Mechanism of antibacterial action: Electron transfer and oxy radicals

1985 Halliwell, 1985 Halliwell, 1985, The importance of free radicals and catalytic metal ions in human diseases, Molec. Aspects Med., 8, 89, 10.1016/0098-2997(85)90001-9 Ames, 1983, Dietary carcinogens and anticarcinogens, Science, 221, 1256, 10.1126/science.6351251 Docampo, 1984, Free-radical intermediates in the antiparasitic action of drugs and phagocytic cells, Volume 6, 244 Mason, 1981, Free radicals in pharmacology and toxicology-selected topics, Pharmacol. Rev., 33, 189 Demopoulos, 1980, The possible role of free radical reactions in carcinogenesis, J. Environ. Path. Toxicol., 3, 273 Kappus, 1986, Overview of enzyme systems involved in bioreduction of drugs and in redox cycling, Biochem. Pharmacol., 35, 1, 10.1016/0006-2952(86)90544-7 1982 Kovacic, 1986, Charge transfer mechanism for carcinogenesis by alkylating and other agents, Bioelectrochem. Bioenerg., 15, 305, 10.1016/0302-4598(86)85020-6 Kovacic, 1986, Charge transfer-oxy radical mechanism for anticancer agents, AntiCancer Drug Design., 1, 196 P. Kovacic, J. R. Ames, and M. D. Ryan. Charge transferoxy radical mechanism for anticancer agents: 9-Anilinoacridines (submitted for publication). P. W. Crawford, P. Lumme, H. Elo, M. D. Ryan, and P. Kovacic. Charge transfer-oxy radical mechanism for anticancer agents: mAMSA derivatives, rhodamine 123 and nickel salicylaldoximate. Free Rad. Res. Commun. (in press). P. W. Crawford, W. O. Foye, M. D. Ryan, and P. Kovacic. Cyclic voltammetry of quinolinium salts and related compounds: Correlation with structure and anticancer activity (submitted for publication). Ames, 1985, Charge transfer and oxy radicals in antimalarial action: Quinones, dapsone metabolites, metal complexes, iminium ions, and peroxides, J. Free Radicals Biol. Med., 1, 353, 10.1016/0748-5514(85)90147-3 Crawford, 1986, Charge transfer mechanism for benzodiazepine (BZ) action. Correlation of reduction potential of BZ iminium with structure and drug activity, Bioelectrochem. Bioenerg., 16, 407, 10.1016/0302-4598(86)80063-0 Ames, 1986, Cyclic voltammetry with cyclic iminium ions: Implications for charge transfer with biomolecules (metabolites of nicotine, phencyclidine and spermine), Bioorg. Chem., 14, 228, 10.1016/0045-2068(86)90034-9 Ames, 1986, Oxidative ionic metabolites of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): Correlation of electroreduction with physiological behavior, Free Rad. Res. Commun., 2, 107, 10.3109/10715768609088061 Ames, 1986, Conjugated and cross-conjugated mesomeric betaines: Correlation of electroreduction with structure and physiological activity, Life Sci., 39, 1085, 10.1016/0024-3205(86)90200-6 Ryan, 1985, Charge transfer in the mechanism of drug action involving quinoxaline diN-oxides, J. Pharm. Sci., 74, 492, 10.1002/jps.2600740427 Crawford, 1986, Cyclic voltammetry of phenazines and quinoxalines including monoand di-N-oxides: Relation to structure and antimicrobial activity, Chem.-Biol. Interactions, 60, 67, 10.1016/0009-2797(86)90018-9 Kovacic, 1984, Does charge transfer by diiminium play a widespread role in living systems?, Kem. Ind., 33, 473 Hamers, 1985, Oxidative stress in human neutrophilic granulocytes: Host defence and self-defence, 351 Halliwell, 1985, Free radicals as useful species, 246 Baehner, 1982, Reduced oxygen by-products and white blood cells, Volume 5, 91 Halliwell, 1985, The chemistry of oxygen radicals and other oxygen-derived species, 20 Fujita, 1985, Implication of hydrogen peroxide in the mutagenicity of coffee, Mutation Res., 144, 227, 10.1016/0165-7992(85)90055-7 Shenep, 1985, Lack of antibacterial activity after intravenous hydrogen peroxide infusion in experimental Escherichia coli species, Infect. Immun., 48, 607, 10.1128/IAI.48.3.607-610.1985 Stierle, 1979, Metabolites of the marine sponge Chondrosia collectrix, J. Org. Chem., 44, 964, 10.1021/jo01320a016 Phillipson, 1983, Antifungal peroxide-ontaining acids from two Caribbean sponges, J. Am. Chem. Soc., 105, 7735, 10.1021/ja00364a045 Matsugo, 1985, Degradation mediated OH radical generation from synthetic cyclic peroxides: ESR studies, FEBS Lett., 184, 25, 10.1016/0014-5793(85)80645-1 Bambury, 1979, Synthetic antibacterial agents, 41 Szent-Györgyi, 1968 Kirkman, 1968, Glucose-6-phosphate dehydrogenase variants and drug-induced hemolysis, NY Acad. Sci. Ann., 151, 753, 10.1111/j.1749-6632.1968.tb11936.x Holtzman, 1982, Role of reactive oxygen and metabolite binding in drug toxicity, Life Sci., 30, 1, 10.1016/0024-3205(82)90629-4 Oliver, 1968, The synthesis and spectroscopic properties of some halogeno-l,2-naphthoquinones, Tetrahedron, 24, 4067, 10.1016/S0040-4020(01)92615-8 Stradyn', 1980, Effect of the heteroatom on the one-electron reduction of α-nitro derivatives of five-membered rings, Chem. Hetero. Cmpds., 16, 1211, 10.1007/BF00501820 Bartak, 1971, The electrochemical study of the formation and decomposition of 2-halo-2-nitropropane anion radicals, J. Electroanal. Chem., 33, 13, 10.1016/S0022-0728(71)80204-8 Müller, 1981, Electrochemical reduction of 2-halo-2-nitro-propane-1,3-diols, Z. Chem., 21, 286, 10.1002/zfch.19810210808 Gavioli, 1971, Solvent effects on the mechanism of polarographic reduction of nitroalkanes, Coll. Czech. Chem. Commun., 36, 730, 10.1135/cccc19710730 Breccia, 1979, Chemical radiosensitization of hypoxic cells and redox potentials: Correlation of voltammetric results with pulse radiolysis data of nitro-compounds and radiosensitizers, Int. J. Radiat. Biol., 36, 85, 10.1080/09553007914550841 Ryan, 1976, Effect of metal ions on the electrochemical reduction of benzil in non-aqueous solvents, J. Eleciroanal. Chem., 67, 333, 10.1016/S0022-0728(76)80049-6 Mishra, 1985, Electrochemical reduction of nitrofurazone and its determination in pharmaceutical dosage forms by D. C. polarography, Analyst, 110, 1373, 10.1039/an9851001373 Olive, 1981, Correlation between the half-wave reduction potentials of nitroheterocycles and their mutagenicity in Chinese hamster V79 spheroids, Mutation Res., 82, 137, 10.1016/0027-5107(81)90145-7 Burmicz, 1976, An ultraviolet spectral and polarographic study of nitrofurantoin, a urinarytract antibiotic, Analyst, 101, 986, 10.1039/an9760100986 Chignell, 1985, Structure-activity relationships in the free-radical metabolism of xenobiotics, Environ. Health Perspect., 61, 133, 10.1289/ehp.8561133 Josephy, 1985, Toxicity of nitroimidazoles, 451 Moreno, 1985, Mechanism of toxicity of nitro compounds used in the chemotherapy of trichomoniasis, Environ. Health Perspect., 64, 199, 10.1289/ehp.8564199 Mason, 1982, Free-radical intermediates in the metabolism of toxic chemicals, Volume 5, 161 Moore, 1976, The metabolism of the antibacterial agent bronopol (2-bromo-2-nitropropane-1,3-diol) given orally to rats and dogs, Food. Cosmet. Toxicol., 14, 183, 10.1016/S0015-6264(76)80421-X Wawzonek, 1961, Polarographic studies in acetonitrile and dimethylformamide. VI: The formation of dihalocarbenes, J. Electrochem. Soc., 108, 1135, 10.1149/1.2427971 Armand, 1966, Controlled-potential polarography and electrolysis of nitro- and nitroso-deri vatives with another group in the geminal position, Bull. Soc. Chim. France., 543 Peover, 1969, Dependence of electrode kinetics on molecular structure: Nitro-compounds in dimethylformamide, J. Eleciroanal. Chem., 20, 427, 10.1016/S0022-0728(69)80172-5 Stewart, 1950, Polarographic study of lower nitroparaffins in nonalkaline media, Anal. Chem., 22, 793, 10.1021/ac60042a014 Russell, 1968, Electron-transfer processes. VIII: Coupling reactions of radicals with chloroform, J. Am. Chem. Soc., 90, 347, 10.1021/ja01004a025 Stretton, 1973, Some aspects of the mode of action of the antibacterial compound bronopol (2-bromo-2-nitropropan-1,3-diol), J. Appl. Bacteriol., 36, 61, 10.1111/j.1365-2672.1973.tb04073.x Lappas, 1976, Substituted 5-nitro-l,3-dioxanes: Correlation of chemical structure and antimicrobial activity, J. Pharm. Sci., 65, 1301, 10.1002/jps.2600650910 Buckley, 1984, Respiratory tract lesions induced by sensory irritants at the RD50 concentration, Toxicol. Appl. Pharmacol., 74, 417, 10.1016/0041-008X(84)90295-3 Kawai, 1973, Inhalation toxicity of phosgene and trichloronitromethane (chloropicrin), Sangyo Igaku., 15, 406, 10.1539/joh1959.15.406 Bond, 1963, The action of fumigants on insects. IV: The effects of oxygen on the toxicity of fumigants to insects, Can. J. Biochem. Physiol., 41, 993, 10.1139/o63-113 Moriya, 1983, Further mutagenicity studies on pesticides in bacterial reversion assay systems, Mutation Res., 116, 185, 10.1016/0165-1218(83)90059-9 Stern, 1985, Red cell oxidative damage, 340 Furst, 1984, New developments in the study of metal carcinogenesis, J. Environ. Sci. Health., C2, 103 Saenger, 1984, Metal ion binding to nucleic acids, 201 Benesch, 1951, Polarographic studies of organic mercury compounds, J. Am. Chem. Soc., 73, 3391, 10.1021/ja01151a115 Page, 1949, Polarographic determination of thiomersalate, Analyst, 74, 292, 10.1039/an9497400292 Hush, 1963, The electroreduction of organic iodides and organomercuric halides, J. Electroanal. Chem., 6, 34, 10.1016/0022-0728(63)80115-1 Stricks, 1961, Ampoterometric titration of sulfhydryl and disulfide groups with organic mercury compounds at the rotated dropping mercury indicator electrode, Anal. Chem., 33, 194, 10.1021/ac60170a009 Vig, 1971, Polarographic current/voltage curves of fluorescein. IV: Effect of concentration, Electrochim. Acta, 16, 157, 10.1016/0013-4686(71)85137-X Omdorff, 1928, The absorption spectra of fluorescein, fluoran and some related compounds, J. Am. Chem. Soc., 50, 819, 10.1021/ja01390a029 Ansel, 1970, Influence of dimethyl sulfoxide on the hemolytic activity of antimicrobial preservatives, J. Pharm. Sci., 59, 478, 10.1002/jps.2600590408 Wozniak, 1984, Inhibition of etoposide-induced DNA damage and cytotoxicity in L1210 cells by dehydrogenase inhibitors and other agents, Cancer Res., 44, 626 Baur, 1983, Inhibition of hemolysis by tricyclic dyestuffsfluorescein-phenothiazine antagonism, Biochem. Pharmacol., 22, 1509, 10.1016/0006-2952(73)90328-6 Moroi, 1963, The respiration of Trichophyton: II. Effects of antifungal agents on the respiration of Trichophyton, Hifu To Hinyo., 25, 221 Venugopal, 1978 Cantoni, 1983, Possible involvement of superoxide free radicals in the HgCl2-induced DNA damage in CHO cells, 42, 1135 Cantoni, 1984, Characterization of DNA lesions produced by HgCl2 in cell culture systems, Chem.-Biol. Interactions, 49, 209, 10.1016/0009-2797(84)90062-0 Ribarov, 1984, HgClj increases the methemoglobin prooxidant activity: Possible mechanism of Hg2+-induced lipid peroxidation in erythrocytes, Chem.-Biol. Interactions, 50, 111, 10.1016/0009-2797(84)90136-4 Ribarov, 1983, Hemoglobin-catalyzed lipid peroxidation in the presence of mercuric chloride, Chem.-Biol. Interactions, 45, 105, 10.1016/0009-2797(83)90046-7 Charland, 1986, Structure of an unusual 5:2 methylmercury : adenine complex, Inorg. Chim. Acta, 124, 161, 10.1016/S0020-1693(00)85867-3 Crumplin, 1980, Mechanisms of action of nalidixic acid and its congeners, Volume 3, 13 Verbist, 1986, Quinolines:Pharmacology, Pharm. Weekbl. Sci. Ed., 8, 22, 10.1007/BF01975474 Cole, 1984, The complexation of transition series metal ions by nalidixic acid, Inorg. Chim. Acta, 92, 91, 10.1016/S0020-1693(00)80004-3 Hill, 1973, Single-strand breaks in deoxyribonucleic acid and viability loss during deoxyribonucleic acid synthesis inhibition in Escherichia coli, J. Bacteriol., 116, 1329, 10.1128/JB.116.3.1329-1335.1973 Divo, 1985, Oxygen- and time-dependent effects of antibiotics and selected mitochondrial inhibitors on Plasmodium falciparum in culture, Antimicrob. Agents Chemother., 27, 21, 10.1128/AAC.27.1.21 Van Oort, 1983, Polarographic reduction and determination of nalidixic acid, Anal. Chim. Acta., 149, 175, 10.1016/S0003-2670(00)83174-8 Shen, 1985, Mechanism of inhibition of DNA gyrase by analogues of nalidixic acid: The target of the drugs is DNA, 82, 307 Irons, 1985, Phenols, catechols and quinones, 259 Albert, 1979, Metal-binding substances, 385 Miriam, 1986, Degradation of DNA by metalloanthracyclines: Requirement for metal ions, Biochem. Biophys. Res. Commun., 136, 1, 10.1016/0006-291X(86)90868-5 Butler, 1964, The polarographic reduction of metal complexes, J. Electroanal. Chem., 8, 463, 10.1016/0022-0728(64)80086-3 Florence, 1984, Algae as indicators of copper speciation, 411 Sweeney, 1979, Antimalarials, 333 Vicente, 1982, Correlation between physical-chemical parameters and the pharmacological behavior of some biguanides, Quim. Ind. (Madrid), 28, 619 Vert, 1983, Polarographic determination of proguanil and chlorhexidine, Talanta, 30, 977, 10.1016/0039-9140(83)80227-6 Pedros, 1985, AC polarographic reduction of biguanides, J. Electroanal. Chem., 182, 413, 10.1016/0368-1874(85)87015-5 Curd, 1946, A possible mode of action of paludrine, Nature, 158, 707, 10.1038/158707b0 Gale, 1962, Pharmacology of certain antimicrobial N1,N5-substiruted biguanides, J. Pharmacol. Exptl. Therap., 138, 277 Datta, 1980, Polarographic investigation of Cu(II) complexes with π donor ligands, Electrochim. Acta, 25, 533, 10.1016/0013-4686(80)87053-8 Halliwell, 1985, Free radicals, aging, and disease, 279 Lown, 1985, Molecular mechanisms of action of anticancer agents involving free radical intermediates, Adv. Free Rad. Biol. Med., 1, 225, 10.1016/8755-9668(85)90009-2 Sinha, 1979, Binding mode of chemically activated semiquinone free radicals from quinone anticancer agents to DNA, Chem.-Biol. Interactions, 28, 301, 10.1016/0009-2797(79)90170-4 Bachur, 1982, Nuclear catalyzed antibiotic free radical formation, Cancer Res., 42, 1078 Youngman, 1984, Role of oxygen activation in Adriamycin-mediated DNA strand scission and the effect of binding on the redox properties of the drug, 131 1979 Grinev, 1985, Synthesis and biological activity of 4-substituted-1,2-naphthoquinones, 1,2-naphthalenediols and their derivatives, Khim.-Farm. Zh., 19, 699 Farashyan, 1985, Influenza virus replication in the presence of bonaphthon and other inhibitors of macromolecule synthesis, Vopr. Virusol., 30, 174 Fujinaga, 1971, Effect of metal ions on the polarographic reduction of organic compounds in dipolar aprotic solvents, J. Electroanal. Chem., 29, 203, 10.1016/S0022-0728(71)80083-9 Fieser, 1935, The reduction potentials of various naphthoquinones, J. Am. Chem. Soc., 57, 491, 10.1021/ja01306a031 Zuman, 1967 Stallings, 1981, Redox chemistry of metal-catechol complexes in aprotic media: 1. Electrochemistry of substituted catechols and their oxidation products, Inorg. Chem., 20, 2655, 10.1021/ic50222a053 Clark, 1985, Antimalarials, 143 Thornalley, 1984, The formation of active oxygen species following activation of 1-naphthol, 1,2- and 1,4-naphthoquinone by rat liver microsomes, Chem.-Biol. Interactions, 48, 195, 10.1016/0009-2797(84)90121-2 Stradins, 1979, Azo, azoxy and diazo compounds, Volume 13, 163 Albert, 1985 Mueller, 1950, The reductive cleavage of 4-dimethylamino-azobenzene by rat liver: Reactivation of carbon dioxide-treated homogenates by riboflavin-adenine dinucleotide, J. Biol. Chem., 185, 145, 10.1016/S0021-9258(18)56402-4 Parent, 1979, Absorption and distribution of C. I. solvent red 24 in rats; intra-tracheal administration of carbon-14-labeled dye, Drug Chem. Toxicol., 2, 409, 10.3109/01480547909016034 Brown, 1978, Mutagenicity testing of certified food colors and related azo, xanthene and triphenylmethane dyes with the salmonella/microsome system, Mutation Res., 56, 249, 10.1016/0027-5107(78)90192-6 Anand, 1979, Sulfonamides and sulfones, 1 Scott, 1973, In vitro action of dapsone and its derivatives on normal and G6PD [glucose-6-phosphate dehydrogenase]-deficient red cells, Br. J. Haematol., 24, 304, 10.1111/j.1365-2141.1973.tb01655.x Weetman, 1980, In vitro inhibition of granulopoiesis by 4-amino-4'-hydroxylaminodiphenyl sulfone, Br. J. Haematol., 45, 361, 10.1111/j.1365-2141.1980.tb07156.x Scholar, 1984, Volume 68/II, 123 Cadenas, 1985, Oxidative stress and formation of excited species, 318 Kaye, 1952, The polarographic reduction of some natural and artificial hydrogen-carriers in bacterial enzyme systems, J. Chem. Soc., 3244, 10.1039/jr9520003244 Binder, 1983, Pyrazine-1,4-dioxides fused to heterocycles: 3. Synthesis and antibacterial activity of substituted pteridine-5,8-dioxides, Arzneim.-Forsch., 33, 803 Johnson, 1984, Studies on 8-aminoquinoline 1-oxide antimalarial agents, J. Heterocyclic Chem., 21, 1093, 10.1002/jhet.5570210434 Kier, 1971 Blacker, 1986, Photochemical cleavage of DNA by 2,7-diazapyrenium cations, Chem. Commun., 1035, 10.1039/c39860001035 Sliwa, 1985, The chemistry of N-substituted pyridinium salts, Heterocycles, 23, 1513, 10.3987/R-1985-06-1513 Morrison, 1978, Flavin model systems: 1. The electrochemistry of 1-hydroxyphenazine and pyocyanine in aprotic solvents, J. Am. Chem. Soc., 100, 207, 10.1021/ja00469a035 Parkanyi, 1975, Charge-transfer spectra of some heterocyclic cations, Zeit. Naturforsch., 30b, 984, 10.1515/znb-1975-11-1237 Caolo, 1979, Benzophenanthridinium salt equilibria, Heterocycles, 12, 11, 10.3987/R-1979-01-0011 Miller, 1983, The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: Recent results with ethyl carbamate and the spice flavors safrole and estragole, Br. J. Cancer, 48, 1, 10.1038/bjc.1983.151 1982 Dryhurst, 1977, 71 Reynolds, 1985, Reaction of the antitumor antibiotic CC-1065 with DNA. Location of the site of thermally induced strand breakage and analysis of DNA sequence specificity, Biochemistry, 24, 6228, 10.1021/bi00343a029 Nelson, 1982, Metabolic activation and drug toxicity, J. Med. Chem., 25, 753, 10.1021/jm00349a001 Mijazaki, 1981, Cyclic voltammetry of aromatic amine N-oxides in nonaqueous solvents and the stability of the free radicals produced, Bull. Chem. Soc. Jpn., 54, 3850, 10.1246/bcsj.54.3850 Neta, 1985, Intramolecular association of covalently linked viologen radicals, J. Chem. Soc. Faraday Trans. 2, 81, 1427, 10.1039/f29858101427 Kinoshita, 1971, Mitomycin derivatives: 1. Preparation of mitosane and mitosene compounds and their biological activities, J. Med. Chem., 14, 103, 10.1021/jm00284a005 Shapovalov, 1980, Polarographic investigation of 6- and 7-nitro derivatives of 9-(methylamino)acridine, which have an antibacterial action, J. Gen. Chem. USSR, 50, 2264 Adams, 1980, Toxicity of nitro compounds toward hypoxic mammalian cells in vitro: Dependence on reduction potential, J. Natl. Cancer Instit., 64, 555 Pernak, 1983, Activity of new quarternary ammonium compounds on strains of bacteria and fungi. Part 5: Synthesis of 3-methyl-n-alkylthiomethylpyridine-, 1-methyl-3-n-alkylthiomethylimidazole- and 1-ethyl-3-n-alkylthiolimidazoline chlorides, Pharmazie, 38, 752 Chesis, 1984, Mutagenicity of quinones: Pathways of metabolic activation and detoxification, 81, 1696 Misra, 1986, Genetic toxicological testing of some dyes by the micronucleus test, Mutation Res., 170, 75, 10.1016/0165-1218(86)90083-2