The generation of free radicals by nitric oxide synthase

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 134, Issue 3, 2003, Pages 281-289

  Porasuphatana, Supatra ^a   Tsai, Pei ^b   Rosen, Gerald M ^b,c  

^a KHON KAEN UNIVERSITY   (Thailand)

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

^c UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE   (United States)

Author keywords

Hydrogen peroxide; Nitric oxide; Nitric oxide synthase; Superoxide; Hydroxyethyl radical

Indexed keywords

ALPHA HYDROXYETHYL; ARGININE; CARBON; CYTOCHROME P450; FREE RADICAL; HEME; HYDROGEN; HYDROGEN PEROXIDE; IRON; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; SUPEROXIDE; UNCLASSIFIED DRUG;

APOPTOSIS; BINDING AFFINITY; CELL DAMAGE; CYTOTOXICITY; ENZYME ACTIVITY; ENZYME METABOLISM; ENZYME SUBSTRATE; HUMAN; HYDROXYLATION; LIVER TOXICITY; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION;

EID: 0037342638     PISSN: 15320456     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1532-0456(02)00271-5     Document Type: Review

References (64)

1. Abu-Soud H.M., Yoho L.L., Stuehr D.J. Calmodulin controls neuronal nitric-oxide synthase by a dual mechanism. J. Biol. Chem. 269:1994;32047-32050.
2. Adak S., Ghosh S., Abu-Soud H.M., Stuehr D.J. Role of reductase domain cluster 1 acidic residues in neuronal nitric oxide synthase. J. Biol. Chem. 274:1999;22313-22320.
3. Adak, S., Aulak, K.S., Stuehr, D.J., 2002a. Direct evidence for nitric oxide production by a nitric oxide synthase-like protein from Bacillus subtilis. J. Biol. Chem. 277, 16167-16171.
4. Adak, S., Bilwes, A.M., Panda, K., et al., 2002b. Cloning, expression, and characterization of a nitric oxide synthase protein from Deinococcus radiodurans. Proc. Natl. Acad. Sci. USA 99, 107-112.
5. Albano E., Parola M., Comoglio A., Dianzani M.U. Evidence for the covalent binding of hydroxyethyl radicals to rat liver microsomal protein. Alcohol. 28:1993;453-459.
6. Albano E., Clot P., Morimoto M., Tomasi A., Ingelman-Sundberg M., French S. Role of cytochrome P450 2E1-dependent formation of hydroxyethyl free radical in the development of liver damage in rats intragastrically fed with ethanol. Hepatology. 23:1996;155-163.
7. Allen R.G., Tresini M. Oxidative stress and gene regulation. Free Radical Biol. Med. 28:2000;463-499.
8. Baek J.K., Thiel B.A., Lucas S., Stuehr D.J. Macrophage nitric oxide synthase subunits. J. Biol. Chem. 268:1993;21120-21129.
9. Bernabe J.C., Tejedo J.R., Rincon P., et al. Sodium nitroprusside-induced mitochondrial apoptotic events in insulin-secreting RINm5F cells are associated with MAP kinases activation. Exp. Cell Res. 269:2001;222-229.
10. Bielski B.H.J., Allen A.O. Mechanism of the disproportionation of superoxide radicals. J. Phys. Chem. 81:1977;1048-1050.
11. Bredt D.S., Hwang P.M., Glatt C.E., Lowenstein C., Reed R.R., Snyder S.H. Cloned and expressed nitric oxide synthase structurally resembles cytochrome P-450 reductase. Nature. 351:1991;714-718.
12. Chartrain N.A., Geller D.A., Koty P.P., et al. Molecular cloning, structure, and chromosomal localization of the human inducible nitric oxide synthase gene. J. Biol. Chem. 269:1994;6765-6772.
13. Cho H.J., Xie Q.-W., Calaycay J., et al. Calmodulin is a subunit of nitric oxide synthase from macrophages. J. Exp. Med. 176:1992;599-604.
14. Clot P., Albano E., Eliasson E., et al. Cytochrome P4502E1 hydroxyethyl radical adducts as the major antigen in autoimmunity formation among alcoholics. Gastroenterology. 111:1996;206-216.
15. Clot P., Parola M., Bellomo G., et al. Plasma membrane hydroxyethyl radical adducts cause antibody-dependent cytotoxicity in rat hepatocytes exposed to alcohol. Gastroenterology. 113:1997;265-276.
16. Cubberley R.R., Alderton W.K., Boyhan A., Charles I.G., Lowe P.N., Old R.W. Cysteine-200 of human inducible nitric oxide synthase is essential for dimerization of haem domains and for binding of haem, nitroarginine and tetrahydrobiopterin. Biochem. J. 323:1997;141-146.
17. Finkelstein E., Rosen G.M., Rauckman E.J. Spin trapping. Kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102:1980;4994-4999.
18. Furchgott R.F. Studies on relaxation of rabbit aorta by sodium nitrite: the basis for the proposal that the acid-activatable inhibitory factor from bovine retractor penis is inorganic nitrite and the endothelium-derived relaxing factor is nitric oxide. Vanhoutte P.M. Vasodilatation: Vascular Smooth Muscle, Peptides, Autonomic Nerves and Endothelium. 1988;401-414 Raven Press, New York.
19. Furchgott R.F., Zawadzki J.V. The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine. Nature. 299:1980;373-376.
20. Grisham M.B., Jourd'heuil D., Wink D.A. Physiological chemistry of nitric oxide and its metabolites: implications in inflammation. Am. J. Physiol. 276:1999;G315-G321.
21. Groves J.T., McClusky G.A. Aliphatic hydroxylation via oxygen rebound. Oxygen transfer catalyzed by iron. J. Am. Chem. Soc. 98:1976;859-861.
22. Guengerich F.P., Macdonald T.L. Chemical mechanisms of catalysis by cytochrome P-450: a unified view. Acc. Chem. Res. 17:1984;9-16.
23. Guengerich F.P. The chemistry of cytochrome P450 reactions. Ioannides C. Cytochrome P450 Metabolic and Toxicological Aspects. 1996;55-74 CRC Press, Inc, Boca Raton, FL.
24. Hall A.V., Antoniou H., Wang Y., et al. Structural organization of the human neuronal nitric oxide synthase gene (NOS1). J. Biol. Chem. 269:1994;33082-33090.
25. 2+/calmodulin-dependent formation of hydrogen peroxide by brain nitric oxide synthase. Biochem. J. 281:1992;627-630.
26. G-hydroxyarginine is not relevant to the mechanism. J. Am. Chem. Soc. 123:2001;2674-2676.
27. Ignarro L.J., Lippton H., Edwards J.C., et al. Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates. J. Pharmacol. Exp. Ther. 218:1981;739-749.
28. Ignarro L.J., Buga G.M., Wood K.S., Byrns R.E., Chaudhuri G. Endothelium-derived relaxing factor produced and released from artery and vein is nitric oxide. Proc. Natl. Acad. Sci. USA. 84:1987;9265-9269.
29. Kissner R., Nauser T., Bugnon P., Lye P.G., Koppenol W.H. Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stop flow technique, and pulse radiolysis. Chem. Res. Toxicol. 10:1997;1285-1292.
30. Kitamura M., Matsuda H., Kimura S., Iyanagi T. One-electron reduction of quinones by the neuronal nitric oxide synthase reductase domain. Adv. Exp. Med. Biol. 500:2001;323-326.
31. Margolis A.S., Porasuphatana S., Rosen G.M. Role of paraquat in the uncoupling of nitric oxide synthase. Biochim. Biophys. Acta. 1524:2000;253-257.
32. Marletta M.A. Nitric oxide synthase function and mechanism. Adv. Exp. Med. Biol. 338:1993;281-284.
33. Marsden P.A., Heng H.H.Q., Scherer S.W., et al. Structure and chromosomal localization of the human constitutive endothelial nitric oxide synthase gene. J. Biol. Chem. 268:1993;17478-17488.
34. Marsden P.A., Heng H.H.Q., Duff C.L., Shi X.-M., Tsui L.-C., Hall V. Localization of the human gene for inducible nitric oxide synthase (NOS2) to chromsome 17q11.2-q.12. Genomics. 19:1994;183-185.
35. 2 inhibition of nitroreduction. Biochem. Biophys. Res. Commun. 75:1975;1267-1274.
36. Mayer B., John M., Heinzel B., et al. Brain nitric oxide synthase is a biopterin- and flavin-containing multi-functional oxido-reductase. FEBS Lett. 288:1991;187-191.
37. Miller R.T., Martasek P., Roman L.J., Nishimura J.S., Masters B.S. Involvement of the reductase domain of neuronal nitric oxide synthase in superoxide anion production. Biochemistry. 36:1997;15277-15284.
38. Moncada S., Palmer R.M.J., Higgs E.A. Nitric oxide: physiology, pathophysiology and pharmacology. Pharmacol. Rev. 43:1991;109-142.
39. Moncada C., Torres V., Vargese E., Albano E., Israel Y. Ethanol-derived immunoreactive species formed by free radical mechanisms. Mol. Pharmacol. 46:1994;786-791.
40. Navasumrit P., Ward T.H., Dodd N.J.F., O'Connor P.J. Ethanol-induced free radicals and hepatic DNA strand breaks are prevented in vivo by antioxidants: effects of acute and chronic ethanol exposure. Carcinogenesis. 21:2000;93-99.
41. G-methyl-L-arginine functions as an alternative substrate and mechanism-based inhibitor of nitric oxide synthase. Biochemistry. 32:1993;9677-9685.
42. Palmer R.M.J., Rees D.D., Ashton D.S., 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.
43. Porasuphatana S., Tsai P., Pou P., Rosen G.M. Involvement of perferryl complex of nitric oxide synthase in the catalysis of secondary free radical formation. Biochim. Biophys. Acta. 1526:2001;95-104.
44. Porasuphatana S., Tsai P., Pou S., Rosen G.M. Perferryl complex of nitric oxide synthase: role in secondary free radical formation. Biochim. Biophys. Acta. 1569:2002;111-116.
45. Pou S., Pou W.S., Bredt D.S., Snyder S.H., Rosen G.M. Generation of superoxide by purified brain nitric oxide synthase. J. Biol. Chem. 267:1992;24173-24176.
46. Pou S., Keaton L., Surichamorn W., Rosen G.M. Mechanism of superoxide generation by neuronal nitric-oxide synthase. J. Biol. Chem. 274:1999;9573-9580.
47. Reinke L.A., Rau J.M., McCay P.B. Possible role of free radicals in alcoholic tissue damage. Free Radical Res. Commun. 9:1990;205-211.
48. Robinson L.J., Weremowicz W., Morton C.C., Michel T. Isolation and chromosomal localization of the human endothelial nitric oxide synthase (NOS3) gene. Genomics. 19:1994;350-357.
49. Roman L.J., Martásek P., Masters B.S.S. Intrinsic and extrinsic modulation of nitric oxide synthase activity. Chem. Rev. 102:2002;1179-1189.
50. Rosen, G.M., Tsai, P., Pou, S., 2002a. Mechanism of free-radical generation by nitric oxide synthase. Chem. Rev. 102, 1191-1199.
51. Rosen, G.M., Tsai, P., Weaver, J.W., Porasuphatana, S., Roman, L.J., Starkov, A.A., Fiskum, G., Pou, S., 2002b. The role of tetrahydrobiopterin in the regulation of neuronal nitric oxide synthase-generated superoxide. J. Biol. Chem. 277, 40275-40280.
52. Rosen G.M., Rauckman E.J., Wilson R.L. Jr., Tschanz C. Production of superoxide during the metabolism of nitrazepam. Xanobiotica. 14:1984;785-794.
53. Siddhanta U., Presta A., Fan B., Wolan D., Rousseau D.L., Stuehr D.J. Domain swapping in inducible nitric-oxide synthase. J. Biol. Chem. 273:1998;18950-18958.
54. Simons T.J.B., Pocock G. Lead enters bovine adrenal medullary cells through calcium channels. J. Neurochem. 48:1987;383-389.
55. 3 and 6-methyl-1,4-naphthoquinone by potassium monopersulfate in aqueous solution. J. Org. Chem. 62:1997;673-678.
56. Stevens-Truss R., Beckingham K., Marletta M.A. Calcium binding sites of calmodulin and electron transfer by neuronal nitric oxide synthase. Biochemistry. 36:1997;12337-12345.
57. G-hydroxy-L-arginine and derived radicals: implications for the mechanism of nitric oxide synthase. J. Am. Chem. Soc. 122:2000;536-537.
58. Tsai P., Porasuphatana S., Pou S., Rosen G.M. Investigations into the spin trapping of nitric oxide and superoxide: models to explore free radical generation by nitric oxide synthase. J. Chem. Soc. Perk. Trans. 2:2000;983-988.
59. Vasquez-Vivar J., Kalyanaraman B., Martasek P., et al. Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Proc. Natl. Acad. Sci. USA. 95:1998;9220-9225.
60. Weaver J., Porasuphatana S., Tsai P., et al. The activation of neuronal nitric-oxide synthase by various divalent cations. J. Pharmacol. Exp. Ther. 302:2002;781-786.
61. Xia Y., Roman L.J., Masters B.S., Zweier J.L. Inducible nitric-oxide synthase generates superoxide from the reductase domain. J. Biol. Chem. 273:1998;22635-22639.
62. Xu W., Gorman P., Sheer D., et al. Regional localization of the gene coding for human brain nitric oxide synthase (NOS1) to 12q24.2->24.31 by fluorescent in situ hybridization. Cytogenet. Cell Genet. 64:1993;62-63.
63. Yoneyama H., Yamamoto A., Kosaka H. Neuronal nitric oxide synthase generates superoxide from the oxygenase domain. Biochem. J. 360:2001;247-253.
64. Zhang L.-Y., van Kuijk F.J.G.M., Misra H.P. EPR studies of spin-trapped free radicals in paraquat-treated lung microsomes. Biochem. Mol. Biol. Int. 37:1995;255-262.