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Review

Developmental and tissue-specific expression of human flavin-containing monooxygenases 1 and 3

Pages 41-49 | Published online: 01 Feb 2006

Bibliography

  • ZIEGLER DM: Microsomal flavin-containing monooxygenase: oxygenation of nucleophilic and sulfur compounds. In: Enzymatic Basis of Detoxication. WB Jakoby (Ed.), Academic Press, Inc., New York City, US (1980):201-227.
  • ZIEGLER DM, MITCHELL CH: Microsomal oxidase IV: properties of a mixed-function amine oxidase isolated from pig liver microsomes. Arch. Biochem. Biophys. (1972) 150:116-125.
  • MASTERS BSS, ZIEGLER DM: The distinct nature and function of NADPH-cytochrome c reductase and the NADPH-dependent mixed-function amine oxidase of porcine liver microsomes. Arch. Biochem. Biophys. (1971) 145:358-364.
  • CASHMAN JR: Flavin monooxygenases. In: Enzyme systems that metabolize drugs and other xenobiotics. C Ionnides (Ed.), John Wiley & Sons, Inc., Indianapolis, IN, USA (2002):67-93.
  • SUH J-K, POULSEN LL, ZIEGLER DM, ROBERTUS JD: Redox regulation of yeast flavin-containing monooxygenase. Arch. Biochem. Biophys. (2000) 381:317-322.
  • PETERS LD, LIVINGSTONE DR, SHEHIN S, HINES RN, SCHLENK D: Characterization of hepatic flavin monooxygenase from the turbot (Scophthalmus maximus L.). Xenobiotica (1995) 25:121-131.
  • KRUEGER SK, WILLIAMS DE: Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism. Pharmacol. Ther. (2005) 106:357-387.
  • DEVEREUX TR, FOUTS JR: Effect of pregnancy or treatment with certain steroids on N,N-dimethylaniline demethylation and N-oxidation by rabbit liver or lung microsomes. Drug Metab. Dispos. (1975) 3:254-258.
  • WILLIAMS DE, HALE SE, MUERHOFFAS, MASTERS BSS: Rabbit lung flavin-containing monooxygenase: purification, characterization, and induction during pregnancy. Mol. Pharmacol. (1985) 28:381-390.
  • WILLIAMS DE, ZIEGLER DM, NORDIN DJ, HALE SE, MASTERS BSS: Rabbit lung flavin-containing monooxygenase is immunochemically and catalytically distinct from the liver enzyme. Biochem. Biophys. Res. Commun. (1984) 125:116-122.
  • TYNES RE, SABOURIN PJ, HODGSONE: Identification of distinct hepatic and pulmonary forms of microsomal flavin-containing monooxygenase in the mouse and rabbit. Biochem. Biophys. Res. Commun. (1985) 126:1069-1075.
  • LAWTON MP, PHILPOT RM: Molecular genetics of the flavin-dependent monooxygenases. Pharmacogenetics (1993) 3:40-44.
  • LAWTON MP, CASHMAN JR, CRESTEIL T etal.: A nomenclature for the mammalian flavin-containing monooxygenase gene family based on amino acid sequence identities. Arch. Biochem. Biophys. (1994) 308:254-257.
  • PHILLIPS IR, DOLPHIN CT, CLAIR P etal.: The molecular biology of the flavin-containing monooxygenases of man. Chem. Biol. Interact. (1995) 96:17-32.
  • HINES RN, HOPP KA, FRANCO J, SAEIAN K, BEGUN FP: Alternative processing of the human hepatic FMO6 gene renders transcripts incapable of encoding a functional flavin-containing monooxygenase. Mol. Pharmacol. (2002) 62:320-325.
  • HERNANDEZ D, JANMOHAMED A, CHANDAN P, PHILLIPS IR, SHEPHARD EA: Organization and evolution of the flavin-containing monooxygenase genes of human and mouse: identification of novel gene and pseudogene clusters. Pharmacogenetics (2004) 14:117-130.
  • POULSEN LL, ZIEGLER DM: Multisubstrate flavin-containing monooxygenases: applications of mechanism to specificity. Chem. Biol. Interact. (1995) 96:57-73.
  • KIM YM, ZIEGLER DM: Size limits of thiocarbamides accepted as substrates by human flavin-containing monooxygenase. Drug Metab. Dispos. (2000) 28:1003-1006.
  • SCHLENK D, CASHMAN JR, YEUNGC, ZHANG X, RETTIE AE: Role of human flavin-containing monooxygenase in the sulfoxidation of 14C-aldicarb. Pesticide Biochem. Physiol. (2002) 73:67-73.
  • CLEMENT B, LUSTIG KL, ZIEGLERDM: Oxidation of desmethylpromethazine catalyzed by pig liver flavin-containing monooxygenase: number and nature of metabolites. Drug Metab. Dispos. (1993) 21:24-29.
  • CASHMAN JR, CELESTIAL JR, LEACHA, NEWDOLL J, PARK SB: Tertiary amines related to brompheniramine: preferred conformations for N-oxygenation by the hog liver flavin-containing monooxygenase. Pharm. Res. (1993) 10:1097-1105.
  • CASHMAN JR, PARK SB, YANG Z-C etal.: Chemical, enzymatic, and human enantioselective S-oxygenation of cimetidine. Drug Metab. Dispos. (1993) 21:587-597.
  • OVERBY LH, CARVER GC, PHILPOTRM: Quantitation and kinetic properties of hepatic microsomal and recombinant flavin-containing monooxygenases 3 and 5 from humans. Chem. Biol. Interact. (1997) 106:29-45.
  • MUSHIRODA T, DOUYA R, TAKAHARA E, NAGATA O: The involvement of flavin-containing monooxygenase, but not CYP3A4 in metabolism of itopride hydrochloride, a gastroprokinetic agent: comparison with cisapride and mosapride citrate. Drug Metab. Dispos. (2000) 28:1231-1237.
  • RING BJ, WRIGHTON SA, ALDRIDGESLK etal.: Flavin-containing monooxygenase-mediated N-oxidation of the M1-muscarinic agonist xanomeline. Drug Metab. Dispos. (1999) 27:1099-1103.
  • HODGSON E, ROSE RL, CAO Y, DEHAL SS, KUPFER D: Flavin-containing monooxygenase isoform specificity for the N-oxidation of tamoxifen determined by product measurement and NADPH oxidation. J. Biochem. Mol. Toxicol. (2000) 14:118-120.
  • TUGNAIT M, HAWES EM, MCKAY G etal.: N-oxygenation of clozapine by flavin-containing monooxygenase. Drug Metab. Dispos. (1997) 25:524-527.
  • HAMMAN MA, HAEHNER-DANIELSBD, WRIGHTON SA, RETTIE AE, HALLSD: Stereoselective sulfoxidation of sulindac sulfide by flavin-containing monooxygenases. Biochem. Pharmacol. (2000) 60:7-17.
  • REID JM, WALKER DL, MILLER JK etal.: The metabolism of pyrazoloacridine (NSC 366140) by cytochromes P450 and flavin monooxygenase in human liver microsomes. Clin. Cancer Res. (2004) 10:1471-1480.
  • YEUNG CK, LANG DH, THUMMELKE, RETTIE AE: Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab. Dispos. (2000) 28:1107-1111.
  • SHIMADA T, YAMAZAKI H, MIMURAM, INUI Y, GUENGERICHFP: Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther. (1994) 270:414-423.
  • MORSELLI PL, FRANCOMORSELLIR, BOSSI L: Clinical pharmacokinetics in newborns and infants: age-related differences and therapeutic implications. Clin. Pharmacokinet. (1980) 5:485-527.
  • HINES RN, MCCARVER DG: The ontogeny of human drug metabolizing enzymes: phase I oxidative enzymes. J. Pharmacol. Exp. Ther. (2002) 300:355-360.
  • MCCARVER DG, HINES RN: The ontogeny of human drug metabolizing enzymes: phase II conjugation enzymes and regulatory mechanisms. J. Pharmacol. Exp. Ther. (2002) 300:361-366.
  • DE WILDT SN, KEARNS GL, LEEDERJS, VAN DEN ANKER JN: Cytochrome P4503A: ontogeny and drug disposition. Clin. Pharmacokinet. (1999) 6:485-505.
  • DE WILDT SN, KEARNS GL, LEEDERJS, VAN DEN ANKER JN: Glucuronidation in humans: pharmacogenetic and developmental aspects. Clin. Pharmacokinet. (1999) 36:439-452.
  • WIRTH PJ, THORGEIRSSON SS: Amine oxidase in mice sex differences and developmental aspects. Biochem. Pharmacol. (1978) 27:601-603.
  • DAS ML, ZIEGLER DM: Rat liver oxidative N-dealkylase and N-oxidase activites as a function of animal age. Arch. Biochem. Biophys. (1970) 140:300-306.
  • UEHLEKE H, REINER O, HELLMERKH: Perinatal development of tertiary amine N-oxidation and NADPH cytochrome c reduction in rat liver microsomes. Res. Commun. Chem. Pathol. Pharmacol. (1971) 2:793-805.
  • DEVEREUX TR, FOUTS JR: N-oxidation and demethylation of N,N,-dimethylaniline by rabbit liver and lung microsomes. Effects of age and metals. Chem. Biol. Interact. (1974) 8:91-105.
  • SHEHIN-JOHNSON SE, WILLIAMSDE, LARSEN-SU S, STRESSER DM, HINES RN: Tissue-specific expression of flavin-containing monooxygenase (FMO) forms 1 and 2 in the rabbit. J. Pharmacol. Exp. Ther. (1995) 272:1293-1299.
  • BURNETT VL, LAWTON MP, PHILPOT RM: Cloning and sequencing of flavin-containing monooxygenases FMO3 and FMO4 from rabbit and characterization of FMO3. J. Biol. Chem. (1994) 269:14314-14322.
  • ATTA-ASAFO-ADJEI E, LAWTON MP, PHILPOT RM: Cloning, sequencing, distribution, and expression in Escherichia coli of flavin-containing monooxygenase 1C1. Evidence for a third gene subfamily in rabbits. J. Biol. Chem. (1993) 268:9681-9689.
  • LARSEN-SU S, KRUEGER SK, YUEHMF etal.: Flavin-containing monooxygenase isoform 2: developmental expression in fetal and neonatal rabbit lung. J. Biochem. Mol. Toxicol. (1999) 13:187-193.
  • CHERRINGTON NJ, CAO Y, CHERRINGTON JW, ROSE RL, HODGSON E: Physiological factors affecting protein expression of flavin-containing monooxygenases 1, 3 and 5. Xenobiotica (1998) 28:673-682.
  • JANMOHAMED A, HERNANDEZ D, PHILLIPS IR, SHEPHARD EA: Cell-, tissue-, sex- and developmental stage-specific expression of mouse flavin-containing monooxygenases (Fmos). Biochem. Pharmacol. (2004) 68:73-83.
  • LOMRI N, GU Q, CASHMAN JR: Molecular cloning of the flavin-containing monooxygenase (form II) cDNA from adult human liver. Proc. Natl. Acad. Sci. USA (1992) 89:1685-1689.
  • DOLPHIN CT, CULLINGFORD TE, SHEPHARD EA, SMITH RL, PHILLIPSIR: Differential developmental and tissue-specific regulation of expression of the genes encoding three members of the flavin-containing monooxygenase family of man, FMO1, FMO3 and FMO4. Eur. J. Biochem. (1996) 235:683-689.
  • KRAUSE RJ, LASH LH, ELFARRA AA: Human kidney flavin-containing monooxygenases and their potential roles in cysteine S-conjugate metabolism and nephrotoxicity. J. Pharmacol. Exp. Ther. (2003) 304:185-191.
  • DOLPHIN CT, BECKETT DJ, JANMOHAMED A etal.: The flavin-containing monooxygenase 2 gene (FMO2) of humans, but not of other primates, encodes a truncated, non-functional protein. J. Biol. Chem. (1998) 273:30599-30607.
  • WHETSTINE JR, YUEH M-F, HOPP KA etal.: Ethnic differences in human flavin-containing monooxygenase 2 (FMO2) polymorphisms: detection of expressed protein in African-Americans. Toxicol. Appl. Pharmacol. (2000) 168:216-224.
  • KRUEGER SK, SIDDENS LK, MARTINSR etal.: Differences in FMO2*1 allelic frequency between Hispanics of Puerto Rican and Mexican descent. Drug Metab Dispos. (2004) 32:1337-1340.
  • KRUEGER SK, SIDDENS LK, HENDERSON MC etal.: Haplotype and functional analysis of four flavin-containing monooxygenase 2 (FMO2) polymorphisms in Hispanics. Pharmacogenetics (2005) 15:245-256.
  • KOUKOURITAKI SB, SIMPSON P, YEUNG CK, RETTIE AE, HINES RN: Human hepatic flavin-containing monooxygenase 1 (FMO1) and 3 (FMO3) developmental expression. Pediatric Res. (2002) 51:236-243.
  • LUO Z, HINES RN: Identification of multiple flavin-containing monooxygenase form 1 (FMO1) gene promoters and observation of tissue-specific DNaseI hypersensitive sites. Arch. Biochem. Biophys. (1996) 336:251-260.
  • SUASEN PJ, DUESCHER RJ, ELFARRAAA: Further characterization and purification of the flavin-dependent S-benzyl-l-cysteine S-oxidase activities of rat liver and kidney microsomes. Mol. Pharmacol. (1993) 43:388-396.
  • DANNAN GA, GUENGERICH FP, WAXMAN DJ: Hormonal regulation of rat liver microsomal enzymes. Role of gonadal steroids in programming, maintenance and suppression of delta4-steroid 5a-reductase, flavin-containing monooxygenase, and sex-specific cytochromes P450. J. Biol. Chem. (1986) 261:10728-10735.
  • STEVENS JC, HINES RN, GU C etal.: Developmental expression of the major human hepatic CYP3A enzymes. J. Pharmacol. Exp. Ther. (2003) 307:573-582.
  • TRLUYER JM, REY E, SONNIER M, PONS G, CRESTEIL T: Evidence of impaired cisapride metabolism in neonates. Br. J. Clin. Pharmacol. (2001) 52:419-425.
  • PEARCE RE, GOTSCHALL RR, KEARNS GL, LEEDER JS: Cytochrome P450 involvement in the biotransformation of cisapride and racemic norcisapride invitro: differential activity of individual CYP3A isoforms. Drug Metab. Dispos. (2001) 29:1548-1554.
  • NONG A, MCCARVER DG, HINES RN, KRISHNAN K: Physicologically-based modeling of inter-child differences in pharmacokinetics on the basis of subject-specific data on hepatic CYP2E1 levels. Toxicol. Appl. Pharmacol. (2005) (In Press).
  • CASHMAN JR, CAMP K, FENNESSEYPV etal.: Biochemical and clinical aspects of the human flavin-containing monooxygenase form 3 (FMO3) related to trimethylaminuria. Curr. Drug Metab. (2003) 4:151-170.
  • CASHMAN JR: The role of flavin-containing monooxygenases in drug metabolism and development. Curr. Opin. Drug Discov. Devel. (2003) 6:486-493.
  • ZIEGLER DM: An overview of the mechanism, substrate specificities, and structure of FMOs. Drug Metab. Rev. (2002) 34:503-511.
  • HINES RN, LUO Z, HOPP KA etal.: Genetic variability at the human FMO1 locus: significance of a yin yang 1 element polymorphism (FMO1*6). J. Pharmacol. Exp. Ther. (2003) 306:1210-1218.
  • LEEDER JS, GAEDIGK R, MARCUCCIKA etal.: Variability of CYP3A7 expression in human fetal liver. J. Pharmacol. Exp. Ther. (2005) 314:626-635.
  • KRUEGER SK, MARTIN SR, YUEHM-F, PEREIRA CB, WILLIAMSDE: Identification of active flavin-containing monooxygenase isoform 2 in human lung and characterization of expressed protein. Drug Metab. Dispos. (2002) 30:34-41.
  • BHAMRE S, BHAGWAT SV, SHANKARSK, BOYD MR, RAVINDRANATH V: Flavin-containing monooxygenase mediated metabolism of psychoactive drugs by human brain microsomes. Brain Res. (1995) 672:276-280.
  • JANMOHAMED A, DOLPHIN CT, PHILLIPS IR, SHEPHARD EA: Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenases and cytochromes P450. Biochem. Pharmacol. (2001) 62:777-786.
  • MAYATEPEK E, KOHLMELLER D: Transient trimethylaminuria in childhood. Acta Paediatr. (1998) 87:1205-1207.
  • JOHNSRUD EK, KOUKOURITAKI SB, DIVAKARAN K etal.: Human hepatic CYP2E1 expression during development. J. Pharmacol. Exp. Ther. (2003) 307:402-407.
  • KOUKOURITAKI SB, MANRO JR, MARSH SA etal.: Developmental expression of human hepatic CYP2C9 and CYP2C19. J. Pharmacol. Exp. Ther. (2004) 308:965-974.

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