Abstract
Free radicals are difficult to detect, identify, and quantitate because of their reactivity. The reactivity of free radicals is also ultimately responsible for their toxicity. A free radical is any reactive organic or inorganic molecule with an odd number of electrons resulting in a species with one unpaired electron. Molecular oxygen with two unpaired electrons (a triplet species) and transition metals and their complexes with one or more unpaired electrons are excluded based on their stability.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Rao, D.N.R., Fischer, V., and Mason, R.P. (1990) Glutathione and ascorbate reduction of the acetaminophen radical formed by peroxidase, J. Biol. Chem. 265, 844–847.
Perez-Reyes, E. and Mason, R.P. (1980) Electron spin resonance study of the autoxidation of 6-aminodopamine, Mol. Pharmacol. 18, 594–597.
Stolze, K. and Nohl, H. (1991) Formation of methemoglobin and phenoxyl radicals from p-hydroxyanisole and oxyhemoglobin, Free Rad. Res. Comms. 11, 321–327.
Kalyanaraman, B., Nemec, J., and Sinha, B.K. (1989) Characterization of free radicals produced during oxidation of etoposide (VP-16) and its catechol and quinone derivatives. An ESR study, Biochemistry 28, 4839–4846.
Josephy, P.D., Eling, T.E., and Mason, R.P. (1983) An electron spin resonance study of the activation of benzidine by peroxidases, Mol. Pharmacol. 23, 766–770.
Eling, T.E., Mason, R.P., and Sivarajah, K. (1985) The formation of aminopyrine cation radical by the peroxidase activity of prostaglandin H synthase and subsequent reactions of the radical, J. Biol. Chem. 260, 1601–1607.
Kolodziejczyk, P., Reszka, K., and Lown, J.W. (1988) Enzymatic oxidative activation and transformation of the antitumor agent mitoxantrone, Free Rad. Biol. Med. 5, 13–25.
Knecht, K.T., Bradford, B.U., Mason, R.P., and Thurman, R.G. (1990) In vivo formation of a free radical metabolite of ethanol, Mol. Pharmacol. 38, 26–30.
Vazquez, A., Tudela, J., Varón, R., and García-Cânovas, F. (1992) A kinetic study of the generation and decomposition of some phenothiazine free radicals formed during enzymatic oxidation of phenothiazines by peroxidase-hydrogen peroxide, Biochem. Pharmacol. 44, 889–894.
Maples, K.R., Jordan, S.J., and Mason, R.P. (1988) In vivo rat hemoglobin thiyl free radical formation following administration of phenylhydrazine and hydrazine-based drugs, Drug Metab. Disp. 16, 799–803.
Kubow, S., Janzen, E.G., and Bray, T.M. (1984) Spin-trapping of free radicals formed during in vitro and in vivo metabolism of 3-methylindole, J. Biol. Chem. 259, 4447–4451.
Kalyanaraman, B., Darley-Usmar, V.M., Woods, J., Joseph, J., and Parthasarathy, S. (1992) Synergistic interaction between the probucol phenoxyl radical and ascorbic acid in inhibiting the oxidation of low density lipoprotein, J. Biol. Chem. 267, 6789–6795.
Reed, G.A., Curtis, J.F., Mottley, C., Eling, T.E., and Mason, R.P. (1986) Epoxidation of (±)-7,8-dihydroxy-7,8-dihydrobenzo[a] pyrene during (bi)sulfite autoxidation: activation of a procarcinogen by a cocarcinogen, Proc. Natl. Acad. Sci. USA 83, 7499–7502.
Fischer, V., Haar, J.A., Greiner, L., Lloyd, R.V., and Mason, R.P. (1991) Possible role of free radical formation in clozapine (clozaril)- induced agranulocytosis, Mol. Pharmacol. 40, 846–853.
Barr, D.P., and Mason, R.P. (1995) Mechanism of radical production from the reaction of cytochrome c with organic hydroperoxides, J. Biol. Chem. 270, 12709–12716.
Barr, D.P., Martin, M.V., Guengerich, F.P., and Mason, R.P. (1996) Reaction of cytochrome P450 with cumene hydroperoxide: ESR spin-trapping evidence for the homolytic scission of the peroxide O-O bond by ferric cytochrome P450 1A2, Chem. Res. Toxicol. 9, 318–325.
Kalyanaraman, B., Mottley, C., and Mason, R.P. (1983) A direct electron spin resonance and spin-trapping investigation of peroxyl free radical formation by hematin/hydroperoxide systems, J. Biol. Chem. 258, 3855–3858.
Van der Zee, J., Barr, D.P., and Mason, R.P. (1996) ESR spin trapping investigation of radical formation from the reaction between hematin and tert-butyl hydroperoxide, Free Rad. Biol. Med. 20, 199–206.
Sies, H. (1974) Biochemistry of the peroxisome in the liver cell, Angew. Chem. Int. 13, 706–718.
Oshino, N., Chance, B., Sies, H., and Bücher, T. (1973) The role of H202 generation in perfused rat liver and the reaction of catalase compound I and hydrogen donors, Arch. Biochem. Biophys. 154, 117–131.
Goldberg, B., Stern, A., Peisach, J., and Blumberg, W.E. (1978) The detection of superoxide anion from the reaction of oxyhemoglobin and phenylhydrazine using EPR spectroscopy, Experientia 35, 488–489.
Mottley, C., Toy, K., and Mason, R.P. (1987) Oxidation of thiol drugs and biochemicals by the lactoperoxidase/hydrogen peroxide system, Mol. Pharmacol. 31, 417–421.
Chance, B., Sies, H., and Boveris, A. (1979) Hydroperoxide metabolism in mammalian organs, Physiol Rev. 59, 527–605.
Flohé, L. (1982) Glutathione peroxidase brought into focus, In: Free Radicals in Biology, Vol. 5, ( Pryor, W.A., Ed. ) pp. 223–254.
Dunford, H.B. and Stillman, J.S. (1976) On the function and mechnism of action of peroxidases, Coord. Chem. Rev. 19, 187–251.
Walling, C. (1975) Fenton’s reagent revisited, Acc. Chem. Res. 8, 125–131.
Koppenol, W.H. and Butler, J. (1985) Energetics of interconversion reactions of oxyradicals, Adv. Free Radical Biol. Med. 1, 91–131.
Hayashi, Y. and Yamazaki, I. (1979) The oxidation-reduction potentials of compound I/compound II and compound II/ferric couples of horseradish peroxidases A2 and C, J. Biol. Chem. 254, 9101–9106.
Yamazaki, I., Mason, H.S., and Piette, L. (1960) Identification, by electron paramagnetic resonance spectroscopy, of free radicals generated from substrates by peroxidase, J. Biol. Chem. 235, 2444–2449.
Maples, K.R., and Mason, R.P. (1988) Free radical metabolite of uric acid, J. Biol. Chem. 263, 1709–1712.
Sipe, H.J. Jr., Jordan, S.J., Hanna, P.M., and Mason, R.P. (1994) The metabolism of 1713-estradiol by lactoperoxidase: a possible source of oxidative stress in breast cancer, Carcinogenesis 15, 2637–2643.
Beutler, E. (1994) G6PD deficiency, Blood 84, 3613–3636.
Hill, H.A.O., and Thornalley, P.J. (1981) Phenyl radical production during the oxidation of phenylhydrazine and in phenylphydrazine-induced haemolysis, FEBS Lett. 125, 235–238.
Sentjurc, M. and Mason, R.P. (1992) Inhibition of radical adduct reduction and reoxidation of the corresponding hydroxylamines in in vivo spin trapping of carbon tetrachloride-derived radicals, Free Rad. Biol. Med. 13, 151–160.
Knecht, K.T., DeGray, J.A., and Mason, R.P. (1992) Free radical metabolism of halothane in vivo: radical adducts detected in bile, Mol. Pharmacol. 41, 943–949.
Horton, J.K., Brigelius, R., Mason, R.P., and Bend, J.R. (1986) Paraquat uptake into freshly isolated rabbit lung epithelial cells and its reduction to the paraquat radical under anaerobic conditions, Mol. Pharmacol. 29, 484–488.
Kalyanaraman, B., Perez-Reyes, E., and Mason, R.P. (1980) Spin-trapping and direct electron spin resonance investigations of the redox metabolism of quinone anticancer drugs, Biochim. Biophys. Acta 630, 119–130.
Powis, G. (1989) Free radical formation by antitumor quinones, Free Rad. Biol. Med. 6, 63–101.
Sinha, B.K. (1989) Free radicals in anticancer drug pharmacology, Chem.-Biol. Interact. 69, 293–317.
Mason, R.P. and Holtzman, J.L. (1975) The role of catalytic superoxide formation in the 02 inhibition of nitroreductase, Biochem. Biophys. Res. Comm. 67, 12671274.
Peterson, F.J., Mason, R.P., Hovsepian, J., and Holtzman, J.L. (1979) Oxygen-sensitive and -insensitive nitroreduction by Escherichia coli and rat hepatic microsomes, J. Biol. Chem. 254, 4009–4014.
Perez-Reyes, E., Kalyanaraman, B., and Mason, R.P. (1980) The reductive metabolism of metronidazole and ronidazole by aerobic liver microsomes, Mol. Pharmacol. 17, 239–244.
Burkitt, M.J. and Mason, R.P. (1991) Direct evidence for in vivo hydroxyl-radical generation in experimental iron overload: an ESR spin-trapping investigation, Proc. Natl. Acad. Sci. USA 88, 8440–8444.
Doelman, C.J.A. and Bast, A. (1990) Oxygen radicals in lung pathology, Free Rad. Biol. Med. 9, 381–400.
Berger, V., Berson, A., Wolf, C., Chachaty, C., Fau, D., Fromenty, B., and Pessayre, D. (1992) Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen, Biochem. Pharmacol. 43, 654–657.
Fau, D., Berson, A., Eugene, D., Fromenty, B., Fisch, C., and Pessayre, D. (1992) Mechanism for the hepatotoxicity of the antiandrogen, nilutamide. Evidence suggesting that redox cycling of this nitroaromatic drug leads to oxidative stress in isolated hepatocytes, J. Pharmacol. Exp. Ther. 263, 69–77.
Litovitz, T. and Manoguerra, A. (1992) Comparison of pediatric poisoning hazards: an analysis of 3.8 million exposure incidents, Pediatrics 89, 999–1006.
Mason, R.P. and Chignell, C.F. (1981) Free radicals in pharmacology and toxicology-selected topics, Pharmacol. Rev. 33, 189–211.
Knecht, K.T. and Mason, R.P. (1993) In vivo spin trapping of xenobiotic free radical metabolites, Arch. Biochem. Biophys. 303, 185–194.
Mason, R.P. and Knecht, K.T. (1994) In vivo detection of radical adducts by electron spin resonance, Meth. Enzymol. 233, 112–117.
DeGray, J.A. and Mason, R.P. (1994) Biological spin trapping, in N.M. Atherton, M.J. Davies, and B.C. Gilbert (eds.), Electron Spin Resonance, Athenaeum Press, Ltd., Cambridge, Vol. 14, pp. 246–301.
Mason, R.P., Hanna, P.M., Burkitt, M.J., and Kadiiska, M.B. (1994) Detection of oxygen-derived radicals in biological systems using electron spin resonance, Environ. Health Perspect. 102, Suppl. 10, 33–36.
Fischer, V., Haar, J.A., Greiner, L., Lloyd, R.V., and Mason, R.P. (1991) Possible role of free radical formation in clozapine (clozaril)-induced agranulocytosis, Mol. Pharmacol. 40, 846–853.
Mason, R.P. and Fischer, V. (1992) Possible role of free radical formation in drug-induced agranulocytosis, Drug Safety 7, Suppl. 1, 45–50.
Uetrecht, J. (1989) Mechanism of hypersensitivity reactions: proposed involvement of reactive metabolites generated by activated leukocytes, Trends in Pharmacological Sciences. 10, 463–467.
Uetrecht, J.P. (1989) Idiosyncratic drug reactions: possible role of reactive metabolites generated by leukocytes, Pharmaceutical Research. 6, 265–273.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Mason, R.P. (1997). Electron Spin Resonance Investigations of Free Radical Toxicology. In: Minisci, F. (eds) Free Radicals in Biology and Environment. NATO ASI Series, vol 27. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-1607-9_1
Download citation
DOI: https://doi.org/10.1007/978-94-017-1607-9_1
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-4831-8
Online ISBN: 978-94-017-1607-9
eBook Packages: Springer Book Archive