Aristolochic acid i metabolism in the isolated perfused rat kidney

Chemical Research in Toxicology

Volumn 25, Issue 1, 2012, Pages 130-139

  Priestap, Horacio A ^a   Torres, M Cecilia ^b   Rieger, Robert A ^b   Dickman, Kathleen G ^b   Freshwater, Tomoko ^c   Taft, David R ^c   Barbieri, Manuel A ^a   Iden, Charles R ^b  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^b STONY BROOK UNIVERSITY   (United States)

^c LONG ISLAND UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARISTOLACTAM 1; ARISTOLACTAM 1A; ARISTOLACTAM 1A O SULFATE; ARISTOLOCHIC ACID; ARISTOLOCHIC ACID 1; ARISTOLOCHIC ACID 1A; ARISTOLOCHIC ACID 1A O GLUCURONIDE; ARISTOLOCHIC ACID 1A O SULFATE; ARISTOLOLACTAM; GLUCURONIDE; SULFATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONCENTRATION (PARAMETERS); DETOXIFICATION; FECES ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KIDNEY CLEARANCE; KIDNEY METABOLISM; KIDNEY PARENCHYMA; KIDNEY PERFUSION; KIDNEY TUBULE; LIVER METABOLISM; MALE; NONHUMAN; RAT; TOXICITY TESTING; URINALYSIS;

ANIMALS; ARISTOLOCHIC ACIDS; BIOTRANSFORMATION; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUGS, CHINESE HERBAL; KIDNEY; LIVER; MALE; PERFUSION; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

ARISTOLOCHIA; RATTUS;

EID: 84855835181     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200333g     Document Type: Article

References (36)

1. Vanherweghem, J.-L., Depierreux, M., Tielemans, C., Abramowicz, D., Dratwa, M., Jadoul, M., Richard, C., Vandervelde, D., Verbeelen, D., Vanhaelen-Fastre, R., and Vanhaelen, M. (1993) Rapidly progressive intersticial renal fibrosis in young woman: association with slimming regimen including Chinese herbs Lancet 341, 387-391 (Pubitemid 23048140)
2. Vanhaelen, M., Vanhaelen-Fastre, R., But, P, and Vanherweghem, J.-L. (1994) Identification of aristolochic acid in Chinese herbs Lancet 343, 174 (Pubitemid 24028653)
3. Hranjec, T., Kovac, A., Kos, J., Mao, W., Chen, J. J., Grollman, A. P., and Jelakovic, B. (2005) Endemic nephropathy: The case for chronic poisoning by Aristolochia Croat. Med. J. 46, 116-125 (Pubitemid 40469936)
4. Mengs, U., Lang, W., and Poch, J. A. (1982) The carcinogenic action of aristolochic acid in rats Arch. Toxicol. 51, 107-119 (Pubitemid 13202139)
5. Nortier, J. L., Muniz, M.-C., Schmeiser, H. H., Arlt, V. M., Bieler, C. A., Petein, M., Depierreux, M. F., de Pauw, L., Abramowicz, D., Vereerstraeten, P., and Vanherweghem, J.-L. (2000) Urothelial carcinoma associated with the use of Chinese herbs (Aristolochia species) N. Eng. J. Med. 342, 1686-1692 (Pubitemid 30354515)
6. 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 (Pubitemid 26119902)
7. Pfau, W., Schmeiser, H. H., and Wiessler, M. (1990) Aristolochic binds covalently to the exocyclic amino group of purine nucleotides in DNA Carcinogenesis 11, 313-319 (Pubitemid 20072170)
8. Arlt, V. M., Stiborova, M., and Schmeiser, H. H. (2002) Aristolochic acid as probable human cancer hazard in herbal remedies: a review Mutagenesis 17, 265-277 (Pubitemid 34814645)
9. Priestap, H. A., de los Santos, C., and Quirke, J. M. E. (2010) Identification of a reduction product of aristolochic acid: implications for the metabolic activation of carcinogenic aristolochic acid J. Nat. Prod. 73, 1979-1986
10. Krumbiegel, G., Hallensleben, J., Mennicke, W. H., Rittmann, N., and Roth, H. J. (1987) Studies on the metabolism of aristolochic acids I and II Xenobiotica 17, 981-991 (Pubitemid 17150543)
11. Chan, W., Cui, L., Xu, G., and Cai, Z. (2006) Study of the phase I and phase II metabolism of nephrotoxin aristolochic acid by liquid chromatography/tandem mass spectrometry Rapid Commun. Mass Spectrom. 20, 1755-1760 (Pubitemid 43793879)
12. Chan, W., Luo, H.-B., Zheng, Y., Cheng, Y.-K., and Cai, Z. (2007) Investigation of the metabolism and reductive activation of carcinogenic aristolochic acids in rats Drug Metab. Dispos. 35, 866-874 (Pubitemid 46798597)
13. Taft, D. R. (2004) The Isolated perfused rat kidney model: A useful tool for drug discovery and development Curr. Drug Discovery Technol. 1, 97-111
14. Stiborova, M., Frei, E., and Schmeiser, H. H. (2008) Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid Kidney Int. 73, 1209-1211 (Pubitemid 351693150)
15. Stiborova, M., Mares, J., Frei, E., Arlt, Martinek, E., V. M., 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
16. Priestap, H. A. (1985) Seven aristololactams from Aristolochia argentina Phytochemistry 24, 849-852
17. Poola, N. R., Kalis, M., Plakogiannis, F. M., and Taft, D. R. (2003) Characterization of pentamidine excretion in the isolated rat kidney J. Antimicrob. Chemother. 52, 397-404 (Pubitemid 37120718)
18. Ajavon, A. D., Bonate, P. L., and Taft, D. R. (2010) Renal excretion of clofarabine: Assesment of dose-linearity and role of renal transport systems on drug excretion Eur. J. Pharm. Sci. 40, 209-216
19. Anders, M. W. (1980) Metabolism of drugs by the kidney Kidney Int. 18, 636-647 (Pubitemid 11204064)
20. Besseghir, K. and Roch-Ramel, F. (1987) Renal excretion of drugs and other xenobiotics Renal Physiol. (Basel, Switz.) 10, 221-241
21. Lohr, J. W., Willsky, G. R., and Acara, M. A. (1998) Renal drug metabolism Pharm. Rev. 50, 107-141 (Pubitemid 28158844)
22. Maack, T. (1980) Physiological evaluation of the isolated perfused rat kidney Am. J. Physiol. 238, F71-F78
23. Shanahan, K. M., Evans, A. M., and Nation, R. L. (1997) Disposition of morphine in the rat isolated perfused kidney: Concentration ranging studies J. Pharmacol. Exp. Ther. 282, 1518-1525 (Pubitemid 27408336)
24. Qi, X., Cai, Y., Gong, L., Liu, L., Chen, F., Xiao, Y., Wu, F., Li, Y., Xue, X., and Ren, J. (2007) Role of mitochondrial permeability transition in human renal tubular epithelial cell death induced by aristolochic acid Toxicol. Appl. Pharmacol. 222, 105-110 (Pubitemid 46962657)
25. Horton, T. L. and Pollack, G. M. (1991) Enterohepatic recirculation and renal metabolism of morphine in the rat J. Pharm. Sci. 80, 1147-1152
26. Stiborova, M., Frei, E., Arlt, V. M., and Schmeiser, H. H. (2008) Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy Mut. Res. 658, 55-67 (Pubitemid 351172880)
27. Stiborova, M., Hudecek, J, Frei, E., and Schmeiser, H. H. (2008) Contribution of biotransformation enzymes to the development of renal injury and urothelial cancer caused by aristolochic acid: Urgent questions, difficult answers Interdiscip. Toxicol. 1, 8-12
28. 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 genotoxycity of aristolochic acid Ia in rodents Int. J. Cancer 127, 1021-1027
29. Xiao, I., Ge, M., Xue, X., Wang, C., Wang, H., Wu, X., Li, L., Liu, L., Qi, X., Zhang, Y., Li, Y., Lou, H., Xie, T., Gu, J., and Ren, G. (2008) Hepatic cytochrome P450s metabolize aristolochic acid and reduce its kidney toxicity Kidney Int. 73, 1231-1239 (Pubitemid 351693146)
30. 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
31. Dickman, K. G., Sweet, D. H., Bonala, R., Ray, T., and Wu, A. (2011) Physiological and molecular characterization of aristolochic acid transport by the kidney J. Pharmacol. Exp. Ther. 338, 588-597
32. Stiborova, 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 (Pubitemid 39628308)
33. Kite, G. C., Yule, M. A., Leon, C., and Simmonds, M. S. J. (2002) Detecting aristolochic acids in herbal remedies by liquid chromatography/serial mass spectrometry Rapid Commun. Mass Spectrom. 16, 585-590 (Pubitemid 34205050)
34. Gu, J., Zhong, D., and Chen, X. (1999) Analysis of O-glucuronide conjugates in urine by electrospray ion trap mass spectrometry Fresenius J. Anal. Chem. 365, 553-558
35. Scott, A. I. (1964) Interpretation of the Ultraviolet Spectra of Natural Products, p 91, Pergamon Press, Oxford.
36. Pit, C. G. and Fowler, M. S. (1967) Electronic absorption spectra of aminosilanes J. Am. Chem. Soc. 89, 6792-6793