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Volumn 33, Issue SUPPL. 3, 2012, Pages 25-32

Theoretical investigation of differences in nitroreduction of aristolochic acid I by cytochromes P450 1A1, 1A2 and 1B1

Author keywords

Aristolochic acid; Aristolochic acid nephropathy; Balkan endemic nephropathy; Cytochromes P450 1A1, 1A2 and 1B1, metabolic activation; Molecular modeling

Indexed keywords

ARISTOLOCHIC ACID; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; HEME;

EID: 84874806270     PISSN: 0172780X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (16)

References (44)
  • 1
    • 0037057532 scopus 로고    scopus 로고
    • Is aristolochic acid a risk factor for Balkan endemic nephropathy-associated urothelial cancer?
    • Arlt VM, Ferluga D, Stiborova M, Pfohl-Leszkowicz A, Vukelic M, Ceovic S, et al. (2002) Is aristolochic acid a risk factor for Balkan endemic nephropathy-associated urothelial cancer? Int J Cancer 101: 500-502.
    • (2002) Int J Cancer , vol.101 , pp. 500-502
    • Arlt, V.M.1    Ferluga, D.2    Stiborova, M.3    Pfohl-Leszkowicz, A.4    Vukelic, M.5    Ceovic, S.6
  • 2
    • 80054742122 scopus 로고    scopus 로고
    • 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
    • Arlt VM, Levova K, Barta F, Shi Z, Evans JD, Frei E, 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.
    • (2011) Chem Res Toxicol , vol.24 , pp. 1710-1719
    • Arlt, V.M.1    Levova, K.2    Barta, F.3    Shi, Z.4    Evans, J.D.5    Frei, E.6
  • 3
    • 36148933380 scopus 로고    scopus 로고
    • Aristolochic acid mutagenesis: Molecular clues to the aetiology of Balkan endemic nephropathy-associated urothelial cancer
    • Arlt VM, Stiborova M, vom Brocke J, Simões ML, Lord GM, Nortier JL, et al. (2007). Aristolochic acid mutagenesis: molecular clues to the aetiology of Balkan endemic nephropathy-associated urothelial cancer. Carcinogenesis. 28: 2253-2261.
    • (2007) Carcinogenesis , vol.28 , pp. 2253-2261
    • Arlt, V.M.1    Stiborova, M.2    Vom Brocke, J.3    Simões, M.L.4    Lord, G.M.5    Nortier, J.I.6
  • 4
    • 41549102309 scopus 로고    scopus 로고
    • Aristolochic acid nephropathy: A worldwide problem
    • DOI 10.1038/ki.2008.129, PII KI2008129
    • Debelle FD, Vanherweghem J-L and Nortier JL (2008) Aristolochic acid nephropathy: a worldwide problem. Kidney Int 74: 158-169. (Pubitemid 351915079)
    • (2008) Kidney International , vol.74 , Issue.2 , pp. 158-169
    • Debelle, F.D.1    Vanherweghem, J.-L.2    Nortier, J.L.3
  • 8
    • 33947716119 scopus 로고    scopus 로고
    • Software news and update a semiempirical free energy force field with charge-based desolvation
    • DOI 10.1002/jcc.20634
    • Huey R, Morris GM, Olson AJ and Goodsell DS (2007) A semiempirical free energy force field with charge-based desolvation. J Comput Chem 28: 1145-1152. (Pubitemid 46506716)
    • (2007) Journal of Computational Chemistry , vol.28 , Issue.6 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 10
    • 80051678011 scopus 로고    scopus 로고
    • Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity
    • Chen M, Gong L, Qi X, Xing G, Luan Y, Wu Y, 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.
    • (2011) Toxicol Sci , vol.122 , pp. 288-296
    • Chen, M.1    Gong, L.2    Qi, X.3    Xing, G.4    Luan, Y.5    Wu, Y.6
  • 12
    • 77953219808 scopus 로고    scopus 로고
    • Linking environmental carcinogen exposure to TP53 mutations in human tumours using the human TP53 knock-in (Hupki) mouse model
    • Kucab JE, Phillips DH, Arlt VM (2010) Linking environmental carcinogen exposure to TP53 mutations in human tumours using the human TP53 knock-in (Hupki) mouse model. FEBS J 277: 2567-2583.
    • (2010) FEBS J , vol.277 , pp. 2567-2583
    • Kucab, J.E.1    Phillips, D.H.2    Arlt, V.M.3
  • 13
    • 79955410481 scopus 로고    scopus 로고
    • 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
    • Levova K, Moserova M, Kotrbova V, Sulc M, Henderson CJ, Wolf CR, Phillips DH, 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.
    • (2011) Toxicol Sci , vol.121 , pp. 43-56
    • Levova, K.1    Moserova, M.2    Kotrbova, V.3    Sulc, M.4    Henderson, C.J.5    Wolf, C.R.6    Phillips, D.H.7
  • 14
  • 15
    • 33846807511 scopus 로고    scopus 로고
    • DNA polymerase beta catalytic efficiency mirrors the Asn279-dCTP H-bonding strength
    • DOI 10.1016/j.febslet.2007.01.042, PII S0014579307000804
    • Martinek V, Bren U, Goodman MF, Warshel A and Florian J (2007) DNA polymerase beta catalytic efficiency mirrors the Asn279-dCTP H-bonding strength. FEBS Lett 581: 775-780. (Pubitemid 46216300)
    • (2007) FEBS Letters , vol.581 , Issue.4 , pp. 775-780
    • Martinek, V.1    Bren, U.2    Goodman, M.F.3    Warshel, A.4    Florian, J.5
  • 16
    • 84857387612 scopus 로고    scopus 로고
    • Comparison of activation of aristolochic acid I and II with NADPH:quinone oxidoreductase, sulphotransferases and N-acetyltranferases
    • Martinek V, Kubickova B, Arlt VM, Frei E, Schmeiser HH, Hudecek J, et al. (2011) Comparison of activation of aristolochic acid I and II with NADPH:quinone oxidoreductase, sulphotransferases and N-acetyltranferases. Neuroendocrinol Lett 32: 57-70.
    • (2011) Neuroendocrinol Lett , vol.32 , pp. 57-70
    • Martinek, V.1    Kubickova, B.2    Arlt, V.M.3    Frei, E.4    Schmeiser, H.H.5    Hudecek, J.6
  • 20
    • 64849096515 scopus 로고    scopus 로고
    • Linear energy relationships for the octahedral preference of Mg, Ca and transition metal ions
    • Pontikis G, Borden J, Martinek V and Florián J (2009) Linear energy relationships for the octahedral preference of Mg, Ca and transition metal ions. J Phys Chem A 113: 3588-3593.
    • (2009) J Phys Chem A , vol.113 , pp. 3588-3593
    • Pontikis, G.1    Borden, J.2    Martinek, V.3    Florián, J.4
  • 24
    • 77955477610 scopus 로고    scopus 로고
    • Detoxification of aristolochic acid I by O-demethylation: Less nephrotoxicity and genotoxicity of aristolochic acid la in rodents
    • Shibutani S, Bonala RR, Rosenquist T, Rieger R, Suzuki N, Johnson F, et al. (2010) Detoxification of aristolochic acid I by O-demethylation: less nephrotoxicity and genotoxicity of aristolochic acid la in rodents. Int J Cancer 127: 1021-1027.
    • (2010) Int J Cancer , vol.127 , pp. 1021-1027
    • Shibutani, S.1    Bonala, R.R.2    Rosenquist, T.3    Rieger, R.4    Suzuki, N.5    Johnson, F.6
  • 25
    • 0029983768 scopus 로고    scopus 로고
    • Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy
    • Schmeiser HH, Bieler CA, Wiessler M, van Ypersele de Strihou C and Cosyns JP (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)
    • (1996) Cancer Research , vol.56 , Issue.9 , pp. 2025-2028
    • Schmeiser, H.H.1    Bieler, C.A.2    Wiessler, M.3    Van Ypersele, D.S.C.4    Cosyns, J.-P.5
  • 26
    • 58449131001 scopus 로고    scopus 로고
    • Chemical and molecular basis of the carcinogenicity of Aristolochia plants
    • Schmeiser HH, Stiborova M and Arlt VM (2009) Chemical and molecular basis of the carcinogenicity of Aristolochia plants. Curr Opin Drug Discov Devel 12: 141-148.
    • (2009) Curr Opin Drug Discov Devel , vol.12 , pp. 141-148
    • Schmeiser, H.H.1    Stiborova, M.2    Arlt, V.M.3
  • 27
    • 0042622380 scopus 로고    scopus 로고
    • SWISS-MODEL: An automated protein homology-modeling server
    • DOI 10.1093/nar/gkg520
    • Schwede T, Kopp J, Guex N and Peitsch MC (2003) SWISS-MODEL: An automated protein homology-modeling server. Nucleic Acids Res 31: 3381-3385. (Pubitemid 37442164)
    • (2003) Nucleic Acids Research , vol.31 , Issue.13 , pp. 3381-3385
    • Schwede, T.1    Kopp, J.2    Guex, N.3    Peitsch, M.C.4
  • 28
    • 79957765003 scopus 로고    scopus 로고
    • The directive of the protein: How does cytochrome P450 select the mechanism of dopamine formation?
    • Schyman P, Lai W, Chen H, Wang Y and Shaik S (2011) The directive of the protein: how does cytochrome P450 select the mechanism of dopamine formation? J Am Chem Soc 133: 7977-7984.
    • (2011) J Am Chem Soc , vol.133 , pp. 7977-7984
    • Schyman, P.1    Lai, W.2    Chen, H.3    Wang, Y.4    Shaik, S.5
  • 29
    • 57149122064 scopus 로고    scopus 로고
    • Human cytochromes P450 1A1 and 1A2 participate in detoxication of carcinogenic aristolochic acid
    • Sistkova J, Hudecek J, Hodek P, Frei E, Schmeiser HH and Stiborova M (2008) Human cytochromes P450 1A1 and 1A2 participate in detoxication of carcinogenic aristolochic acid. Neuroendocrinol Lett 29: 733-737.
    • (2008) Neuroendocrinol Lett , vol.29 , pp. 733-737
    • Sistkova, J.1    Hudecek, J.2    Hodek, P.3    Frei, E.4    Schmeiser, H.H.5    Stiborova, M.6
  • 30
    • 38649109829 scopus 로고    scopus 로고
    • Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy
    • DOI 10.1016/j.mrrev.2007.07.003, PII S1383574207000282
    • Stiborova M, Frei E, Arlt VM and Schmeiser HH (2008a) Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy. Mutat Res 658: 55-67. (Pubitemid 351172880)
    • (2008) Mutation Research - Reviews in Mutation Research , vol.658 , Issue.1-2 , pp. 55-67
    • Stiborova, M.1    Frei, E.2    Arlt, V.M.3    Schmeiser, H.H.4
  • 31
    • 10344258034 scopus 로고    scopus 로고
    • 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
    • DOI 10.1002/ijc.20564
    • Stiborova M, Frei E, Hodek P, Wiessler M and Schmeiser HH (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)
    • (2005) International Journal of Cancer , vol.113 , Issue.2 , pp. 189-197
    • Stiborova, M.1    Frei, E.2    Hodek, P.3    Wiessler, M.4    Schmeiser, H.H.5
  • 32
    • 43749112968 scopus 로고    scopus 로고
    • Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid
    • DOI 10.1038/ki.2008.125, PII KI2008125
    • Stiborova M, Frei E and Schmeiser HH (2008b) Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid. Kidney Int 73: 1209-1211. (Pubitemid 351693150)
    • (2008) Kidney International , vol.73 , Issue.11 , pp. 1209-1211
    • Stiborova, M.1    Frei, E.2    Schmeiser, H.H.3
  • 33
    • 0142185373 scopus 로고    scopus 로고
    • Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: Evidence for reductive activation by human NAD(P)H:quinone oxidoreductase
    • DOI 10.1093/carcin/bgg119
    • Stiborova M, Frei E, Sopko B, Sopkova K, Markova V, Lankova M, et al. (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. (Pubitemid 37304677)
    • (2003) Carcinogenesis , vol.24 , Issue.10 , pp. 1695-1703
    • Stiborova, M.1    Frei, E.2    Sopko, B.3    Sopkova, K.4    Markova, V.5    Lankova, M.6    Kumstyrova, T.7    Wiessler, M.8    Schmeiser, H.H.9
  • 34
    • 0034861029 scopus 로고    scopus 로고
    • Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: Evidence for reductive activation by cytochromes P450 1A1 and 1A2
    • DOI 10.1021/tx010059z
    • Stiborova M, Frei E, Wiessler M and Schmeiser HH (2001). Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: evidence for reductive activation by cytochromes P450 1A1 and 1A2. Chem. Res. Toxicol. 14: 1128-1137. (Pubitemid 32800169)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.8 , pp. 1128-1137
    • Stiborova, M.1    Frei, E.2    Wiessler, M.3    Schmeiser, H.H.4
  • 35
    • 84856118524 scopus 로고    scopus 로고
    • Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2
    • Stiborova M, Levova K, Barta F, Shi Z, Frei E, Schmeiser HH, et al. (2012) Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2. Toxicol Sci 125: 345-358.
    • (2012) Toxicol Sci , vol.125 , pp. 345-358
    • Stiborova, M.1    Levova, K.2    Barta, F.3    Shi, Z.4    Frei, E.5    Schmeiser, H.H.6
  • 36
    • 79955436820 scopus 로고    scopus 로고
    • 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
    • Stiborova M, Mares J, Frei E, Arlt VM, Martinek V and Schmeiser HH (2011a) 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.
    • (2011) Environ Mol Mutagen , vol.52 , pp. 448-459
    • Stiborova, M.1    Mares, J.2    Frei, E.3    Arlt, V.M.4    Martinek, V.5    Schmeiser, H.H.6
  • 37
    • 84857427527 scopus 로고    scopus 로고
    • Role of cytochromes P450 in metabolism of carcinogenic aristolochic acid I: Evidence of their contribution to aristolochic acid I detoxication and activation in rat liver
    • Stiborova M, Mares J, Levova K, Pavlickova J, Barta F, Hodek P, et al. (2011b) Role of cytochromes P450 in metabolism of carcinogenic aristolochic acid I: evidence of their contribution to aristolochic acid I detoxication and activation in rat liver. Neuro Endocrinol Lett 32 (Suppl 1): 121-130.
    • (2011) Neuro Endocrinol Lett , vol.32 , Issue.SUPPL. 1 , pp. 121-130
    • Stiborova, M.1    Mares, J.2    Levova, K.3    Pavlickova, J.4    Barta, F.5    Hodek, P.6
  • 38
    • 0037108678 scopus 로고    scopus 로고
    • Sudan I is a potential carcinogen for humans: Evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes
    • Stiborova M, Martinek V, Rydlova 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. (Pubitemid 35204721)
    • (2002) Cancer Research , vol.62 , Issue.20 , pp. 5678-5684
    • Stiborova, M.1    Martinek, V.2    Rydlova, H.3    Hodek, P.4    Frei, E.5
  • 40
    • 78649447922 scopus 로고    scopus 로고
    • Cytochrome P450- and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency
    • Stiborova M, Rupertova M and Frei E (2011c) Cytochrome P450- and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency. Biochim Biophys Acta 1814: 175-185.
    • (2011) Biochim Biophys Acta , vol.1814 , pp. 175-185
    • Stiborova, M.1    Rupertova, M.2    Frei, E.3
  • 42
    • 79953126762 scopus 로고    scopus 로고
    • Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1
    • Wang A, Savas U, Stout CD and Johnson EF (2011) Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1. J Biol Chem 286: 5736-5743.
    • (2011) J Biol Chem , vol.286 , pp. 5736-5743
    • Wang, A.1    Savas, U.2    Stout, C.D.3    Johnson, E.F.4
  • 44
    • 84861325737 scopus 로고    scopus 로고
    • Biomonitoring of aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-trap mass spectrometry
    • Yun BH, Rosenquist TA, Sidorenko V, Iden CR, Chen C-H, Pu Y-S, 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.
    • (2012) Chem Res Toxicol , vol.25 , pp. 1119-1131
    • Yun, B.H.1    Rosenquist, T.A.2    Sidorenko, V.3    Iden, C.R.4    Chen, C.-H.5    Pu, Y.-S.6


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