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Contributions of Human Enzymes in Carcinogen Metabolism

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Rendic, Slobodan, Guengerich, F. Peter·2012·Chemical Research in Toxicology

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Abstract

Considerable support exists for the roles of metabolism in modulating the carcinogenic properties of chemicals. In particular, many of these compounds are pro-carcinogens that require activation to electrophilic forms to exert genotoxic effects. We systematically analyzed the existing literature on the metabolism of carcinogens by human enzymes, which has been developed largely in the past 25 years. The metabolism and especially bioactivation of carcinogens are dominated by cytochrome P450 enzymes (66% of bioactivations). Within this group, six P450s--1A1, 1A2, 1B1, 2A6, 2E1, and 3A4--accounted for 77% of the P450 activation reactions. The roles of these P450s can be compared with those estimated for drug metabolism and should be considered in issues involving enzyme induction, chemoprevention, molecular epidemiology, interindividual variations, and risk assessment.

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Items 201–314 of 314

Metabolic activation of the potent carcinogen dibenzo[a, l]pyrene by human recombinant cytochromes P450, lung and liver microsomes
Shou, M., Krausz, K. W., Gonzalez, F. J., & Gelboin, H. V. (1996) · Carcinogenesis · doi:10.1093/carcin/17.11.2429 · Cited by 68
Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases
Chou, H., Lang, N. P., & Kadlubar, F. F. (1995) · Carcinogenesis · doi:10.1093/carcin/16.2.413 · Cited by 67
Human Cytochrome P450 Enzymes of Importance for the Bioactivation of Methyleugenol to the Proximate Carcinogen 1‘-Hydroxymethyleugenol
Jeurissen, S. M. F., Bogaards, J. J. P., Boersma, M. G., et al. (2005) · Chemical Research in Toxicology · doi:10.1021/tx050267h · Cited by 67
ATF4 and the integrated stress response are induced by ethanol and cytochrome P450 2E1 in human hepatocytes
Magne, L., Blanc, É., Legrand, B., Lucas, D., Barouki, R., Rouach, H., & Garlatti, M. (2010) · Journal of Hepatology · doi:10.1016/j.jhep.2010.07.023 · Cited by 67
Hydroxymethyl-substituted furans: mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases
Glatt, H. R., Schneider, H., Murkovic, M., Monien, B. H., & Meinl, W. (2011) · Mutagenesis · doi:10.1093/mutage/ger054 · Cited by 67
Bioactivation of diesel exhaust particle extracts and their major nitrated polycyclic aromatic hydrocarbon components, 1-nitropyrene and dinitropyrenes, by human cytochromes P450 1A1, 1A2, and 1B1
Yamazaki, H., Hatanaka, N., Kizu, R., Hayakawa, K., Shimada, N., Guengerich, F. P., Nakajima, M., & Yokoi, T. (2000) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/s1383-5718(00)00138-8 · Cited by 66
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Contribution of human cytochrome P450 to benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol metabolism, as predicted from heterologous expression in yeast
Gautier, J., Lecoeur, S., Cosme, J., Perret, A., Urban, P., Beaune, P. H., & Pompon, D. (1996) · Pharmacogenetics · doi:10.1097/00008571-199612000-00002 · Cited by 66
Production of DNA strand breaks by N-nitrosodimethylamine and 2-amino-3-methylimidazo[4,5-f]quinoline in THLE cells expressing human CYP isoenzymes and inhibition by sulforaphane
Barcelo, S., Macé, K., Pfeifer, A. M. A., & Chipman, J. K. (1998) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/s0027-5107(97)00288-1 · Cited by 65
A Potential Role for the Estrogen-metabolizing Cytochrome P450 Enzymes in Human Breast Carcinogenesis
Modugno, F., Knoll, C. A., Kanbour‐Shakir, A., & Romkes, M. (2003) · Breast Cancer Research and Treatment · doi:10.1023/b:brea.0000004376.21491.44 · Cited by 65
Competing Roles of Cytochrome P450 1A1/1B1 and Aldo−Keto Reductase 1A1 in the Metabolic Activation of (±)-7,8-Dihydroxy-7,8-dihydro-benzo[a]pyrene in Human Bronchoalveolar Cell Extracts
Jiang, H., Shen, Y.-M., Quinn, A. M., & Penning, T. M. (2005) · Chemical Research in Toxicology · doi:10.1021/tx0497245 · Cited by 65
Glucuronidation of PhIP and N-OH-PhIP by UDP-glucuronosyltransferase 1A10
Dellinger, R. W., Chen, G., Blevins‐Primeau, A. S., Krzeminski, J., AMIN, S. G., & Lazarus, P. (2007) · Carcinogenesis · doi:10.1093/carcin/bgm164 · Cited by 65
Differential activation of promutagens by alloenzymes of human sulfotransferase 1A2 expressed in Salmonella typhimurium
Meinl, W., Meerman, J. H. N., & Glatt, H. R. (2002) · Pharmacogenetics · doi:10.1097/00008571-200212000-00002 · Cited by 63
Metabolic activation of heterocyclic aromatic amines catalyzed by human arylamine N-acetyltransferase isozymes (NAT1 and NAT2) expressed in Salmonella typhimurium
WILD, D., Feser, W., Michel, S., et al. (1995) · Carcinogenesis · doi:10.1093/carcin/16.3.643 · Cited by 63
Investigation of the mechanistic basis of N,N-dimethylformamide toxicity. Metabolism of N,N-dimethylformamide and its deuterated isotopomers by cytochrome P450 2E1
Mráz, J., Jheeta, P., Gescher, A., Hyland, R., Thummel, K. E., & Threadgill, M. D. (1993) · Chemical Research in Toxicology · doi:10.1021/tx00032a009 · Cited by 62
Cytochrome P450- and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency
Stiborová, M., Rupertová, M., & Frei, E. (2010) · Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics · doi:10.1016/j.bbapap.2010.05.016 · Cited by 62
BIOTRANSFORMATION OF 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE (NNK) IN PERIPHERAL HUMAN LUNG MICROSOMES
Smith, G. B. J., Bend, J. R., Bedard, L. L., Reid, K. R., Petsikas, D., & Massey, T. E. (2003) · Drug Metabolism and Disposition · doi:10.1124/dmd.31.9.1134 · Cited by 61
Experimentelle studie uber die pathogenese der epithelialgeschwulste
Yamagiwa, K. (1915) · Cited by 61
Metabolism of Chloroform in the Human Liver and Identification of the Competent P450s
Gemma, S., Vittozzi, L., & Testai, E. (2003) · Drug Metabolism and Disposition · doi:10.1124/dmd.31.3.266 · Cited by 60
Size Limits of Thiocarbamides Accepted as Substrates by Human Flavin-Containing Monooxygenase 1
Kim, Y. M., & Ziegler, D. M. (2000) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(24)15176-8 · Cited by 60
Characterization of a human cell line expressing high levels of cDNA-derived CYP2D6
Penman, B. W., Reece, J., Smith, T. J., Yang, C., Gelboin, H. V., Gonzalez, F. J., & Crespi, C. L. (1993) · Pharmacogenetics · doi:10.1097/00008571-199302000-00003 · Cited by 59
Lack of evidence for metabolism of p-phenylenediamine by human hepatic cytochrome P450 enzymes
Stanley, L. A., Skare, J. A., Doyle, E., Powrie, R. H., D’Angelo, D., & Elcombe, C. R. (2005) · Toxicology · doi:10.1016/j.tox.2005.01.019 · Cited by 59
ROLE OF HUMAN CYTOCHROME P450 (CYP) IN THE METABOLIC ACTIVATION OF NITROSAMINE DERIVATIVES: APPLICATION OF GENETICALLY ENGINEEREDSALMONELLAEXPRESSING HUMAN CYP
Kamataki, T., Fujita, K., Nakayama, K., Yamazaki, Y., Miyamoto, M., & Ariyoshi, N. (2002) · Drug Metabolism Reviews · doi:10.1081/dmr-120005668 · Cited by 58
Bioactivation of 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone: evidence for DNA adduct formation mediated by cytochrome P450 enzymes and peroxidases
Arlt, V. M., Henderson, C. J., Wolf, C. R., Schmeiser, H. H., Phillips, D. H., & Stiborová, M. (2005) · Cancer Letters · doi:10.1016/j.canlet.2005.03.035 · Cited by 58
In vitro-in vivo correlations of human (s)-nicotine metabolism
Berkman, C. E., Park, S. B., Wrighton, S. A., & Cashman, J. R. (1995) · Biochemical Pharmacology · doi:10.1016/0006-2952(95)00168-y · Cited by 57
Evaluation of Xenobiotic N- and S-Oxidation by Variant Flavin-Containing Monooxygenase 1 (FMO1) Enzymes
Furnes, B. (2004) · Toxicological Sciences · doi:10.1093/toxsci/kfh079 · Cited by 56
METABOLISM AND CYTOTOXICITY OF AFLATOXIN B 1 IN CYTOCHROME P-450-EXPRESSING HUMAN LUNG CELLS
Vleet, T. R. V., Klein, P. J., & Coulombe, R. A. (2002) · Journal of Toxicology and Environmental Health · doi:10.1080/00984100290071216 · Cited by 55
Characterization of human soluble high and low activity catechol-O-methyltransferase catalyzed catechol estrogen methylation
Goodman, J. E., Jensen, L. T., He, P., & Yager, J. D. (2002) · Pharmacogenetics · doi:10.1097/00008571-200210000-00003 · Cited by 55
Characterization of Common CYP1B1 Variants with Different Capacity for Benzo[a]pyrene-7,8-Dihydrodiol Epoxide Formation from Benzo[a]pyrene
Aklillu, E., Øvrebø, S., Botnen, I. V., Otter, C. A., & Ingelman‐Sundberg, M. (2005) · Cancer Research · doi:10.1158/0008-5472.can-05-0113 · Cited by 55
The contribution of UDP-glucuronosyltransferase 1A9 on CYP1A2-mediated genotoxicity by aromatic and heterocyclic amines
Yueh, M. (2001) · Carcinogenesis · doi:10.1093/carcin/22.6.943 · Cited by 55
Metabolic activation of furfuryl alcohol: formation of 2-methylfuranyl DNA adducts in Salmonella typhimurium strains expressing human sulfotransferase 1A1 and in FVB/N mice
Monien, B. H., Herrmann, K., Florian, S., et al. (2011) · Carcinogenesis · doi:10.1093/carcin/bgr126 · Cited by 55
Covalent binding of the anticancer drug ellipticine to DNA in V79 cells transfected with human cytochrome P450 enzymes
Frei, E., Bieler, C. A., Arlt, V. M., Wießler, M., & Stiborová, M. (2002) · Biochemical Pharmacology · doi:10.1016/s0006-2952(02)01072-9 · Cited by 54
Role of cytochrome P450 in estradiol metabolism in vitro.
Cheng, Z., Shu, Y., Liu, Z., Wang, L., Ouyang, D., & Zhou, H.-H. (2001) · PubMed · Cited by 54
N-Nitrosodimethylamine-Mediated Cytotoxicity in a Cell Line Expressing P450 2E1: Evidence for Apoptotic Cell Death
Lin, H.-L., Parsels, L. A., Maybaum, J., et al. (1999) · Toxicology and Applied Pharmacology · doi:10.1006/taap.1999.8651 · Cited by 53
Update Information on Drug Metabolism Systems— 2009, Part I
Guengerich, F. P., & Rendić, S. (2010) · Current Drug Metabolism · doi:10.2174/138920010791110908 · Cited by 53
Self-citation
The mode of cisplatin-induced cell death in CYP2E1-overexpressing HepG2 cells: Modulation by ERK, ROS, glutathione, and thioredoxin
Lu, Y., & Cederbaum, A. I. (2007) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2007.06.021 · Cited by 52
Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA
Jacobson, P. A., Green, K., Birnbaum, A. K., et al. (2002) · Cancer Chemotherapy and Pharmacology · doi:10.1007/s00280-002-0453-3 · Cited by 52
Gastrointestinally Distributed UDP-glucuronosyltransferase 1A10, Which Metabolizes Estrogens and Nonsteroidal Anti-inflammatory Drugs, Depends upon Phosphorylation
Basu, N. K., Kubota, S., Meselhy, M. R., Ciotti, M., Chowdhury, B., Hartori, M., & Owens, I. S. (2004) · Journal of Biological Chemistry · doi:10.1074/jbc.m401396200 · Cited by 51
Paradoxical Enhancement of the Toxicity of 1,2-Dibromoethane byO 6-Alkylguanine-DNA Alkyltransferase
Liu, L., Pegg, A. E., Williams, K. M., & Guengerich, F. P. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m205548200 · Cited by 50
Self-citation
Elucidation of Catalytic Specificities of Human Cytochrome P450 and Glutathione S-Transferase Enzymes and Relevance to Molecular Epidemiology
Guengerich, F. P., Shimada, T., Raney, K. D., Yun, C., Meyer, D. J., KETTERER, B., Harris, T. M., Groopman, J. D., & Kadlubar, F. F. (1992) · Environmental Health Perspectives · doi:10.1289/ehp.929875 · Cited by 50
Self-citation
Quaternary ammonium-linked glucuronidation of trans-4-hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4
Ogura, K., Ishikawa, Y. T., Kaku, T., Nishiyama, T., Ohnuma, T., Muro, K., & Hiratsuka, A. (2006) · Biochemical Pharmacology · doi:10.1016/j.bcp.2006.01.004 · Cited by 50
Thiourea toxicity in mouse C3H/10T12 cells expressing human flavin-dependent monooxygenase 3
Smith, P. B., & Crespi, C. L. (2002) · Biochemical Pharmacology · doi:10.1016/s0006-2952(02)00978-4 · Cited by 49
Cytochrome b5 shifts oxidation of the anticancer drug ellipticine by cytochromes P450 1A1 and 1A2 from its detoxication to activation, thereby modulating its pharmacological efficacy
Černá, V., Mrázová, B., Moserová, M., Martínek, V., Hodek, P., Hudeček, J., Frei, E., & Stiborová, M. (2011) · Biochemical Pharmacology · doi:10.1016/j.bcp.2011.06.003 · Cited by 49
Interspecies differences in metabolism of heterocyclic aromatic amines by rat and human P450 1A2
Turesky, R. J., Constable, A., Fay, L. B., & Guengerich, F. P. (1999) · Cancer Letters · doi:10.1016/s0304-3835(99)00137-8 · Cited by 49
Self-citation
Functional Characterization of Human Cytochrome P450 2S1 Using a Synthetic Gene-Expressed Protein in Escherichia coli
Bui, P. H., & Hankinson, O. (2009) · Molecular Pharmacology · doi:10.1124/mol.109.057752 · Cited by 49
Fatty Acid Hydroperoxides Support Cytochrome P450 2S1-Mediated Bioactivation of Benzo[a]pyrene-7,8-dihydrodiol
Bui, P. H., Hsu, E. L., & Hankinson, O. (2009) · Molecular Pharmacology · doi:10.1124/mol.109.057760 · Cited by 49
Activation of Dihaloalkanes by Thiol-dependent Mechanisms
Guengerich, F. P. (2003) · BMB Reports · doi:10.5483/bmbrep.2003.36.1.020 · Cited by 48
Self-citation
Bioactivation of Tamoxifen by Recombinant Human Cytochrome P450 Enzymes
Notley, L. M., de Wolf, C. J. F., Wunsch, R. M., Lancaster, R. G., & Gillam, E. M. J. (2002) · Chemical Research in Toxicology · doi:10.1021/tx0100439 · Cited by 47
Expression of Cytochrome P450 3A7 inEscherichia coli:Effects of 5′ Modification and Catalytic Characterization of Recombinant Enzyme Expressed in Bicistronic Format with NADPH-Cytochrome P450 Reductase
Gillam, E. M. J., Wunsch, R. M., Ueng, Y., Shimada, T., Reilly, P. E. B., Kamataki, T., & Guengerich, F. P. (1997) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1997.0286 · Cited by 47
Self-citation
IDENTIFICATION OF CRITICAL AMINO ACID RESIDUES OF HUMAN CYP2A13 FOR THE METABOLIC ACTIVATION OF 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE, A TOBACCO-SPECIFIC CARCINOGEN
He, X., Shen, J., Ding, X., Lu, A. Y. H., & Hong, J. (2004) · Drug Metabolism and Disposition · doi:10.1124/dmd.104.001370 · Cited by 47
CYP2E1-dependent hepatotoxicity and oxidative damage after ethanol administration in human primary hepatocytes
Liu, L. (2005) · World Journal of Gastroenterology · doi:10.3748/wjg.v11.i29.4530 · Cited by 46
Aldo-Keto Reductases and Formation of Polycyclic Aromatic Hydrocarbon o-Quinones
Penning, T. M. (2004) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(04)78003-9 · Cited by 46
Mutagenicity and DNA Adduct Formation by the Urban Air Pollutant 2-Nitrobenzanthrone
Arlt, V. M., Glatt, H. R., da Costa, G. G., Reynisson, J., Takamura‐Enya, T., & Phillips, D. H. (2007) · Toxicological Sciences · doi:10.1093/toxsci/kfm103 · Cited by 46
Comparative aflatoxin B(1) activation and cytotoxicity in human bronchial cells expressing cytochromes P450 1A2 and 3A4.
Vleet, T. R. V., Macé, K., & Coulombe, R. A. (2002) · PubMed · Cited by 46
Activation of bis-Electrophiles to Mutagenic Conjugates by Human O6-Alkylguanine-DNA Alkyltransferase
Valadez, J. G., Liu, L., Loktionova, N. A., Pegg, A. E., & Guengerich, F. P. (2004) · Chemical Research in Toxicology · doi:10.1021/tx049897u · Cited by 45
Self-citation
Human glutathione S-transferase-expressing Salmonella typhimurium tester strains to study the activation/detoxification of mutagenic compounds: studies with halogenated compounds, aromatic amines and aflatoxin B1
Simula, T. P., Glancey, M. J., & Wolf, C. R. (1993) · Carcinogenesis · doi:10.1093/carcin/14.7.1371 · Cited by 45
The sparteine/debrisoquine (CYP2D6) oxidation polymorphism and the risk of lung cancer: A meta- analysis
Christensen, P. M., Gøtzsche, P. C., & Brøsen, K. (1997) · European Journal of Clinical Pharmacology · doi:10.1007/s002280050219 · Cited by 45
Dynamics of Glutathione Conjugation and Conjugate Efflux in Detoxification of the Carcinogen, 4-Nitroquinoline 1-Oxide: Contributions of Glutathione, GlutathioneS-Transferase, and MRP1
Peklak-Scott, C., Townsend, A. J., & Morrow, C. S. (2005) · Biochemistry · doi:10.1021/bi047810y · Cited by 44
Metabolic activation of phenanthrene by human and mouse cytochromes P450 and pharmacokinetics in CYP1A2 knockout mice
Schöber, W., Pusch, G., Oeder, S., Reindl, H., Behrendt, H., & Buters, J. (2009) · Chemico-Biological Interactions · doi:10.1016/j.cbi.2009.09.008 · Cited by 44
A Transgenic Mouse Expressing Human CYP4B1 in the Liver
Imaoka, S., Hayashi, K., Hiroi, T., Yabusaki, Y., Kamataki, T., & Funae, Y. (2001) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.2001.5055 · Cited by 43
Competing Roles of Aldo-Keto Reductase 1A1 and Cytochrome P4501B1 in Benzo[a]pyrene-7,8-diol Activation in Human Bronchoalveolar H358 Cells: Role of AKRs in P4501B1 Induction
Jiang, H., Vudathala, D. K., Blair, I. A., & Penning, T. M. (2005) · Chemical Research in Toxicology · doi:10.1021/tx0502488 · Cited by 42
Rapid induction of colon carcinogenesis in CYP1A-humanized mice by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and dextran sodium sulfate
Cheung, C., Loy, S., Li, G. X., Liu, A. B., & Yang, C. S. (2010) · Carcinogenesis · doi:10.1093/carcin/bgq235 · Cited by 42
Identification of a genotoxic mechanism for the carcinogenicity of the environmental pollutant and suspected human carcinogeno-anisidine
Stiborová, M., Martínková, M., Šulc, M., Dračínská, H., Schmeiser, H. H., & Frei, E. (2005) · International Journal of Cancer · doi:10.1002/ijc.21122 · Cited by 41
High promutagen activating capacity of yeast microsomes containing human cytochrome P-450 1A and human NADPH-cytochrome P-450 reductase
Sengstag, C., Eugster, H., & Würgler, F. E. (1994) · Carcinogenesis · doi:10.1093/carcin/15.5.837 · Cited by 40
Characterizing Proteins of Unknown Function: Orphan Cytochrome P450 Enzymes as a Paradigm
Guengerich, F. P., Tang, Z., Salamanca-Pinzon, S. G., & Cheng, Q. (2010) · Molecular Interventions · doi:10.1124/mi.10.3.6 · Cited by 40
Self-citation
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
Stiborová, M., Sopko, B., Hodek, P., Frei, E., Schmeiser, H. H., & Hudeček, J. (2005) · Cancer Letters · doi:10.1016/j.canlet.2005.06.038 · Cited by 40
Risk assessment: toxicity from chemical exposure resulting from enhanced expression of CYP2E1
Raucy, J. L. (1995) · Toxicology · doi:10.1016/0300-483x(95)03216-3 · Cited by 40
Metabolism of Ethyl Carbamate by Pulmonary Cytochrome P450 and Carboxylesterase Isozymes: Involvement of CYP2E1 and Hydrolase A
Forkert, P., & Lee, R. P. (1997) · Toxicology and Applied Pharmacology · doi:10.1006/taap.1997.8233 · Cited by 39
Metabolic oxidation and toxification of N-methylformamide catalyzed by the cytochrome P450 isoenzyme CYP2E1.
Hyland, R., Gescher, A., Thummel, K. E., Schiller, C., Jheeta, P., Mynett, K. J., Smith, A. W., & Mráz, J. (1992) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)08872-8 · Cited by 39
Advantages of Human Hepatocyte-Derived Transformants Expressing a Series of Human Cytochrome P450 Isoforms for Genotoxicity Examination
Hashizume, T., Yoshitomi, S., Asahi, S., Uematsu, R., Matsumura, S., Chatani, F., & Oda, H. (2010) · Toxicological Sciences · doi:10.1093/toxsci/kfq154 · Cited by 36
2-Amino-3,8-Dimethylimidazo-[4,5-f]Quinoxaline–Induced DNA Adduct Formation and Mutagenesis in DNA Repair–Deficient Chinese Hamster Ovary Cells Expressing Human Cytochrome P4501A1 and Rapid or Slow AcetylatorN-Acetyltransferase 2
Bendaly, J., Zhao, S., Neale, J. R., Metry, K. J., Doll, M. A., States, J. C., Pierce, W. M. J., & Hein, D. W. (2007) · Cancer Epidemiology Biomarkers & Prevention · doi:10.1158/1055-9965.epi-07-0305 · Cited by 35
Use of genetically manipulated Salmonella typhimurium strains to evaluate the role of sulfotransferases and acetyltransferases in nitrofen mutagenicity
Glatt, H. R. (2003) · Carcinogenesis · doi:10.1093/carcin/bgh070 · Cited by 35
Characterization of UDP-glucuronosyltransferase 2A1 (UGT2A1) variants and their potential role in tobacco carcinogenesis
Bushey, R. T., Chen, G., Blevins‐Primeau, A. S., Krzeminski, J., Amin, S., & Lazarus, P. J. (2010) · Pharmacogenetics and Genomics · doi:10.1097/fpc.0b013e328341db05 · Cited by 34
Oxidation pattern of the anticancer drug ellipticine by hepatic microsomes - similarity between human and rat systems.
Stiborová, M., Bořek-Dohalská, L., Aimová, D., Kotrbová, V., Kukacková, K., Janouchová, K., Rupertová, M., Ryšlavá, H., Hudeček, J., & Frei, E. (2006) · PubMed · Cited by 33
Expression of sulfotransferase isoform 1A1 (SULT1A1) in breast cancer cells significantly increases 4-hydroxytamoxifen-induced apoptosis.
Mercer, K. E., Apostolov, E. O., da Costa, G. G., Yu, X., Lang, P. Y., Roberts, D. W., Davis, W., Basnakian, A. G., Kadlubar, F. F., & Kadlubar, S. A. (2010) · PubMed · Cited by 32
Reductive Detoxification of Arylhydroxylamine Carcinogens by Human NADH Cytochrome b5 Reductase and Cytochrome b5
Kurian, J. R., Chin, N. A., Longlais, B. J., Hayes, K., & Trepanier, L. A. (2006) · Chemical Research in Toxicology · doi:10.1021/tx060106t · Cited by 32
The stimulatory role of human cytochrome b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a new cell expression system to study cytochrome P450 mediated biotransformation
Duarte, M. P., Palma, B. B., Gilep, A. A., Laires, A., Oliveira, J. S., Usanov, S. A., Rueff, J., & Kranendonk, M. (2005) · Mutagenesis · doi:10.1093/mutage/gei012 · Cited by 31
Genotoxicity of acrylamide in vitro: Acrylamide is not metabolically activated in standard in vitro systems
Koyama, N., Yasui, M., Oda, Y., Suzuki, S., Satoh, T., Suzuki, T., Matsuda, T., Masuda, S., Kinae, N., & Honma, M. (2010) · Environmental and Molecular Mutagenesis · doi:10.1002/em.20560 · Cited by 30
In vitro micronucleus test in HepG2 transformants expressing a series of human cytochrome P450 isoforms with chemicals requiring metabolic activation
Hashizume, T., Yoshitomi, S., Asahi, S., Matsumura, S., Chatani, F., & Oda, H. (2009) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/j.mrgentox.2009.03.009 · Cited by 29
Expression of human glutathione S-transferase P1 confers resistance to benzo[a]pyrene or benzo[a]pyrene-7,8-dihydrodiol mutagenesis, macromolecular alkylation and formation of stable N2-Gua-BPDE adducts in stably transfected V79MZ cells co-expressing hCYP1A1
Kushman, M. E., Kabler, S. L., Fleming, M. H., Ravoori, S., Gupta, R. C., Doehmer, J., Morrow, C. S., & Townsend, A. J. (2006) · Carcinogenesis · doi:10.1093/carcin/bgl125 · Cited by 29
Oxidation of N,N-dimethylformamide and N,N-diethylformamide by human liver microsomes and human recombinant P450s
Amato, G., Grasso, E., Longo, V. G., & Gervasi, P. G. (2001) · Toxicology Letters · doi:10.1016/s0378-4274(01)00324-1 · Cited by 29
Cytochrome P450 2S1 is Reduced by NADPH-Cytochrome P450 Reductase
Xiao, Y., Shinkyo, R., & Guengerich, F. P. (2011) · Drug Metabolism and Disposition · doi:10.1124/dmd.111.039321 · Cited by 29
Self-citation
In vivo activation of aflatoxin B1 in C57BL/6N mice carrying a human fetus-specific CYP3A7 gene.
Li, Y., Yokoi, T., Katsuki, M., et al. (1997) · PubMed · Cited by 28
Regulation of Benzo[a]pyrene-Mediated DNA- and Glutathione-Adduct Formation by 2,3,7,8-Tetrachlorodibenzo-p-dioxin in Human Lung Cells
Gelhaus, S. L., Harvey, R. G., Penning, T. M., & Blair, I. A. (2010) · Chemical Research in Toxicology · doi:10.1021/tx100297z · Cited by 28
Problematic Detoxification of Estrogen Quinones by NAD(P)H-Dependent Quinone Oxidoreductase and Glutathione-S-transferase
Chandrasena, R. E. P., Edirisinghe, P. D., Bolton, J. L., & Thatcher, G. R. J. (2008) · Chemical Research in Toxicology · doi:10.1021/tx8000797 · Cited by 28
Detoxication of Structurally Diverse Polycyclic Aromatic Hydrocarbon (PAH) o-Quinones by Human Recombinant Catechol-O-methyltransferase (COMT) via O-Methylation of PAH Catechols
Zhang, L., Jin, Y., Chen, M., Huang, M. T., Harvey, R. G., Blair, I. A., & Penning, T. M. (2011) · Journal of Biological Chemistry · doi:10.1074/jbc.m111.240739 · Cited by 28
PULMONARY BIOACTIVATION OF TRICHLOROETHYLENE TO CHLORAL HYDRATE: RELATIVE CONTRIBUTIONS OF CYP2E1, CYP2F, AND CYP2B1
Forkert, P., Baldwin, R. M., Millen, B., Lash, L. H., Putt, D. A., Shultz, M. A., & Collins, K. S. (2005) · Drug Metabolism and Disposition · doi:10.1124/dmd.105.005074 · Cited by 28
Comparison of three different in vitro mutation assays used for the investigation of cytochrome P450-mediated mutagenicity of nitro-polycyclic aromatic hydrocarbons
Kappers, W. A., van Och, F. M. M., de Groene, E. M., & Horbach, G. J. (2000) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/s1383-5718(00)00015-2 · Cited by 27
Evaluation of nitroreductase and acetyltransferase participation in N-nitrosodiethylamine genotoxicity
Aiub, C. A. F., Mazzei, J. L., Pinto, L. F. R., et al. (2006) · Chemico-Biological Interactions · doi:10.1016/j.cbi.2006.03.012 · Cited by 27
Establishment of ten strains of genetically engineered Salmonella typhimurium TA1538 each co-expressing a form of human cytochrome P450 with NADPH-cytochrome P450 reductase sensitive to various promutagens
Yamazaki, Y., Fujita, K., Nakayama, K., Suzuki, A., Nakamura, K., Yamazaki, H., & Kamataki, T. (2004) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/j.mrgentox.2004.06.003 · Cited by 26
The Metabolic Rate Constants and Specific Activity of Human and Rat Hepatic Cytochrome P-450 2E1 Toward Toluene and Chloroform
Lipscomb, J. C., Barton, H. A., Tornero‐Velez, R., Evans, M. V., Alcasey, S., SNAWDER, J. E., & Laskey, J. W. (2004) · Journal of Toxicology and Environmental Health · doi:10.1080/15287390490425588 · Cited by 26
Cytochrome P450 catalyzed oxidation of monochlorobenzene, 1,2- and 1,4-dichlorobenzene in rat, mouse, and human liver microsomes
Nedelcheva, V., Gut, I., Souček, P., et al. (1998) · Chemico-Biological Interactions · doi:10.1016/s0009-2797(98)00058-1 · Cited by 25
Roles of human sulfotransferases in genotoxicity of carcinogens using genetically engineeredumutest strains
Oda, Y., Zhang, Y., Buchinger, S., Reifferscheid, G., & Yang, M. (2011) · Environmental and Molecular Mutagenesis · doi:10.1002/em.20696 · Cited by 25
O 6-Alkylguanine-DNA Alkyltransferase Has Opposing Effects in Modulating the Genotoxicity of Dibromomethane and Bromomethyl Acetate
Liu, L., Williams, K. M., Guengerich, F. P., & Pegg, A. E. (2004) · Chemical Research in Toxicology · doi:10.1021/tx049958o · Cited by 25
Self-citation
SULT1C3, an orphan sequence of the human genome, encodes an enzyme activating various promutagens
Meinl, W., Donath, C., Schneider, H., Sommer, Y., & Glatt, H. R. (2007) · Food and Chemical Toxicology · doi:10.1016/j.fct.2007.08.040 · Cited by 24
Genotoxic activation of benzophenone and its two metabolites by human cytochrome P450s in SOS/umu assay
Takemoto, K., Yamazaki, H., Nakajima, M., & Yokoi, T. (2002) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/s1383-5718(02)00141-9 · Cited by 22
The metabolism of β-chloroprene: preliminary in-vitro studies using liver microsomes
Himmelstein, M. W., Carpenter, S. C., Hinderliter, P. M., Snow, T. A., & Valentine, R. (2001) · Chemico-Biological Interactions · doi:10.1016/s0009-2797(01)00214-9 · Cited by 22
Escherichia coli MTC, a NADPH cytochrome P450 reductase competent mutagenicity tester strain for the expression of human cytochrome P450: Comparison of three types of expression systems
Kranendonk, M., Fisher, C., Roda, R., Carreira, F., Theisen, P., Laires, A., Rueff, J., Vermeulen, N. P. E., & Estabrook, R. W. (1999) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/s1383-5718(98)00193-4 · Cited by 22
UDP-Glucuronosyltransferase 1A10: Activity against the Tobacco-Specific Nitrosamine, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, and a Potential Role for a Novel UGT1A10 Promoter Deletion Polymorphism in Cancer Susceptibility
Balliet, R. M., Chen, G., Dellinger, R. W., & Lazarus, P. J. (2009) · Drug Metabolism and Disposition · doi:10.1124/dmd.109.030569 · Cited by 22
Role of induction of specific hepatic cytochrome P450 isoforms in epoxidation of 4-vinylcyclohexene.
Fontaine, S. M., Hoyer, P. B., Halpert, J. R., & Sipes, I. G. (2001) · PubMed · Cited by 22
Escherichia coli BTC, a human cytochrome P450 competent tester strain with a high sensitivity towards alkylating agents: involvement of alkyltransferases in the repair of DNA damage induced by aromatic amines
Duarte, M. P., Palma, B. B., Laires, A., Oliveira, J. S., Rueff, J., & Kranendonk, M. (2005) · Mutagenesis · doi:10.1093/mutage/gei028 · Cited by 21
N-Acetyltransferase and sulfotransferase activity in human prostate: potential for carcinogen activation
Al‐Buheissi, S., Patel, H., Meinl, W., Hewer, A. J., Bryan, R. L., Glatt, H. R., Miller, R. A., & Phillips, D. H. (2006) · Pharmacogenetics and Genomics · doi:10.1097/01.fpc.0000204998.22301.09 · Cited by 20
Analysis of the involvement of human N-acetyltransferase 1 in the genotoxic activation of bladder carcinogenic arylamines using a SOS/umu assay system
Oda, Y. (2004) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/j.mrfmmm.2004.06.033 · Cited by 20
Antigenotoxic activity of naturally occurring furanocoumarins
Marumoto, S., Oda, Y., & Miyazawa, M. (2011) · Environmental and Molecular Mutagenesis · doi:10.1002/em.20665 · Cited by 20
Conjugation of Butadiene Diepoxide with Glutathione Yields DNA Adducts in Vitro and in Vivo
Cho, S., & Guengerich, F. P. (2011) · Chemical Research in Toxicology · doi:10.1021/tx200471x · Cited by 18
Self-citation
Characterization of Dibenzo[a,l]pyrene-trans-11,12-diol (Dibenzo[def,p]chrysene) Glucuronidation by UDP-Glucuronosyltransferases
Olson, K. C., Sun, D., Chen, G., Sharma, A. K., Amin, S., Ropson, I. J., Spratt, T. E., & Lazarus, P. J. (2011) · Chemical Research in Toxicology · doi:10.1021/tx200178v · Cited by 18
Heterologous expression of human cytochrome P450 2E1 in HepG2 cell line
Zhuge, J. (2003) · World Journal of Gastroenterology · doi:10.3748/wjg.v9.i12.2732 · Cited by 18
The stimulatory role of human cytochrome b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a new cell expression system to study cytochrome P450-mediated biotransformation (a corrigendum report on Duarte et al. (2005) Mutagenesis 20, 93-100)
Duarte, M. P., Palma, B. B., Gilep, A. A., Laires, A., Oliveira, J. S., Usanov, S. A., Rueff, J., & Kranendonk, M. (2006) · Mutagenesis · doi:10.1093/mutage/gel054 · Cited by 17
Genotoxic activation of 2-phenylbenzotriazole-type compounds by human cytochrome P4501A1 and N-acetyltransferase expressed in Salmonella typhimurium umu strains
Oda, Y., Watanabe, T., Terao, Y., et al. (2008) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/j.mrgentox.2008.04.013 · Cited by 16
The Effects of Single Nucleotide Polymorphisms in CYP2A13 on Metabolism of 5-Methoxypsoralen
Goto, T., Moriuchi, H., Fu, X., Ikegawa, T., Matsubara, T., Chang, G., Uno, T., Morigaki, K., Isshiki, K., & Imaishi, H. (2010) · Drug Metabolism and Disposition · doi:10.1124/dmd.110.034553 · Cited by 16
Intestinal carcinogenesis of two food processing contaminants, 2‐amino‐1‐methyl‐6‐phenylimidazo[4,5‐b]pyridine and 5‐hydroxymethylfurfural, in transgenic FVB min mice expressing human sulfotransferases
Svendsen, C., Meinl, W., Glatt, H. R., Alexander, J., Knutsen, H. K., Hjertholm, H., Rasmussen, T., & Husøy, T. (2011) · Molecular Carcinogenesis · doi:10.1002/mc.20869 · Cited by 14
Mutual inhibition between quinine and etoposide by human liver microsomes. Evidence for cytochrome P4503A4 involvement in their major metabolic pathways.
Zhao, X., Kawashiro, T., & Ishizaki, T. (1998) · PubMed · Cited by 11
Role of P4502E1 in the metabolism of 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)-ethane
Herbst, J., Köster, U., Kerssebaum, R., & Dekant, W. (1994) · Xenobiotica · doi:10.3109/00498259409043253 · Cited by 11
MOLECULAR MECHANISM OF GENOTOXICITY OF THE ENVIRONMENTAL POLLUTANT 3-NITROBENZANTHRONE
Stiborová, M., Arlt, V. M., Henderson, C. J., Wolf, C. R., Frei, E., Schmeiser, H. H., & Phillips, D. H. (2005) · Biomedical Papers · doi:10.5507/bp.2005.025 · Cited by 10
Aromatase and Estrogen 2-Hydroxylase Activities of Human Placental Microsomes in Pregnancy-Induced Hypertension.
OKUBO, K., 神保, 正., Toma, Y., Shimizu, Y., & Yanaihara, T. (1996) · Endocrine Journal · doi:10.1507/endocrj.43.363 · Cited by 8

Formation and Biological Targets of Quinones: Cytotoxic versus Cytoprotective Effects
Bolton, J. L., & Dunlap, T. (2017) · Chemical Research in Toxicology · doi:10.1021/acs.chemrestox.6b00256 · Cited by 522
Survey of Human Oxidoreductases and Cytochrome P450 Enzymes Involved in the Metabolism of Xenobiotic and Natural Chemicals
Rendic, S., & Guengerich, F. P. (2015) · Chemical Research in Toxicology · doi:10.1021/tx500444e · Cited by 477
Self-citation
Characterization of cytochrome P450s (CYP)-overexpressing HepG2 cells for assessing drug and chemical-induced liver toxicity
Chen, S., Wu, Q., Li, X., Li, D., Mei, N., Ning, B., Puig, M., Ren, Z., Tolleson, W. H., & Guo, L. (2021) · Journal of Environmental Science and Health, Part C · doi:10.1080/26896583.2021.1880242 · Cited by 44

See all 279

Authors: Rendic, S., & Guengerich, F. P.
Venue: Chemical Research in Toxicology
Publisher: American Chemical Society (ACS)
Published: 2012-05-10
Volume: 25
Issue: 7
Pages: 1316-1383
ISSN: 0893-228X (ISSN-L)
1520-5010
DOI: 10.1021/tx300132k
OpenAlex: W1998118464
Cited by: 279
References: 314
FWCI: 22.61
Type: journal article
Language: en
Open access: green

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Contributions of Human Enzymes in Carcinogen Metabolism

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