Phagomimetic action of antimicrobial agents

Free Radical Research

Volumn 28, Issue 1, 1998, Pages 1-14

  Gutteridge, John M C ^a   Quinlan, Gregory J ^a   Kovacic, Peter ^b  

^a ROYAL BROMPTON HOSPITAL   (United Kingdom)

^b SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

Antibiotics; DNA damage; Electron transfer; Phagocytosis; Reactive oxygen species; Transition metal ions

Indexed keywords

ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; HYDROGEN PEROXIDE; HYDROXYL RADICAL; REACTIVE OXYGEN METABOLITE; SUPEROXIDE;

ANTIFUNGAL ACTIVITY; BACTERICIDAL ACTIVITY; CANCER CELL DESTRUCTION; DRUG MECHANISM; ELECTRON TRANSPORT; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; OXIDATION REDUCTION REACTION; PHAGOCYTOSIS; REVIEW;

EID: 0031968712     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769809097871     Document Type: Review

References (121)

1. Ames, J. R., Ryan, M. D. and Kovacic, P. (1986). Mechanism of antibacterial action: electron transfer and oxy radicals, Journal of Free Radicals in Biology and Medicine, 2, 337-391.
2. Halliwell, B. and Gutteridge, J. M. C. (1985). Free radicals in biology and medicine, University press New York, 306-313.
3. th edition, Chapman Hall Press London.
4. Edberg, S. C. and Berger, S. A. (1983). Antibiotics and infection, Churchill Livingstone Press New York.
5. Root, R. K. and Sande, M. A. (1984). Contemporary issues in infectious diseases, Vol. 1, Churchill Livingstone press, New York.
6. Greenwood, D. and Grady, F. O. (1985). The scientific basis of antimicrobial chemotherapy, The society for general microbiology symposium (38), Cambridge university press, Cambridge.
7. Hecht, (1979). Bleomycin, chemical, biochemical and biological aspects, Springer Verlag press, New York.
8. Butler, J. and Hoey, B. M. (1993). Redox cycling drugs and DNA damage. In B. Halliwell and O. I. Aruoma (eds) DNA and Free Radicals. Eillis Horwood, Sussex, 243-273.
9. Neilands, J. B. and Valenta, J. R. (1985). Iron-containing antibiotics. In Metal ions in biological systems, Vol. 19, (Sigel, H. ed), Marcel Dekker Inc, New York 313-333.
10. Albert, A. and Rees, C. W. (1956). Avidity of the tetracyclines for the cations of metals. Nature, 177, 433-434.
11. Lambs, L., Brionand, M. and Berthon, G. (1984). Metal ion-tetracycline interactions in biological fluids, part 3. Formation of mixed-metal ternary complexes of tetracycline, oxytetracycline, doxycycline and minocycline with calcium and magnesium, and their involvement in the bioavailability of these antibiotics in blood plasma. Agents and Actions, 14, 743-750.
12. 13C NMR and spectroscopic studies. Structure and bonding properties of the streptidine fraction. Journal of Inorganic Biochemistry, 40, 201-215.
13. Kays, S. E., Crowell, W. A. and Johnson, M. A. (1991). Iron supplementation increases gentamycin nephrotoxicity in rats. Journal of Nutrition, 121, 1869-1875.
14. Ismail, T. H. B., Ali, B. H. and Bashir, A. A. (1994). Influence of iron, desferrioxamine and ascorbic acid on gentamycin-induced nephrotoxicity in rats. General Pharmacology, 25, 1249-1252.
15. Pierson, M. G. and Møller, A. R. (1981). Prophylaxis of kanamycin-induced ototoxicity by a radioprotectant. Hearing Research, 4, 79-87.
16. Priuska, E. M. and Schacht, J. (1995). Formation of free radicals by gentamycin and iron and evidence for an iron/gentamycin complex. Biochemical Pharmacology, 11, 1749-1752.
17. Gartez, S. L., Altschuler, R. A. and Schacht, J. (1994). Attenuation of gentamycin ototoxicity by glutathione in the guinea pig in vivo. Hearing Research, 77, 81-87.
18. L'Herminez-van Krimpen, P. C. (1995). Metal-antibiotic interactions. In Handbook of metal-ligand interactions in biological fluids, Bioinorganic chemistry, Vol. 2 (Berthon, G. ed), Marcel Dekker, New York, 920-925.
19. Quinlan, G. J. and Gutteridge, J. M. C. (1995). Antibiotics, metal ions, and the generation of free radicals. In Handbook of Metal-Ligand Interactions in Biological Fluids, (ed Berthon, G). Macel Dekker, New York, vol 2, 1336-1345.
20. Plas, G. and Desbuquois, B. (1982). Receptor-mediated insulin degradation and insulin-stimulated glycogenesis in cultured foetal hepatocytes. Biochemical Journal, 202, 333-341.
21. Hajdu, J. (1985). In Metal ions in biological systems (H. Sigel ed), Marcel Dekker, New York, vol 19, 53-80.
22. Gutteridge, J. M. C. (1984). Streptonigrin-induced deoxyribose degradation: inhibition by Superoxide dismutase, hydroxyl radical scavengers and iron chelators. Biochemical Pharmacology, 33, 3059-3062.
23. Rao, K. V., Biemann, K. and Woodard, R. B. (1963). Journal of the American Chemical society, 85, 2532-2533.
24. Lown, J. W., Joshua, A. V. and Clen, H. H. (1982). Reactive oxygen species leading to lipid peroxidation and DNA lesions implicated in the cytotoxic action of certain antitumor antibiotics. In Free radicals lipid peroxidation and cancer (D, C, H, McBrian and T, T, Slater, eds), Academic press London. 304-328.
25. Sugioka, K. and Nakano, M. (1982). Mechanism of phospholipid peroxidation induced by ferric ion-ADP-adriamycin-co-ordination complex. Biochimica Biophysica Acta, 713, 333-343.
26. Gutteridge, J. M. C. (1984). Lipid peroxidation and possible hydroxyl radical formation stimulated by the self-reduction of a doxorubicin-iron (III) complex. Biochemical Pharmacology, 33, 1725-1728.
27. Gutteridge, J. M. C., Quinlan, G. J., Swain, J. A. and Cox, J. (1994). Ferrous ion formation by Ferrioxamine prepared from agedesferroxamine: a potential prooxidant property. Free Radical Biology and Medicine, 16, 733-739.
28. Gutteridge, J. M. C. (1991). Hydroxyl radical formation from the autoreduction of a ferric citrate complex. Free Radical Biology and Medicine, 11, 401-406.
29. Gutteridge, J. M. C. (1990). Superoxide-dependent formation of hydroxyl radicals from ferric complexes: an evaluation of fourteen iron chelators. Free Radical Research Communications, 9, 119-125.
30. Caspary, W. J., Niziak, C., Lanzo, A., Friedman, R. and Bachur, N. R. (1979). Bleomycin A2: a ferrous oxidase. Molecular Pharmacology, 16, 256-260.
31. Takeshita, M., Grollman, A. P., Ohtsubo, E. and Ohtsubo, H. (1978). Interaction of bleomycin with DNA. Proceedings of the National Academy of Sciences, USA, 75, 5983-5987.
32. Giloni, L., Takeshita, M., Johnson, F., Iden, C. and Grollman, A. P. (1981). Bleomycin-induced strandscission of DNA. Mechanism of deoxyribose cleavage. Journal of Biological Chemistry, 256, 8608-8615.
33. Quinlan, G. J. and Gutteridge, J. M. C. (1989). Bacitracin and bacitracin-zinc complex damage DNA and carbohydrate in the presence of iron and copper salts. Free Radical Research Communications, 7, 37-44.
34. Babior, B. M. (1987). The respiratory burst oxidase. Trends in Biochemical Sciences, June: 241-243.
35. Folkes, L. K., Candeias, L. P. and Wardman, P. (1995). Kinetics and mechanisms of HOCl reactions. Archives of biochemistry and Biophysics, 323, 120-126.
36. Kovacic, P. (1959). An integrated concept of carcinogenic - anticarcinogenic action. Ohio Journal of Science, 59, 318-320.
37. Kovacic, P., Ames, J. R., Lumme, P., Elo, H., Cox, O., Jackson, H., Rivera, L. A. and Ryan, M. D. (1986). Charge-transfer - oxy radical mechanism for anti-cancer agents. Anti-cancer Drug Design, 1, 197-214.
38. Kovacic, P., Popp, W. J., Ames, J. R. and Ryan, M. D. (1988). Anti-cancer action of metal complexes: electron transfer and oxidative stress? Anti-cancer Drug Design, 3, 205-216.
39. Crawford, P. W., Lumme, P., Elo, H., Ryan, M. D. and Kovacic, P. (1987). Charge transfer-oxy radical mechanism for anti-cancer agents: mAMSA derivatives, rhodamine 123, and nickel salicyaldoximate. Free Radical Research Communications, 3, 347-356.
40. Kovacic, P., Ames, J. R. and Ryan, M. D. (1988). Electron transfer-oxy radical mechanism for anticancer agents: Etopside, Cu DIPS, and bis (9-aminoacridines). In Redox Chemistry and Interfacial Behaviour of Biological Molecules, (eds Dryhurst, G and Niki, K) Plenum press New York. 345-357.
41. Clarke, M. J. and Limauro, S. (1995). In Handbook of Metal Ligand Interactions in Biological Fluids. (G. Berthon ed) Marcell Dekker New York vol 2:1010-1018.
42. Speranskii, S. D., Zorin, V. P., Pogirnitskaya, A. V., Speranskaya, E. C. and Cherenkevich, S. N. (1991). Mechanism of the cytotoxic action of 1,2-benzoquinones on tumour cells. Experimental Oncology, 13, 55-58.
43. Kovacic, P., Ames, J. R., Grogan, J. W., Hazra, B. and Ryan, M. D. (1988). Anticancer quinones and quinolines: Mode of action via electron transfer and oxidative stress. Redox Chemistry and Interfacial Behaviour of Biological Molecules. (G. Dryhurst and K. Niki eds) Plenum press New York. 295-307.
44. Redman, C., LeFevre, J. and MacDonald, M. L. (1995). Inhibition of diacylglycerol kinase by the antitumour agent calphostin-C : evidence for similarity between the active site of diacylglycerol kinase and the regularity site of protein kinase-C. Biochemical Pharmacology, 50, 235-241.
45. Beall, H. D., Liu, Y., Siegel, D., Bolton, E. M., Gibson, N. W. and Ross, D. (1996). Role of NAD(P)H-Quinone oxoreductase (DT-Diaphorase) cyotoxicity and induction of DNA damage by streptonigrin. Biochemical Pharmacology, 51, 645-652.
46. Kovacic, P., Ames, J. R., Taylor, E. C. and Ryan, M. D. (1988). Electrochemistry of the anticancer agents methotrexate and a-difluoromethylornithine in iminium form. Journal of Pharmaceutical Sciences, 77, 999-1002.
47. Crawford, P. W., Foye, W. O., Ryan, M. D. and Kovacic, P. (1987). Cyclic voltammetry of quinolinium salts and related compounds: Correlation with structure and anticancer activity. Journal of Pharmaceutical Sciences, 76, 481-484.
48. Kovacic, P., Ames, J. R. and Ryan, M. D. (1987). Electron transfer-oxy radical mechanism for anti-cancer agents. Anti-Cancer Drug Design, 2, 37-46.
49. Chin, D.-H. and Goldberg, I. H. (1992). Internal hydrogen abstraction by activated neocarzinostatin: quenching of the radical at C2 by hydrogen atom transfer from the α carbon of the adducted thiol. Journal of the American Chemical society, 114, 1914-1915.
50. Goldberg, I. H. (1991). Mechanism of neocarzinostatin action: role of DNA microstructure in determination of chemistry of bistranded oxidative damage. Accounts of Chemical Research. 24, 191-198.
51. Takahara, P. M., Rosenzweig, A. C., Frederick, C. A. and Lippard, S. J. (1995). Crystal structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature, 377, 649-652.
52. Baum, R. (1992). Protein found that binds to cisplatin-DNA adducts. Chemical and Engineering News, 70, 19-21.
53. Hernandez, L., Cholody, W. M., Hudson, E. A., Resau, J. H., Pauly, G. and Michejda, C. J. (1995). Mechanism of action of bisimidazoacridones. New drugs with potent selective activity against colon cancer. Cancer Research, 55, 2338-2345.
54. Pindur, U., Haber, M. and Sattler, K. (1993). Antitumour active drugs as intercalators of deoxyribonucleic acid. Journal of Chemical Education, 70, 263-272.
55. Corbett, A. H. and Osheroff, N. (1993). When good enzymes go bad: conversion of topoisomerase II to a cellular toxin by antineoplastic drugs. Chemical Research in Toxicology, 6, 585-597.
56. Bienvenu, P. (1992). Assessing and counteracting the prooxidant effects of anticancer drugs. (I. Emerit and B. Chance eds). In Free Radicals and Aging. Birkauser, Boston, Experientia. 62S: 257-265.
57. Pamatong, F. V., Detmer, C. A. and Bocarsly, J. R. (1996). Double-strand DNA cleavage agent. Journal of the American Chemical Society, 118, 5339-5345.
58. Hoffmann, T. A. and Ladik, J. (1964). Quantum mechanical considerations on some properties of DNA. Advances in Chemical Physics, 7, 84-158.
59. Kovacic, P., Crawford, P. W., Ryan, M. D. and Nelson, V. (1986). Charge transfer mechanism for carcinogenesis by alkylating and other agents. Bioelectrochemistry and Bioenergetics, 15, 305-316.
60. Murphy, C. J., Arkin, M. R., Jenkins, Y., Ghatlia, N. D., Bossmann, S. H., Turro, N. J. and Barton, J. K. (1993). Long-range photoinduced electron transfer through a DNA helix. Science, 262, 1025-1029.
61. Chen, E. C. M., Chen, E. S. D. and Wentworth, W. E. (1990). The role of electron donors and acceptors in base stacking in DNA and RNA. Biochemical and Biophysical Research Communications, 171, 97-101.
62. Mizumoto, K., Glascott, P. A. Jr. and Farber, J. L. (1993). Roles of oxidative stress and poly (adp-ribosyl)ation in the killing of cultured hepatocytes by methyl methansulphonate. Biochemical Pharmacology, 46, 1811-1818.
63. Katoh, T., Higashi, K., Inoue, N. and Tanaka, I. (1988). Effects of chronic inhalation of ethylene oxide on lipid peroxidation and glutathione redox cycle in rat liver. Research Communications in Chemical Pathology and Pharmacology, 61, 281-284.
64. Hadi, S. M. (1991). Anti-cancer drugs and DNA degradation. Medical Sciences Research, 19, 627-632.
65. Kurose, J., Saito, H., Suematsu, M., Fukumura, D., Muira, S., Morizane, T. and Tsuchiya, M. (1991). Kupffer cell-mediated oxidative stress on colon cancer cell line visualised by digital imaging fluorescence microscopy. Cancer Letters, 59, 201-209.
66. Gressier, B., Lebegue, S., Brunet, C., Luyckx, M., Dine, T., Cazin, M. and Cazin, J. C. (1994). Prooxidant properties of methotrexate-evaluation and prevention by an antioxidant drug. Pharmazie, 49, 679-681.
67. Handa, K. and Sato, S. (1975). Generation of free radicals of quinone group containing anti-cancer chemicals in NADPH-microsome system as evidenced by initiation of sulfite oxidation. Gann, 66, 43-17.
68. Bachur, N. R., Gordon, S. L., Gee, M. V. and Kon, H. (1979). NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals. Proceedings of the National Academy of Sciences, USA, 76, 954-957.
69. Lown, J. W., Sim, S. K. and Chen, H. H. (1978). Hydroxyl radical production by free and DNA-bound aminoquinone antibiotics and its role in DNA degradation. Electron spin resonance detection of hydroxyl radicals by spin trapping. Canadian Journal of Biochemistry, 56, 1042-1047.
70. Kalyanaraman, E., Reyes, E. P. and Mason, R. P. (1980). Spin-trapping and direct electron spin resonance investigations of the redox metabolism of quinone anticancer drugs. Biochimica Biphysica Acta, 630, 119-130.
71. Rowley, D. A. and Halliwell, B. (1983). DNA damage by superoxide-generating systems in relation to the mechanism of action of the anti-tumour antibiotic adriamycin. Biochimica Biophysica Acta, 761, 86-93.
72. Powis, G. (1987). Metabolism and action of Anticancer Drugs. (G. Powis and R. Prough, eds). Taylor and Francis London. 211-260.
73. Kang, J. Y., Chen, Y. and Epstein, P. N. (1996). Suppression of doxorubicin cardiotoxicity by over expression of catalase in the heart of trangenic mice. Journal of Biological Chemistry, 271, 12610-12616.
74. Yen, H.-C., Oberley, T. D., Vichitbandha, S., Ho, Y.-S. and St Clair, D. K. (1996). The protective role of manganese Superoxide dismutase against adrimycin-induced acute cardiac toxicity in transgenic mice. Journal of Clinical Investigation, 98, 1253-1260.
75. Richards, R. W., Smith, R. M. and Golding, B. T. (1970). Macrolide antibiotic studies XV. The autoxidation of polyenes of the filipin complex and lagosin. The Journal of Antibiotics, XXIII, 603-612.
76. Gutteridge, J. M. C. and Thomas, A. H. (1980). Thiobarbituric acid reactivity of autoxidised candicidin. Biochemical Medicine, 24, 194-200.
77. Andrews, F. A., Sarosi, G. A. and Beggs, W. H. (1979). Enhancement of amphotericin B activity by a series of compounds related to phenolic antioxidants. Journal of Antimicrobial Chemotherapy, 5, 173-177.
78. Gutteridge, J. M. C., Thomas, A. H. and Cuthbert, A. (1983). Free radical damage to polyene antifungal antibiotics: changes in biological activity and thiobarbituric acid reactivity. Journal of Applied Biochemistry, 4, 53-58.
79. Brajtburg, J., Elberg, S., Schwartz, D. R., Vertut-Croquin, A., Schlessinger, D., Kobayashi, G. S. and Medoff, G. (1985). Involvement of oxidative damage in erythrocyte lysis induced by Amphotericin B. Antimicrobial Agents and Chemotherapy, 27, 172-176.
80. Tomasz, A. (1983). Handbook of Experimental Pharmacology. Antibiotics containing the β-lactam structure, (eds Demain, A. L. and Solomon, N. A.), Springer-Verlag, New York, vol 67, part 2, chapt 2.
81. Bertina, V. (1983). The Chemistry and Biology of Antibiotics. Elsevier, New York, Chapt 11.
82. Kovacic, P., Jawdosiuk, M., Ames, J. R. and Ryan, M. D. (1987). A novel approach to β-lactam chemistry in vivo: electron transfer and oxy-radical formation by iminium. Bioorganic Chemistry, 15, 423-441.
83. Van Dyke, C., Kovacic, P. and Bowen, J. P. (1991). Computational studies on isomerization of imine from penicillin and electron transfer by carboxyiminium derived from β-lactams. Bioorganic Chemistry, 19, 314-326.
84. Kovacic, P., Ames, J. R. and Ryan, M. D. (1989). Electron transfer mechanism for β-lactam antibiotic action via side-chain imine. Bioogarnic Chemistry, 16, 149-164.
85. Kovacic, P., Ames, J. R. and Ryan, M. D. (1988). Minimum essential structural requirements for lactam antibiotic action. Free Radical Research Communications, 7, 19-26.
86. Jouenne, T. and Junter, G.-A. (1989). Electro-chemical classification of antibacterial effects of β-lactam antibiotics on Escherichia coli cultures. Bioelectrochemistry and Bioenergetics, 22, 331-340.
87. Uri, J. V., Phillips, L. and Pitkin, D. H. (1986). Comparative laboratory studies on α-methoxyimino furyl- and phenylacetamido cephalosporines: structure-activity relationships. Acta Microbiologica Hungarica, 33, 131-140.
88. Burks, J. E. Jr., Chelius, E. C. and Johnson, R. A. (1994). Kinetic differences in the chlorination of cephalosporin versus carbcephalsporin enols: evidence of sulfur neighbouring group participation. Journal of Organic Chemistry, 59, 5724-5728.
89. Bhanot, S. K., Chatterjee, R. N. and Naik, S. R. (1994). Synthesis and antimicrobial activities of some new quinolonyl-3′-penicillin and 4′-cephalosporin derivatives. Arzneimittel-Forschung, 44, 663-667.
90. Miller, M. J. and Malouin, F. (1993). Microbial iron chelators as drug delivery agents: the rational design and synthesis of siderophore-drug conjugates. Accounts of Chemical Research, 26, 241-249.
91. Pu, Y., Lowe, C., Sailer, M. and Vederas, J. C. (1994). Synthesis, stability and antimicrobial activity of (+)-obafluorin and related β-lactone antibiotics. Journal of Organic Chemistry, 59, 3642-3655.
92. Quinlan, G. J. and Gutteridge, J. M. C. (1988). Oxidative damage to DNA and deoxyribose by β-lactam antibiotics in the presence of iron and copper salts. Free Radical Research Communications, 5, 149-158.
93. Tune, B. M., Fravert, D. and Hsu, C.-Y. (1989). Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochemical Pharmacology, 38, 795-802.
94. Quinlan, G. J. and Gutteridge, J. M. C. (1988). Hydroxyl radical generation by tetracycline antibiotics with free radical damage to DNA, lipids and carbohydrate in the presence of iron and copper salts. Free Radical Biology and Medicine, 5, 344-348.
95. Buschfort, C. and Witte, I. (1994). Induction and mechanism of DNA single- and double-strand breaks by tetracycline/Cu(II) in the absence of light. Carcinogenesis, 15, 2927-2930.
96. Quinlan, G. J. and Gutteridge, J. M. C. (1991). DNA base damage by β-lactam, tetracycline, bacitracin, and rifamycin antibacterial antibiotics. Biochemical Pharmacology, 42, 1595-1599.
97. Wasil, M., Halliwell, B. and Moorehouse, C. P. (1988). Scavenging of hypochlorous acid by tetracyline, rifampicin, and some other antibiotics: a possible antioxidant action of rifampicin and tetracycline? Biochemical Pharmacology, 37, 775-778.
98. Scrutton, M. C. (1977). Divalent metal catalysis of the oxidation of rifamycin SV to rifamycin S. Federation of Biochemists Letters, 78, 216-220.
99. Kono, Y. (1982). Oxygen enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to rifamycin S catalysed by mmanganous ions: the role of Superoxide. Journal of Biochemistry-Tokoyo, 91, 381-395.
100. Quinlan, G. J. and Gutteridge, J. M. C. (1987). Oxygen radical damage by Rifamycin SV and copper ions. Biochemical Pharmacology, 36, 3629-3633.
101. Kukielka, E. and Cederbaum, A. I. (1995). Stimulation of NADH-dependent microsomal DNA strand cleavage by rifamycin SV. Biochemical Journal, 307, 361-367.
102. Okai, Y. and Ishizaka, I. (1994). A possible immunomodulating activity of arbekacin (ABK), a newly synthesized antibiotic against methicillin-resistant Staphylococcus aureus (MRSA). International Journal of lmmunopharmacology, 16, 321-327.
103. Shapira, L., Soskoline, W. A., Houri, Y., Barak, V., Halabi, A. and Stabholz, A. (1996). Protection against endotoxic shock and lipopolysaccharide-induced local inflamation by tetracycline: correlation with inhibition of cytokine secretion. Infection and Immunity, 64, 835-828.
104. Tufano, M. A., Cipollaro-de, L., Ero, G., Ianniello, R., Baroni, A. and Galdiero, F. (1992). Antimicrobial agents induce monocytes to release IL-α, IL-6, and TNF and induce lymphocytes to release IL-4 and TNF. Immunopharntacology and Immunotoxicology, 14, 769-782.
105. Bailly, S., Pocidalo, J. J., Fay, M. and Gourerot-Pocidalo, M. A. (1991). Differential modulation of cytokine production by macrolides: interleukin-6 production is increased by spiramycin and erthythromycin. Antimicrobial Agents and Chemotherapy, 35, 2016-2019.
106. Halliwell, B. and Gutteridge, J. M. C. (1985). Free Radicals in Biology and Medicine. University press New York. 306-313.
107. Ames, J. R., Ryan, M. D. and Kovacic, P. (1986). Mechanism of antibacterial action: electron transfer and oxy radicals. Journal of Free Radicals in Biology and Medicine, 2, 377-391.
108. Crawford, P, W., Scamehorn, R. G., Hollstein, U., Ryan, M. D. and Kovacic, P. (1986). Cyclic voltammetry of phenazines and quinoxalines including mono- and di-N-oxides. Relation to structure and antimicrobial activity. Chemico- Biological Interactions, 60, 67-84.
109. Ryan, M. D., Scamehorn, R. D. and Kovacic, P. (1985). Charge transfer in the mechanism of drug action involving quinoxaline di-N-oxides. Journal of Pharmaceutical Sciences, 74, 492-495.
110. Kovacic, P., Kassel, M. A., Ames, J. R., Feinberg, B. A. and Silva, W. (1990). Reduction potentials of antibacterial agents. Journal of Biopharmaceutical Sciences, 1, 331-342.
111. Petering, D. H., Byrne, R. W. and Antholine, W. (1995). Transition metal requirements for the action of antibiotics. In Handbook of Metal-Ligand Interactions in Biological Fluids, (ed Berthon, G), Marcel Dekker, New York, vol 2: 1325-1335.
112. Parwana, H. K. and Gurdev, S. (1985). Antifungal activity of metal complexes of thiosemicarbazones. Inorganica Chimica Acta, 108, 87-89.
113. Okazaki, K., Nomura, K. and Yoshii, E. (1989). Total synthesis of naturally occurring granacitin. Chemical Communications, 354-356.
114. Scannel, R. T., Barr, J. R., Murty, V. S., Reddy, K. S. and Hecht, S. M. (1988). DNA strand scission by naturally occurring 5-alkylresorcinols. Journal of the American Chemical Society, 110, 3650-3651.
115. Bockholt, H., Udvarnoki, G. and Rohr, J. (1994). Biosynthetic studies on the xanthone antibiotics Iysolipins X and I. Journal of Organic Chemistry, 59, 2064-2069.
116. Parker, K. A. and Casteel, D. A. (1988). Isoquinoline quinones, preparation of saframycin intermediates and a total synthesis of mimosamycin. Journal of Organic Chemistry, 53, 2847-2850.
117. Schmidt, U., Leitenberger, V., Meyer, R. and Griesser, H. (1992). The synthesis of biphenomycin A. Chemical Communications, 951-953.
118. Reszka, F. S., Cruz, F. S. and Docampo, R. (1986). Photosensitization by the trypanocidal agent crystal violet. Type 1 versus type II reactions. Chemico-Biohgical Interactions, 58, 161-172.
119. Rocca, P., Marsais, F., Godard, A. and Queguiner, G. (1993). A short synthesis of the antimicrobial marine sponge pigment fascaplysin. Tetrahedron Letters, 7917-7918.
120. Shoji, J., Hinoo, H., Terui, Y., Kikuchi, J., Hattori, T., Ishii, K., Matsumoto, K. and Yoshida, T. (1989). Isolation of azomycin from Pseudomonas fluorescens. Journal of Antibiotics, 42, 1513-1514.
121. Ehlhardt, W. J., Beaulieu, B. B. Jr. and Goldman, P. (1988). Nitrosoimidazoles: highly bactericidal analogues of 5-nitroimidazole drugs. Journal of Medicinal Chemistry, 31, 323-329.