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Part of the book series: Antibiotics ((1512,volume 5 / 2))

Abstract

At the outbreak of the Second World War, Japanese troops overran the Dutch East Indies, thereby cutting off the Allied Forces from their major source of the antimalarial drug quinine. Faced with entirely inadequate supplies of quinine coupled with the grim prospect of waging tropical warfare in some of the world’s worst malaria-infested regions, the Allied Powers instituted a comprehensive program of research in the chemotherapy of malaria. This program, sponsored and supported by the Committee on Medical Research of the Office of Scientific Research and Development, involved active participation and joint cooperation by academic institutions, pharmaceutical firms, private individuals, and the United States Army, Navy, and Public Health Service.

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References

  • Ball, E.G., Anfinsen, C.B., Cooper, O.: The inhibitory action of naphthoquinones on respiratory processes. J. Biol. Chem. 168, 257–270 (1947)

    PubMed  CAS  Google Scholar 

  • Berberian, D.A., Slighter, R.G., Jr.: The schizonticidal activity of hydroxynaphthoquinones against Plasmodium berghei infections in mice. J. Parasitol. 54, 999–1005 (1968)

    Article  PubMed  CAS  Google Scholar 

  • Bishop, D.H.L., Pandya, K.P., King, H.K.: Ubiquinone and vitamin K in bacteria. Biochem. J. 83, 606–614 (1962)

    PubMed  CAS  Google Scholar 

  • Brodie, A.F.: Vitamin K and other quinones as coenzymes in oxidative phosphorylation in bacterial systems. Fed. Proc. 20, 995–1004 (1961)

    PubMed  CAS  Google Scholar 

  • Brodie, A.F., Ballantine, J.: Oxidative phosphorylation in fractionated bacterial systems. III. Specificity of vitamin K reactivation. J. Biol. Chem. 235, 232–237 (1960)

    PubMed  CAS  Google Scholar 

  • Brodie, A.F., Weber, M.M., Gray, C.T.: The role of vitamin K1 in coupled oxidative phosphorylation. Biochim. Biophys. Acta 25, 448–449 (1957)

    Article  PubMed  CAS  Google Scholar 

  • Chmielewska, I.: Oxidative and photosynthetic phosphorylation involving 2-methylquinones. Biochim. Biophys. Acta 39, 170–171 (1960)

    Article  PubMed  CAS  Google Scholar 

  • Crane, F.L.: Quinones in electron transport. I. Coenzymatic activity of plastoquinones, Coenzyme Q and related natural quinones. Arch. Biochem. Biophys. 87, 198–202 (1960)

    Article  PubMed  CAS  Google Scholar 

  • Crane, F.L., Hatefi, Y., Lester, R.L., Widmer, C.: Isolation of a quinone from beef heart mitochondria. Biochim. Biophys. Acta 25, 220–221 (1957)

    Article  PubMed  CAS  Google Scholar 

  • Crane, F.L., Widmer, C., Lester, R.L., Hatefi, Y.: Studies on the electron transport system. XV. Coenzyme Q (Q275) and the succinoxidase activity of the electron transport particle. Biochim. Biophys. Acta 31, 476–489 (1959)

    Article  PubMed  CAS  Google Scholar 

  • Estabrook, R.W.: The spectral and enzymatic characterization of cytochrome c1 of liver mitochondria. J. Biol. Chem. 230, 735–750 (1958)

    PubMed  CAS  Google Scholar 

  • Fieser, L.F., Berliner, E., Bondrus, F.J., Chang, F.C., Dauben, W.G., Ettlinger, M.G., Fawaz, G., Fields, M., Fieser, M., Heidelberger, C., Heymann, H., Seligman, A.M., Vaughan, W.R., Wilson, A.G., Wilson, E., Wu, M., Leffler, M.T., Hamlin, K.E., Hathaway, R.J., Matson, E.J., Moore, E.E., Moore, M.B., Rapala, R.T., Zaugg, H.E.: Naphthoquinone antimalarials. I. General survey. J. Am. Chem. Soc. 70, 3151–3155 (1948)

    Article  PubMed  CAS  Google Scholar 

  • Gutnick, D.L., Brodie, A.F.: Phosphate-dependent incorporation of tritium into a naphthoquinone during oxidative phosphorylation. J. Biol. Chem. 240, PC 3698–3699 (1965)

    PubMed  CAS  Google Scholar 

  • Hatefi, Y., Haavik, A.G., Jurtshuk, P.: Studies on the electron transport system. XXX. DPNH-cytochrome c reductase I. Biochim. Biophys. Acta 52, 106–118 (1961)

    Article  PubMed  CAS  Google Scholar 

  • Hendlin, D., Cook, T.M.: The reversible inhibition of succinoxidase by naphthoquinones. Biochem. Biophys. Res. Commun. 2, 71–75 (1960)

    Article  PubMed  CAS  Google Scholar 

  • Heymann, H., Fieser, L.F.: Naphthoquinone antimalarials. J. Biol. Chem. 176, 1359–1362 (1948)

    PubMed  CAS  Google Scholar 

  • Howland, J.L.: The reversibility of inhibition by 2-heptyl-4-hydroxyquinoline-N-oxide and 2-hydroxy-3-(3-methylbutyl)-l,4-naphthoquinone of succinate oxidation. Biochim. Biophys. Acta 73, 665–667 (1963 a)

    Article  PubMed  CAS  Google Scholar 

  • Howland, J.L.: Uncoupling and inhibition of oxidative phosphorylation by 2-hydroxy-3-alkyl-1,4-naphthoquinones. Biochim. Biophys. Acta 77, 659–662 (1963 b)

    Article  CAS  Google Scholar 

  • HĂĽlsmann, W.C.: Over het mechanisme van de ademhalingsketenphosphorylering. M.D. Thesis, Klein Offset Drukkerij, Amsterdam (1958)

    Google Scholar 

  • Jacobsen, B.K., Dam, H.: Vitamin K in bacteria. Biochim. Biophys. Acta 40, 211–216 (1960)

    Article  PubMed  CAS  Google Scholar 

  • Leahy, G.J., Currie, D.J., Holmes, H.L., Maltman, J.R.: Growth-inhibitory activities of some 1,4-naphthoquinones and related compounds on Staphylococcus aureus and Escherichia coli. Can. J. Microbiol. 14, 661–666 (1968)

    Article  PubMed  CAS  Google Scholar 

  • Lester, R.L., Crane, F.L.: The natural occurrence of Coenzyme Q and related compounds. J. Biol. Chem. 234, 2169–2175 (1959)

    PubMed  CAS  Google Scholar 

  • Olenick, J.G., Hahn, F.E.: Bactericidal action of a 2-hydroxy-3-alkyl-1,4-naphthoquinone: Blockade of metabolite permeation across the membrane. Ann. N.Y. Acad. Sci. 235, 542–552 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Olenick, J.G., Cook, T.M., Hahn, F.E.: Bactericidal action of 2-hydroxy-3-(cyclohexylpropyl)-1,4 naphthoquinone on Bacillus megaterium. J. Bacteriol 107, 528–534 (1971)

    PubMed  CAS  Google Scholar 

  • Reif, A.E., Potter, V.R.: Studies on succinoxidase inhibition I. Pseudoirreversible inhibition by a naphthoquinone and by antimycin A. J. Biol. Chem. 205, 279–290 (1953)

    PubMed  CAS  Google Scholar 

  • Takemori, S., King, T.E.: Reconstitution of respiratory chain enzyme systems. XIII. Sequential fragmentation of succinate oxidase: preparation and properties of succinate-cytochrome c reductase and the cytochrome b-c1 particle. J. Biol. Chem. 239, 3546–3558 (1964)

    PubMed  CAS  Google Scholar 

  • Tappel, A.L.: Inhibition of electron transport by antimycin A, alkyl hydroxynaphthoquinones and metal coordination compounds. Biochem. Pharmacol. 3, 289–296 (1960)

    Article  PubMed  CAS  Google Scholar 

  • Vilkas, M., Lederer, E.: Sur un mecanisme possible de la phosphorylation oxydative. Experientia 18, 546–549 (1962)

    Article  PubMed  CAS  Google Scholar 

  • Wendel, W.B.: The influence of naphthoquinones upon the respiratory and carbohydrate metabolism of malarial parasites. Fed. Proc. 5, 406–407 (1946)

    PubMed  CAS  Google Scholar 

  • Widmer, C., Clark, H.W., Neufeld, H.A., Stotz, E.: Cytochrome components of the soluble SC factor preparation. J. Biol. Chem. 210, 861–867 (1954)

    PubMed  CAS  Google Scholar 

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© 1979 Springer-Verlag Berlin · Heidelberg

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Olenick, J.G. (1979). 2-Hydroxy-3-Alkyl-1,4-Naphthoquinones. In: Hahn, F.E. (eds) Mechanism of Action of Antieukaryotic and Antiviral Compounds. Antibiotics, vol 5 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46407-2_9

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  • DOI: https://doi.org/10.1007/978-3-642-46407-2_9

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46409-6

  • Online ISBN: 978-3-642-46407-2

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