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New 4-Hydroxypyridine and 4-Hydroxyquinoline Derivatives as Inhibitors of NADH-Ubiquinone Oxidoreductase in the Respiratory Chain II

  • Kun Hoe Chung
  • Kwang Yun Cho
  • Yasuko Asami
  • Nobutaka Takahashi
  • Shigeo Yoshida

Summary

For elucidation of structural requisites of piericidin-like compounds for inhibitors to NADH-UQ oxidoreductase biomimetic derivatives of 4-hydroxypyridine and 4-hydroxyquinoline were systematically designed, synthesized and examined with mitochondria and submitochondria. The modification of arylalkyl sidechains were revealed to show high inhibitory activity of compounds. Also, sidechains of alkoxy-ω-phenylalkyl and alkyl-ω-phenylalkyl groups were regarded as good templates for examination of inhibitors to NADH-ubiquinone oxidoreductase. Among synthetic compounds 6-phenylhexyl derivatives of hydroxypyridine and hydroxyquinoline showed highest inhibitory activity as much as ubicidins. The modification of hydrophilic part did not increase the activity well, but combination of methoxy, ethoxy and propoxy groups maintained their activity like dimethoxy compound. Especially inhibition activity of 6-substituted hydroxyquinolines was diminished dramatically.

Keywords

Quinoline Derivative High Inhibitory Activity Hydrophilic Part Respiratory Electron Transport Lipophilic Part 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

RET

respiratory electron transport

ETP

electron transport particles

NADH-UQ oxidoreductase

NADH-ubiquinone oxidoreductase

Tris

Tris(hydroxymethyl)amino-methane

EDTA

ethylenediaminetetraacetic acid

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Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Kun Hoe Chung
    • 1
  • Kwang Yun Cho
    • 1
  • Yasuko Asami
    • 2
  • Nobutaka Takahashi
    • 2
  • Shigeo Yoshida
    • 3
  1. 1.Korea Research Institute of Chemical TechnologyDaedeog Danji, TaejonKorea
  2. 2.Department of Agricultural ChemistryThe University of TokyoBunkyo-ku, Tokyo 113Japan
  3. 3.Chemical Regulation of Biomechanisms Lab.The Institute of Chemical and Physical Research (RIKEN)Wako-shi, SaitamaJapan

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