메뉴 건너뛰기




Volumn 17, Issue 2, 2016, Pages

Active site mutations as a suitable tool contributing to explain a mechanism of aristolochic acid I nitroreduction by cytochromes P450 1A1, 1A2 and 1B1

Author keywords

1A2 and 1B1; Aristolochic acid I; Aristolochic acid nephropathy; DNA adduct formation; Nitroreduction; Site directed mutagenesis of cytochromes P450 1A1

Indexed keywords

7 METHOXYRESORUFIN O DEMETHYLASE; ARISTOLOCHIC ACID; BIOLOGICAL MARKER; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; PLASMID VECTOR; SUDAN I; UNCLASSIFIED DRUG; ARISTOLOCHIC ACID I; DNA ADDUCT; RECOMBINANT PROTEIN; UNSPECIFIC MONOOXYGENASE;

EID: 84957560992     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms17020213     Document Type: Article
Times cited : (15)

References (64)
  • 1
    • 0036020624 scopus 로고    scopus 로고
    • Aristolochic acid as a probable human cancer hazard in herbal remedies
    • [CrossRef] [PubMed]
    • Arlt, V.M.; Stiborova, M.; Schmeiser, H.H. Aristolochic acid as a probable human cancer hazard in herbal remedies: A review. Mutagenesis 2002, 17, 265–277. [CrossRef] [PubMed]
    • (2002) A Review. Mutagenesis , vol.17 , pp. 265-277
    • Arlt, V.M.1    Stiborova, M.2    Schmeiser, H.H.3
  • 2
    • 58449131001 scopus 로고    scopus 로고
    • Chemical and molecular basis of the carcinogenicity of Aristolochia plants. Curr. Opin
    • Schmeiser, H.H.; Stiborová, M.; Arlt, V.M. Chemical and molecular basis of the carcinogenicity of Aristolochia plants. Curr. Opin. Drug Discov. Dev. 2009, 12, 141–148.
    • (2009) Drug Discov. Dev , vol.12 , pp. 141-148
    • Schmeiser, H.H.1    Stiborová, M.2    Arlt, V.M.3
  • 6
    • 84861325737 scopus 로고    scopus 로고
    • Biomonitoring of aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-trap mass spectrometry
    • [CrossRef] [PubMed]
    • Yun, B.H.; Rosenquist, T.A.; Sidorenko, V.; Iden, C.R.; Chen, C.H.; Pu, Y.S.; Bonala, R.; Johnson, F.; Dickman, K.G.; Grollman, A.P. et al. Biomonitoring of aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-trap mass spectrometry. Chem. Res. Toxicol. 2012, 25, 1119–1131. [CrossRef] [PubMed]
    • (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    Bonala, R.7    Johnson, F.8    Dickman, K.G.9    Grollman, A.P.10
  • 7
    • 84957563069 scopus 로고    scopus 로고
    • A review of human CARCINOGENS: Pharmaceuticals
    • International Agency for Research on Cancer (IARC), Geneva, Switzerland
    • International Agency for Research on Cancer (IARC). A review of human CARCINOGENS: Pharmaceuticals. In Environ. Health Criteria Monographs; World Health Organization: Geneva, Switzerland, 2012.
    • Environ. Health Criteria Monographs; World Health Organization , pp. 2012
  • 8
  • 10
    • 84867399463 scopus 로고    scopus 로고
    • Evidence of exposure to aristolochic acid in patients with urothelial cancer from a Balkan endemic nephropathy region of Romania. Environ. Mol
    • [CrossRef] [PubMed]
    • Schmeiser, H.H.; Kucab, J.E.; Arlt, V.M.; Phillips, D.H.; Hollstein, M.; Gluhovschi, G.; Gluhovschi, C.; Modilca, M.; Daminescu, L.; Petrica, L. et al. Evidence of exposure to aristolochic acid in patients with urothelial cancer from a Balkan endemic nephropathy region of Romania. Environ. Mol. Mutagen. 2012, 53, 636–641. [CrossRef] [PubMed]
    • (2012) Mutagen , vol.53 , pp. 636-641
    • Schmeiser, H.H.1    Kucab, J.E.2    Arlt, V.M.3    Phillips, D.H.4    Hollstein, M.5    Gluhovschi, G.6    Gluhovschi, C.7    Modilca, M.8    Daminescu, L.9    Petrica, L.10
  • 12
    • 38649109829 scopus 로고    scopus 로고
    • Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy. Mutat
    • Stiborová, M.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy. Mutat. Res. 2008, 658, 55–67.
    • (2008) Res , vol.658 , pp. 55-67
    • Stiborová, M.1    Frei, E.2    Arlt, V.M.3    Schmeiser, H.H.4
  • 13
    • 43749112968 scopus 로고    scopus 로고
    • Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Schmeiser, H.H. Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid. Kidney Int. 2008, 73, 1209–1211. [CrossRef] [PubMed]
    • (2008) Kidney Int , vol.73 , pp. 1209-1211
    • Stiborová, M.1    Frei, E.2    Schmeiser, H.H.3
  • 14
    • 84882303544 scopus 로고    scopus 로고
    • Enzymes metabolizing aristolochic acid and their contribution to the development of Aristolochic acid nephropathy and urothelial cancer
    • [CrossRef] [PubMed]
    • Stiborová, M.; Martínek, V.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. Enzymes metabolizing aristolochic acid and their contribution to the development of Aristolochic acid nephropathy and urothelial cancer. Curr. Drug Metab. 2013, 14, 695–705. [CrossRef] [PubMed]
    • (2013) Curr. Drug Metab , vol.14 , pp. 695-705
    • Stiborová, M.1    Martínek, V.2    Frei, E.3    Arlt, V.M.4    Schmeiser, H.H.5
  • 15
    • 84893070184 scopus 로고    scopus 로고
    • Knock-out and humanized mice as suitable tools to identify enzymes metabolizing the human carcinogen aristolochic acid
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. Knock-out and humanized mice as suitable tools to identify enzymes metabolizing the human carcinogen aristolochic acid. Xenobiotica 2014, 44, 135–145. [CrossRef] [PubMed]
    • (2014) Xenobiotica , vol.44 , pp. 135-145
    • Stiborová, M.1    Frei, E.2    Arlt, V.M.3    Schmeiser, H.H.4
  • 16
    • 0029983768 scopus 로고    scopus 로고
    • Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy
    • [PubMed]
    • Schmeiser, H.H.; Bieler, C.A.; Wiessler, M.; Ypersele de Strihou, C.; Cosyns, J.P. Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy. Cancer Res. 1996, 56, 2025–2028. [PubMed]
    • (1996) Cancer Res , vol.56 , pp. 2025-2028
    • Schmeiser, H.H.1    Bieler, C.A.2    Wiessler, M.3    Ypersele De Strihou, C.4    Cosyns, J.P.5
  • 17
    • 0032780946 scopus 로고    scopus 로고
    • Aristolactam I a metabolite of aristolochic acid I upon activation forms an adduct found in DNA of patients with Chinese herbs nephropathy. Exp. Toxic
    • [CrossRef]
    • Stiborová, M.; Frei, E.; Breuer, A.; Bieler, C.A.; Schmeiser, H.H. Aristolactam I a metabolite of aristolochic acid I upon activation forms an adduct found in DNA of patients with Chinese herbs nephropathy. Exp. Toxic. Pathol. 1999, 51, 421–427. [CrossRef]
    • (1999) Pathol , vol.51 , pp. 421-427
    • Stiborová, M.1    Frei, E.2    Breuer, A.3    Bieler, C.A.4    Schmeiser, H.H.5
  • 20
  • 21
    • 58149459327 scopus 로고    scopus 로고
    • TP53 mutation signature supports involvement of aristolochic acid in the aetiology of endemic nephropathy-associated tumours
    • [CrossRef] [PubMed]
    • Nedelko, T.; Arlt, V.M.; Phillips, D.H.; Hollstein, M. TP53 mutation signature supports involvement of aristolochic acid in the aetiology of endemic nephropathy-associated tumours. Int. J. Cancer 2009, 124, 987–990. [CrossRef] [PubMed]
    • (2009) Int. J. Cancer , vol.124 , pp. 987-990
    • Nedelko, T.1    Arlt, V.M.2    Phillips, D.H.3    Hollstein, M.4
  • 22
    • 77953219808 scopus 로고    scopus 로고
    • Linking environmental carcinogen exposure to TP53 mutations in human tumours using the human TP53 knock-in (Hupki) mouse model
    • [CrossRef] [PubMed]
    • Kucab, J.E.; Phillips, D.H.; Arlt, V.M. Linking environmental carcinogen exposure to TP53 mutations in human tumours using the human TP53 knock-in (Hupki) mouse model. FEBS J. 2010, 277, 2567–2583. [CrossRef] [PubMed]
    • (2010) FEBS J , vol.277 , pp. 2567-2583
    • Kucab, J.E.1    Phillips, D.H.2    Arlt, V.M.3
  • 25
    • 84864351166 scopus 로고    scopus 로고
    • Upper urinary tract urothelial cancer: Where it is A:T
    • [CrossRef]
    • Olivier, M.; Hollstein, M.; Schmeiser, H.H.; Straif, K.; Wild, C.P. Upper urinary tract urothelial cancer: Where it is A:T. Nat. Rev. 2012, 12, 503–504. [CrossRef]
    • (2012) Nat. Rev , vol.12 , pp. 503-504
    • Olivier, M.1    Hollstein, M.2    Schmeiser, H.H.3    Straif, K.4    Wild, C.P.5
  • 27
    • 0036257348 scopus 로고    scopus 로고
    • Carcinogenic aristolochic acids upon activation by DT-diaphorase form adducts found in DNA of patients with Chinese herbs nephropathy
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Sopko, B.; Wiessler, M.; Schmeiser, H.H. Carcinogenic aristolochic acids upon activation by DT-diaphorase form adducts found in DNA of patients with Chinese herbs nephropathy. Carcinogenesis 2002, 23, 617–625. [CrossRef] [PubMed]
    • (2002) Carcinogenesis , vol.23 , pp. 617-625
    • Stiborová, M.1    Frei, E.2    Sopko, B.3    Wiessler, M.4    Schmeiser, H.H.5
  • 28
    • 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
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Sopko, B.; Sopková, K.; Marková, V.; Laˇnková, M.; Kumstýˇrová, T.; Wiessler, M.; Schmeiser, H.H. Human cytosolic enzymes involved in the metabolic activation of carcinogenic aristolochic acid: Evidence for reductive activation by human NAD(P)H:quinone oxidoreductase. Carcinogenesis 2003, 24, 1695–1703. [CrossRef] [PubMed]
    • (2003) Carcinogenesis , vol.24 , pp. 1695-1703
    • Stiborová, M.1    Frei, E.2    Sopko, B.3    Sopková, K.4    Marková, V.5    Laˇnková, M.6    Kumstýˇrová, T.7    Wiessler, M.8    Schmeiser, H.H.9
  • 29
    • 80051678011 scopus 로고    scopus 로고
    • Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity
    • [CrossRef] [PubMed]
    • Chen, M.; Gong, L.; Qi, X.; Xing, G.; Luan, Y.; Wu, Y.; Xiao, Y.; Yao, J.; Li, Y.; Xue, X. et al. Inhibition of renal NQO1 activity by dicoumarol suppresses nitroreduction of aristolochic acid I and attenuates its nephrotoxicity. Toxicol. Sci. 2011, 122, 288–296. [CrossRef] [PubMed]
    • (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    Xiao, Y.7    Yao, J.8    Li, Y.9    Xue, X.10
  • 30
    • 84898847123 scopus 로고    scopus 로고
    • The influence of dicoumarol on the bioactivation of the carcinogen aristolochic acid I in rats
    • [CrossRef] [PubMed]
    • Stiborová, M.; Levová, K.; Bárta, F.; Šulc, M.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. The influence of dicoumarol on the bioactivation of the carcinogen aristolochic acid I in rats. Mutagenesis 2014, 29, 189–200. [CrossRef] [PubMed]
    • (2014) Mutagenesis , vol.29 , pp. 189-200
    • Stiborová, M.1    Levová, K.2    Bárta, F.3    Šulc, M.4    Frei, E.5    Arlt, V.M.6    Schmeiser, H.H.7
  • 31
    • 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
    • Stiborová, M.; Mareš, J.; Frei, E.; Arlt, V.M.; Martínek, V.; Schmeiser, H.H. 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. 2011, 52, 448–459.
    • (2011) Environ. Mol. Mutagen , vol.52 , pp. 448-459
    • Stiborová, M.1    Mareš, J.2    Frei, E.3    Arlt, V.M.4    Martínek, V.5    Schmeiser, H.H.6
  • 32
    • 84857387612 scopus 로고    scopus 로고
    • Comparison of activation of aristolochic acid I and II with NADPH:Quinone oxidoreductase, sulphotransferases and N-acetyltransferases
    • Martínek, V.; Kubickova, B.; Arlt, V.M.; Frei, E.; Schmeiser, H.H.; Hudeˇcek, J.; Stiborova, M. Comparison of activation of aristolochic acid I and II with NADPH:quinone oxidoreductase, sulphotransferases and N-acetyltransferases. Neuro. Endocrinol. Lett. 2011, 32 (Suppl. 1), S57–S70.
    • (2011) Neuro. Endocrinol. Lett , vol.32 , pp. S57-S70
    • Martínek, V.1    Kubickova, B.2    Arlt, V.M.3    Frei, E.4    Schmeiser, H.H.5    Hudeˇcek, J.6    Stiborova, M.7
  • 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
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Wiessler, M.; Schmeiser, H.H. Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: Evidence for reductive activation by cytochromes P450 1A1 and 1A2. Chem. Res. Toxicol. 2001, 14, 1128–1137. [CrossRef] [PubMed]
    • (2001) Chem. Res. Toxicol , vol.14 , pp. 1128-1137
    • Stiborová, M.1    Frei, E.2    Wiessler, M.3    Schmeiser, H.H.4
  • 35
    • 0035721136 scopus 로고    scopus 로고
    • Carcinogenic and nephrotoxic alkaloids aristolochic acids upon activation by NADPH:Cytochrome P450 reductase form adducts found in DNA of patients with Chinese herbs nephropathy. Gen. Physiol
    • [PubMed]
    • Stiborová, M.; Hájek, M.; Frei, E.; Schmeiser, H.H. Carcinogenic and nephrotoxic alkaloids aristolochic acids upon activation by NADPH:cytochrome P450 reductase form adducts found in DNA of patients with Chinese herbs nephropathy. Gen. Physiol. Biophys. 2001, 20, 375–392. [PubMed]
    • (2001) Biophys , vol.20 , pp. 375-392
    • Stiborová, M.1    Hájek, M.2    Frei, E.3    Schmeiser, H.H.4
  • 36
    • 10344258034 scopus 로고    scopus 로고
    • Human hepatic and renal microsomes, cytochromes P450 1A1/2, NADPH:CYP reductase and prostaglandin H synthase mediate the formation of aristolochic acid DNA-adducts found in patients with urothelial cancer
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Hodek, P.; Wiessler, M.; Schmeiser, H.H. Human hepatic and renal microsomes, cytochromes P450 1A1/2, NADPH:CYP reductase and prostaglandin H synthase mediate the formation of aristolochic acid DNA-adducts found in patients with urothelial cancer. Int. J. Cancer 2005, 113, 189–197. [CrossRef] [PubMed]
    • (2005) Int. J. Cancer , vol.113 , pp. 189-197
    • Stiborová, M.1    Frei, E.2    Hodek, P.3    Wiessler, M.4    Schmeiser, H.H.5
  • 37
    • 84874806270 scopus 로고    scopus 로고
    • Theoretical investigation of differences in nitroreduction of aristolochic acid I by cytochromes P450 1A1, 1A2 and 1B1
    • Jerabek, P.; Martinek, V.; Stiborova, M. Theoretical investigation of differences in nitroreduction of aristolochic acid I by cytochromes P450 1A1, 1A2 and 1B1. Neuro Endocrinol. Lett. 2012, 33 (Suppl. 3), S25–S32.
    • (2012) Neuro Endocrinol. Lett. , vol.33 , pp. S25-S32
    • Jerabek, P.1    Martinek, V.2    Stiborova, M.3
  • 38
    • 84902268459 scopus 로고    scopus 로고
    • Mechanisms of enzyme-catalyzed reduction of two carcinogenic nitro-aromatics, 3-nitrobenzanthrone and aristolochic acid I: Experimental and theoretical approaches
    • [CrossRef] [PubMed]
    • Stiborová, M.; Frei, E.; Schmeiser, H.H.; Arlt, V.M.; Martínek, V. Mechanisms of enzyme-catalyzed reduction of two carcinogenic nitro-aromatics, 3-nitrobenzanthrone and aristolochic acid I: Experimental and theoretical approaches. Int. J. Mol. Sci. 2014, 15, 10271–10295. [CrossRef] [PubMed]
    • (2014) Int. J. Mol. Sci. , vol.15 , pp. 10271-10295
    • Stiborová, M.1    Frei, E.2    Schmeiser, H.H.3    Arlt, V.M.4    Martínek, V.5
  • 39
    • 57149122064 scopus 로고    scopus 로고
    • Human cytochromes P450 1A1 and 1A2 participate in detoxication of carcinogenic aristolochic acid
    • [PubMed]
    • Sistkova, J.; Hudecek, J.; Hodek, P.; Frei, E.; Schmeiser, H.H.; Stiborova, M. Human cytochromes P450 1A1 and 1A2 participate in detoxication of carcinogenic aristolochic acid. Neuro Endocrinol. Lett. 2008, 29, 733–737. [PubMed]
    • (2008) Neuro Endocrinol. 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
  • 40
    • 77950936385 scopus 로고    scopus 로고
    • Cytochrome P450 1A2 detoxicates aristolochic acid in the mouse. Drug Metab
    • [CrossRef] [PubMed]
    • Rosenquist, T.A.; Einolf, H.J.; Dickman, K.G.; Wang, L.; Smith, A.; Grollman, A.P. Cytochrome P450 1A2 detoxicates aristolochic acid in the mouse. Drug Metab. Dispos. 2010, 38, 761–768. [CrossRef] [PubMed]
    • (2010) Dispos , vol.38 , pp. 761-768
    • Rosenquist, T.A.1    Einolf, H.J.2    Dickman, K.G.3    Wang, L.4    Smith, A.5    Grollman, A.P.6
  • 41
    • 77955477610 scopus 로고    scopus 로고
    • Detoxification of aristolochic acid I by O-demethylation: Less nephrotoxicity and genotoxicity of aristolochic acid Ia in rodents
    • [CrossRef] [PubMed]
    • Shibutani, S.; Bonala, R.R.; Rosenquist, T.; Rieger, R.; Suzuki, N.; Johnson, F.; Miller, F.; Grollman, A.P. Detoxification of aristolochic acid I by O-demethylation: Less nephrotoxicity and genotoxicity of aristolochic acid Ia in rodents. Int. J. Cancer 2010, 127, 1021–1027. [CrossRef] [PubMed]
    • (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    Miller, F.7    Grollman, A.P.8
  • 42
    • 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
    • [CrossRef] [PubMed]
    • Arlt, V.M.; Levova, K.; Barta, F.; Shi, Z.; Evans, J.D.; Frei, E.; Schmeiser, H.H.; Nebert, D.W.; Phillips, D.H.; Stiborova, M. 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. 2011, 24, 1710–1719. [CrossRef] [PubMed]
    • (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    Schmeiser, H.H.7    Nebert, D.W.8    Phillips, D.H.9    Stiborova, M.10
  • 43
    • 84856118524 scopus 로고    scopus 로고
    • Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2
    • [CrossRef] [PubMed]
    • Stiborová, M.; Levová, K.; Bárta, F.; Shi, Z.; Frei, E.; Schmeiser, H.H.; Nebert, D.W.; Phillips, D.H.; Arlt, V.M. Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2. Toxicol. Sci. 2012, 125, 345–358. [CrossRef] [PubMed]
    • (2012) Toxicol. Sci , vol.125 , pp. 345-358
    • Stiborová, M.1    Levová, K.2    Bárta, F.3    Shi, Z.4    Frei, E.5    Schmeiser, H.H.6    Nebert, D.W.7    Phillips, D.H.8    Arlt, V.M.9
  • 44
    • 84947564784 scopus 로고    scopus 로고
    • Contributions of cytochromes P450 to detoxification of a human carcinogen aristolochic acid I in human and rat livers: Experimental and theoretical approaches
    • [CrossRef] [PubMed]
    • Stiborová, M.; Bárta, F.; Levová, K.; Hodek, P.; Schmeiser, H.H.; Arlt, V.M.; Martínek, V. Contributions of cytochromes P450 to detoxification of a human carcinogen aristolochic acid I in human and rat livers: Experimental and theoretical approaches. Int. J. Mol. Sci. 2015, 16, 27561–27575. [CrossRef] [PubMed]
    • (2015) Int. J. Mol. Sci. , vol.16 , pp. 27561-27575
    • Stiborová, M.1    Bárta, F.2    Levová, K.3    Hodek, P.4    Schmeiser, H.H.5    Arlt, V.M.6    Martínek, V.7
  • 45
    • 79957765003 scopus 로고    scopus 로고
    • The directive of the protein: How does cytochrome P450 select the mechanism of dopamine formation
    • [CrossRef] [PubMed]
    • Schyman, P.; Lai, W.; Chen, H.; Wang, Y.; Shaik, S. The directive of the protein: How does cytochrome P450 select the mechanism of dopamine formation? J. Am. Chem. Soc. 2011, 133, 7977–7984. [CrossRef] [PubMed]
    • (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
  • 46
    • 0033814819 scopus 로고    scopus 로고
    • Purification of proteins using polyhistidine affinity tags
    • [PubMed]
    • Bornhorst, J.A.; Falke, J.J. Purification of proteins using polyhistidine affinity tags. Methods Enzymol. 2000, 326, 245–254. [PubMed]
    • (2000) Methods Enzymol , vol.326 , pp. 245-254
    • Bornhorst, J.A.1    Falke, J.J.2
  • 47
    • 0034687092 scopus 로고    scopus 로고
    • Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants
    • [CrossRef] [PubMed]
    • Yun, C.H.; Miller, G.P.; Guengerich, F.P. Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants. Biochemistry 2000, 39, 11319–11329. [CrossRef] [PubMed]
    • (2000) Biochemistry , vol.39 , pp. 11319-11329
    • Yun, C.H.1    Miller, G.P.2    Guengerich, F.P.3
  • 48
    • 0024518203 scopus 로고
    • Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis
    • [PubMed]
    • Shen, A.L.; Porter, T.D.; Wilson, T.E.; Kasper, C.B. Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis. J. Biol. Chem. 1989, 264, 7584–7589. [PubMed]
    • (1989) J. Biol. Chem , vol.264 , pp. 7584-7589
    • Shen, A.L.1    Porter, T.D.2    Wilson, T.E.3    Kasper, C.B.4
  • 49
    • 0016333916 scopus 로고
    • Ethoxyresorufin: Direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab
    • [PubMed]
    • Burke, M.D.; Mayer, R.T. Ethoxyresorufin: Direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab. Dispos. 1974, 2, 583–588. [PubMed]
    • (1974) Dispos , vol.2 , pp. 583-588
    • Burke, M.D.1    Mayer, R.T.2
  • 50
    • 0037108678 scopus 로고    scopus 로고
    • Is a potential carcinogen for humans: Evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes
    • [PubMed]
    • Stiborová, M.; Martínek, V.; Rýdlová, H.; Hodek, P.; Frei, E. 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. 2002, 62, 5678–5684. [PubMed]
    • (2002) Cancer Res , vol.62 , pp. 5678-5684
    • Stiborová, M.1    Martínek, V.2    Rýdlová, H.3    Hodek, P.4    Frei, E.5    Sudan, I.6
  • 51
    • 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. Toxicol
    • [CrossRef] [PubMed]
    • Levová, K.; Mizerovská, M.; Kotrbová, V.; Šulc, M.; Henderson, C.J.; Wolf, C.R.; Philips, D.H.; Frei, E.; Schmeiser, H.H.; Mareš, J. et al. 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. 2011, 121, 43–56. [CrossRef] [PubMed]
    • (2011) Sci , vol.121 , pp. 43-56
    • Levová, K.1    Mizerovská, M.2    Kotrbová, V.3    Šulc, M.4    Henderson, C.J.5    Wolf, C.R.6    Philips, D.H.7    Frei, E.8    Schmeiser, H.H.9    Mareš, J.10
  • 52
    • 26444446947 scopus 로고    scopus 로고
    • The binding of aristolochic acid I to the active site of human cytochromes P450 1A1 and 1A2 explains their potential to reductively activate this human carcinogen
    • [CrossRef] [PubMed]
    • Stiborová, M.; Sopko, B.; Hodek, P.; Frei, E.; Schmeiser, H.H.; Hudeˇcek, J. The binding of aristolochic acid I to the active site of human cytochromes P450 1A1 and 1A2 explains their potential to reductively activate this human carcinogen. Cancer Lett. 2005, 229, 193–204. [CrossRef] [PubMed]
    • (2005) Cancer Lett , vol.229 , pp. 193-204
    • Stiborová, M.1    Sopko, B.2    Hodek, P.3    Frei, E.4    Schmeiser, H.H.5    Hudeˇcek, J.6
  • 53
    • 0031284662 scopus 로고    scopus 로고
    • 32P-postlabelling analysis of DNA adducts formed by aristolochic acid in tissues from patients with Chinese herbs nephropathy
    • [CrossRef] [PubMed]
    • Bieler, C.A.; Stiborová, M.; Wiessler, M.; Cosyns, J.-P.; van Ypersele Strihou, C.; Schmeiser, H.H. 32P-postlabelling analysis of DNA adducts formed by aristolochic acid in tissues from patients with Chinese herbs nephropathy. Carcinogenesis 1997, 18, 1063–1067. [CrossRef] [PubMed]
    • (1997) Carcinogenesis , vol.18 , pp. 1063-1067
    • Bieler, C.A.1    Stiborová, M.2    Wiessler, M.3    Cosyns, J.-P.4    Van Ypersele Strihou, C.5    Schmeiser, H.H.6
  • 55
    • 0028071497 scopus 로고
    • Expression of modified human cytochrome P450 1A1 in Escherichia coli: Effects of 5’ substitution, stabilization, purification, spectral characterization, and catalytic properties. Arch. Biochem
    • [CrossRef] [PubMed]
    • Guo, Z.; Gillam, E.M.; Ohmori, S.; Tukey, R.H.; Guengerich, F.P. Expression of modified human cytochrome P450 1A1 in Escherichia coli: Effects of 5’ substitution, stabilization, purification, spectral characterization, and catalytic properties. Arch. Biochem. Biophys. 1994, 312, 436–446. [CrossRef] [PubMed]
    • (1994) Biophys , vol.312 , pp. 436-446
    • Guo, Z.1    Gillam, E.M.2    Ohmori, S.3    Tukey, R.H.4    Guengerich, F.P.5
  • 56
    • 0028358220 scopus 로고
    • Expression of modified human cytochrome P450 1A2 in Escherichia coli: Stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch. Biochem
    • [CrossRef] [PubMed]
    • Sandhu, P.; Guo, Z.; Baba, T.; Martin, M.V.; Tukey, R.H.; Guengerich, F.P. Expression of modified human cytochrome P450 1A2 in Escherichia coli: Stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch. Biochem. Biophys. 1994, 309, 168–177. [CrossRef] [PubMed]
    • (1994) Biophys , vol.309 , pp. 168-177
    • Sandhu, P.1    Guo, Z.2    Baba, T.3    Martin, M.V.4    Tukey, R.H.5    Guengerich, F.P.6
  • 57
    • 0032168855 scopus 로고    scopus 로고
    • Recombinant human cytochrome P450 1B1 expression in Escherichia coli. Arch
    • [CrossRef] [PubMed]
    • Shimada, T.; Wunsch, R.M.; Hanna, I.H.; Sutter, T.R.; Guengerich, F.P.; Gillam, E.M.J. Recombinant human cytochrome P450 1B1 expression in Escherichia coli. Arch. Biochem. Biophys. 1998, 357, 111–120. [CrossRef] [PubMed]
    • (1998) Biochem. Biophys , vol.357 , pp. 111-120
    • Shimada, T.1    Wunsch, R.M.2    Hanna, I.H.3    Sutter, T.R.4    Guengerich, F.P.5    Gillam, E.6
  • 58
    • 84957594188 scopus 로고    scopus 로고
    • The Human Cytochrome P450 (CYP): Allele Nomenclature Database, accessed on 29 January 2016
    • The Human Cytochrome P450 (CYP): Allele Nomenclature Database. Available online: http://www.cypalleles.ki.se/ (accessed on 29 January 2016).
  • 59
    • 0031041652 scopus 로고    scopus 로고
    • Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4: Role of residues 210 and 211 in flavonoid activation and substrate specifity
    • [CrossRef] [PubMed]
    • Harlow, G.R.; Halpert, J.R. Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4: Role of residues 210 and 211 in flavonoid activation and substrate specifity. J. Biol. Chem. 1997, 272, 5396–5402. [CrossRef] [PubMed]
    • (1997) J. Biol. Chem , vol.272 , pp. 5396-5402
    • Harlow, G.R.1    Halpert, J.R.2
  • 60
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes: I Evidence for its hemoprotein nature
    • [PubMed]
    • Omura, T.; Sato, R. The carbon monoxide-binding pigment of liver microsomes: I Evidence for its hemoprotein nature. J. Biol. Chem. 1964, 239, 2370–2378. [PubMed]
    • (1964) J. Biol. Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 62
    • 84884943157 scopus 로고    scopus 로고
    • The relationship between DNA adduct formation by benzo[a]pyrene and expression of its activation enzyme cytochrome P450 1A1 in rats. Environ. Toxicol
    • [CrossRef] [PubMed]
    • Hodek, P.; Koblihova, J.; Kizek, R.; Frei, E.; Arlt, V.M.; Stiborova, M. The relationship between DNA adduct formation by benzo[a]pyrene and expression of its activation enzyme cytochrome P450 1A1 in rats. Environ. Toxicol. Pharmacol. 2013, 36, 989–996. [CrossRef] [PubMed]
    • (2013) Pharmacol , vol.36 , pp. 989-996
    • Hodek, P.1    Koblihova, J.2    Kizek, R.3    Frei, E.4    Arlt, V.M.5    Stiborova, M.6
  • 63
    • 0035894174 scopus 로고    scopus 로고
    • The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem
    • [CrossRef]
    • Stiborová, M.; Bieler, C.A.; Wiessler, M.; Frei, E. The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem. Pharmacol. 2001, 62, 1675–1684. [CrossRef]
    • (2001) Pharmacol , vol.62 , pp. 1675-1684
    • Stiborová, M.1    Bieler, C.A.2    Wiessler, M.3    Frei, E.4
  • 64
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem
    • [CrossRef] [PubMed]
    • Guengerich, F.P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 2001, 14, 611–650. [CrossRef] [PubMed]
    • (2001) Res. Toxicol , vol.14 , pp. 611-650
    • Guengerich, F.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.