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Original Article

Reduction Potentials of Imine-Substituted, Biologically Active Pyridines: Possible Relation To Activity

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Pages 185-192 | Received 16 Jan 1990, Accepted 19 Feb 1990, Published online: 07 Jul 2009

References

  • Halliwell B., Gutteridge J. M.C. Free Radicals in Biology and Medicine. Oxford University Press, Oxford 1985
  • Oxidative Stress, H. Sies. Academic Press, New York 1985
  • Kovacic P., Ames J. R., Rector D. L., Jawdosiuk M., Ryan M. D. Reduction potentials of anthelmintic drugs. Possible relationship to activity. Journal of Free Radicals in Biology and Medicine 1988; 6: 131, and references therein
  • Kovacic P., Ames J. R., Ryan M. D. Reduction potentials of antimycobacterial agents: Relationship to activity. Bioeleclrochemistry Bioenergelics 1989; 21: 269
  • Salem L. The sudden polarization effect and its possible role in vision. Accounts of Chemical Research 1979; 12: 87
  • Bonacic-Koutecky V., Koutecky J., Michl J. Neutral and charged biradicals, zwitterions, funnels in S1, and proton translocation: Their role in photochemistry, photophysics, and vision. Angewandte Chemie International Edition Engl. 1979; 26: 170
  • Kovacic P., Kiser P. F., Smith K. M., Feinberg B. A. Iminium: A missing link in the primary process of the photosynthetic chain?. 1989, unpublished work
  • Medicinal Chemistry., A. Burger. Wiley-Interscience, New York 1970; 21–23; 26–28, Pt. 1, Ch. 19
  • Brandänge S., Lindblom L. N-Vinyl as N-H protecting group-convenient synthesis of myosmine. Acta Chemica Scandanavia B. 1976; 30: 93
  • Mundy B. P., Larsen B. R. A new approach to pyrrolidine and piperidine alkaloids. Synthetic Communications 1972; 2: 197
  • Leete E. Biosynthesis and metabolism of the tobacco alkaloids. Alkaloids: Chemical and Biological Perspectives., S. W. Pelletier. Wiley, New York 1983; Vol. 1: 85–153, Ch. 3
  • Riebe M., Westphal K., Fortnagel P. Mutagenicity testing in bacterial test systems of some constituents of tobacco. Mutation Research 1982; 101: 39
  • Ryan M. D., Scamehorn R. G., Kovacic P. Charge transfer in the mechanism of drug action involving quinoxaline di-N-oxides. Journal of Pharmaceutical Science 1985; 74: 492
  • Ames J. R., Brandange S., Rodriguez B., Castagnoli N., Jr., Ryan M. D., Kovacic P. Cyclic voltammetry with cyclic iminium ions. Implications for charge transfer with biomolecules (metabolites of nicotine, phencyclidine, and spermine). Bioorganic Chemistry 1986; 14: 228
  • Kern W. R., Abbott B. C., Coates R. M. Isolation and Structure of a Hoplonemertine. Toxin. Toxicon. 1971; 9: 15–22
  • Kem W. R. A study of the Occurrence of Anabaseine in Paramemertesand Other Nemertines. Toxicon. 1971; 9: 23–32
  • Kamimura H., Yamamato I. Studies on nicotinoids as insecticides. III. Structure of anabaseine. Agricultural and Biological Chemistry. 1963; 27: 450
  • Keeler R. F., Crowe M. W., Lambert E. A. The tobacco alkaloid anabasine isolated from nicotiana-gluca. Teratology 1984; 30: 61
  • Lin J.-K., Huang I.-H., Lee K.-W., Lin-Shiau S.-Y. Mutagenicity of dipyridyls and their methylated derivatives in Salmonella typhimurium/rat liver microsome system. Proceedings of National Science Council B. ROC. 1989; 13: 56–63, and references therein
  • Claxton L. D., Dearfield K. L., Spanggord R. T., Riccio E. S., Mortelmans K. Comparative mutagenicity of halogenated pyridines in the Salmonella typhimurium/mammalian microsome test. Mutation Research 1987; 176: 185–198
  • Kern W. R., Scott K. N., Duncan J. H. Hoplonemertine worms - A new source of pyridine neurotoxins. Experientia 1976; 32: 684
  • Ginsburg H., Nissani E., Krugliak M. Alkalinization of the food vacuole of malaria parasites by quinoline drugs and alkylamines is not correlated with their antimalarial activity. Biochemical Pharmacology 1989; 38: 2645
  • Krogstad D. J., Schlesinger P. H., Gluzman I. Y. Chloroquine and acid vesicle function. Progress in Clinical Biological Research 1989; 313: 53
  • Ames J. R., Ryan M. D., Klayman D. L., Kovacic P. Charge transfer and oxy radicals in antimalarial action. Quinones, dapsone metabolites, metal complexes, iminium ions and peroxides. Journal of Free Radicals in Biolology and Medicine 1985; 1: 353
  • Vennerstrom J. L. Oxidants, oxidant drugs, and malaria. Journal of Medicinal Chemistry 1988; 31: 1269
  • Scheiner S., Hillenbrand E. A. Modification of pK values caused by change in H-bond geometry. Proceedings of National Academy of Science USA 1985; 82: 2741
  • Kovacic P., Popp W. J., Ames J. R., Ryan M. D. Anti-cancer action of metal complexes: electron transfer and oxidative stress?. Anti-Cancer Drug Design 1988; 3: 205–216, and references therein.
  • Gaisser H.-D., de Vries J., van der Goot H., Timmerman H. Inhibition of NADH oxidase and lactate dehydrogenase of Mycoplasma gallisepticumby copper complexes of 2, 2′-bipyridyl analogues. Biochemical Pharmacology 1987; 36: 3237
  • Floridi A., Castiglione S., Bianchi C. Sites of inhibition of mitochondrial electron transport by rhein. Biochemical Pharmacology 1989; 38: 743
  • Kawashima T., Yoshida K., Tohda Y., Ariga M., Mori Y., Sakata Y., Misumi S. The chemistry of constrained heteroaromatics. I. The synthesis and properties of a methylviologen analog. Tetrahedron Letters 1984; 25: 1585
  • Anderson R. F., Partel K. B. Radical cations of some low-potential viologen compounds-reduction potentials and electron transfer reactions. Journal of the Chemical Society, Faraday Transactions, I 1984; 80: 2693
  • Sandy M. S., Moldeus P., Ross D., Smith M. T. Cycling and lipid-peroxidation in bipyridyl herbicide cytotoxicity studies with a compromised isolated hepatocyte model system. Biochemical Pharmacology 1986; 35: 3095
  • Fridovich I. Biology of oxygen radicals. Science 1978; 201: 875
  • Kovacic P., Ames J. R., Taylor E. C., Ryan M. D. Electrochemistry of the anticancer agents methotrexate and α-diflurormethylornithine in iminium form. Journal of Pharmaceutical Science 1988; 77: 999
  • Frank D. M., Arora P. K., Blumer J. L., Sayre L. M. Model study on the bioreduction of paraquat, MPP, and analogs. Evidence against a “Redox Cycling” mechanism in MPTP neurotoxicity. Biochemical and Biophysical Research Communications 1987; 147: 1095–1104

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