Organization and evolution of the flavin-containing monooxygenase genes of human and mouse: Identification of novel gene and pseudogene clusters

Pharmacogenetics

Volumn 14, Issue 2, 2004, Pages 117-130

  Hernandez, Diana ^a   Janmohamed, Azara ^a   Chandan, Pritpal ^a   Phillips, Ian R ^b   Shephard, Elizabeth A ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Chromosome 1; Evolution; Flavin containing monooxygenase; FMO; Gene family; Human; Mouse; Pseudogene

Indexed keywords

QUERCETIN; UNSPECIFIC MONOOXYGENASE;

CHROMOSOME; GENE CLUSTER; GENE EXPRESSION; GENE FUNCTION; GENE IDENTIFICATION; GENE STRUCTURE; HUMAN; MULTIGENE FAMILY; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PRIORITY JOURNAL; PSEUDOGENE; REVIEW;

AMINO ACID SEQUENCE; ANIMALS; BASE SEQUENCE; CHROMOSOMES, ARTIFICIAL, BACTERIAL; CHROMOSOMES, HUMAN, PAIR 1; CLONING, MOLECULAR; DNA; EVOLUTION, MOLECULAR; FEMALE; GENE LIBRARY; HUMANS; MALE; MICE; MICE, INBRED C57BL; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; OPEN READING FRAMES; OXYGENASES; PHYLOGENY; PSEUDOGENES; RATS; SEQUENCE HOMOLOGY, AMINO ACID; SEQUENCE HOMOLOGY, NUCLEIC ACID; TISSUE DISTRIBUTION;

MAMMALIA;

EID: 1342309263     PISSN: 0960314X     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008571-200402000-00006     Document Type: Review

References (53)

1. Ziegler DM. Recent studies on the structure and function of multisubstrate flavin-containing monooxygenases. Ann Rev Pharmacol Toxicol 1993; 33:179-199.
2. Rettie AE, Meier GP, Sadeque AJ. Prochiral sulfides as in vitro probes for multiple forms of the flavin-containing monooxygenase. Chem Biol Interact 1995; 96:3-15.
3. Cashman JR. Stereoselectivity in S- and N-oxygenation by the mammalian flavin-containing and cytochrome P-450 monooxygenases. Drug Met Rev 1998; 30:675-707.
4. Cashman JR. Human flavin-containing monooxygenase: substrate specificity and role in drug metabolism. Curr Drug Metab 2000; 1:181-191.
5. Marks R, Greaves MW, Prottey C, Hartop PJ. Trimethylaminuria: the use of choline as an aid to diagnosis. Br J Dermatol 1977; 96:399-402.
6. Cashman JR, Ziegler DM. Contribution of N-oxygenation to the metabolism of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) by various liver preparations. Mol Pharmacol 1986; 29:163-167.
7. Duffel MW, Logan DJ, Ziegler DM. Cysteamine and cystamine. Methods Enzymol 1987; 143:149-154.
8. Suh JK, Poulsen LL, Ziegler DM, Robertus JD. Redox regulation of yeast flavin-containing monooxygenase. Arch Biochem Biophys 2000; 381:317-321.
9. Ziegler DM, Duffel MW, Poulsen LL. Studies on the nature and regulation of the cellular thio:disulphide potential. Ciba Found Symp 1979; 2:191-204.
10. Guo WX, Ziegler DM. Estimation of flavin-containing monooxygenase activities in crude tissue preparations by thiourea-dependent oxidation of thiocholine. Anal Biochem 1991; 198:143-148.
11. Kim YM, Ziegler DM. Size limits of thiocarbamides accepted as substrates by human flavin-containing monooxygenase 1. Drug Metab Dispos 2000; 28:1003-1006.
12. Dolphin CT, Janmohamed A, Smith RL, Shephard EA, Phillips IR. Missense mutation in flavin-containing mono-oxygenase 3 gene, FMO3, underlies fish-odour syndrome. Nat Genet 1997; 17:491-494.
13. Hernandez D, Addou S, Lee D, Orengo C, Shephard EA, Phillips IR. Trimethylaminuria and a human FMO3 mutation database. Hum Mutat 2003; 22:201-213.
14. Mitchell SC, Smith RL. Trimethylaminuria: the fish malodor syndrome. Drug Metab Dispos 2001; 29:517-521.
15. Cashman JR, Camp K, Fakharzadeh SS, Fennessey PV, Hines RN, Mamer OA, et al. Biochemical and clinical aspects of the human flavin-containing monooxygenase form 3 (FMO3) related to trimethylaminuria. Curr Drug Metab 2003; 4:151-170.
16. Phillips IR, Dolphin CT, Clair P, Hadley MR, Hutt AJ, McCombie RR, et al. The molecular biology of the flavin-containing monooxygenases of man. Chem Biol Interact 1995; 96:17-32.
17. Dolphin C, Shephard EA, Povey S, Palmer CN, Ziegler DM, Ayesh R, et al. Cloning, primary sequence, and chromosomal mapping of a human flavin-containing monooxygenase (FMO1). J Biol Chem, 1991; 266:12379-12385.
18. Dolphin CT, Beckett DJ, Janmohamed A, Cullingford TE, Smith RL, Shephard EA, et al. The flavin-containing monooxygenase 2 gene (FMO2) of humans, but not of other primates, encodes a truncated, nonfunctional protein. J Biol Chem 1998; 273:30599-30607.
19. Dolphin CT, Cullingford TE, Shephard EA, Smith RL, Phillips IR. 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; 235:683-693.
20. Dolphin CT, Shephard EA, Povey S, Smith RL, Phillips IR. Cloning, primary sequence and chromosomal localization of human FMO2, a new member of the flavin-containing mono-oxygenase family. Biochem J 1992; 287:261-267.
21. 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.
22. Fourney RM, Miyakoshi J, Day RS, Paterson MC. Northern blotting: efficient RNA staining and transfer. Focus (BRL) 1988; 10:5-7.
23. Osoegawa K, Tateno M, Woon PY, Frengen E, Mammoser AG, Catanese JJ, et al. Bacterial artificial chromosome libraries for mouse sequencing and functional analysis. Genome Res 2000; 10:116-128.
24. Overby LH, Buckpitt AR, Lawton MP, Atta-Asafo-Adjei E, Schulze J, Philpot RM. Characterization of flavin-containing monooxygenase 5 (FMO5) cloned from human and guinea pig: evidence that the unique catalytic properties of FMO5 are not confined to the rabbit ortholog. Arch Biochem Biophys 1995; 317:275-284.
25. Cherrington NJ, Falls JG, Rose RL,Clements KM, Philpot RM, Levi PE, et al. Molecular cloning, sequence, and expression of mouse flavin-containing monooxygenases 1 and 5 (FMO1 and FMO5). J Biochem Mol Toxicol 1998; 12:205-212.
26. Falls JG, Cherrington NJ, Clements KM, Philpot RM, Levi PE, Rose RL, et al. Molecular cloning, sequencing, and expression in Escherichia coli of mouse flavin-containing monooxygenase 3 (FMO3): comparison with the human isoform. Arch Biochem Biophys 1997; 347:9-18.
27. Reese MG, Eeckman FH, Kulp D, Haussler D. Improved splice site detection in Genie. J Comput Biol 1997; 4:311-323.
28. Swofford, DL, PAUP*: Phylogenetic Analysis Using Parsimony (and Other Methods) 4.0 Beta. 2002, Sunderland, MA: Sinauer Associates, Inc.
29. Lomri N, Gu Q, Cashman JR. Molecular cloning of the flavin-containing monooxygenase (form II) cDNA from adult human liver. Proc Natl Acad Sci U S A 1992; 89:1685-1689.
30. Lawton MP, Cashman JR, Cresteil T, Dolphin CT, Elfarra AA, Hines RN, et al. A nomenclature for the mammalian flavin-containing monooxygenase gene family based on amino acid sequence identities. Arch Biochem Biophys 1994; 308:254-257.
31. Itoh K, Nakamura K, Kimura T, Itoh S, Kamataki T. Molecular cloning of mouse liver flavin containing monooxygenase (FMO1) cDNA and characterization of the expression product: metabolism of the neurotoxin, 1,2,3,4- tetrahydroisoquinoline (TIQ). J Toxicol Sci 1997; 22:45-56.
32. Karoly ED, Rose RL. Sequencing, expression, and characterization of cDNA expressed flavin-containing monooxygenase 2 from mouse. J Biochem Mol Toxicol 2001; 15:300-308.
33. Janmohamed A, Hernandez D, Chandan P, Phillips IR, Shephard EA. Cell type-specific expression of the flavin-containing mono-oxygenase family of mouse, submitted.
34. Dolphin CT, Riley JH, Smith RL, Shephard EA, Phillips IR. Structural organization of the human flavin-containing monooxygenase 3 gene (FMO3), the favored candidate for fish-odor syndrome, determined directly from genomic DNA. Genomics 1997; 46:260-267.
35. Lattard V, Longin-Sauvageon C, Benoit E. Cloning, sequencing and tissue distribution of rat flavin-containing monooxygenase 4: two different forms are produced by tissue-specific alternative splicing. Mol Pharmacol 2003; 63:253-261.
36. Luo Z, Hines RN. Identification of multiple rabbit flavin-containing monooxygenase form 1 (FMO1) gene promoters and observation of tissue-specific DNase 1 hypersensitive sites. Arch Biochem Biophys 1996; 336:251-260.
37. Koukouritaki SB, Simpson P, Yeung CK, Rettie AE, Hines RN. Human hepatic flavin-containing monooxygenases 1 (FMO1) and 3 (FMO3) developmental expression. Pediatr Res 2002; 51:236-243.
38. Falls JG, Blake BL, Cao Y, Levi PE, Hodgson E. Gender differences in hepatic expression of flavin-containing monooxygenase isoforms (FMO1, FMO3, and FMO5) in mice. J Biochem Toxicol 1995; 10:171-177.
39. Falls JG, Ryu DY, Cao Y, Levi PE, Hodgson E. Regulation of mouse liver flavin-containing monooxygenases 1 and 3 by sex steroids. Arch Biochem Biophys 1997; 342:212-223.
40. Whetstine JR Yueh M, McCarver DG, Williams DE, Park C, Kang JH, et al. Ethnic differences in human flavin-containing monooxygenase 2 (FMO2) polymorphisms: detection of expressed protein in African-Americans. Toxicol Appl Pharmacol 2000; 168:216-224.
41. Krueger SK, Martin SR, Yueh MF, Pereira CB, Williams DE. Identification of active flavin-containing monooxygenase isoform 2 in human lung and characterization of expressed protein. Drug Metab Dispos 2002; 30:34-41.
42. Williams DE, Ziegler DM, Nordin DJ, Hale SE, Masters BS. Rabbit lung flavin-containing monooxygenase is immunochemically and catalytically distinct from the liver enzyme. Biochem Biophys Res Commun 1984; 125:116-122.
43. Yeung CK, Lang DH, Thummel KE, Rettie AE. Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab Dispos 2000; 28:1107-1111.
44. Lang DH, Rettie AE. In vitro evaluation of potential in vivo probes for human flavin-containing monooxygenase (FMO): metabolism of benzydamine and caffeine by FMO and P450 isoforms. Br J Clin Pharmacol 2000; 50:311-314.
45. Attar M, Dong D, Ling KH, Tang-Liu DD. Cytochrome P450 2C8 and Flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. Drug Metab Dispos 2003; 31:476-481.
46. Lang DH, Yeung CK, Peter RM, Ibarra C, Gasser R, Itagaki K, et al. Isoform specificity of trimethyiamine N-oxygenation by human flavin-containing monooxygenase (FMO) and P450 enzymes: selective catalysis by FMO3. Biochem Pharmacol 1998; 56:1005-1012.
47. Ripp SL, Itagaki K, Philpot RM, Elfarra AA. Methionine S-oxidation in human and rabbit liver microsomes: evidence for a high-affinity methionine S-oxidase activity that is distinct from flavin-containing monooxygenase 3. Arch Biochem Biophys 1999; 367:322-332.
48. Phillips IR, Dolphin CT, McCombie RR, Beckett DJ, Janmohamed A, Smith RL, et al. Molecular genetics of the flavin-containing monooxygenases. In First International Workshop on Trimethylaminuria 1999; Bethesda, MD, USA.
49. Hines RN, Hopp KA, Franco J, Saeian K, Begun FP. Alternative processing of the human FMO6 gene renders transcripts incapable of encoding a functional flavin-containing monooxygenase. Mol Pharmacol 2002; 62:320-325.
50. Shephard EA, Dolphin CT, Fox MF, Povey S, Smith R, Phillips IR. Localization of genes encoding three distinct flavin-containing monooxygenases to human chromosome 1q. Genomics 1993; 16:85-89.
51. McCombie RR, Dolphin CT, Povey S, Phillips IR, Shephard EA. Localization of human flavin-containing monooxygenase genes FMO2 and FMO5 to chromosome 1q. Genomics 1996; 34:426-429.
52. Carver EA, Stubbs L. Zooming in on the human-mouse comparative map: genome conservation re-examined on a high resolution scale. Genome Res 1997; 7:1123-1137.
53. Gelb BD, Zhang J, Cotter PD, Gershin IF, Desnick RJ. Physical mapping of the human connnexin 40 (GJA5), flavin-containing monooxygenase 5, and natriuretic peptide receptor genes on 1q21. Genomics 1997; 39:409-411.