Role of MGMT in protecting against cyclophosphamide-induced toxicity in cells and animals

DNA Repair

Volumn 6, Issue 8, 2007, Pages 1145-1154

  Hansen, Ryan J ^a   Ludeman, Susan M ^b   Paikoff, Sari J ^b   Pegg, Anthony E ^c   Dolan, M Eileen ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b DUKE CANCER INSTITUTE   (United States)

^c PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

Acrolein; Alkyltransferase; Chloroacetaldehyde; DNA repair; Ifosfamide; Oxazaphosphorines

Indexed keywords

ACROLEIN; CARBOPLATIN; CHLOROACETALDEHYDE; CISPLATIN; CYCLOPHOSPHAMIDE; CYSTEINE; DOXORUBICIN; GLUTATHIONE; IFOSFAMIDE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; OXAZAPHOSPHORINE; STREPTOZOCIN; TEMOZOLOMIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL LEVEL; COMBINATION CHEMOTHERAPY; CYTOTOXICITY; DNA CROSS LINKING; DNA DAMAGE; DNA REPAIR; DRUG DOSE REDUCTION; DRUG EFFICACY; DRUG MEGADOSE; DRUG METABOLISM; DRUG STRUCTURE; EWING SARCOMA; GENE EXPRESSION; HUMAN; IMMUNOSUPPRESSIVE TREATMENT; IN VITRO STUDY; LIPID PEROXIDATION; LUNG CANCER; NONHUMAN; OVARY CANCER; OVARY CELL; PRIORITY JOURNAL; PROSTATE CANCER; TUMOR BIOPSY; UTERUS SARCOMA;

ACETALDEHYDE; ACROLEIN; ALKYLATING AGENTS; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; CYCLOPHOSPHAMIDE; DNA REPAIR; DRUG RESISTANCE, NEOPLASM; IFOSFAMIDE; MICE; MICE, KNOCKOUT; MUTATION; NEOPLASMS, EXPERIMENTAL; O(6)-METHYLGUANINE-DNA METHYLTRANSFERASE; RECOMBINANT PROTEINS; TRANSFECTION; TRANSPLANTATION, HETEROLOGOUS;

ANIMALIA; CRICETULUS GRISEUS; MUS;

EID: 34447342240     PISSN: 15687864     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dnarep.2007.03.010     Document Type: Article

References (95)

1. Kaina B. Mechanisms and consequences of methylating agent-induced SCEs and chromosomal aberrations: a long road traveled and still a far way to go. Cytogenet. Genome Res. 104 (2004) 77-86
2. Davies S.M. Therapy-related leukemia associated with alkylating agents. Med. Pediatr. Oncol. 36 (2001) 536-540
3. Wiencke J.K., and Wiemels J. Genotoxicity of 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU). Mutat. Res. 339 (1995) 91-119
4. Zhang J., Tian Q., Chan S.Y., Duan W., and Zhou S. Insights into oxazaphosphorine resistance and possible approaches to its circumvention. Drug Resist. Updat. 8 (2005) 271-297
5. Hilton J. Deoxyribonucleic acid crosslinking by 4-hydroperoxycyclophosphamide in cyclophosphamide-sensitive and -resistant L1210 cells. Biochem. Pharmacol. 33 (1984) 1867-1872
6. Kohn K.W. Interstrand cross-linking of DNA by 1,3-bis(2-chloroethyl)-1-nitrosourea and other 1-(2-haloethyl)-1-nitrosoureas. Cancer Res. 37 (1977) 1450-1454
7. 6-alkylguanine by alkyltransferases. Mutat. Res. 462 (2000) 83-100
8. 6-alkylguanine-DNA alkyltransferase. Prog. Nucleic Acid Res. Mol. Biol. 51 (1995) 167-223
9. Daniels D.S., Mol C.D., Arvai A.S., Kanugula S., Pegg A.E., and Tainer J.A. Active and alkylated human AGT structures: a novel zinc site, inhibitor and extrahelical base binding. EMBO J. 19 (2000) 1719-1730
10. 6-methylguanine-DNA methyltransferase upon alkylation of its active site by SN1 (indirect-acting) and SN2 (direct-acting) alkylating agents: breaking a "salt-link". Biochemistry 35 (1996) 12259-12266
11. 6-benzylguanine or 1,3-bis(2-chloroethyl)-1-nitrosourea. Biochemistry 35 (1996) 1328-1334
12. 6-methylguanine-DNA methyltransferase gene MGMT in human normal and tumor tissues. J. Natl. Cancer Inst. 84 (1992) 337-340
13. 6-Alkylguanine-DNA alkyltransferase activity in human myeloid cells. J. Clin. Invest. 76 (1985) 2106-2114
14. 6-benzylguanine plus BCNU. Blood 88 (1996) 1649-1655
15. 6-alkylguanine-DNA alkyltransferase: regulation and importance in response to alkylating carcinogenic and therapeutic agents. Cancer Res. 50 (1990) 6119-6129
16. 6-Methylguanine-DNA methyltransferase protein levels in pediatric brain tumors. Clin. Cancer Res. 3 (1997) 2459-2463
17. 6-methylguanine-DNA methyltransferase activity in brain tumors and adjacent normal brain. Cancer Res. 53 (1993) 3416-3420
18. Belanich M., Pastor M., Randall T., Guerra D., Kibitel J., Alas L., Li B., Citron M., Wasserman P., White A., Eyre H., Jaeckle K., Schulman S., Rector D., Prados M., Coons S., Shapiro W., and Yarosh D. Retrospective study of the correlation between the DNA repair protein alkyltransferase and survival of brain tumor patients treated with carmustine. Cancer Res. 56 (1996) 783-788
19. Gerson S.L. Clinical relevance of MGMT in the treatment of cancer. J. Clin. Oncol. 20 (2002) 2388-2399
20. 6-Alkylguanine-DNA alkyltransferase activity of human malignant glioma and its clinical implications. J. Neurooncol. 21 (1994) 135-140
21. 6-benzylguanine analogues on sensitivity of human tumor cells to the cytotoxic effects of alkylating agents. Cancer Res. 51 (1991) 3367-3372
22. 6-benzylguanine provides a means to evaluate the role of this protein in protection against carcinogenic and therapeutic alkylating agents. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 5368-5372
23. 6-benzylguanine on the sensitivity of human colon tumor xenografts to 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU). Biochem. Pharmacol. 46 (1993) 285-290
24. 6-(hetarylmethyl)guanines having basic rings in the side chain. J. Med. Chem. 41 (1998) 5265-5271
25. 6-alkylguanine-DNA alkyltransferase. Mol. Cancer Ther. 3 (2004) 1215-1220
26. Barvaux V.A., Ranson M., Brown R., McElhinney R.S., McMurry T.B., and Margison G.P. Dual repair modulation reverses Temozolomide resistance in vitro. Mol. Cancer Ther. 3 (2004) 123-127
27. 6-(4-Bromothenyl)guanine reverses temozolomide resistance in human breast tumour MCF-7 cells and xenografts. Br. J. Cancer 93 (2005) 1152-1156
28. 6-alkylguanine DNA alkyl-transferase, increases the inhibitory activity of temozolomide against human acute leukaemia cells in vitro. Pharmacol. Res. 53 (2006) 317-323
29. Colvin O.M. An overview of cyclophosphamide development and clinical applications. Curr. Pharm. Des. 5 (1999) 555-560
30. Fraiser L.H., Kanekal S., and Kehrer J.P. Cyclophosphamide toxicity. Characterising and avoiding the problem. Drugs 42 (1991) 781-795
31. Ludeman S.M. The chemistry of the metabolites of cyclophosphamide. Curr. Pharm. Des. 5 (1999) 627-643
32. Malet-Martino M., Gilard V., and Martino R. The analysis of cyclophosphamide and its metabolites. Curr. Pharm. Des. 5 (1999) 561-586
33. 6-Methylguanine-DNA methyltransferase in ovarian malignancy and its correlation with postoperative response to chemotherapy. Gynecol. Oncol. 52 (1994) 172-174
34. Codegoni A.M., Broggini M., Pitelli M.R., Pantarotto M., Torri V., Mangioni C., and D'Incalci M. Expression of genes of potential importance in the response to chemotherapy and DNA repair in patients with ovarian cancer. Gynecol. Oncol. 65 (1997) 130-137
35. 6-methylguanine-DNA methyltransferase in relation to p53 status and therapeutic response in ovarian cancer. Int. J. Cancer 84 (1999) 388-395
36. 6-methylguanine DNA methyltransferase and survival of patients with diffuse large B-cell lymphoma. J. Natl. Cancer Inst. 94 (2002) 26-32
37. 6-methylguanine DNA methyltransferase silencing in diffuse large B-cell lymphomas from the Middle East. Hum. Pathol. 37 (2006) 742-748
38. 6-methylguanine-DNA methyltransferase protein expression is a favorable prognostic marker in diffuse large B-cell lymphoma. Int. J. Hematol. 83 (2006) 341-347
39. 6-Methylguanine-DNA methyl transferase gene expression and prognosis in breast carcinoma. Int. J. Oncol. 21 (2002) 1125-1131
40. 6-methylguanine-DNA methyl transferase (MGMT) and p53 in breast cancer. Jpn. J. Clin. Oncol. 35 (2005) 121-125
41. 6-alkylguanine-DNA-alkyltransferase of human tumour xenografts. EORTC SPG and PAMM Groups. Eur. J. Cancer 34 (1998) 1749-1755
42. 6-alkylguanine-DNA alkyltransferase. Cancer Chemother. Pharmacol. 43 (1999) 80-85
43. 6-Methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int. J. Cancer 77 (1998) 919-922
44. 6-benzylguanine on nitrogen mustard-induced toxicity, apoptosis, and mutagenicity in Chinese hamster ovary cells. Mol. Cancer Ther. 1 (2001) 21-28
45. 6-alkylguanine-DNA alkyltransferase in protecting against cyclophosphamide-induced toxicity and mutagenicity. Cancer Res. 59 (1999) 3059-3063
46. 6-alkylguanine-DNA alkyltransferases. Cancer Res. 60 (2000) 5464-5469
47. Smith S.M., Ludeman S.M., Wilson L.R., Springer J.B., Gandhi M.C., and Dolan M.E. Selective enhancement of ifosfamide-induced toxicity in Chinese hamster ovary cells. Cancer Chemother. Pharmacol. 52 (2003) 291-302
48. Zhang J., Tian Q., Yung Chan S., Chuen Li S., Zhou S., Duan W., and Zhu Y.Z. Metabolism and transport of oxazaphosphorines and the clinical implications. Drug Metab. Rev. 37 (2005) 611-703
49. Dong Q., Barsky D., Colvin M.E., Melius C.F., Ludeman S.M., Moravek J.F., Colvin O.M., Bigner D.D., Modrich P., and Friedman H.S. A structural basis for a phosphoramide mustard-induced DNA interstrand cross-link at 5′-d(GAC). Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 12170-12174
50. Struck R.F., Davis Jr. R.L., Berardini M.D., and Loechler E.L. DNA guanine-guanine crosslinking sequence specificity of isophosphoramide mustard, the alkylating metabolite of the clinical antitumor agent ifosfamide. Cancer Chemother. Pharmacol. 45 (2000) 59-62
51. Cox P.J. Cyclophosphamide cystitis-identification of acrolein as the causative agent. Biochem. Pharmacol. 28 (1979) 2045-2049
52. Brock N. The development of mesna for the inhibition of urotoxic side effects of cyclophosphamide, ifosfamide, and other oxazaphosphorine cytostatics. Recent Results Cancer Res. 74 (1980) 270-278
53. Takamoto S., Sakura N., Namera A., and Yashiki M. Monitoring of urinary acrolein concentration in patients receiving cyclophosphamide and ifosphamide. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 806 (2004) 59-63
54. Brock N., Pohl J., Stekar J., and Scheef W. Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention. III. Profile of action of sodium 2-mercaptoethane sulfonate (mesna). Eur. J. Cancer Clin. Oncol. 18 (1982) 1377-1387
55. Ormstad K., Orrenius S., Lastbom T., Uehara N., Pohl J., Stekar J., and Brock N. Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat. Cancer Res. 43 (1983) 333-338
56. Batista C.K., Mota J.M., Souza M.L., Leitao B.T., Souza M.H., Brito G.A., Cunha F.Q., and Ribeiro R.A. Amifostine and glutathione prevent ifosfamide- and acrolein-induced hemorrhagic cystitis. Cancer Chemother. Pharmacol. 59 (2007) 71-77
57. Bruggemann S.K., Kisro J., and Wagner T. Ifosfamide cytotoxicity on human tumor and renal cells: role of chloroacetaldehyde in comparison to 4-hydroxyifosfamide. Cancer Res. 57 (1997) 2676-2680
58. Goren M.P., Wright R.K., Pratt C.B., and Pell F.E. Dechloroethylation of ifosfamide and neurotoxicity. Lancet 2 (1986) 1219-1220
59. Lewis L.D., and Meanwell C.A. Ifosfamide pharmacokinetics and neurotoxicity. Lancet 335 (1990) 175-176
60. Skinner R., Sharkey I.M., Pearson A.D., and Craft A.W. Ifosfamide, mesna, and nephrotoxicity in children. J. Clin. Oncol. 11 (1993) 173-190
61. Williams M.L., and Wainer I.W. Cyclophosphamide versus ifosfamide: to use ifosfamide or not to use, that is the three-dimensional question. Curr. Pharm. Des. 5 (1999) 665-672
62. Aleksa K., Halachmi N., Ito S., and Koren G. A tubule cell model for ifosfamide nephrotoxicity. Can. J. Physiol. Pharmacol. 83 (2005) 499-508
63. Aleksa K., Matsell D., Krausz K., Gelboin H., Ito S., and Koren G. Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr. Nephrol. 20 (2005) 872-885
64. McCune J.S., Risler L.J., Phillips B.R., Thummel K.E., Blough D., and Shen D.D. Contribution of CYP3A5 to hepatic and renal ifosfamide N-dechloroethylation. Drug Metab. Dispos. 33 (2005) 1074-1081
65. Aleksa K., Ito S., and Koren G. Renal-tubule metabolism of ifosfamide to the nephrotoxic chloroacetaldehyde: pharmacokinetic modeling for estimation of intracellular levels. J. Lab. Clin. Med. 143 (2004) 159-162
66. Nicolao P., and Giometto B. Neurological toxicity of ifosfamide. Oncology 65 Suppl 2 (2003) 11-16
67. Aeschlimann C., Kupfer A., Schefer H., and Cerny T. Comparative pharmacokinetics of oral and intravenous ifosfamide/mesna/methylene blue therapy. Drug Metab. Dispos. 26 (1998) 883-890
68. Pelgrims J., De Vos F., Van den Brande J., Schrijvers D., Prove A., and Vermorken J.B. Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature. Br. J. Cancer 82 (2000) 291-294
69. Schwerdt G., Gordjani N., Benesic A., Freudinger R., Wollny B., Kirchhoff A., and Gekle M. Chloroacetaldehyde- and acrolein-induced death of human proximal tubule cells. Pediatr. Nephrol. 21 (2006) 60-67
70. Liu X.L., Chen K., Ye Y.P., Peng X.Y., and Qian B.C. Glutathione antagonized cyclophosphamide- and acrolein-induced cytotoxicity of PC3 cells and immunosuppressive actions in mice. Zhongguo Yao Li Xue Bao 20 (1999) 643-646
71. Gamcsik M.P., Dolan M.E., Andersson B.S., and Murray D. Mechanisms of resistance to the toxicity of cyclophosphamide. Curr. Pharm. Des. 5 (1999) 587-605
72. Wu C.C., Hsieh C.W., Lai P.H., Lin J.B., Liu Y.C., and Wung B.S. Upregulation of endothelial heme oxygenase-1 expression through the activation of the JNK pathway by sublethal concentrations of acrolein. Toxicol. Appl. Pharmacol. 214 (2006) 244-252
73. Liu-Snyder P., McNally H., Shi R., and Borgens R.B. Acrolein-mediated mechanisms of neuronal death. J. Neurosci. Res. 84 (2006) 209-218
74. 2+-signaling by chloroacetaldehyde: a possible cause for chronic ifosfamide nephrotoxicity. Kidney Int. 68 (2005) 2029-2041
75. Luo J., and Shi R. Acrolein induces oxidative stress in brain mitochondria. Neurochem. Int. 46 (2005) 243-252
76. Uchida K. Current status of acrolein as a lipid peroxidation product. Trends Cardiovasc. Med. 9 (1999) 109-113
77. Misonou Y., Asahi M., Yokoe S., Miyoshi E., and Taniguchi N. Acrolein produces nitric oxide through the elevation of intracellular calcium levels to induce apoptosis in human umbilical vein endothelial cells: implications for smoke angiopathy. Nitric Oxide 14 (2006) 180-187
78. Chung F.L., Young R., and Hecht S.S. Formation of cyclic 1,N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44 (1984) 990-995
79. Eder E., Hoffman C., Bastian H., Deininger C., and Scheckenbach S. Molecular mechanisms of DNA damage initiated by alpha, beta-unsaturated carbonyl compounds as criteria for genotoxicity and mutagenicity. Environ. Health Perspect. 88 (1990) 99-106
80. Dosanjh M.K., Chenna A., Kim E., Fraenkel-Conrat H., Samson L., and Singer B. All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 1024-1028
81. Oesch F., and Doerjer G. Detection of N2,3-ethanoguanine in DNA after treatment with chloroacetaldehyde in vitro. Carcinogenesis 3 (1982) 663-665
82. Dypbukt J.M., Atzori L., Edman C.C., and Grafstrom R.C. Thiol status and cytopathological effects of acrolein in normal and xeroderma pigmentosum skin fibroblasts. Carcinogenesis 14 (1993) 975-980
83. Gros L., Ishchenko A.A., and Saparbaev M. Enzymology of repair of etheno-adducts. Mutat. Res. 531 (2003) 219-229
84. Kisby G.E., Lesselroth H., Olivas A., Samson L., Gold B., Tanaka K., and Turker M.S. Role of nucleotide- and base-excision repair in genotoxin-induced neuronal cell death. DNA Repair (Amst.) 3 (2004) 617-627
85. Flowers J.L., Ludeman S.M., Gamcsik M.P., Colvin O.M., Shao K.L., Boal J.H., Springer J.B., and Adams D.J. Evidence for a role of chloroethylaziridine in the cytotoxicity of cyclophosphamide. Cancer Chemother. Pharmacol. 45 (2000) 335-344
86. 6-methylguanine-DNA methyltransferase (MGMT) on the cytotoxic and recombinogenic activity of different antineoplastic drugs. Int. J. Cancer 65 (1996) 506-512
87. Links M., and Lewis C. Chemoprotectants: a review of their clinical pharmacology and therapeutic efficacy. Drugs 57 (1999) 293-308
88. a and high reactivity of cysteine 145. Biochemistry 42 (2003) 10965-10970
89. 6-alkylguanine-DNA alkyltransferase activity in peripheral lymphocytes of patients undergoing bone marrow transplantation. Br. J. Cancer 66 (1992) 331-336
90. 6-methylguanine-DNA methyltransferase by various aldehydes in cultured human bronchial fibroblasts. Carcinogenesis 6 (1985) 1755-1759
91. 6-benzyl-8-oxoguanine. Biochem. Pharmacol. 58 (1999) 237-244
92. 6-benzylguanine. Biochemistry 34 (1995) 7113-7119
93. Borner K., Kisro J., Bruggemann S.K., Hagenah W., Peters S.O., and Wagner T. Metabolism of ifosfamide to chloroacetaldehyde contributes to antitumor activity in vivo. Drug Metab. Dispos. 28 (2000) 573-576
94. Shiraishi A., Sakumi K., and Sekiguchi M. Increased susceptibility to chemotherapeutic alkylating agents of mice deficient in DNA repair methyltransferase. Carcinogenesis 21 (2000) 1879-1883
95. Glassner B.J., Weeda G., Allan J.M., Broekhof J.L., Carls N.H., Donker I., Engelward B.P., Hampson R.J., Hersmus R., Hickman M.J., Roth R.B., Warren H.B., Wu M.M., Hoeijmakers J.H., and Samson L.D. DNA repair methyltransferase (Mgmt) knockout mice are sensitive to the lethal effects of chemotherapeutic alkylating agents. Mutagenesis 14 (1999) 339-347