Mutation, polymorphism and perspectives for the future of human flavin-containing monooxygenase 3

Mutation Research - Reviews in Mutation Research

Volumn 612, Issue 3, 2006, Pages 165-171

  Zhou, Jianhua ^a   Shephard, Elizabeth A ^b  

^a SOOCHOW UNIVERSITY   (China)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

FMO3; Mutation; Polymorphism

Indexed keywords

FLAVIN CONTAINING MONOOXYGENASE 3; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TRIMETHYLAMINE OXIDE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

DETOXIFICATION; ETHNIC DIFFERENCE; GENE EXPRESSION; GENE MUTATION; GENETIC POLYMORPHISM; GENETIC VARIABILITY; HUMAN; HUMAN TISSUE; LIVER; METABOLIC DISORDER; NUCLEOTIDE SEQUENCE; OXYGENATION; PRIORITY JOURNAL; REVIEW; TRIMETHYLAMINURIA;

ADULT; CHILD; CHILD, PRESCHOOL; HUMANS; LIVER; METHYLAMINES; MUTATION; ODORS; OXYGENASES; POLYMORPHISM, GENETIC;

EID: 33646812867     PISSN: 13835742     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrrev.2005.09.001     Document Type: Review

References (53)

1. Ziegler D.M. Microsomal Flavin-containing Monooxygenase: Oxygenation of Nucleophilic Nitrogen and Sulfur Compounds in Enzymatic Basis of Detoxication vol. 1 (1980), Academic Press, New York pp. 210-277
2. Cashman J.A., Park S.B., Berkman C., and Cashman L.E. Role of hepatic flavin-containing monooxygenase 3 in drug and chemical metabolism in adult humans. Chem. Biol. Interact. 96 (1995) 33-46
3. Chung W.G., Park C.S., Roh H.K., Lee W.K., and Cha Y.N. Oxidation of rantidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn. J. Pharmacol. 84 (2000) 213-220
4. Hodgson E., Rose R.L., Cao Y., Dehal S.S., and Kupfer D. Flavin-containing monooxygenase isoform specificity for the N-oxidation of tamoxifen determined by product measurement and NADPH oxidation. J. Biochem. Mol. Toxicol. 14 (2000) 118-120
5. Ziegler-Skylakakis K., Nill S., Pan J.F., and Andrae U. S-oxygenation of thiourea results in the formation of genotoxic products. Environ. Mol. Mutagen. 31 (1998) 362-373
6. Hodgson E., Rose R.L., Falls G., Blake B.L., and Levi P.E. Pesticide-metabolizing enzymes. Toxicol. Lett. 83 (1995) 73-81
7. Al-Waiz M., Ayesh R., Mitchell S.C., Idle J.R., and Smith R.L. A genetic polymorphism of the N-oxidation of trimethylamine in humans. Clin. Pharmacol. Ther. 42 (1987) 588-594
8. Phillips I.R., Dolphin C.T., Clair P., Hadley M.R., Hutt A.J., McCombie R.R., Smith R.L., and Shephard E.A. The molecular biology of the flavin-containing monooxygenases of man. Chem. Biol. Interact. 96 (1995) 17-32
9. Shephard E.A., Dolphin C.T., Povey S., Smith R.L., and Philips I.R. Localization of genes encoding three distinct flavin-containing monooxygenases to human chromosome 1q. Genomics 16 (1993) 85-89
10. McCombie R.R., Dolphin C.T., Povey S., Phillips I.R., and Shephard E.A. Localization of human flavin-containing monooxygenase genes FMO2 and FMO5 to chromosome lq. Genomics 15 (1996) 426-429
11. Humber J.R., Hammond K.B., Hathaway W.E., Marcoux J.G., and O'Brien D. Trimethylaminuria: the fish-odour syndrome. Lancet 1 (1970) 770-771
12. Bain M.D., Jones M., Boriello S.P., Reed P.J., Tracey B.M., Chalmers R.A., and Stacey T.E. Contribution of gut bacterial metabolism to human metabolic disease. Lancet 1 (1988) 1079
13. Ayesh R., Mitchell S.C., Zhang A.Q., and Smith R.L. The fish odour syndrome: biochemical, familial and clinical aspects. Br. Med. J. 307 (1993) 655-657
14. Zhang A.Q., Mitchell S., and Smith R. Fish odour syndrome: verification of carrier detection test. J. Inherit. Metab. Dis. 18 (1995) 669-674
15. Shelley E.D., and Shelley W.B. The fish odor syndrome. Trimethylaminuria. JAMA 251 (1984) 253-255
16. Todd W.A. Psychosocial problems as the major complication of an adolescent with trimethylaminuria. J. Pediatr. 94 (1997) 936-937
17. Haddi H.F., Cholerton S., Atkinson S., Irshaid Y.M., Rawashdeh N.M., and Ide J.R. The N-oxidation of trimethylamine in a Jordanian population. Br. J. Clin. Pharmacol. 39 (1995) 179-181
18. Cashman J.R., Park S.B., Yang Z.C., Washington S.A., Gomez D.Y., Giacomini K.M., and Brett C.M. Chemical, enzymatic, and human enantioselective S-oxygenation of cimetidine. Drug Metab. Dispos. 21 (1993) 587-597
19. Murphy H.C., Dolphin C.T., Janmohamed A., Holmes H.C., Michelakakis H., Shephard E.A., Chalmers R.A., Phillips I.R., and Iles R.A. A novel mutation in the flavin-containing monooxygenase 3 gene, FMO3, that causes fish-odour syndrome: activity of the mutant enzyme assessed by proton NMR spectroscopy. Pharmacogenetics 10 (2000) 439-451
20. Mitchell S.C., and Smith R.L. Trimethylamuria: the fish malodor syndrome. Drug Metab. Dispos. 29 (2001) 517-521
21. Mazon R.A., Gil-Setas A., Berrade A.S., Bandres E.T., Wevers R., Engelke U., and Aschocke J. Primary trimethylaminuria or fish odor syndrome. A novel mutation in the first documented case in Spain. Med. Clin. (Barc) 22 (2003) 219-221
22. Dolphin C.T., Janmohamed A., Smith R.L., Shephard E.A., and Phillips I.R. Missense mutation in flavin-containing monooxygenase 3 gene, FMO3, underlies fish-odour syndrom. Nat. Genet. 17 (1997) 491-494
23. Akerman B.R., Forrest S., Chow L., Youil R., Knight M., and Treacy E.P. Two novel mutations of the FMO3 gene in a proband with trimethylaminuria. Hum. Mutat. 13 (1999) 376-379
24. Treacy E.P., Akerman B.R., Chow LML, Youil R., Bibeau C., Lin J., Bruce A.G., Knight M., Danks D.M., Cashman J.R., and Forrest S.M. Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication. Hum. Mol. Genet. 7 (1998) 839-845
25. Akerman B.R., Lemass H., Chow L.M., Lambert D.M., Greenburg C., Bibeau C., Mamer O.A., and Treacy E.P. Trimethylaminuria is caused by mutations of the FMO3 gene in a North American population. Mol. Genet. Metab. 68 (1999) 24-31
26. Basarab T., Ashton G.H., Menage H.P., and McGrath J.A. Sequence variations in the flavin-containing mono-oxygenase 3 gene (FMO3) in fish odour syndrome. Br. J. Dermatol. 140 (1999) 164-167
27. Dolphin C.T., Janmohamed A., Smith R.L., Shephard E.A., and Phillips I.R. Compound heterozygosity for missense mutations in the flavin-containing monooxygenase 3 (FMO3) gene in patients with fish-odor syndrome. Pharmacogenetics 10 (2000) 799-807
28. Park C.S., Chung W.G., Kang J.H., Roh H.K., Lee K.H., and Cha Y.N. Phenotyping of flavin-containing monooxygenase using caffeine metabolism of FMO3 in a Korean population. Pharmacogenetics 9 (1999) 155-164
29. Zschocke J., Kohlmueller D., Quak E., Meissner T., Hoffman G.F., and Mayatepek E. Mild trimethylaminuria caused by common variants in FMO3 gene. Lancet 354 (1999) 834-835
30. Hernandez D., Addou S., Lee D., Orengo C., Shephard E.A., and Phillips I.R. Trimethylaminuria and a human FMO3 mutation database. Hum. Mutat. 22 3 (2003) 209-213
31. Agundez J.A., Gallardo L., Ledesma M.C., Lozano L., Rodriguez-Lescure A., Pontes J.C., Iglesias-Moreno M.C., Poch J., Ladero J.M., and Benitez. Functionally active duplications of the CYP2D6 gene was more prevalent among larynx and lung cancer patients. Oncology 61 (2001) 59-63
32. Park S.B., Jacob P., Benowitz N.L., and Cashman J.R. Stereoselective metabolism of (S)-()-nicotine in humans: formation of trans (S)-()-nicotine N-1′-oxide. Chem. Res. Toxicol. 6 (1993) 880-888
33. Lattard W., Zhang J., Tran Q., Furnes B., Schlenk D., and Cashman J.R. Two new polymorphisms of the FMO3 gene in Caucasian and African-American populations; comparative genetic and functional studies. Drug Metab. Dispos. 31 (2003) 854-860
34. Cashman J.R., Zhang J., Leushner J., and Braun A. Population distribution of human flavin-containing monooxygenase, form 3: gene polymorphisms. Drug Metab. Dispos. 29 (2001) 1629-1637
35. Zeng W.M., Tang J., Dong Y.L., Shi H., Gao L., Yang Z.L., Lu J., Hao Z.J., and Xiao C.J. The frequency distribution of flavin-containing monooxygenase 3 mutant alleles in 28 population from Yunnan. Zhonghua Yi Xue Yi Zhuan Xue Za Zhi 20 (2003) 318-321
36. Bourd P., Blackbum A., Jermin L.S., and Chelvanayagam G. Polymorphism of phase II enzymes: identification of new enzymes and polymorphic variants by database analysis. Toxicol. Lett. 102-103 (1998) 149-154
37. Bertilsson L., Dahl M.L., Dalen P., and Al-Shurbaji A. Molecular genetics of CYP2D6: clinical relevance with focus on psychotropic drug. Br. J. Clin. Pharmacol. 53 (2002) 111-122
38. Dolphin C.T., Riley J.H., Smith R.L., Shephard E.A., and Phillips I.R. Structural organization of the human flavin-containing monooxygenase 3 gene (FMO3), the favored candidate for fish-odor syndrome, determined directly from genomic DNA. Genomics 46 (1997) 260-267
39. Lambert D.M., Mamer O.A., Akerman B.R., Luc Choinie' re, Gaudet D., Hamet P., and Treacy E.P. In vivo variability of TMA oxidation is partially mediated by polymorphisms of the FMO3 gene. Mol. Genet. Metab. 73 (2001) 224-229
40. Furnes B., Feng J., Sommer S.S., and Schlenk D. Identification of novel variants of the flavin-containing monooxygenase gene family in Afrivan Americans. Drug Metab. Dispos. 32 (2003) 187-752
41. Cashman J.R., Xiong Y.N., Xu L., and Janowsky A. N-Oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication. J. Pharmacol. Exp. Ther. 288 (1999) 1251-1260
42. Stormer E., Roots I., and Brockmoller J. Benzydamine N-oxidation as an index reaction reflecting FMO activity in human liver microsomes and impact of FMO3 polymorphisms on enzyme activity. Br. J. Clin. Pharmacol. 50 (2000) 553-561
43. Mayatepek E., Flock B., and Zschocke J. Benzydamine metabolism in vivo is impaired in patients with deficiency of flavin-containing monooxygenase 3. Pharmacogenetics 14 (2004) 775-777
44. Park C.S., Kang J.H., Chung W.G., Yi H.G., Pie J.E., Park D.K., Hines R.N., McCarver D.G., and Cha Y.N. Ethnic differences in allelic frequency of two flavin-containing monooxgenase 3 (FMO3) polymorphisms: linkage and effects on in vivo and in vitro FMO activities. Pharmacogenetics 12 (2002) 77-80
45. Cashman J.R., and Zhang J. Interindividual differences of human flavin-containing monooxygenease 3: genetic polymorphisms and functional variation. Drug Metab. Dispos. 30 (2002) 1043-1049
46. Janmohamed A., Dolphic C.T., Philip I.R., and Shephard E.A. Quantification and cellular localization of expression in human skin of genes encoding flavin-containing monooxygenase and cytochromes P450. Biochem. Pharmacol. 62 (2001) 777-786
47. Elfarra A.A., and Krause R.J. Potential roles of flavin-containing monooxygenases in sulfoxidation reactions of l-methionine, N-acetyl-l-methionine and peptides containing l-methionine. Biochim. Biophys. Acta 1703 2 (2005) 183-189
48. Hisamuddin I.M., Wehbi M.A., Chao A., Wyre H.W., Hylind L.M., Giardiello F.M., and Yang V.W. Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposis. Clin. Cancer Res. 10 24 (2004) 8357-8362
49. Phillips I.R., and Shephard E.A. Flavin-containing monooxygenases. In: Creighton T.E. (Ed). Wiley Encyclopedia of Molecular Medicine (2002), John Wiley and Sons, New York, New York, USA 1297-1299
50. Koukouritaki S.B., Poch M.T., Cabacungan E.T., McCarver D.G., and Hines R.N. Discovery of novel flavin-containing monooxygenase 3 (FMO3) single nucleotide polymorphisms and functional analysis of upstream haplotype variants. Mol. Pharmacol. 106 3 (2005) 357-387
51. Mayatepek E., and Kohlmueller D. Transient trimethylaminuria in childhood. Acta Paediatr. Int. J. Paediatr. 87 (1998) 1205-1207
52. Zhang J., Tran Q., Lattard V., and Cashman J.R. Deleterious mutations in the flavin-containing monooxygenase 3 (FMO3) gene causing trimethylaminuria. Pharmacogenetics 13 (2003) 49-50
53. Coecke S., Debast G., Phillips I.R., Vercruysse A., Shephard E.A., and Rogiers V. Hormonal regulation of microsomal flavin-containing monooxygenase activity by sex steroids and growth hormone in co-cultured adult male rat hepatocytes. Biochem. Pharmacol. 56 (1998) 1047-1051