Isoform specificity of trimethylamine N-oxygenation by human flavin-containing monooxygenase (FMO) and P450 enzymes Selective catalysis by fmo3

Biochemical Pharmacology

Volumn 56, Issue 8, 1998, Pages 1005-1012

  Lang, Dieter H ^a   Yeung, Catherine K ^a   Peter, Raimund M ^a   Ibarra, Catherine ^a   Gasser, Rodolfo ^b   Itagaki, Kiyoshi ^c   Philpot, Richard M ^c   Rettie, Allan E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

Benzydamine; Cytochrome P450; Flavin containing monooxygenase; N oxidation; Trimethylamine; Trimethylaminuria

Indexed keywords

BENZYDAMINE; CYTOCHROME P450; TRIMETHYLAMINE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; HUMAN; HUMAN TISSUE; KINETICS; LIVER MICROSOME METABOLISM; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; XENOBIOTIC METABOLISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; INTESTINES; KIDNEY; KINETICS; LIVER; METHYLAMINES; MICROSOMES; MICROSOMES, LIVER; OXIDANTS; OXYGENASES;

EID: 0032531915     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00218-4     Document Type: Article

References (33)

1. Mitchell S.C. The fish-odor syndrome. Perspect Biol Med. 39:1996;514-526.
2. Tjoa S., Fennessy P. The identification of trimethylamine excess in man Quantitative analysis and biochemical origins . Anal Biochem. 197:1991;77-82.
3. Holmes H.C., Burns S.P., Michelakakis H., Kordoni V., Bain M.D., Chalmers R.A., Rafter J.E.M., Iles R.A. Choline and L-carnitine as precursors of trimethylamine. Biochem Soc Trans. 25:1997;96S.
4. Zhang A.Q., Mitchell S.C., Ayesh R., Smith R.L. Determination of trimethylamine and related aliphatic amines in human urine by head-space gas chromatography. J Chromatogr. 584:1992;141-145.
5. 14C-labelled trimethylamine and its N-oxide in man. Xenobiotica. 17:1987;551-558.
6. Poulsen L.L., Ziegler D.M. The liver microsomal FAD-containing monooxygenase. J Biol Chem. 254:1979;6449-6455.
7. Ziegler D.M. Recent studies on the structure and function of multisubstrate flavin-containing monooxygenases. Annu Rev Pharmacol Toxicol. 33:1993;179-199.
8. Lawton M.P., Cashman J.R., Cresteil T., Dolphin C.T., Elfarra A.A., Hines R.N., Hodgson E., Kimura T., Ozols J., Phillips I.R., Philpot R.M., Poulsen L.L., Rettie A.E., Shephard E.A., Williams D.E., Ziegler D.M. A nomenclature for the mammalian flavin-containing monooxygenase gene family based on amino acid sequence identities. Arch Biochem Biophys. 308:1994;254-257.
9. Dolphin C.T., Cullingford T.E., Shephard E.A., Smith R.L., Phillips I.R. 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. 235:1996;683-689.
10. Overby L.H., Buckpitt A.R., Lawton M.P., Atta-Asafo-Adjei E., Schulze J., Philpot R.M. 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. 317:1995;275-284.
11. Al-Waiz M., Ayesh R., Mitchell S.C., Idle J.R., Smith R.L. Disclosure of the metabolic retroversion of trimethylamine N-oxide in humans - A pharmacogenetic approach. Clin Pharmacol Ther. 42:1987;608-612.
12. Wranne L. Urinary excretion of trimethylamine and trimethylamine oxide following trimethylamine-administration to normals and to patients with liver disease. Acta Med Scand. 153:1956;433-441.
13. Dolphin C.T., Janmohamed A., Smith R.L., Shepard E.A., Phillips I.R. Missense mutation in flavin-containing mono-oxygenase 3 gene FMO3, underlies fish-odour syndrome. Nat Genet. 17:1997;491-494.
14. Baker J.R., Chaykin S. The biosynthesis of trimethylamine-N-oxide. J Biol Chem. 237:1962;1309-1313.
15. Lang D.H., Rettie A.E., Böcker R.H. Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes. Chem Res Toxicol. 10:1997;1037-1044.
16. Rettie A.E., Bogucki B.D., Lim I., Meier G.P. Stereoselective sulfoxidation of a series of alkyl p-tolyl sulfides by microsomal and purified flavin-containing monooxygenases. Mol Pharmacol. 37:1990;643-651.
17. Itagaki K., Carver G.T., Philpot R.M. Expression and characterization of a modified flavin-containing monooxygenase 4 from humans. J Biol Chem. 271:1996;20102-20107.
18. Haining R.L., Hunter A.P., Sadeque A.J.M., Philpot R.M., Rettie A.E. Baculovirus-mediated expression and purification of human FMO3. Drug Metab Dispos. 25:1997;790-797.
19. Wills R.B.H., Silalahi J., Wooton M. Simultaneous determination of food-related amines by high-performance liquid chromatography. J Liq Chromatog. 10:1987;3183-3191.
20. Baldock G.A., Brodie R.R., Chasseaud L.F., Taylor T. Determination of benzydamine and its N-oxide in biological fluids by high-performance liquid chromatography. J Chromatogr. 529:1990;113-123.
21. Batey D.W., Eckhert C.D. Identification of FAD, FMN and riboflavin in the retina by microextraction and high-performance liquid chromatography. J Anal Biochem. 188:1990;164-167.
22. Segel IH, Enzyme Kinetics, pp. 54-59. John Wiley, New York, 1975.
23. Powis G., Svingen B.A., Degraw C. Iron-EDTA stimulated reduction of indicine N-oxide by the hepatic microsomal fraction, isolated hepatocytes and the intact rat. Biochem Pharmacol. 31:1982;293-299.
24. Kataoka S., Naito T. Reduction of benzydamine N-oxide by rat liver xanthine oxidase. Chem Pharm Bull (Tokyo). 27:1979;2913-2920.
25. Sugiura M., Iwasaki K., Kato R. Reduction of tertiary amine N-oxides by liver microsomal cytochrome P-450. Mol Pharmacol. 12:1976;322-334.
26. Burka L.T., Guengerich F.P., Willard R.J., Macdonald T.L. Mechanism of cytochrome P-450 catalysis. Mechanism of N-dealkylation and amine oxide deoxygenation. J Am Chem Soc. 107:1985;2549-2551.
27. cam. J Am Chem Soc. 106:1984;1514-1515.
28. Higgins T., Chaykin S., Hammond K.B., Humbert J.R. Trimethylamine N-oxide synthesis A human variant . Biochem Med. 6:1972;392-396.
29. Cashman J.R., Bi Y., Lin J., Youil R., Knight M., Forrest S., Treacy E. Human flavin-containing monooxygenase form 3 cDNA expression of the enzymes containing amino acid substitutions observed in individuals with trimethylaminuria . Chem Res Toxicol. 10:1997;837-841.
30. Poulsen L.L., Ziegler D.M. Multisubstrate flavin-containing monooxygenases Applications of mechanism to specificity . Chem Biol Interact. 96:1995;57-73.
31. Ziegler D.M., Mitchell C.H. Microsomal oxidase IV Properties of a mixed-function amine oxidase isolated from pig liver microsomes . Arch Biochem Biophys. 150:1972;116-125.
32. Lomri N., Yang Z., Cashman J.R. Expression in Escherichia coli of the flavin-containing monooxygenase D (form II) from adult human liver Determination of a distinct tertiary amine substrate specificity . Chem Res Toxicol. 6:1993;425-429.
33. Weast RC, Handbook of Chemistry and Physics, p. D-166. CRC Press, Boca Raton, FL, 1984.