The influence of dicoumarol on the bioactivation of the carcinogen aristolochic acid I in rats

Mutagenesis

Volumn 29, Issue 3, 2014, Pages 189-200

  Stiborová, Marie ^a   Levová, Kateřina ^a   Bárta, František ^a   Šulc, Miroslav ^a   Frei, Eva ^b   Arlt, Volker M ^c   Schmeiser, Heinz H ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^c Imperial College London   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARISTOLOCHIC ACID; CARCINOGEN; CYTOCHROME P450; DICOUMAROL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); ARISTOLOCHIC ACID I; CYP1A2 PROTEIN, RAT; CYTOCHROME; CYTOCHROME P450 1A1; DNA ADDUCT; MUTAGENIC AGENT; NQO1 PROTEIN, RAT;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CYTOSOL; DETOXIFICATION; DNA ADDUCT; ENZYME ACTIVITY; GENOTOXICITY; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONTENT; RAT; WISTAR RAT; ANIMAL; DRUG EFFECTS; HUMAN; KIDNEY; LIVER; METABOLIC ACTIVATION; METABOLISM; MOUSE; MUTAGEN TESTING;

ACTIVATION, METABOLIC; ANIMALS; ARISTOLOCHIC ACIDS; CARCINOGENS; CYTOCHROME P-450 CYP1A1; CYTOCHROMES; CYTOSOL; DICUMAROL; DNA ADDUCTS; HUMANS; KIDNEY; LIVER; MALE; MICE; MICROSOMES, LIVER; MUTAGENICITY TESTS; MUTAGENS; NAD(P)H DEHYDROGENASE (QUINONE); RATS; RATS, WISTAR;

EID: 84898847123     PISSN: 02678357     EISSN: 14643804     Source Type: Journal    
DOI: 10.1093/mutage/geu004     Document Type: Article

References (58)

1. Arlt, V. M., Stiborova, M. and Schmeiser, H. H. (2002) Aristolochic acid as a probable human cancer hazard in herbal remedies: A review. Mutagenesis, 17, 265-277
2. Debelle, F. D., Vanherweghem, J. L. and Nortier, J. L. (2008) Aristolochic acid nephropathy: A worldwide problem. Kidney Int., 74, 158-169
3. Schmeiser, H. H., Stiborovà, M. and Arlt, V. M. (2009) Chemical and molecular basis of the carcinogenicity of Aristolochia plants. Curr. Opin. Drug Discov. Devel., 12, 141-148
4. Gökmen, M. R., Cosyns, J. P., Arlt, V. M., et al. (2013) The epidemiology, diagnosis, and management of aristolochic acid nephropathy: A narrative review. Ann. Intern. Med., 158, 469-477
5. Nortier, J. L., Martinez, M. C., Schmeiser, H. H., et al. (2000) Urothelial carcinoma associated with the use of a Chinese herb (Aristolochia fangchi). N. Engl. J. Med., 342, 1686-1692
6. Yun, B. H., Rosenquist, T. A., Sidorenko, V., et al. (2012) Biomonitoring of aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-Trap mass spectrometry. Chem. Res. Toxicol., 25, 1119-1131
7. Arlt, V. M., Stiborová, M., vom Brocke, J., Simões, M. L., Lord, G. M., Nortier, J. L., Hollstein, M., Phillips, D. H. and Schmeiser, H. H. (2007) Aristolochic acid mutagenesis: Molecular clues to the aetiology of Balkan endemic nephropathy-Associated urothelial cancer. Carcinogenesis, 28, 2253-2261
8. Grollman, A. P., Shibutani, S., Moriya, M., et al. (2007) Aristolochic acid and the etiology of endemic (Balkan) nephropathy. Proc. Natl. Acad. Sci. U.S.A., 104, 12129-12134
9. Moriya, M., Slade, N., Brdar, B., et al. (2011) TP53 Mutational signature for aristolochic acid: An environmental carcinogen. Int. J. Cancer, 129, 1532-1536
10. Schmeiser, H. H., Bieler, C. A., Wiessler, M., van Ypersele de Strihou, C. and Cosyns, J. P. (1996) Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy. Cancer Res., 56, 2025-2028
11. Arlt, V. M., Ferluga, D., Stiborova, M., Pfohl-Leszkowicz, A., Vukelic, M., Ceovic, S., Schmeiser, H. H. and Cosyns, J. P. (2002) Is aristolochic acid a risk factor for Balkan endemic nephropathy-Associated urothelial cancer? Int. J. Cancer, 101, 500-502
12. Jelakovic, B., Karanovic, S., Vukovic-Lela, I., et al. (2012) Aristolactam-DNA adducts are a biomarker of environmental exposure to aristolochic acid. Kidney Int., 81, 559-567
13. Lord, G. M., Hollstein, M., Arlt, V. M., Roufosse, C., Pusey, C. D., Cook, T. and Schmeiser, H. H. (2004) DNA adducts and p53 mutations in a patient with aristolochic acid-Associated nephropathy. Am. J. Kidney Dis., 43, e11-e17
14. Chen, C. H., Dickman, K. G., Moriya, M., et al. (2012) Aristolochic acidassociated urothelial cancer in Taiwan. Proc. Natl. Acad. Sci. U.S.A., 109, 8241-8246
15. Hoang, M. L., Chen, C. H., Sidorenko, V. S., et al. (2013) Mutational signature of aristolochic acid exposure as revealed by whole-exome sequencing. Sci. Transl. Med., 5, 197ra102
16. Poon, S. L., Pang, S. T., McPherson, J. R., et al. (2013) Genome-wide mutational signatures of aristolochic acid and its application as a screening tool. Sci. Transl. Med., 5, 197ra101
17. Olivier, M., Hollstein, M., Schmeiser, H. H., Straif, K. and Wild, C. P. (2012) Upper urinary tract urothelial cancers: Where it is A:T. Nat. Rev. Cancer, 12, 503-504
18. Stiborová, M., Frei, E., Sopko, B., Sopková, K., Marková, V., Lanková, M., Kumstýrová, T., Wiessler, M. and Schmeiser, H. H. (2003) Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: Evidence for reductive activation by human NAD(P)H:quinone oxidoreductase. Carcinogenesis, 24, 1695-1703
19. Stiborová, M., Frei, E., Arlt, V. M. and Schmeiser, H. H. (2008) Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy. Mutat. Res., 658, 55-67
20. Stiborová, M., Mareîs, J., Frei, E., Arlt, V. M., Martínek, V. and Schmeiser, H. H. (2011) The human carcinogen aristolochic acid I is activated to form DNA adducts by human NAD(P)H:quinone oxidoreductase without the contribution of acetyltransferases or sulfotransferases. Environ. Mol. Mutagen., 52, 448-459
21. Stiborová, M., Martínek, V., Frei, E., Arlt, V. M. and Schmeiser, H. H. (2013) Enzymes metabolizing aristolochic acid and their contribution to the development of aristolochic acid nephropathy and urothelial cancer. Curr. Drug Metab., 14, 695-705
22. Chen, M., Gong, L., Qi, X., et al. (2011) Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity. Toxicol. Sci., 122, 288-296
23. Stiborová, M., Frei, E., Hodek, P., Wiessler, M. and Schmeiser, H. H. (2005) Human hepatic and renal microsomes, cytochromes P450 1A1/2, NADPH:cytochrome P450 reductase and prostaglandin H synthase mediate the formation of aristolochic acid-DNA adducts found in patients with urothelial cancer. Int. J. Cancer, 113, 189-197
24. Stiborová, M., Levová, K., Bárta, F., Shi, Z., Frei, E., Schmeiser, H. H., Nebert, D. W., Phillips, D. H. and Arlt, V. M. (2012) Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2. Toxicol. Sci., 125, 345-358
25. Arlt, V. M., Levová, K., Bárta, F., et al. (2011) Role of P450 1A1 and P450 1A2 in bioactivation versus detoxication of the renal carcinogen aristolochic acid I: Studies in Cyp1a1-/-, Cyp1a2-/-, and Cyp1a1/1a2-/-mice. Chem. Res. Toxicol., 24, 1710-1719
26. Levová, K., Moserová, M., Kotrbová, V., et al. (2011) Role of cytochromes P450 1A1/2 in detoxication and activation of carcinogenic aristolochic acid I: Studies with the hepatic NADPH:cytochrome P450 reductase null (HRN) mouse model. Toxicol. Sci., 121, 43-56
27. Shibutani, S., Bonala, R. R., Rosenquist, T., Rieger, R., Suzuki, N., Johnson, F., Miller, F. and Grollman, A. P. (2010) Detoxification of aristolochic acid I by O-demethylation: Less nephrotoxicity and genotoxicity of aristolochic acid Ia in rodents. Int. J. Cancer, 127, 1021-1027
28. Levova, K., Moserova, M., Nebert, D. W., Phillips, D. H., Frei, E., Schmeiser, H. H., Arlt, V. M. and Stiborova, M. (2012) NAD(P)H:quinone oxidoreductase expression in Cyp1a-knockout and CYP1A-humanized mouse lines and its effect on bioactivation of the carcinogen aristolochic acid I. Toxicol. Appl. Pharmacol., 265, 360-367
29. Arlt, V. M., Zuo, J., Trenz, K., Roufosse, C. A., Lord, G. M., Nortier, J. L., Schmeiser, H. H., Hollstein, M. and Phillips, D. H. (2011) Gene expression changes induced by the human carcinogen aristolochic acid I in renal and hepatic tissue of mice. Int. J. Cancer, 128, 21-32
30. Wiechelman, K. J., Braun, R. D. and Fitzpatrick, J. D. (1988) Investigation of the bicinchoninic acid protein assay: Identification of the groups responsible for color formation. Anal. Biochem., 175, 231-237
31. Schmeiser, H. H., Stiborova, M. and Arlt, V. M. (2013) 32P-postlabeling analysis of DNA adducts. Methods Mol. Biol., 1044, 389-401
32. Stiborová, M., Martínek, V., Rýdlová, H., Hodek, P. and Frei, E. (2002) Sudan I is a potential carcinogen for humans: Evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Cancer Res., 62, 5678-5684
33. Stiborová, M., Dracínská, H., Hájková, J., Kaderábková, P., Frei, E., Schmeiser, H. H., Soucek, P., Phillips, D. H. and Arlt, V. M. (2006) The environmental pollutant and carcinogen 3-nitrobenzanthrone and its human metabolite 3-Aminobenzanthrone are potent inducers of rat hepatic cytochromes P450 1A1 and-1A2 and NAD(P)H:quinone oxidoreductase. Drug Metab. Dispos., 34, 1398-1405
34. Burke, M. D., Thompson, S., Weaver, R. J., Wolf, C. R. and Mayer, R. T. (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol., 48, 923-936
35. Kobayashi, K., Urashima, K., Shimada, N. and Chiba, K. (2002) Substrate specificity for rat cytochrome P450 (CYP) isoforms: Screening with cDNAexpressed systems of the rat. Biochem. Pharmacol., 63, 889-896
36. Yamazaki, H., Shimizu, M., Nagashima, T., Minoshima, M. and Murayama, N. (2006) Rat cytochrome P450 2C11 in liver microsomes involved in oxidation of anesthetic agent propofol and deactivated by prior treatment with propofol. Drug Metab. Dispos., 34, 1803-1805
37. Rendic, S. and Di Carlo, F. J. (1997) Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab. Rev., 29, 413-580
38. Laursen, T., Jensen, K. and Møller, B. L. (2011) Conformational changes of the NADPH-dependent cytochrome P450 reductase in the course of electron transfer to cytochromes P450. Biochim. Biophys. Acta, 1814, 132-138
39. Pudney, C. R., Khara, B., Johannissen, L. O. and Scrutton, N. S. (2011) Coupled motions direct electrons along human microsomal P450 Chains. PLoS Biol., 9, e1001222
40. Rosenquist, T. A., Einolf, H. J., Dickman, K. G., Wang, L., Smith, A. and Grollman, A. P. (2010) Cytochrome P450 1A2 detoxicates aristolochic acid in the mouse. Drug Metab. Dispos., 38, 761-768
41. Nedelcheva, V. and Gut, I. (1994) P450 in the rat and man: Methods of investigation, substrate specificities and relevance to cancer. Xenobiotica., 24, 1151-1175
42. Vecera, R., Zacharová, A., Orolin, J., Strojil, J., Skottová, N. and Anzenbacher, P. (2011) Fenofibrate-induced decrease of expression of CYP2C11 and CYP2C6 in rat. Biopharm. Drug Dispos., 32, 482-487
43. Zacharová, A., Siller, M., Spicáková, A., Anzenbacherová, E., Skottová, N., Anzenbacher, P. and Vecera, R. (2012) Rosuvastatin suppresses the liver microsomal CYP2C11 and CYP2C6 expression in male Wistar rats. Xenobiotica., 42, 731-736
44. Crow, J. W., Gibaldi, M. and Levy, G. (1979) Comparative pharmacokinetics of coumarin anticoagulants. XLII: Effect of phenobarbital on systemic availability of orally administered dicumarol in rats with ligated bile ducts. J. Pharm. Sci., 68, 1309-1312
45. Lai, C. M., Yacobi, A. and Levy, G. (1976) Relationship between dicumarol distribution and the effect of enzyme induction on dicumarol elimination in rats. J. Pharmacol. Exp. Ther., 199, 74-81
46. Pearce, R., Greenway, D. and Parkinson, A. (1992) Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: Effects on coumarin, dicumarol, and testosterone oxidation. Arch. Biochem. Biophys., 298, 211-225
47. Wallin, R., Wajih, N. and Hutson, S. M. (2008) VKORC1: A warfarinsensitive enzyme in vitamin K metabolism and biosynthesis of vitamin K-dependent blood coagulation factors. Vitam. Horm., 78, 227-246
48. Rajan, L. and Moliterno, D. J. (2012) New anticoagulants in ischemic heart disease. Curr. Cardiol. Rep., 14, 450-456
49. Talalay, P. and Prochaska, H. J. (1998) Mechanism of induction of NAD(P) H:quinone reductase. Chem. Scr., 27A, 61-66
50. Jaiswal, A. K. (2000) Regulation of genes encoding NAD(P)H:quinone oxidoreductases. Free Radic. Biol. Med., 29, 254-262
51. Dinkova-Kostova, A. T., Fahey, J. W. and Talalay, P. (2004) Chemical structures of inducers of nicotinamide quinone oxidoreductase 1 (NQO1). Meth. Enzymol., 382, 423-448
52. Ross, D. (2004) Quinone reductases multitasking in the metabolic world. Drug Metab. Rev., 36, 639-654
53. Dinkova-Kostova, A. T. and Talalay, P. (2010) NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1), a multifunctional antioxidant enzyme and exceptionally versatile cytoprotector. Arch. Biochem. Biophys., 501, 116-123
54. Yu, F. Y., Wu, T. S., Chen, T. W. and Liu, B. H. (2011) Aristolochic acid I induced oxidative DNA damage associated with glutathione depletion and ERK1/2 activation in human cells. Toxicol. In Vitro, 25, 810-816
55. Zhu, S., Wang, Y., Jin, J., et al. (2012) Endoplasmic reticulum stress mediates aristolochic acid I-induced apoptosis in human renal proximal tubular epithelial cells. Toxicol. In Vitro, 26, 663-671
56. Gong, X., Gutala, R. and Jaiswal, A. K. (2008) Quinone oxidoreductases and vitamin K metabolism. Vitam. Horm., 78, 85-101
57. Tie, J. K., Jin, D. Y., Straight, D. L. and Stafford, D. W. (2011) Functional study of the vitamin K cycle in mammalian cells. Blood, 117, 2967-2974
58. Radjendirane, V., Joseph, P., Lee, Y. H., Kimura, S., Klein-Szanto, A. J., Gonzalez, F. J. and Jaiswal, A. K. (1998) Disruption of the DT diaphorase (NQO1) gene in mice leads to increased menadione toxicity. J. Biol. Chem., 273, 7382-7389.