Repair of 2′-C-cyano-2′-deoxy-1-β-D-arabino- pentofuranosylcytosine-induced DNA single-strand breaks by transcription-coupled nucleotide excision repair

Cancer Research

Volumn 68, Issue 10, 2008, Pages 3881-3889

  Wang, Yaqing ^a   Liu, Xiaojun ^a   Matsuda, Akira ^b   Plunkett, William ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2' C CYANO 2' DEOXY 1 BETA ARABINOPENTOFURANOSYLCYTOSINE; ENDONUCLEASE; EXCISION REPAIR CROSS COMPLEMENTING PROTEIN 1; HELICASE; NUCLEOSIDE ANALOG; PROTEIN P53; SINGLE STRANDED DNA; SMALL INTERFERING RNA; UNCLASSIFIED DRUG; XERODERMA PIGMENTOSUM GROUP C PROTEIN; 1,3 DIOXOLANE DERIVATIVE; 2' CYANO 2' DEOXYARABINOFURANOSYLCYTOSINE; 2'-CYANO-2'-DEOXYARABINOFURANOSYLCYTOSINE; ANTINEOPLASTIC AGENT; CYTARABINE; CYTOSINE; DRUG DERIVATIVE; TP53 PROTEIN, HUMAN; TROXACITABINE;

ANIMAL CELL; ARTICLE; CANCER CELL CULTURE; CELL SURVIVAL; CLONOGENESIS; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DNA STRAND BREAKAGE; EXCISION REPAIR; HUMAN; HUMAN CELL; IC 50; IMMUNOBLOTTING; IMMUNOHISTOCHEMISTRY; MISMATCH REPAIR; NONHUMAN; PRIORITY JOURNAL; ULTRAVIOLET IRRADIATION; ANIMAL; CHEMISTRY; CHO CELL; CRICETULUS; DNA REPAIR; GENETIC TRANSCRIPTION; HAMSTER; HELA CELL; METABOLISM; MOUSE; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHO CELLS; CRICETINAE; CRICETULUS; CYTARABINE; CYTOSINE; DIOXOLANES; DNA DAMAGE; DNA REPAIR; HELA CELLS; HUMANS; MICE; TRANSCRIPTION, GENETIC; TUMOR SUPPRESSOR PROTEIN P53;

EID: 45549100917     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-07-6885     Document Type: Article

References (50)

1. Sampath D, Rao VA, Plunkett W. Mechanisms of apoptosis induction by nucleoside analogs. Oncogene 2003;22:9063-74.
2. Matsuda A, Nakajima Y, Azuma A, Tanaka M, Sasaki T. Nucleosides and nucleotides. 100. 2′-C-cyano-2′-deoxy-1-β-D- arabinofuranosyl-cytosine (CNDAC): design of a potential mechanism-based DNA-strand-breaking antineoplastic nucleoside. J Med Chem 1991;34:2917-9.
3. Matsuda A. 2′-C-Cyano-2′-deoxy-1-b-d-arabinofuranosyl- cytosine(CNDAC): a mechanism-based DNA-strand-breaking antitumor nucleoside. Nucleosides Nucleotides 1995;14:461-71.
4. Hayakawa Y, Kawai R, Otsuki K, Kataoka M, Matsuda A. Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-D-arabino- pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation. Bioorg Med Chem Lett 1998;8:2559-62.
5. Azuma A, Huang P, Matsuda A, Plunkett W. 2′-C-cyano-2′-deoxy- 1-β-D-arabino-pentofuranosylcytosine: a novel anticancer nucleoside analog that causes both DNA strand breaks and G(2) arrest. Mol Pharmacol 2001;59:725-31.
6. Azuma A, Huang P, Matsuda A, Plunkett W. Cellular pharmacokinetics and pharmacodynamics of the deoxycytidine analog 2′-C-cyano-2′-deoxy-1- β-D-arabino-pentofuranosylcytosine (CNDAC). Biochem Pharmacol 2001;61:1497-507.
7. Hanaoka K, Suzuki M, Kobayashi T, et al. Antitumor activity and novel DNA-self-strand-breaking mechanism of CNDAC (1-(2-C-cyano-2-deoxy-β- D-arabino-pentofuranosyl) cytosine) and its N4-palmitoyl derivative (CS-682). Int J Cancer 1999;82:226-36.
8. Sampath D, Cortes J, Estrov Z, et al. Pharmacodynamics of cytarabine alone and in combination with 7-hydroxystaurosporine (UCN-01) in AML blasts in vitro and during a clinical trial. Blood 2006;107:2517-24.
9. Shi Z, Azuma A, Sampath D, Li YX, Huang P, Plunkett W. S-phase arrest by nucleoside analogues and abrogation of survival without cell cycle progression by 7-hydroxystaurosporine. Cancer Res 2001;61:1065-72.
10. Liu X, Guo Y, Li Y, et al. Molecular basis for G2 arrest induced by 2′-C-cyano-2′-deoxy-1-β-D-arabino- pentofuranosylcytosine and consequences of checkpoint abrogation. Cancer Res 2005;65:6874-81.
11. Liu X, Matsuda A, Plunkett W. Ataxia-telangiectasia and Rad3-related and DNA-dependent protein kinase cooperate in G2 checkpoint activation by the DNA strand-breaking nucleoside analogue 2′-C-cyano-2′-deoxy-1- D-arabino-pentofuranosylcytosine. Mol Cancer Ther 2008;7:133-42.
12. Kamiya K, Huang P, Plunkett W. Inhibition of the 3′→′ exonuclease of human DNA polymerase ε by fludarabine-terminated DNA. J Biol Chem 1996;271:19428-35.
13. Kramata P, Downey KM, Paborsky LR. Incorporation and excision of 9-(2-phosphonylmethoxyethyl)guanine (PMEG) by DNA polymerase δ and ε in vitro. J Biol Chem 1998;273:21966-71.
14. Perrino FW, Mazur DJ, Ward H, Harvey S. Exonucleases and the incorporation of aranucleotides into DNA. Cell Biochem Biophys 1999;30:331-52.
15. Johnson AA, Ray AS, Hanes J, et al. Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase. J Biol Chem 2001;276:40847-57.
16. Krokan HE, Standal R, Slupphaug G. DNA glycosylases in the base excision repair of DNA. Biochem J 1997; 325:1-16.
17. Lindahl T. Suppression of spontaneous mutagenesis in human cells by DNA base excision-repair. Mutat Res 2000;462:129-35.
18. Chou KM, Kukhanova M, Cheng YC. A novel action of human apurinic/apyrimidinic endonuclease: excision of L-configuration deoxyribonucleoside analogs from the 3′ termini of DNA. J Biol Chem 2000;275:31009-15.
19. Iyer RR, Pluciennik A, Burdett V, Modrich PL. DNA mismatch repair: functions and mechanisms. Chem Rev 2006;106:302-23.
20. Chaney SG, Sancar A. DNA repair: enzymatic mechanisms and relevance to drug response. J Natl Cancer Inst 1996;88:1346-60.
21. Yamauchi T, Nowak BJ, Keating MJ, Plunkett W. DNA repair initiated in chronic lymphocytic leukemia lymphocytes by 4-hydroperoxycyclophosphamide is inhibited by fludarabine and clofarabine. Clin Cancer Res 2001;7:3580-9.
22. Sandoval A, Consoli U, Plunkett W. Fludarabine-mediated inhibition of nucleotide excision repair induces apoptosis in quiescent human lymphocytes. Clin Cancer Res 1996;2:1731-41.
23. Busch DB, Cleaver JE, Glaser DA. Large-scale isolation of UV-sensitive clones of CHO cells. Somat Cell Genet 1980;6:407-18.
24. Legerski R, Peterson C. Expression cloning of a human DNA repair gene involved in xeroderma pigmentosum group C. Nature 1992;360:610.
25. Doetsch PW, Cunningham RP. The enzymology of apurinic/apyrimidinic endonucleases. Mutat Res 1990; 236:173-201.
26. Madhusudan S, Smart F, Shrimpton P, et al. Isolation of a small molecule inhibitor of DNA base excision repair. Nucleic Acids Res 2005;33:4711-24.
27. Wyatt MD, Pittman DL. Methylating agents and DNA repair responses: Methylated bases and sources of strand breaks. Chem Res Toxicol 2006;19:1580-94.
28. Thompson LH, Brookman KW, Dillehay LE, et al. A CHO-cell strain having hypersensitivity to mutagens, a defect in DNA strand-break repair, and an extraordinary baseline frequency of sister-chromatid exchange. Mutat Res 1982;95:427-40.
29. Koi M, Umar A, Chauhan DP, et al. Human chromosome 3 corrects mismatch repair deficiency and microsatellite instability and reduces N-methyl-N′-nitro-N-nitrosoguanidine tolerance in colon tumor cells with homozygous hMLH1 mutation. Cancer Res 1994;54:4308-12.
30. Gaillard PH, Wood RD. Activity of individual ERCC1 and XPF subunits in DNA nucleotide excision repair. Nucleic Acids Res 2001;29:872-9.
31. Kufe DW, Munroe D, Herrick D, Egan E, Spriggs D. Effects of 1-β-D-arabinofuranosylcytosine incorporation on eukaryotic DNA template function. Mol Pharmacol 1984;26:128-34.
32. Kukhanova M, Liu SH, Mozzherin D, Lin TS, Chu CK, Cheng YC. L- and D-Enantiomers of 2′,3′-dideoxycytidine 5′-triphosphate analogs as substrates for human DNA polymerases. Implications for the mechanism of toxicity. J Biol Chem 1995;270:23055-9.
33. Townsend AJ, Cheng YC. Sequence-specific effects of ara-5-aza-CTP and ara-CTP on DNA synthesis by purified human DNA polymerases in vitro: visualization of chain elongation on a defined template. Mol Pharmacol 1987;32:330-9.
34. Wood RD. Nucleotide excision repair in mammalian cells. J Biol Chem 1997;272:23465-8.
35. Kufe DW, Major PP, Egan EM, Beardsley GP. Correlation of cytotoxicity with incorporation of ara-C into DNA. J Biol Chem 1980;255:8997-900.
36. Major PP, Egan EM, Beardsley GP, Minden MD, Kufe DW. Lethality of human myeloblasts correlates with the incorporation of arabinofuranosylcytosine into DNA. Proc Natl Acad Sci U S A 1981; 78:3235-9.
37. Huang P, Chubb S, Hertel LW, Grindey GB, Plunkett W. Action of 2′,2′-difluorodeoxycytidine on DNA synthesis. Cancer Res 1991;51:6110-7.
38. Huang P, Chubb S, Plunkett W. Termination of DNA synthesis by 9-β-D-arabinofuranosyl-2-fluoroadenine. A mechanism for cytotoxicity. J Biol Chem 1990;265: 16617-25.
39. Wang Y, Matsuda A, Plunkett W. Excision of 2′-C-cyano-2′- deoxy-1-β-D-arabino-pentofuranosylcytosine (CNDAC) residues from DNA [abstract 516]. In: Proceedings of the 97th Annual Meeting of the American Association for Cancer Research; AACR; 2006. p. 122.
40. Robson CN, Hickson ID. Isolation of cDNA clones encoding a human apurinic/apyrimidinic endonuclease that corrects DNA repair and mutagenesis defects in E. coli xth (exonuclease III) mutants. Nucleic Acids Res 1991;19:5519-23.
41. Sobol RW, Horton JK, Kuhn R, et al. Requirement of mammalian DNA polymerase-β in base-excision repair. Nature 1996;379:183-6.
42. Fang WH, Modrich P. Human strand-specific mismatch repair occurs by a bidirectional mechanism similar to that of the bacterial reaction. J Biol Chem 1993;268:11838-44.
43. Dzantiev L, Constantin N, Genschel J, Iyer RR, Burgers PM, Modrich P. A defined human system that supports bidirectional mismatch-provoked excision. Mol Cell 2004;15:31-41.
44. Constantin N, Dzantiev L, Kadyrov FA, Modrich P. Human mismatch repair: reconstitution of a nick-directed bidirectional reaction. J Biol Chem 2005;280:39752-61.
45. Bernstein C, Bernstein H, Payne CM, Garewal H. DNA repair/pro-apoptotic dual-role proteins in five major DNA repair pathways: fail-safe protection against carcinogenesis. Mutat Res 2002;511:145-78.
46. Saxowsky TT, Doetsch PW. RNA polymerase encounters with DNA damage: transcription-coupled repair or transcriptional mutagenesis? Chem Rev 2006; 106:474-88.
47. Poltoratsky V, Horton JK, Prasad R, Wilson SH. REV1 mediated mutagenesis in base excision repair deficient mouse fibroblast. DNA Repair (Amst) 2005;4:1182-8.
48. Friedberg EC, Wagner R, Radman M. Specialized DNA polymerases, cellular survival, and the genesis of mutations. Science 2002;296:1627-30.
49. Heller RC, Marians KJ. Replication fork reactivation downstream of a blocked nascent leading strand. Nature 2006;439:557-62.
50. Kantarjian H, Garcia-Manero G, Faderi S, et al. Phase I study of sapacitabine, an oral nucleoside analogue, in patients with advanced leukemias or myelodysplastic syndromes (MDS) [abstract]. Blood 2007;110:270a.