Inducible nitric oxide synthase catalyzes ethanol oxidation to α-hydroxyethyl radical and acetaldehyde

Toxicology

Volumn 223, Issue 3, 2006, Pages 167-174

  Porasuphatana, Supatra ^a   Weaver, John ^b,c   Rosen, Gerald M ^b,c,d  

^a KHON KAEN UNIVERSITY   (Thailand)

^b UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^c UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE   (United States)

^d UNIVERSITY OF MARYLAND   (United States)

Author keywords

Hydroxyethyl radical; Acetaldehyde; Ethanol; Nitric oxide synthase

Indexed keywords

ACETALDEHYDE; ALCOHOL; ARGININE; FREE RADICAL; INDUCIBLE NITRIC OXIDE SYNTHASE;

ARTICLE; CATALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; METABOLISM; OXIDATION; PRIORITY JOURNAL;

ACETALDEHYDE; ARGININE; CATALASE; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ETHANOL; HYDRAZONES; NITRIC OXIDE SYNTHASE TYPE II; OXIDATION-REDUCTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPIN TRAPPING; SUPEROXIDE DISMUTASE;

EID: 33744508055     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2006.02.022     Document Type: Article

References (24)

1. Bell-Parikh L.C., and Guengerich F.P. Kinetics of cytochrome P450 2E1-catalyzed oxidation of ethanol to acetic acid via acetaldehyde. J. Biol. Chem. 274 (1999) 23833-23840
2. Chartrain N.A., Geller D.A., Koty P.P., Sitrin N.F., Nussler A.K., Hoffman E.P., Billiar T.R., Hutchinson N.I., and Mudgett J.S. Molecular cloning, structure, and chromosomal localization of the human inducible nitric oxide synthase gene. J. Biol. Chem. 269 (1994) 6765-6772
3. De Montellano P.R.O., Nishida C., Rodriguez-Crespo I., and Gerber N. Nitric oxide synthase structure and electron transfer. Drug Met. Dispos. 26 (1998) 1185-1189
4. Diaz Gomez M.I., Castro G.D., de Layno A.M., Costantini M.H., and Castro J.A. Cytochrome P450 reductase-mediated anaerobic biotransformation of ethanol to 1-hydroxyethyl-free radicals and acetaldehyde. Toxicology 154 (2000) 113-122
5. Förstermann U., Closs E.I., Pollock J.S., Nakane M., Schwarz P., Gath I., and Kleinert H. Nitric oxide synthase isozymes. Characterization, purification, molecular cloning and functions. Hypertension 23 (1994) 1121-1131
6. Guengerich F.P., and Macdonald T.L. Chemical mechanisms of catalysis by cytochrome P-450: A unified view. Acc. Chem. Res. 17 (1984) 9-16
7. G-hydroxyarginine is not relevant to the mechanism. J. Am. Chem. Soc. 123 (2001) 2675-2676
8. Kozutsumi D., Arita M., Kawashima A., Adachi M., and Takami A. An improved method for acetaldehyde determination in blood by high-performance liquid chromatography and solid-phase extraction. J. Chromatogr. Sci. 40 (2002) 477-482
9. 3CHO) production in rodent lung after exposure to metal-rich particles. Free Radical Biol. Med. 26 (1999) 1569-1577
10. Marletta M.A. Nitric oxide synthase structure and mechanism. J. Biol. Chem. 268 (1993) 12231-12234
11. Marsden P.A., Heng H.H., Scherer S.W., Stewart R.J., Hall A.V., Shi X.M., Tsui L.C., and Schappert K.T. Structure and chromosomal localization of the human constitutive endothelial nitric oxide synthase gene. J. Biol. Chem. 268 (1993) 17478-17488
12. Masters B.S.S., McMillan K., Sheta E.A., Nishimura J.S., Roman L.J., and Martasek P. Neuronal nitric oxide synthase, a modular enzyme formed by convergent evolution: structure studies of a cysteine thiolate-ligand heme protein that hydroxylates l-arginine to produce {radical dot}NO as a cellular signal. Fed. Am. Soc. Exp. Biol. J. 10 (1996) 552-558
13. Moncada S., and Higgs A. The l-arginine-nitric oxide pathway. N. Engl. J. Med. 329 (1993) 2002-2012
14. Nathan C. Nitric oxide as a secretory product of mammalian cells. Fed. Am. Soc. Exp. Biol. J. 6 (1992) 3051-3064
15. G-methyl-l-arginine functions as an alternative substrate and mechanism-based inhibitor of nitric oxide synthase. Biochemical 32 (1993) 9677-9685
16. Palmer R.M.J., Rees D.D., Ashton D.S., and Moncada S. l-arginine is the physiological precursor for the formation of nitric oxide in endothelium-dependent relaxation. Biochem. Biophys. Res. Commun. 153 (1988) 1251-1256
17. Pou S., Ramos C.L., Gladwell T., Renks E., Centra M., Young D., Cohen M.S., and Rosen G.M. A kinetic approach to the selection of a sensitive spin trapping system for the detection of hydroxyl radical. Anal. Biochem. 217 (1994) 76-83
18. Porasuphatana S., Tsai P., Pou S., and Rosen G.M. Involvement of the perferryl complex of nitric oxide synthase in the catalysis of secondary free radical formation. Biochim. Biophys. Acta 1526 (2001) 95-104
19. Porasuphatana S., Tsai P., Pou S., and Rosen G.M. Perferryl complex of nitric oxide synthase: role in secondary free radical formation. Biochim. Biophys. Acta 1569 (2002) 111-116
20. Sakuragawa A., Yoneno T., Inoue K., and Okutani T. Trace analysis of carbonyl compounds by liquid chromatography-mass spectrometry after collections as 2,4-dinitrophenyl hydrazone derivatives. J. Chromatogr. A. 844 (1999) 403-408
21. Thomas M.J., Robison T.Q., Samuel M., and Forman H.J. Detecting and identifying volatile aldehydes as dinitrophenylhydrazines using gas chromatography mass spectrometry. Free Radical Biol. Med. 18 (1995) 553-557
22. Uchiyama S., Ando M., and Aoyagi S. Isomerization of aldehyde-2,4-dinitrophenylhydrazone derivatives and validation of high-performance liquid chromatographic analysis. J. Chromatogr. A. 996 (2003) 95-102
23. Xia Y., Roman L.J., Masers B.S.S., and Zweier J.L. Inducible nitric-oxide synthase generates superoxide from the reductase domain. J. Biol. Chem. 273 (1998) 22635-22639
24. Xu W., Gorman P., Sheer D., Bates G., Kishimoto J., Lizhi L., and Emson P. Regional localization of the gene coding for human brain nitric oxide synthase (NOS1) to 12q24.2 → 24.31 by fluorescent in situ hydridization. Cytogenet. Genome Res. 64 (1993) 62-63