Mammalian flavin-containing monooxygenase (FMO) as a source of hydrogen peroxide

Cashman, 2006, Human flavin-containing monooxygenases, Annual Review of Pharmacology and Toxicology, 46, 65, 10.1146/annurev.pharmtox.46.120604.141043 Krueger, 2005, Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism, Pharmacology and Therapeutics, 106, 357, 10.1016/j.pharmthera.2005.01.001 Yeung, 2000, Immunoquantitation of FMO1 in human liver, kidney, and intestine, Drug Metabolism and Disposition, 28, 1107 Zhang, 2006, Quantitative analysis of FMO gene mRNA levels in human tissues, Drug Metabolism and Disposition, 34, 19, 10.1124/dmd.105.006171 Dolphin., 1998, The flavin-containing monooxygenase 2 gene (FMO2) of humans, but not other primates, encodes a truncated nonfunctional protein, Journal of Biological Chemistry, 273, 30599, 10.1074/jbc.273.46.30599 Krueger, 2002, Identification of active flavin-containing monooxygenase isoform 2 in human lung and characterization of expressed protein, Drug Metabolism and Disposition, 30, 34, 10.1124/dmd.30.1.34 Krueger, 2004, Differences in FMO2*1 allelic frequency between Hispanics of Puerto Rican and Mexican descent, Drug Metabolism and Disposition, 32, 1337, 10.1124/dmd.104.001099 Krueger, 2005, Haplotype and functional analysis of four flavin-containing monooxygenase isoform 2 (FMO2) polymorphisms in Hispanics, Pharmacogenetics and Genomics, 15, 245, 10.1097/01213011-200504000-00008 Veeramah, 2008, The potentially deleterious functional variant flavin-containing monooxygenase 2*1 is at high frequency throughout sub-Saharan Africa, Pharmacogenetics and Genomics, 18, 877, 10.1097/FPC.0b013e3283097311 Whetstine, 2000, Ethnic differences in human flavin-containing monooxygenase 2 (FMO2) polymorphisms: detection of expressed protein in African-Americans, Toxicology and Applied Pharmacology, 168, 216, 10.1006/taap.2000.9050 Koukouritaki, 2002, Human hepatic flavin-containing monooxygenase 1 (FMO1) and 3 (FMO3) developmental expression, Pediatric Research, 50, 1 Lang, 1998, Isoform specificity of trimethylamine N-oxygenation by human flavin-containing monooxygenase (FMO) and P450 enzymes, Biochemical Pharmacology, 56, 1005, 10.1016/S0006-2952(98)00218-4 Hernandez, 2003, Trimethylaminuria and a human FMO3 mutation database, Human Mutation, 22, 209, 10.1002/humu.10252 Treacy, 1998, Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication, Human Molecular Genetics, 7, 839, 10.1093/hmg/7.5.839 Zhang, 2003, Deleterious mutations in the flavin-containing monooxygenase 3 (FMO3) gene causing trimethylaminuria, Pharmacogenetics, 13, 495, 10.1097/00008571-200308000-00007 Dolphin, 1997, Missense mutation in flavin-containing mono-oxygenase 3 gene, FMO3, underlies fisk-odour syndrome, Nature Genetics, 17, 491, 10.1038/ng1297-491 Hisamuddin, 2007, Genetic polymorphisms of human flavin-containing monooxygenase 3: implications for drug metabolism and clinical perspectives, Pharmacogenomics, 8, 635, 10.2217/14622416.8.6.635 Yamazaki, 2013, Survey of variants of human flavin-containing monooxygenase 3 (FMO3) and their drug oxidation activities, Biochemical Pharmacology, 85, 1588, 10.1016/j.bcp.2013.03.020 Mayatepek, 2004, Benzydamine metabolism in vivo is impaired in patients with deficiency of flavin-monooxygenase 3, Pharmacogenetics, 14, 775, 10.1097/00008571-200411000-00009 Jones, 1986, Reactions of the 4a-hydroperoxide of liver microsomal flavin-containing monooxygenase with nucleophilic and electrophilic substrates, Journal of Biological Chemistry, 261, 2553, 10.1016/S0021-9258(17)35823-4 Poulsen, 1995, Multisubstrate flavin-containing monooxygenase: application of mechanism to specificity, Chemical–Biological Interactions, 96, 57, 10.1016/0009-2797(94)03583-T Cashman, 1995, Structural and catalytic properties of the mammalian flavin-containing monooxygenase, Chemical Research in Toxicology, 8, 165, 10.1021/tx00044a001 Zielger, 2002, An overview of the mechanism, substrate specificities and structure of FMOs, Drug Metabolism Reviews, 34, 503, 10.1081/DMR-120005650 Rauckman, 1979, Superoxide radical as an intermediate in the oxidation of hydroxylamines by mixed function amine oxidase, Molecular Pharmacology, 15, 131 Tynes, 1986, Formation of hydrogen peroxide and N-hydroxylated amines catalyzed by pulmonary flavin-containing monooxygenase in the presence of primary alkylamines, Archives of Biochemistry and Biophysics, 251, 654, 10.1016/0003-9861(86)90375-9 Krueger, 2009, Characterization of sulfoxygenation and structural implications of human flavin-containing monooxygenase isoform 2 (FMO2.1) variants S195L and N413K, Drug Metabolism and Disposition, 37, 1785, 10.1124/dmd.109.027201 Mishin, 2010, Application of the Amplex Red/horseradish peroxidase assay to measure hydrogen peroxide generation by recombinant microsomal enzymes, Free Radicals in Biology and Medicine, 48, 1485, 10.1016/j.freeradbiomed.2010.02.030 Bienert, 2006, Membrane transport of hydrogen peroxide, Biochimistry Biophysica Acta, 1758, 994, 10.1016/j.bbamem.2006.02.015 Henderson, 2008, Metabolism of the anti-tuberculosis drug ethionamide by mouse and human FMO1, FMO2 and FMO3 and mouse and human lung microsomes, Toxicology and Applied Pharmacology, 233, 420, 10.1016/j.taap.2008.09.017 Guengerich, 1989, Analysis and characterization of enzymes, 777 Bradford, 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Analytical Biochemistry, 72, 248, 10.1016/0003-2697(76)90527-3 Henderson, 2004, Flavin-containing monooxygenase form 2 S-oxygenation: sulfenic acid formation from thioureas and oxidation of glutathione, Chemical Research in Toxicology, 17, 633, 10.1021/tx034253s Zhou, 1997, A stable nonfluorescent derivative of resorufin for the fluorometric determination of trace hydrogen peroxide: applications in detecting the activity of phagocyte NADPH oxidase and other oxidases, Analytical Biochemistry, 253, 162, 10.1006/abio.1997.2391 Francois, 2009, Human flavin-containing monooxygenase 2.1 catalyzes oxygenation of the antitubercular drugs thiacetazone and ethionamide, Drug Metabolism and Disposition, 37, 178, 10.1124/dmd.108.024158 Nishida, 2011, Bioactivation of antituberculosis thioamide and thiourea prodrugs by bacterial and mammalian flavin monooxygenases, Chemical–Biological Interactions, 192, 21, 10.1016/j.cbi.2010.09.015 Eswaramoorthy, 2006, Mechanism of action of a flavin-containing monooxygenase, Proceedings of the National Academy of Sciences of the United States of America, 103, 9832, 10.1073/pnas.0602398103 Alfieri, 2008, Revealing the moonlighting role of NADP in the structure of a flavin-containing monooxygenase, Proceedings of the National Academy of Sciences of the United States of America, 105, 6572, 10.1073/pnas.0800859105 Kim, 2000, Size limits of thiocarbamides accepted as substrates by human flavin-containing monooxygenase 1, Drug Metabolism and Disposition, 28, 1003 Nagata, 1990, Substrate specificities of rabbit lung and porcine liver flavin-containing monooxygenases: differences due to substrate size, Chemical Research in Toxicology, 3, 372, 10.1021/tx00016a016 Massey, 1994, Activation of molecular oxygen by flavins and flavoproteins, Journal of Biological Chemistry, 269, 22459, 10.1016/S0021-9258(17)31664-2 Tynes, 1985, Catalytic activity and substrate specificity of the flavin-containing monooxygenase in microsomal systems: characterization of the hepatic, pulmonary and renal enzymes of the mouse, rabbit and rat, Archives of Biochemistry and Biophysics, 240, 77, 10.1016/0003-9861(85)90010-4 Ziegler, 1980, Microsomal flavin-containing monooxygenase: oxygenation of nucleophilic nitrogen and sulfur compounds, vol. 1, 201, 10.1016/B978-0-12-380001-5.50015-3 Ziegler, 1993, Recent studies on the structure and function of multisubstrate flavin-containing monooxygenase, Annual Review of Pharmacology and Toxicology, 33, 179, 10.1146/annurev.pa.33.040193.001143 Ziegler, 1998, Catalytic mechanism of FMO-catalyzed N- and S-oxidations, 30 Furnes, 2003, Identification of novel variants of the flavin-containing monooxygenase gene family in African Americans, Drug Metabolism and Disposition, 31, 187, 10.1124/dmd.31.2.187