Investigation of the reaction of peroxynitrite with propofol at acid pH: Predominant production of oxidized, nitrated, and halogenated derivatives

Nitric Oxide - Biology and Chemistry

Volumn 8, Issue 3, 2003, Pages 170-181

  Kohnen, Stephan L ^a   Mouithys Mickalad, Ange A ^a   Deby Dupont, Ginette P ^a,b   Deby, Carol M T ^a   Hans, Pol ^a,b   Lamy, Maurice L ^a,b   Noels, Alfred F ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Peroxynitrate; Peroxynitrite; Phenol halogenation; Phenol nitration; Phenol oxidation; Propofol

Indexed keywords

1,4 BENZOQUINONE; 4 NITROPROPOFOL; ANESTHETIC AGENT; CHLORIDE ION; CHLORINE; CHLORINE DERIVATIVE; DIPHENYLQUINONE; HALIDE; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; METHANOL; NITROSYLCHLORIDE; NITRYL CHLORIDE; PEROXYNITRITE; PROPOFOL; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ELECTRON SPIN RESONANCE; HALOGENATION; NITRATION; OXIDATION; PH; PRIORITY JOURNAL; SYNTHESIS;

EID: 0038121601     PISSN: 10898603     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1089-8603(03)00013-2     Document Type: Article

References (42)

1. Beckman J.S., Beckman T.W., Chen J., Marshall P.A., Freeman B.A. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA. 87:1990;1620-1624.
2. Pryor W.A., Squadrito G.L. The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268:1995;L699-L722.
3. Radi R., Peluffo G., Alvarez M.N., Naviliat M., Cayota A. Unraveling peroxynitrite formation in biological systems. Free Radic. Biol. Med. 33:2001;463-488.
4. Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288:1991;481-487.
5. Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. J. Biol. Chem. 266:1991;4244-4250.
6. Bartlett D., Church D.F., Bounds P.L., Koppenol W.H. The kinetics of the oxidation of L-ascorbic acid by peroxynitrite. Free Radic. Biol. Med. 18:1995;85-92.
7. Yermilov V., Yoshie Y., Rubio J., Ohshima H. Effects of carbon dioxide/bicarbonate on induction of DNA single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine and base-propenal mediated by peroxynitrite. FEBS Lett. 399:1996;67-70.
8. O'Donnell V.B., Eiserich J.P., Chumley P.H., Jablonsky M.J., Krishna N.R., Kirk M., Barnes S., Darley-Usmar V.M., Freeman B.A. Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion. Chem. Res. Toxicol. 12:1999;83-92.
9. Ischiropoulos H., Zhu L., Chen J., Tsai M., Martin J.C., Smith C.D., Beckman J.S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298:1992;431-437.
10. Alvarez B., Rubbo H., Kirk M., Barnes S., Freeman B.A., Radi R. Peroxynitrite-dependent tryptophan nitration. Chem. Res. Toxicol. 9:1996;390-396.
11. Ramazanian M.S., Padmaja S., Koppenol W.H. Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9:1996;232-240.
12. Nonoyama N., Chiba K., Hisatome K., Suzuki H., Shintani F. Nitration, hydroxylation of substituted phenols by peroxynitrite. Kinetic feature and an alternative mechanism view. Tetrahedron Lett. 40:1999;6933-6937.
13. - ) and singlet oxygen in aqueous solution Proc. Natl. Acad. Sci. USA. 97:2000;2984-2989.
14. - ) Proc. Natl. Acad. Sci. USA. 97:2000;10307-10312.
15. 2: evidence for carbonate radical production J. Am. Chem. Soc. 120:1998;3458-3463.
16. Uppu R.M., Lemercier J.-N., Squadrito G.L., Zhang H., Bolzan R.M., Pryor W.A. Nitrosation by peroxynitrite: use of phenol as a probe. Arch. Biochem. Biophys. 358:1998;1-16.
17. Yenes S., Messeguer A. A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite. Tetrahedron. 55:1999;14111-14122.
18. Bryson H.M., Fulton B.R., Faulds D. Propofol: an update of its use in anaesthesia and conscious sedation. Drugs. 50:1995;513-559.
19. Mathy-Hartert M., Deby-Dupont G., Hans P., Deby C., Lamy M. Protective activity of propofol. Diprivan and intralipid against active oxygen species. Mediators Inflamm. 7:1998;327-333.
20. Kahraman S., Demiryürek A.T. Propofol is a peroxynitrite scavenger. Anesth. Analg. 84:1997;1127-1129.
21. Mouithys-Mickalad A., Hans P., Deby-Dupont G., Hoebeke M., Deby C., Lamy M. Propofol reacts with peroxynitrite to form a phenoxyl radical: demonstration by electron spin resonance. Biochem. Biophys. Res. Commun. 249:1998;833-837.
22. Mathy-Hartert M., Mouithys-Mickalad A., Kohnen S., Deby-Dupont G., Lamy M., Hans P. Effects of propofol on endothelial cells subjected to a peroxynitrite donor (SIN-1). Anaesthesia. 55:2000;1066-1071.
23. Cudic M., Ducrocq C. Transformations of 2,6-diisopropylphenol by NO-derived nitrogen oxides, particularly peroxynitrite. Nitric Oxide. 4:2000;147-156.
24. Bohle D.S., Glassbrenner P.A., Hansert B. Syntheses of pure tetramethylammonium peroxynitrite. Methods Enzymol. 269:1996;302-311.
25. Koppenol W.H. 100 years of peroxynitrite chemistry and 11 years of peroxynitrite biochemistry. Redox Rep. 6:2001;339-341.
26. Uppu R.M., Pryor W.A. Synthesis of peroxynitrite in a two-phase system using isoamyl nitrite and hydrogen peroxide. Anal. Biochem. 236:1996;242-249.
27. 2 ): a novel synthesis and some chemical and spectroscopic properties Inorg. Chem. 34:1995;787-791.
28. Regimbal J.-M., Mozurkewich M. Peroxynitric acid decay mechanisms and kinetics at low pH. J. Phys. Chem. A. 101:1997;8822-8829.
29. A receptors J. Med. Chem. 41:1998;1846-1854.
30. Vaughan W.R., Kirkwood Finch G. The effect of alkyl groups on 4-nitro and 4-nitroso-phenols. J. Org. Chem. 21:1956;1201-1210.
31. Kharasch M.S., Joshi B.S. Reactions of hindered phenols. III. Reaction of nitrous acid with hindered phenols. J. Org. Chem. 27:1962;651-653.
32. Erschov V.V., Zlobina G.A., Nikiforov G.A. Nitration and nitrosation of 2,6-dialkylphenols. Izv. Akad. Nauk SSSR, Ser. Khim. 10:1963;1877-1880.
33. Wheatley W.B., Holdrege C.T. Dialkylaminoalkyl ethers of some 2,6-dialkylphenols. J. Org. Chem. 23:1958;568-571.
34. 4 surfaces J. Org. Chem. 50:1985;3927-3928.
35. Fatiadi A.J. Facile coupling of sterically hindered 2,6-dialkylphenols with periodic acid. Synthesis. 1973;357-358.
36. Omura K. Rapid conversion of phenols to p-benzoquinones under acidic conditions with lead dioxide. Synthesis. 1998;1145-1148.
37. Petranek J., Pilar J. One-electron oxidation of 2,6-dialkyl-4-alkoxyphenols; effect of alkyl substituents. Collection Czechoslov. Chem. Commun. 35:1970;830-837.
38. Hazen S.L., Heinecke J.W. 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation. is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. J. Clin. Invest. 99:1997;2075-2081.
39. Dunford H.B. Peroxidase-catalyzed halide ion oxidation. Redox Rep. 5:2000;169-171.
40. Deby-Dupont G., Deby C., Lamy M. Neutrophil myeloperoxidase revisited: its role in health and disease. Intensivmed. 36:1999;500-513.
41. Eiserich J.P., Cross C.E., Jones A.D., Halliwell B., van der Vliet A. Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric protein modification. J. Biol. Chem. 271:1996;19199-19208.
42. Alvarez B., Radi R. Peroxynitrite decay in the presence of hydrogen peroxide, mannitol and ethanol: a reappraisal. Free Radic. Res. 34:2001;467-475.