Photosensitization by antitumor agents 2: Anthrapyrazole-photosensitized oxidation of ascorbic acid and 3,4-dihydroxyphenylalanine

Journal of Free Radicals in Biology & Medicine - Tập 2 - Trang 203-211 - 1986
Krzysztof Reszka1, Pawel Kolodziejczyk1, J. William Lown1
1Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Tài liệu tham khảo

Lown, 1982, Synthesis and redox properties of chromophore modified glycosides related to anthracyclines, J. Org. Chem., 47, 4304, 10.1021/jo00143a026 Lown, 1979, Diminished Superoxide anion generation by reduced 5-iminodaunorubicin relative to daunorubicin and the relationship to cardiotoxicity of the anthracycline antitumor agents, Biochem. Pharmacol., 28, 2563, 10.1016/0006-2952(79)90027-3 Murdock, 1979, Antitumor agents: I. 1,4-bis[(aminoalkyl)amino]-9, 10-anthracenediones, J. Med. Chem., 22, 1024, 10.1021/jm00195a002 Showalter, 1985, Design, biochemical pharmacology, electrochemistry and tumor biology of antitumor anthrapyrazoles, Anticancer Drug Design, 1, 73 Fry, 1985, In vitro DNA strand scission and inhibition of nucleic acid synthesis in L1210 leukemia cells by a new class of DNA complexers the anthra [1,9-cd]pyrazol-6(2H)-ones (anthrapyrazoles), Biochem. Pharmacol., 34, 3499, 10.1016/0006-2952(85)90724-5 Reszka, 1986, Horseradish peroxidase-catalyzed oxidation of mitoxantrone: Spectrophotometric and electron paramagnetic resonance studies, J. Free Radicals in Biol. Med., 2, 25, 10.1016/0748-5514(86)90120-0 Reszka, 1986, Photosensitization by antitumor agents. 1: Production of singlet oxygen during irradiation of anthrapyrazoles with visible light, Photochem. Photobiol., 43, 499, 10.1111/j.1751-1097.1986.tb09526.x Davies, 1972, Primary processes in the methylene blue photosensitized oxidation of L-ascorbic acid, J. Photochem., 1, 423, 10.1016/0047-2670(72)80039-X Chou, 1983, L-Ascorbic acid quenching of singlet delta molecular oxygen in aqueous media: Generalized antioxidant property of vitamin C, Biochem. Biophys. Res. Commun., 115, 932, 10.1016/S0006-291X(83)80024-2 Buettner, 1984, Hydrogen peroxide and hydroxyl radical formation by methylene blue in the presence of ascorbic acid, Radiat. Environ. Biophys., 23, 235, 10.1007/BF01407595 Buettner, 1985, Hydrogen peroxide and hydroxyl free radical production by hematoporphyrin derivatives, ascorbate and light, Cancer Lett., 25, 297, 10.1016/S0304-3835(15)30009-4 Jahnke, 1978, Photooxidation of epinephrine sensitized by methylene blue—evidence for the involvement of singlet oxygen and of Superoxide, Photochem. Photobiol., 28, 517, 10.1111/j.1751-1097.1978.tb06961.x De Mol, 1979, Formation of singlet molecular oxygen by 8-methoxypsoralen, Photochem. photobiol., 30, 331, 10.1111/j.1751-1097.1979.tb07364.x Reszka, 1984, Photooxidation of 3,4-dihydroxyphenylalanine by hematoporphyrin in aqueous solutions: An electron spin resonance study using 2,2,6,6-tetramethyl-4-piperidone-1-oxyl (TEMPONE), Photochem. Photobiol., 39, 293, 10.1111/j.1751-1097.1984.tb08180.x Felix, 1983, Free radicals from photoreduction of hematoporphyrin in aqueous solution, Photochem. Photobiol., 37, 141, 10.1111/j.1751-1097.1983.tb04449.x Halliwell, 1976, Ascorbic acid, metal ions and the Superoxide radical, Biochem. J., 155, 697, 10.1042/bj1550697 Redpath, 1973, Reducing compounds in radioprotection and radiosensitization: Model experiments using ascorbic acid, Int. J. Radiat. Biol., 23, 51, 10.1080/09553007314550051 Magnus, 1976 Borg, 1984, Cytotoxicity from coupled redox cycling of autooxidizing xenobiotics and metals, Israel J. Chem., 24, 38, 10.1002/ijch.198400007 Laroff, 1972, The electron spin resonance spectra of radical intermediates in the oxidation of ascorbic acid and related substances, J. Am. Chem. Soc., 94, 9062, 10.1021/ja00781a013 Krasna, 1979, Proflavin catalyzed photoproduction of hydrogen from organic compounds, Photochem. Photobiol., 29, 267, 10.1111/j.1751-1097.1979.tb07048.x Buettner, 1978, The effect of iron on the distribution of Superoxide and hydroxyl radicals as seen by spin trapping and on the Superoxide dismutase assay, Photochem. Photobiol., 28, 693, 10.1111/j.1751-1097.1978.tb07001.x Buettner, 1978, Considerations in the spin trapping of Superoxide and hydroxyl radicals in aqueous systems using 5,5-dimethyl-1-pyrroline-1-oxide, Biochem. Biophys. Res. Commun., 83, 69, 10.1016/0006-291X(78)90398-4 Morimitsu, 1977, Oxidations of ascorbic acid and αtocopherol by Superoxide, 79 Cabelli, 1983, Kinetics and mechanism for the oxidation of ascorbic acid/ascorbate by HO2/O2− radicals: A pulse radiolysis and stopped-flow photolysis study, J. Phys. Chem., 87, 1809, 10.1021/j100233a031 Bielski, 1975, Some properties of the ascorbate free radical, Ann. NY Acad. Sci., 258, 231, 10.1111/j.1749-6632.1975.tb29283.x Yamazaki, 1977, Free radicals in enzyme-substrate reactions, Volume 3, 183 Finkelstein, 1979, Spin trapping of Superoxide, Mol. Pharmacol., 16, 676 Winterbourn, 1979, Comparison of Superoxide with other reducing agents in the biological production of hydroxyl radicals, Biochem. J., 182, 625, 10.1042/bj1820625 Rao, 1973, Ionization constants and spectral characteristics of some semiquinone radicals in aqueous solutions, J. Phys. Chem., 77, 2274, 10.1021/j100638a003 Kalyanaraman, 1982, Electron spin resonancespin stabilization in enzymatic systems: Detection of semiquinones produced during peroxidatic oxidation of catechols and catecholamines, Biochem. Biophys. Res. Commun., 106, 1119, 10.1016/0006-291X(82)91228-1 Bors, 1979, Pulse-radiolytic investigations of catechols and catecholamines: 4. 3,4-dihydroxybenzaldehyde and 3,4-dihydroxyacetophenone, J. Phys. Chem., 83, 3084, 10.1021/j100487a005 Misra, 1972, The role of Superoxide anion in the autooxidation of epinephrine and a simple assay for suproxide dismutase, J. Biol. Chem., 247, 3170, 10.1016/S0021-9258(19)45228-9 Patel, 1973, Semiquinone free radicals and oxygen, J. Chem. Soc. Faraday Trans. 1, 69, 814, 10.1039/f19736900814