Evaluation of the Antioxidant Properties of Propofol and its Nitrosoderivative. Comparison with Homologue Substituted Phenols

References

• Bindoli, A., Rigobello, M.P. and Scutari, G. (2001) "Effects of general anesthetics on isolated mitochondria", Chapter 10, In: Ebadi, M., Marwah, J. and Chopra, R., eds, Mitochondrial Ubiquinone (Coenzyme Qv): Biochemical, Functional, Medical and Therapeutic Apects in Human Health and Diseases (Prominent Press, Scottsdale, AZ) II, pp 171–187.
   Google Scholar
• Musacchio, E., Rizzoli, V, Bianchi, M., Bindoli, A. and Galzigna, L. (1991) "Antioxidant action of propofol on liver microsomes, mitochondria and brain synaptosomes in the rat", Pharmacol. Toxicol. 69, 75–77.
   PubMedGoogle Scholar
• Bao, Y.P., Williamson, G., Tew, D., Plumb, G.W., Lambert, N., Jones, J.G. and Menon, D.K. (1998) "Antioxidant effects of propofol in human hepatic microsomes: concentration effects and clinical relevance", Br. J. Anaesth. 81, 584–589.
   PubMed Web of Science ®Google Scholar
• Murphy, P.G., Davies, M.J., Columb, M.O. and Stratford, N. (1996) "Effect of propofol and thiopentone on free radical mediated oxidative stress of the erythrocyte", Br. J. Anaesth. 76, 536–543.
   PubMed Web of Science ®Google Scholar
• Stevanato, R., Momo, F., Marian, M., Rigobello, M.P., Bindoli, A., Bragadin, M., Vincenti, E. and Scutari, G. (2002) "Effects of nitrosopropofol on mitochondrial energy-converting system", Biochem. Pharmacol. 64, 1133–1138.
   PubMed Web of Science ®Google Scholar
• Momo, F., Fabris, S., Bindoli, A., Scutari, G. and Stevanato, R. (2002) "Different effects of propofol and nitrosopropofol on DMPC multilamellar liposomes", Biophys. Chem. 95, 145–155.
   PubMed Web of Science ®Google Scholar
• Momo, F., Fabris, S., Wisniewska, A., Fiore, C., Bindoli, A., Scutari, G. and Stevanato, R. (2003) "Correlation between fluidising effects on phospholipid membranes and mito-chondrial respiration of propofol and p-nitrosophenol homologues", Biophys. Chem. 103, 213–222.
   PubMed Web of Science ®Google Scholar
• Kharash, M.S. and Joshi, B.S. (1962) "Reactions of hindered phenols. DI Reactions of nitrous acid with hindered phenols", J. Org. Chem. 27, 651–653.
   Web of Science ®Google Scholar
• Blois, M.S. (1958) "Antioxidant determinations by the use of a stable free radical", Nature 181, 1199–1200.
   Web of Science ®Google Scholar
• Horakova, L., Schaur, R.J., Balgavy, P. and Egger, G. (1995) "Interaction of the pyridoindole stobadine with alkoxyl and stable free radicals", Redox Rep. 1, 369–372.
   PubMed Web of Science ®Google Scholar
• Kruk, J., Schmid, G.H. and Strzalka, K. (1994) "Antioxidant properties of plastoquinol and other biological prenylquinols in liposomes and solution", Free Radic. Res. 21, 409–416.
   PubMed Web of Science ®Google Scholar
• Ernster, L. and Nordenbrand, K. (1967) "Microsomal lipid permddation", Meth. Enzymol. 10, 574–580.
   Google Scholar
• Buege, J.D. and Aust, S.D. (1978) "Microsomal lipid peroxidation", Meth. Enzymol. 52, 302–310.
   PubMedGoogle Scholar
• Damiani, E., Belaid, C., Carloni, P. and Greci, L. (2003) "Comparison of antioxidant activity between aromatic indolinonic nitroxides and natural and synthetic antioxi-dants", Free Radic. Res. 37, 731–741.
   PubMed Web of Science ®Google Scholar
• O'Brien, P.J. and Rahimtula, A.D. (1980) "The permddase function of cytochrome P450 with possible implications for carcinogenesis", In: Gustafsson, J.A., Carlstedt-Duke, J., Mode, A. and Rafter, J., eds, Biochemistry, Biophysics and Regulation of Cytochrome P-450 (Elsevier/North Holland, Amsterdam), pp 273–281.
   Google Scholar
• Barr, D.P., Martin, M.V., Guengerich, F.P. and Mason, R.P. (1996) "Reaction of cytochrome P450: ESR spin trapping evidence for the homolytic scission of the peroxide 0-0 bond by ferric cytochrome P4501A2", Chem. Res. Toxicol. 9, 318–325.
   PubMed Web of Science ®Google Scholar
• Murdoch, J.A.C., Grant, S.A. and Kenny, G.N.C. (2000) "Safety of patient-maintained propofol sedation using a target-controlled system in healthy volunteers", Br. J. Anaesth. 85, 299–301.
   PubMed Web of Science ®Google Scholar
• Stuart, P.C., Stott, S.M., Millar, A., Kenny, G.N.C. and Russel, D. (2000) "Cp50 of propofol with and without nitrous oxide 67%", Br. J. Anaesth. 84, 638–639.
   PubMed Web of Science ®Google Scholar
• Burton, G.W. and Ingold, K.U. (1983) "Mechanisms of antioxidant action. Studies on vitamin E and related anti-oxidants in biological systems", In: McBrien, D.C.H. and Slater, T.F., eds, Protective Agents in Cancer (Academic Press, London), pp 81–92.
   Google Scholar
• Hogg, J.S., Lohman, D.H. and Russel, K.E. (1961) "The kinetics of reaction of 2,2-dipheny1-1-picrylhydrazyl with phenols", Can. J. Chem. 39, 1588–1594.
   Web of Science ®Google Scholar
• Moncada, S., Palmer, R. and Higgs, E.A. (1991) "Nitric oxide: physiology, pathophysiology and pharmacology", Pharmacol. Rev. 43, 109–142.
   PubMed Web of Science ®Google Scholar
• Koppenol, W.H. (1996) "Thermodynamics of reactions involving nitrogen—oxygen compounds", Methods Enzymol. 268, 7–12.
   PubMed Web of Science ®Google Scholar
• Wink, D.A., Hanbauer, I., Grisham, M.B., Laval, F., Nims, R.W., Laval, J., Cook, J., Pacelli, R., Liebmarm, J., Krishna, M., Ford, P.C. and Mitchell, J.B. (1996) "Chemical biology of nitric oxide: regulation and protective and toxic mechanisms", Curr. Top. Cell. Regul. 34, 159–187.
   PubMedGoogle Scholar
• Arteel, G.E., Briviba, K. and Sies, H. (1999) "Protection against peroxynitrite", FEBS Lett. 445, 226–230.
   PubMed Web of Science ®Google Scholar
• Wink, D.A. and Mitchell, J.B. (2003) "Nitric oxide and cancer: an introduction", Free Radic. Biol. Med. 34, 951–954.
   PubMed Web of Science ®Google Scholar
• Tokimoto, T. and Shinagawa, K. (2001) "Nitric oxide generation in aqueous solutions of cigarette smoke and approaches to its origin", Biol. Chem. 382, 1613–1619.
   PubMed Web of Science ®Google Scholar
• Hogg, N. and Kalyanaraman, B. (1999) "Nitric oxide and lipid permddation", Biochim. Biophys. Acta 1411, 378–384.
   PubMed Web of Science ®Google Scholar
• Rigobello, M.P., Scutari, G., Boscolo, R. and Bindoli, A. (2002) "Inhibition of lipid permddation by S-nitrosoglutathione and copper", Free Radic. Res. 36, 1071–1077.
   PubMed Web of Science ®Google Scholar
• Klotz, L.O. and Sies, H. (2003) "Defenses against peroxy-nitrite: selenocompounds and flavonoids", Toxicol. Lett. 140–141, 125–132.
   Web of Science ®Google Scholar
• Arteel, G.E., Schroeder, P. and Sies, H. (2000) "Reactions of peroxynitrite with cocoa procyanidin oligomers", J. Nutr. 130, 2100S–2104S.
   Google Scholar