Mutation spectra induced by α-acetoxytamoxifen-DNA adducts in human DNA repair proficient and deficient (Xeroderma pigmentosum complementation group A) cells

Biochemistry

Volumn 44, Issue 22, 2005, Pages 8198-8205

  McLuckie, Keith I E ^a   Crookston, Robert J R ^a   Gaskell, Margaret ^a   Farmer, Peter B ^a   Routledge, Michael N ^b   Martin, Elizabeth A ^a,c   Brown, Karen ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGENS; CELLS; DISEASES; DNA; DRUG PRODUCTS; HEALTH RISKS; MUTAGENESIS; TUMORS;

BREAST CANCER; DNA ADDUCTS; MUTATION SPECTRA; TAMOXIFEN;

BIOCHEMISTRY;

ADENINE; ALPHA ACETOXYTAMOXIFEN; CYTOSINE; ESTER; GUANINE; PHOSPHORUS 32; PLASMID DNA; TAMOXIFEN; TAMOXIFEN DERIVATIVE; THYMINE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; BREAST CANCER; CELL LINE; CELL STRAIN GM00637; CELL STRAIN GM04429; CONTROLLED STUDY; DNA ADDUCT; DNA DAMAGE; DNA REPAIR; DNA SEQUENCE; ENDOMETRIUM CANCER; ENDOMETRIUM TUMOR; EXCISION REPAIR; FIBROBLAST; GENE; GENETIC TRANSFECTION; GENOTOXICITY; HUMAN; HUMAN CELL; ISOTOPE LABELING; LIVER; LIVER CARCINOMA; MUTATION; MUTATION RATE; NONHUMAN; NUCLEIC ACID BASE SUBSTITUTION; PRIORITY JOURNAL; RAT; SUPF GENE; XERODERMA PIGMENTOSUM; XERODERMA PIGMENTOSUM COMPLEMENTATION GROUP A;

BASE SEQUENCE; CELL LINE, TRANSFORMED; DNA ADDUCTS; DNA MUTATIONAL ANALYSIS; DNA REPAIR; GENES, SUPPRESSOR; GENETIC COMPLEMENTATION TEST; GENETIC PREDISPOSITION TO DISEASE; HUMANS; MOLECULAR SEQUENCE DATA; MUTAGENESIS; MUTAGENICITY TESTS; PHOSPHORUS RADIOISOTOPES; PLASMIDS; RNA, TRANSFER; TAMOXIFEN; TRANSFECTION; XERODERMA PIGMENTOSUM;

EID: 20144376201     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi047399e     Document Type: Article

References (48)

1. Fisher, B., Costantino, J. P., Wickerham, D. L., Redmond, C. K., Kavanah, M., Cronin, W. M., Vogel, V., Robidoux, A., Dimitrov, N., Atkins, J., Daly, M., Wieand, S., Tan-Chiu, E., Ford, L., Wolmark, N., and other National Surgical Adjuvant Breast and Bowel Project Investigators (1998) Tamoxifen for prevention of breast cancer: Report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study, J. Natl. Cancer Inst. 90, 1371-1388.
2. Fornander, T., Cedermark, B., Mattsson, A., Skoog, L., Theve, T., Askergren, J., Rutqvist, L. E., Glas, U., Silfversward, C., Somell, A., Wilking, N., and Hjalmar, M. L. (1989) Adjuvant tamoxifen in early breast cancer-Occurrence of new primary cancers, Lancet 1, 117-120.
3. Fisher, B., Costantino, J. P., Redmond, C. K., Fisher, E. R., Wickerham, D. L., Cronin, W. M., and other National Surgical Adjuvant Breast and Bowel Project Investigators (1994) Endometrial cancer in tamoxifen-treated breast cancer patients: Findings from the National Adjuvant Breast and Bowel Project (NSABP) B-14, J. Natl. Cancer Inst. 86, 527-537.
4. Han, X., and Liehr, J. G. (1992) Induction of covalent DNA adducts in rodents by tamoxifen, Cancer Res. 52, 1360-1363.
5. Greaves, P., Goonetilleke, R., Nunn, G., Topham, J., and Orton, T. (1993) Two-year carcinogenicity study of tamoxifen in Alderley Park Wistar-derived rats, Cancer Res. 53, 3919-3924.
6. Carthew, P., Martin, E. A., White, I. N. H., de Matteis, F., Edwards, R. E., Dorman, B. M., Heydon, R. T., and Smith, L. L. (1995) Tamoxifen induces short-term cumulative DNA damage and liver tumours in rats: Promotion by phenobarbital, Cancer Res. 55, 544-547.
7. Shibutani, S., Suzuki, N., Terashima, I., Sugarman, S. M., Grollman, A. P., and Pearl, M. L. (1999) Tamoxifen-DNA adducts detected in the endometrium of women treated with tamoxifen, Chem. Res. Toxicol 12, 646-653.
8. Shibutani, S., Ravindernath, A., Suzuki, N., Terashima, I., Sugarman, S. M., Grollman, A. P., and Pearl, M. L. (2000) Identification of tamoxifen-DNA adducts in the endometrium of women treated with tamoxifen, Carcinogenesis 21, 1461-1467.
9. Umemoto, A., Monden, Y., Lin, C.-X., Momen, M. A., Ueyama, Y., Komaki, K., Laxmi, Y. R. S., and Shibutani, S. (2004) Determination of tamoxifen-DNA adducts in leukocytes from breast cancer patients treated with tamoxifen, Chem. Res. Toxicol. 17, 1577-1583.
10. Martin, E. A., Brown, K., Gaskell, M., Al-Azzawi, F., Garner, R. C., Boocock, D. J., Mattock, E., Pring, D. W., Dingley, K., Turteltaub, K. W., Smith, L. L., and White, I. N. H. (2003) Tamoxifen DNA damage detected in human endometrium using accelerator mass spectrometry, Cancer Res. 63, 8461-8465.
11. Carmichael, P. L., Ugwumadu, A. H. N., Neven, P., Hewer, A. J., Poon, G. K., and Phillips, D. H. (1996) Lack of genotoxicity of tamoxifen in human endometrium, Cancer Res. 56, 1475-1479.
12. 32P-post-labelling for tamoxifen-IDNA adducts in the human endometrium, Carcinogenesis 20, 339-342.
13. 32P-postlabeling analyses of tamoxifen-DNA adducts in humans, J. Nat. Cancer Inst. 96, 1099-1104.
14. Phillips, D. H., Carmichael, P. L., Hewer, A., Cole, K. J., and Poon, G. K. (1994) α-Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes, Cancer Res. 54, 5518-5522.
15. Potter, G. A., McCague, R., and Jarman, M. (1994) A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative-metabolism, Carcinogenesis 15, 439-442.
16. Jarman, M., Poon, G. K., Rowlands, M. G., Grimshaw, R. M., Horton, M. N., Potter, G. A., and McCague, R. (1995) The deuterium-isotope effect for the α-hydroxylation of tamoxifen by rat-liver microsomes accounts for the reduced genotoxicity of D-5-ethyl tamoxifen, Carcinogenesis 16, 683-688.
17. Phillips, D. H., Carmichael, P. L., Hewer, A., Cole, K. J., Hardcastle, I. R., Poon, G. K., Keough, A., and Strain, A. J. (1996) Activation of tamoxifen and its metabolite α-hydroxytamoxifen to DNA-binding products: Comparisons between human, rat, and mouse hepatocytes, Carcinogenesis 17, 89-94.
18. Shibutani, S., Dasaradhi, L., Terashima, I., Banoglu, E., and Duffel, M. W. (1998) α-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts, Cancer Res. 58, 647-653.
19. Davis, W., Venitt, S., and Phillips, D. H. (1998) The metabolic activation of tamoxifen and α-hydroxytamoxifen to DNA-binding species in rat hepatocytes proceeds via sulphation, Carcinogenesis 19, 861-866.
20. Osborne, M. R., Hewer, A., Hardcastle, I. R., Carmichael, P. L., and Phillips, D. H. (1996) Identification of the major tamoxifen-deoxyguanosine adduct formed in the liver DNA of rats treated with tamoxifen, Cancer Res. 56, 66-71.
21. Rajaniemi, H., Rasanen, I., Koivisto, P., Peltonen, K., and Hemminki, K. (1999) Identification of the major tamoxifen-DNA adducts in rat liver by mass spectroscopy. Carcinogenesis 20, 305-309.
22. Dasaradhi, L., and Shibutani, S. (1997) Identification of tamoxifen-DNA adducts formed by α-sulfate tamoxifen and α-acetoxytamoxifen, Chem. Res. Toxicol. 10, 189-196.
23. 2-deoxyguanosinyl)tamoxifen lesions, the major DNA adducts detected in endometrial tissues of patients treated with tamoxifen. Cancer Res. 59, 2091-2095.
24. Davies, R., Oreffo, V. I. C., Martin, E. A., Festing, M. F. W., White, I. N. H., Smith, L. L., and Styles, J. A. (1997) Tamoxifen causes gene mutations in the livers of λ/lacI transgenic rats, Cancer Res. 57, 1288-1293.
25. Davies, R., Gant, T. W., Smith, L. L., and Styles, J. A. (1999) Tamoxifen induces G:C>T:A mutations in the cII gene in the liver of λ/lacI transgenic rats but not at 5′-CpG-3′ dinucleotide sequences as found in the lacI transgene, Carcinogenesis 20, 1351-1356.
26. McLuckie, K. I. E., Routledge, M. N., Brown, K., Gaskell, M., Farmer, P. B., Roberts, G. C. K., and Martin, E. A. (2002) DNA adducts formed from 4-hydroxytamoxifen are more mutagenic than those formed by α- acetoxytamoxifen in a shuttle vector target gene replicated in human Ad293 cells, Biochemistry 41, 8899-8906.
27. Kraemer, K. H., Lee, M. M., and Scotto, J. (1987) Xeroderma pigmentosum: Cutaneous, ocular, and neurologic abnormalities in 830 published cases, Arch. Dermatol. 123, 241-250.
28. Seidman, M. M., Dixon, K., Razzaque, A., Zagursky, R. J., and Berman, M. L. (1985) A shuttle vector plasmid for studying carcinogen-induced point mutations in mammalian cells, Gene 38, 233-237.
29. Foster, A. B., Jarman, M., Leung, O.-T., McCague, R., Leclerq, G., and Devleeschouwer, N. (1985) Hydroxy derivatives of tamoxifen, J. Med. Chem. 28, 1491-1497.
30. Parris, C. N., and Seidman, M. M. (1992) A signature element distinguishes sibling and independent mutations in a shuttle vector plasmid, Gene 117, 1-5.
31. 32P-post-labelled DNA adducts by the development of a novel automated on-line solid-phase extraction HPLC method, Carcinogenesis 19, 1061-1069.
32. Graham, F. L., and van der Eb, A. J. (1973) A new technique for the assay of infectivity of human adenovirus 5 DNA. Virology 52, 456-467.
33. Routledge, M. N., McLuckie, K. I. E., Jones, G. D. D., Farmer, P. B., and Martin, E. A. (2001) Presence of benzo[a]pyrene diol epoxide adducts in target DNA leads to an increase in UV-induced DNA single strand breaks and supF gene mutations, Carcinogenesis 22, 1231-1238.
34. Cariello, N. F., Piegorsch, W. W., Adams, W. T., and Skopek, T. R. (1994) Computer program for the analysis of mutational spectra: Application top53 mutations, Carcinogenesis 15, 2281-2285.
35. Brown, K., Heydon, R. T., Jukes, R., White, I. N. H., and Martin, E. A. (1999) Further characterization of the DNA adducts formed in rat liver after the administration of tamoxifen, N-desmethyltamoxifen, or N,N-didesmethyltamoxifen, Carcinogenesis 20, 2011-2016.
36. Lowes, D. A., Brown, K., Heydon, R. T., Martin, E. A., and Gant, T. W. (1999) Site-specific tamoxifen-DNA adduct formation: Lack of correlation with mutational ablility in Escherichia coli, Biochemistry 38, 10989-10996.
37. Lewis, P. D., Harvey, J. S., Waters, E. M., Skibinski, D. O. F., and Parry, J. M. (2001) Spontaneous mutation spectra in supF: Comparative analysis of mammalian cell line base substitution spectra, Mutagenesis 16, 503-515.
38. 1-induced mutations in a plasmid replicated in xeroderma pigmentosum and DNA repair proficient human cells. Cancer Res. 52, 5668-5673.
39. Bubley, G. J., Ashburner, B. P., and Teicher, B. A. (1991) Spectrum of cis-Diamminedichloroplatinum(II) induced mutations in a shuttle vector propagated in human cells, Mol. Carcinog. 4, 397-406.
40. Bredberg, A., Kraemer, K. H., and Seidman, M. M. (1986) Restricted ultraviolet mutational spectrum in a shuttle vector propagated in xeroderma pigmentosum cells, Proc. Natl. Acad. Sci. U.S.A. 83, 8273-8277.
41. Shibutani, S., Reardon, J. T., Suzuki, N., and Sancar, A. (2000) Excision of tamoxifen-DNA adducts by the human nucleotide excision repair system, Cancer Res. 60, 2607-2610.
42. Osborne, M. R., Hardcastle, I. R., and Phillips, D. H. (1997) Minor products of reaction of DNA with α-acetoxytamoxifen, Carcinogenesis 18, 539-543.
43. 2-Deoxyguanosinyl)tamoxifen, Biochemistry 36, 13010-13017.
44. 1 have different properties than single mutations and may be generated during translesion synthesis. Mutat. Res. 430, 23-36.
45. Seidman, M. M., Bredberg, A., Seetharam, S., and Kraemer, K. H. (1987) Multiple point mutations in a shuttle vector propagated in human cells: Evidence for an error-prone DNA polymerase activity, Proc. Natl. Acad. Sci. U.S.A. 84, 4944-4948.
46. Yadollahi-Farsani, M., Davies, D. S., and Boobis, A. R. (2002) The mutational signature of α-hydroxytamoxifen at Hprt locus in Chinese hamster cells, Carcinogenesis 23, 1947-1952.
47. Chen, T., da Costa, G. G., Marques, M. M., Shelton, S. D., Beland, F. A., and Manjanatha, M. G. (2002) Mutations induced by α-hydroxytamoxifen in the lacI and cII genes of Big Blue transgenic rats, Carcinogenesis 23, 1751-1757.
48. Brown, K., Pearson, H., Farmer, P. B., Neven, P., and Carmichael, P. L. (2004) Analysis of p53 mutations in endometrial tumors from tamoxifen-treated women, Proc. AACR 45, 1123.