6
15. Garibyan L., Huang T., Kim M., Wolff E., Nguyen A., Nguyen T., Diep A., Hu K., Iverson A., Yang H., and Miller J.H. Use of the rpoB gene to determine the specificity of base substitution mutations on the Escherichia coli chromosome. DNA Repair (Amst.) 2 (2003) 593-608
16. Munch-Petersen A. Metabolism of Nucleotides, Nucleosides and Nucleobases in Microorganisms (1983), Academic Press
17. M. Kanehisa, The KEGG database, Novartis Found Symp. 247 (2002) 91-101 (discussion 101-103, 119-128, 244-152).
18. Neuhard J. Pyrimidine nucleotide metabolism and pathways of thymidine triphosphate biosynthesis in Salmonella typhimurium. J. Bacteriol. 96 (1968) 1519-1527
19. Munch-Petersen B., Piskur J., and Sondergaard L. The single deoxynucleoside kinase in Drosophila melanogaster, Dm-dNK, is multifunctional and differs from the mammalian deoxynucleoside kinases. Adv. Exp. Med. Biol. 431 (1998) 465-469
20. Munch-Petersen B., Knecht W., Lenz C., Sondergaard L., and Piskur J. Functional expression of a multisubstrate deoxyribonucleoside kinase from Drosophila melanogaster and its C-terminal deletion mutants. J. Biol. Chem. 275 (2000) 6673-6679
21. Johansson M., van Rompay A.R., Degreve B., Balzarini J., and Karlsson A. Cloning and characterization of the multisubstrate deoxyribonucleoside kinase of Drosophila melanogaster. J. Biol. Chem. 274 (1999) 23814-23819
22. Zheng X., Johansson M., and Karlsson A. Retroviral transduction of cancer cell lines with the gene encoding Drosophila melanogaster multisubstrate deoxyribonucleoside kinase. J. Biol. Chem. 275 (2000) 39125-39129
23. Wang J., Neuhard J., and Eriksson S. An Escherichia coli system expressing human deoxyribonucleoside salvage enzymes for evaluation of potential antiproliferative nucleoside analogs. Antimicrob. Agents Chemother. 42 (1998) 2620-2625
24. Godson G.N., and Vapnek D. A simple method of preparing large amounts of phiX174 RF 1 supercoiled DNA. Biochim. Biophys. Acta 299 (1973) 516-520
25. Bhagwat A.S., and Roberts R.J. Genetic analysis of the 5-azacytidine sensitivity of Escherichia coli K-12. J. Bacteriol. 169 (1987) 1537-1546
26. Marquez V.E., Barchi Jr. J.J., Kelley J.A., Rao K.V., Agbaria R., Ben-Kasus T., Cheng J.C., Yoo C.B., and Jones P.A. Zebularine: a unique molecule for an epigenetically based strategy in cancer chemotherapy. The magic of its chemistry and biology. Nucleosides Nucleotides Nucleic Acids 24 (2005) 305-318
27. 5K. Eur. J. Org. Chem. 2006 (2006) 924-931
28. Barbe J., Gibert I., and Guerrero R. 5-Azacytidine: survival and induction of the SOS response in Escherichia coli K-12. Mutat. Res. 166 (1986) 9-16
29. Birnboim H.C., and Doly J. A rapid alkaline extraction procedure for screening recombinant plasmid DNA. Nucleic Acids Res. 7 (1979) 1513-1523
30. Pitsikas P., Polosina Y.Y., and Cupples C.G. Interaction between the mismatch repair and nucleotide excision repair pathways in the prevention of 5-azacytidine-induced CG-to-GC mutations in Escherichia coli. DNA Repair (Amst.) 8 (2009) 354-359
31. Glickman B., van den Elsen P., and Radman M. Induced mutagenesis in dam-mutants of Escherichia coli: a role for 6-methyladenine residues in mutation avoidance. Mol. Gen. Genet. 163 (1978) 307-312
32. Glickman B.W., and Radman M. Escherichia coli mutator mutants deficient in methylation-instructed DNA mismatch correction. Proc. Natl. Acad. Sci. U.S.A. 77 (1980) 1063-1067
33. Matic I., Ekiert D., Radman M., and Kohiyama M. Generation of DNA-free Escherichia coli cells by 2-aminopurine requires mismatch repair and nonmethylated DNA. J. Bacteriol. 188 (2006) 339-342
34. Barchi Jr. J.J., Cooney D.A., Hao Z., Weinberg Z.H., Taft C., Marquez V.E., and Ford Jr. H. Improved synthesis of zebularine [1-(beta-d-ribofuranosyl)-dihydropyrimidin-2-one] nucleotides as inhibitors of human deoxycytidylate deaminase. J. Enzyme Inhib. 9 (1995) 147-162
35. Votruba I., Holy A., and Wightman R.H. The mechanism of inhibition of DNA synthesis in Escherichia coli by pyrimidin-2-one beta-d-ribofuranoside. Biochim. Biophys. Acta 324 (1973) 14-23
36. Dowd C.L., Sutch B.T., Haworth I.S., Eritja R., Marquez V.E., and Yang A.S. Incorporation of zebularine from its 2′-deoxyribonucleoside triphosphate derivative and activity as a template-coding nucleobase. Nucleosides Nucleotides Nucleic Acids 27 (2008) 131-145
37. Galmarini C.M., Jordheim L., and Dumontet C. Pyrimidine nucleoside analogs in cancer treatment. Expert Rev. Anticancer Ther. 3 (2003) 717-728
38. Mini E., Nobili S., Caciagli B., Landini I., and Mazzei T. Cellular pharmacology of gemcitabine. Ann. Oncol. 17 Suppl. 5 (2006) v7-v12
39. Wood R.D., Mitchell M., and Lindahl T. Human DNA repair genes. Mutat. Res. 577 (2005) 275-283
40. Lamers M.H., Perrakis A., Enzlin J.H., Winterwerp H.H., de Wind N., and Sixma T.K. The crystal structure of DNA mismatch repair protein MutS binding to a G × T mismatch. Nature. 407 (2000) 711-717
41. Warren J.J., Pohlhaus T.J., Changela A., Iyer R.R., Modrich P.L., and Beese L.S. Structure of the human MutSalpha DNA lesion recognition complex. Mol. Cell 26 (2007) 579-592