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Xenobiotica
the fate of foreign compounds in biological systems
Volume 33, 2003 - Issue 1
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Research Article

CYP2A13-catalysed coumarin metabolism: comparison with CYP2A5 and CYP2A6

L. B. VON WEYMARN Department of Biochemistry, Molecular Biology & Biophysics, University of Minnesota Cancer Center, Mayo Mail Code 806, 420 Delaware Street SE., Minneapolis, MN 55455, USA
&
S. E. MURPHY Department of Biochemistry, Molecular Biology & Biophysics, University of Minnesota Cancer Center, Mayo Mail Code 806, 420 Delaware Street SE., Minneapolis, MN 55455, USA
Pages 73-81 | Published online: 22 Sep 2008

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Shotaro Uehara, Norie Murayama, Yuichiro Higuchi, Nao Yoneda, Hiroshi Yamazaki & Hiroshi Suemizu. (2022) Comparison of mouse and human cytochrome P450 mediated-drug metabolising activities in hepatic and extrahepatic microsomes. Xenobiotica 52:3, pages 229-239.
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Risto O. Juvonen, Elmeri M. Jokinen, Juhani Huuskonen, Olli Kärkkäinen, Hannu Raunio & Olli T. Pentikäinen. (2021) Molecular docking and oxidation kinetics of 3-phenyl coumarin derivatives by human CYP2A13. Xenobiotica 51:11, pages 1207-1216.
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Shu-Feng Zhou, Jun-Ping Liu & Balram Chowbay. (2009) Polymorphism of human cytochrome P450 enzymes and its clinical impact. Drug Metabolism Reviews 41:2, pages 89-295.
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Caitlin M. Brown, Brad Reisfeld & Arthur N. Mayeno. (2008) Cytochromes P450: A Structure-Based Summary of Biotransformations Using Representative Substrates. Drug Metabolism Reviews 40:1, pages 1-100.
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J. R. Jalas, M. Seetharaman, S. S. Hecht & S. E. Murphy. (2004) Molecular modelling of CYP2A enzymes: application to metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Xenobiotica 34:6, pages 515-533.
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Koichi Kato, Tomoki Nakayoshi, Sho Hioki, Masahiro Hiratsuka, Yoshinobu Ishikawa, Eiji Kurimoto & Akifumi Oda. (2024) Structural Impact Assessment of Cytochrome P450 2A13 Polymorphisms Using Molecular Dynamics Simulations. Biological and Pharmaceutical Bulletin 47:3, pages 620-628.
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Yujie Lu, Man Zhang, Jin Zhang, Min Jiang & Gang Bai. (2023) Psoralen prevents the inactivation of estradiol and treats osteoporosis via covalently targeting HSD17B2. Journal of Ethnopharmacology 311, pages 116426.
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Brett R. Winters, Phillip W. Clapp, Steven O. Simmons, Tavleen K. Kochar, Ilona Jaspers & Michael C. Madden. (2023) E-Cigarette Liquids and Aldehyde Flavoring Agents Inhibit CYP2A6 Activity in Lung Epithelial Cells. ACS Omega 8:12, pages 11261-11266.
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Takashi Yamada, Naruo Katsutani, Taeko Maruyama, Tomoko Kawamura, Hiroshi Yamazaki, Norie Murayama, Weida Tong, Yasushi Yamazoe & Akihiko Hirose. (2022) Combined Risk Assessment of Food-derived Coumarin with <i>in Silico</i> Approaches. Food Safety 10:3, pages 73-82.
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Radim Vrzal. (2021) Genetic and Enzymatic Characteristics of CYP2A13 in Relation to Lung Damage. International Journal of Molecular Sciences 22:22, pages 12306.
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You Lv, Hanlu Liu, Lifan Wang, Kun Li, Wei Gao, Xiaoyu Liu, Liangfu Tang, Tatiana A. Kalinina, Tatiana V. Glukhareva & Zhijin Fan. (2021) Discovery of Novel 3,4-Dichloroisothiazole-Containing Coumarins as Fungicidal Leads. Journal of Agricultural and Food Chemistry 69:14, pages 4253-4262.
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Gentao Li, Hui Xiong, Khawar Saeed, Ruicong Ma, Yufeng Xing, Yajuan Bi, Caiyu Li, Jianhui Huang & Youcai Zhang. (2020) Comparative toxicity analysis of corannulene and benzo[a]pyrene in mice. Toxicology Letters 331, pages 130-142.
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Eko Aditya Rifai, Valerio Ferrario, Jürgen Pleiss & Daan P. Geerke. (2020) Combined Linear Interaction Energy and Alchemical Solvation Free-Energy Approach for Protein-Binding Affinity Computation. Journal of Chemical Theory and Computation 16:2, pages 1300-1310.
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Shotaro Uehara, Yasuhiro Uno & Hiroshi Yamazaki. (2020) The marmoset cytochrome P450 superfamily: Sequence/phylogenetic analyses, genomic structure, and catalytic function. Biochemical Pharmacology 171, pages 113721.
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ChingYi Jennifer Hsieh, Meng Sun, Gwendolyn Osborne, Karin Ricker, Feng C. Tsai, Kate Li, Rajpal Tomar, Jimmy Phuong, Rose Schmitz & Martha S. Sandy. (2019) Cancer Hazard Identification Integrating Human Variability: The Case of Coumarin. International Journal of Toxicology 38:6, pages 501-552.
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Medjda Bellamri, Lihua Yao, Radha Bonala, Francis Johnson, Linda B. Von Weymarn & Robert J. Turesky. (2019) Bioactivation of the tobacco carcinogens 4-aminobiphenyl (4-ABP) and 2-amino-9H-pyrido[2,3-b]indole (AαC) in human bladder RT4 cells. Archives of Toxicology 93:7, pages 1893-1902.
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Maryam Foroozesh, Jayalakshmi Sridhar, Navneet Goyal & Jiawang Liu. (2019) Coumarins and P450s, Studies Reported to-Date. Molecules 24:8, pages 1620.
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X. Ding, L. Li, L.S. Van Winkle & Q.-Y. Zhang. 2018. Comprehensive Toxicology. Comprehensive Toxicology 171 193 .
Shufeng Zhou. 2016. Cytochrome P450 2D6. Cytochrome P450 2D6 1 100 .
S. C. Narayanapillai, L. B. von Weymarn, S. G. Carmella, P. Leitzman, J. Paladino, P. Upadhyaya, S. S. Hecht, S. E. Murphy & C. Xing. (2016) Dietary Dihydromethysticin Increases Glucuronidation of 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol in A/J Mice, Potentially Enhancing Its Detoxification. Drug Metabolism and Disposition 44:3, pages 422-427.
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Shotaro Uehara, Yasuhiro Uno, Takashi Inoue, Erika Sasaki & Hiroshi Yamazaki. (2015) Substrate Selectivities and Catalytic Activities of Marmoset Liver Cytochrome P450 2A6 Differed from Those of Human P450 2A6. Drug Metabolism and Disposition 43:7, pages 969-976.
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F. Peter Guengerich. 2015. Cytochrome P450. Cytochrome P450 523 785 .
Linda C. Blake, Anuradha Roy, David Neul, Frank J. Schoenen, Jeffrey Aubé & Emily E. Scott. (2013) Benzylmorpholine Analogs as Selective Inhibitors of Lung Cytochrome P450 2A13 for the Chemoprevention of Lung Cancer in Tobacco Users. Pharmaceutical Research 30:9, pages 2290-2302.
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Linda B. von Weymarn, Cassandra Retzlaff & Sharon E. Murphy. (2012) CYP2A6- and CYP2A13-Catalyzed Metabolism of the Nicotine Δ 5′(1′) Iminium Ion . Journal of Pharmacology and Experimental Therapeutics 343:2, pages 307-315.
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Valerie M. Kramlinger, Linda B. von Weymarn & Sharon E. Murphy. (2012) Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol. Chemico-Biological Interactions 197:2-3, pages 87-92.
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Tatsushi Goto, Hiroshi Moriuchi, Xuejun Fu, Tomoyo Ikegawa, Toshiyuki Matsubara, Gang Chang, Tomohide Uno, Kenichi Morigaki, Kunio Isshiki & Hiromasa Imaishi. (2010) The Effects of Single Nucleotide Polymorphisms in CYP2A13 on Metabolism of 5-Methoxypsoralen. Drug Metabolism and Disposition 38:12, pages 2110-2116.
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Nohemí Salinas-Jazmín, Marisol de la Fuente, Ruth Jaimez, Mayra Pérez-Tapia, Armando Pérez-Torres & Marco A. Velasco-Velázquez. (2009) Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model. Cancer Chemotherapy and Pharmacology 65:5, pages 931-940.
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Antoinette Chougnet, Wolf‐D. Woggon, Esther Locher & Boris Schilling. (2009) Synthesis and in vitro Activity of Heterocyclic Inhibitors of CYP2A6 and CYP2A13, Two Cytochrome P450 Enzymes Present in the Respiratory Tract. ChemBioChem 10:9, pages 1562-1567.
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N. M. DeVore, B. D. Smith, J. L. Wang, G. H. Lushington & E. E. Scott. (2009) Key Residues Controlling Binding of Diverse Ligands to Human Cytochrome P450 2A Enzymes. Drug Metabolism and Disposition 37:6, pages 1319-1327.
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Kari E. Schlicht, Jeannette Zinggeler Berg & Sharon E. Murphy. (2009) Effect of CYP2A13 Active Site Mutation N297A on Metabolism of Coumarin and Tobacco-Specific Nitrosamines. Drug Metabolism and Disposition 37:3, pages 665-671.
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Sharon E. Murphy & Linda B. von Weymarn. 2008. Advances in Bioactivation Research. Advances in Bioactivation Research 1 29 .
Linda B. von Weymarn, Jamie A. Chun, Gabriel A. Knudsen & Paul F. Hollenberg. (2007) Effects of Eleven Isothiocyanates on P450 2A6- and 2A13-Catalyzed Coumarin 7-Hydroxylation. Chemical Research in Toxicology 20:9, pages 1252-1259.
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Tatsuki Fukami, Miki Nakajima, Haruko Sakai, Miki Katoh & Tsuyoshi Yokoi. (2007) CYP2A13 Metabolizes the Substrates of Human CYP1A2, Phenacetin, and Theophylline. Drug Metabolism and Disposition 35:3, pages 335-339.
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Jason K. Yano, Travis T. Denton, Matthew A. Cerny, Xiaodong Zhang, Eric F. Johnson & John R. Cashman. (2006) Synthetic Inhibitors of Cytochrome P-450 2A6:  Inhibitory Activity, Difference Spectra, Mechanism of Inhibition, and Protein Cocrystallization. Journal of Medicinal Chemistry 49:24, pages 6987-7001.
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Linda B. von Weymarn, Jamie A. Chun & Paul F. Hollenberg. (2006) Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. Carcinogenesis 27:4, pages 782-790.
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Sompop Peamkrasatam, Kampon Sriwatanakul, Kazuma Kiyotani, Masaki Fujieda, Hiroshi Yamazaki, Tetsuya Kamataki & Krongtong Yoovathaworn. (2006) In vivo Evaluation of Coumarin and Nicotine as Probe Drugs to Predict the Metabolic Capacity of CYP2A6 Due to Genetic Polymorphism in Thais. Drug Metabolism and Pharmacokinetics 21:6, pages 475-484.
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Sharon E. Murphy, Vytautas Raulinaitis & Kathryn M. Brown. (2005) NICOTINE 5′-OXIDATION AND METHYL OXIDATION BY P450 2A ENZYMES. Drug Metabolism and Disposition 33:8, pages 1166-1173.
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Ivonne M. C. M. Rietjens, Martijn J. Martena, Marelle G. Boersma, Wim Spiegelenberg & Gerrit M. Alink. (2005) Molecular mechanisms of toxicity of important food-borne phytotoxins. Molecular Nutrition & Food Research 49:2, pages 131-158.
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Hansen L. Wong, Sharon E. Murphy & Stephen S. Hecht. (2004) Cytochrome P450 2A-Catalyzed Metabolic Activation of Structurally Similar Carcinogenic Nitrosamines:  N‘ -Nitrosonornicotine Enantiomers, N -Nitrosopiperidine, and N- Nitrosopyrrolidine . Chemical Research in Toxicology 18:1, pages 61-69.
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F. Peter Guengerich. 2005. Cytochrome P450. Cytochrome P450 377 530 .
. (2004) Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Coumarin. EFSA Journal 2:12, pages 104.
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Xiao-Yang He, Jian Shen, Wen-Yu Hu, Xinxin Ding, Anthony Y.H Lu & Jun-Yan Hong. (2004) Identification of Val117 and Arg372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation. Archives of Biochemistry and Biophysics 427:2, pages 143-153.
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