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Pharmaceutical Chemistry Journal

, Volume 17, Issue 4, pp 252–260 | Cite as

Ubiquinones: Prospects for use in medicine (review)

  • L. M. Kogan
  • E. A. Obol'nikova
  • G. I. Samokhvalov
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Keywords

Organic Chemistry Ubiquinone 
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.

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Literature cited

  1. 1.
    “Nomenclature of quinones with isoprenoid side chains,” Eur. J. Biochem.,53, 15–18 (1975).Google Scholar
  2. 2.
    R. A. Morton, Biol. Rev.,46, 47–49 (1971); T. Ramasarma, J. Scient. Indust. Res.,27, No. 4, 147–164 (1968).Google Scholar
  3. 3.
    R. A. Morton, Nature,182, 1764–1767 (1958).Google Scholar
  4. 4.
    B. O. Linn, A. C. Page. E. L. Worg, et al., J. Am. Chem. Soc.,81, 4007–4010 (1959).Google Scholar
  5. 5.
    J. Jayaraman and T. Ramasarma, J. Sci. Indust. Res.,20C, No. 3, 69–77 (1961).Google Scholar
  6. 6.
    CIBA Foundation Symposium on Quinones in Electron Transport, Boston (1961).Google Scholar
  7. 7.
    P. Mitchell, Chemiosmotic Coupling in Oxidative and Photosynthetic Phosphorylation, Bodmin (1966); P. Mitchell, J. Theoret. Biol.,62, 327–367 (1976).Google Scholar
  8. 8.
    A. Kroger and M. Klingenberg, Eur. J. Biochem.,34, 358–368 (1973); A. Kroger and M. Klingenberg, ibid., 313–323.Google Scholar
  9. 9.
    M. Gutman and N. Silman, FEBS Lett.,26, 207–210 (1972).Google Scholar
  10. 10.
    M. Gutman, in: Bioenergetics of Membranes, Amsterdam (1977), p. 165.Google Scholar
  11. 11.
    B. L. Trumpower, J. Bioenerg. Biochem.,13, 1–24 (1981).Google Scholar
  12. 12.
    M. Gutman, Biochim. Biophys. Acta,594, 53–84 (1980).Google Scholar
  13. 13.
    J. Scholler, T. M. Farley, and K. Folkers, Int. Z. Vitaminforsch,38, 362–368 (1968); J. B. Boler, T. M. Farley, J. Scholler, et al., ibid.,39, 281–288 (1969). M. Larsen, J. R. Coush, F. Enzmann, et al., ibid., 447–456; R. Nakamura, D. Jones, J. Sholler, et al., Biochem. Biophys. Res. Commun.,47, 1451–1457 (1972).Google Scholar
  14. 14.
    J. S. Dinning, C. D. Fitch, C. H. Shunk, et al., J. Am. Chem. Soc.,84, 2007–2008 (1962).Google Scholar
  15. 15.
    T. Isiyama, Bitamii,52, 511–517 (1978).Google Scholar
  16. 16.
    K. Folkers and Y. Yamamura, eds., Biomedical and Clinical Aspects of Coenzyme Q, Amsterdam (1977).Google Scholar
  17. 17.
    K. Folkers and Y. Yamamura, eds., Biomedical and Clinical Aspects of Coenzyme Q, in: Biomedical and Clinical Aspects of Coenzyme Q, Amsterdan (1977), pp. 299–313.Google Scholar
  18. 18.
    K. Folkers, T. Watanabe, V. Pinphanichakarn, et al., in: Biomedical and Clinical Aspects of Coenzyme Q (K. Folkers and Y. Yamamura, eds.), Amsterdam (1977).Google Scholar
  19. 19.
    T. Kishi, T. Watanabe, and K. Folkers, Proc. Natl. Acad. Sci. USA,73, 4653–4656 (1976).Google Scholar
  20. 20.
    T. Kishi, K. Makino, T. Okamoto, et al., J. Pharm. Dyn.,3, No. 7, S11, S23 (1980).Google Scholar
  21. 21.
    L. Block, A. Georgopulos, P. Mayer, et al., J. Exp. Med.,148, 1228-l240 (1978).Google Scholar
  22. 22.
    A. C. Casey and E. G. Bliznakov, Chem. Biol. Interact.,5, 1–12 (1972).Google Scholar
  23. 23.
    M. Kobayashi, Y. Shimomura, M. Tanaka, et al., Chem. Abstr.92, No. 1626w (1980).Google Scholar
  24. 24.
    G. Lenaz, P. Pasquai, E. Bertoli, et al., Arch. Biochem. Biophys.,169, 217–226 (1975).Google Scholar
  25. 25.
    G. Lenaz, E. Bertoli, G. Parenti-Castelli, et al., Boll. Soc. Ital. Biol. Sper.,55, 1033–1038 (1979); M. D. Espositii, E. Bertoli, G. Parenti-Castelli, et al., J. Bioenerg. Biomemed.,13, 37–50 (1981).Google Scholar
  26. 26.
    G. Parenti-Castelli, E. M. Degli, E. Bertoli, et al., Boll. Soc. Ital. Biol. Sper.,55, 1988–1992 (1979); L. Landi, P. Pasquali, L. Cabrini, et al., ibid., 2142–2148.Google Scholar
  27. 27.
    E. M. Degli and G. Lenaz, Boll. Soc. Ital. Biol. Sper.,55, 1607–1611 (1979).Google Scholar
  28. 28.
    E. M. Degli, E. Bertoli, and G. Lenaz, Boll. Soc. Ital. Biol. Sper.,55, 1612–1617 (1979).Google Scholar
  29. 29.
    K. Folkers, H. W. Moore, G. Lenaz, et al., Biochem. Biophys. Res. Commun.,23, 386–391 (1966); G. D. Daves, K. Folkers, Lenaz, et al., Int. Z. Vitaminforsch,38, 65–70 (1968).Google Scholar
  30. 30.
    G. P. Littaru, L. Ho, and K. Folkers, Int. J. Vitam. Nutr. Res.,42, 291–305 (1972).Google Scholar
  31. 31.
    G. P. Littaru, L. Ho, and K. Folkers, Int. J. Vitam. Nutr. Res.,42, 413–434 (1972).Google Scholar
  32. 32.
    K. Folkers, T. Watanabe, and M. Kaji, J. Molec. Med.,2, 431–460 (1977).Google Scholar
  33. 33.
    T. Ishiyama, Y. Morita, S. Toyama, et al., Jpn. Heart. J.,17, 32–42 (1976).Google Scholar
  34. 34.
    E. Takeuchi, Y. Ioymasa, and H. Tsuchioka, et al., in: Biomedical and Clinical Aspects of Coenzyme Q, Amsterdam (1980), pp. 95–108.Google Scholar
  35. 35.
    T. Ozawa and S. Sugiyama, ibid., pp. 349–364.Google Scholar
  36. 36.
    T. Nakamura, H. Samma, M. Himeno, et al., ibid., pp. 3–14.Google Scholar
  37. 37.
    S. Shinozawa, Y. Araki, and T. Oda, Acta Med. Okayama,34, 255–261 (1980). Cited in Chem. Abstr.93, N198496c (1980).Google Scholar
  38. 38.
    W. G. Nayler, in: Biomedical and Clinical Aspects of Coenzyme Q, Amsterdam (1980), pp. 409–425.Google Scholar
  39. 39.
    T. Abe, F. Okamoto, M. Chiba, et al., ibid., pp. 77–93.Google Scholar
  40. 40.
    H. Ohara, H. Kanaide, R. Yoshimura, et al., J. Molec. Cell. Cardiol.,13, 65–74 (1981).Google Scholar
  41. 41.
    H. Matsunaga, H. Matzumoto, T. Yoshitaka, et al., in: Biomedical and Clinical Aspects of Coenzyme Q, Amsterdam (1980), pp. 67–76.Google Scholar
  42. 42.
    T. Yamagami, Y. Uwamoto, K. Folkers, et al., Int. J. Vitam. Nutr. Res.,44, 404–414 (1972).Google Scholar
  43. 43.
    Y. Iwamoto, T. Yamagami, K. Folkers, et al., Biochem. Biophys. Res. Commun.,58, 743–748 (1974).Google Scholar
  44. 44.
    T. Igarashi, Y. Tanabe, Y. Nakajima, et al., Folia Pharmacol. Jpn.,68, 460–472 (1972).Google Scholar
  45. 45.
    T. Nomura, H. Hayashi, K. Hirabayashi, et al., Oyo Yakuri,19, 701–707 (1980). Cited in Chem. Abstr.93, N230934g (1980).Google Scholar
  46. 46.
    T. Igarashi, Y. Nakojima, M. Tanaka et al., J. Pharmacol. Exp. Ther.,189, 149–156 (1974).Google Scholar
  47. 47.
    K. Folkers, J. Drzeworski, P. S. Richardson, et al., Res. Commun. Chem. Pathol. Pharmacol.,31, 129–140 (1981).Google Scholar
  48. 48.
    H. Tajima, Japanese Patent No. 77-99222; Chem. Abstr.88, N27812v (1978).Google Scholar
  49. 49.
    Japanese Patent No. 52-130922 (1977); RZh Khim. 130259p (1979).Google Scholar
  50. 50.
    S. K. Carter, J. Natl. Cancer Inst.,55, 1265–1274 (1975).Google Scholar
  51. 51.
    E. A. Lefrak, J. Pitha, S. Rosenheim, et al., Cancer (Philadelphia),32, 302–314 (1973); E. P. Cortes, G. Lutman, J. Wanka, et al., Cancer Chemotherap. Rep.,6, 215–226 (1975); A. C. Gilladoga, C. Manuel, C. T. T. Tan, et al., Cancer (Philadelphia),37, 1070–1078 (1976).Google Scholar
  52. 52.
    Y. Iwamoto, I. L. Hansen, T. H. Porter, et al., Biochem Biophys. Res. Commun.,58, 633–638 (1974). C. Bertassoli, L. Ballerini, T. Watanabe, et al., Res. Commun. Chem. Pathol. Pharmcol.,15, 797 (1976).Google Scholar
  53. 53.
    M. Gonsalvez, M. Blanko, J. Hunter, et al., Eur. J. Cancer,10, 567–578 (1974).Google Scholar
  54. 54.
    N. Yamanaka, T. Kato, K. Nishida, et al., Cancer Chemother. Pharmacol.,3, 223–227 (1979).Google Scholar
  55. 55.
    K. Takahashi, N. Takeda, T. Okubo, et al., in: Biomedical and Clinical Aspects of Coenzyma Q, Amsterdam (1980), pp. 205–212.Google Scholar
  56. 56.
    I. B. Afanas'ev, N. I. Polozova, and G. I. Samokhvalov, Bioorg. Chem.,9, 434–439 (1980).Google Scholar
  57. 57.
    I. Kishi and K. Folkers, Cancer Treat. Rep.,60, 223–224 (1976).Google Scholar
  58. 58.
    I. Folkers, M. Lie, T. Watanaba, et al., Biochem. Biophys. Res. Commun.,77, 1536–1542 (1977).Google Scholar
  59. 59.
    M. Ghione and C. Bertazzoli, in: Biomedical and Clinical Aspects of Cosenzyme Q (K. Folkers and Y. Yamamura, eds.), Amsterdam (1977), pp. 183–199.Google Scholar
  60. 60.
    R. Ogura, H. Toyama, T. Shimada, et al., J. Appl. Biochem.,1, 325–335 (1979); Kurume Igakki Zasshi,42, 603–625 (1979). Cited in Chem. Abstr.92, N174345f (1980); J. Shaeffer, A. M. El-Mahdi, and R. K. Nichols, Res. Commun. Chem. Pathol. Pharmacol.,29, 309–315 (1980); H. Ohara, H. Kamaide, and M. Nakamura, J. Molec. Cell. Cardiol.,13, 741–752(1981); N. Domae, H. Sawada, E. Matsuyama, et al., Cancer Treat. Rep.,65, 79–91 (1981).Google Scholar
  61. 61.
    K. Folkers, J. Choe, and A. B. Combs, Proc. Natl. Acad. Sci. USA,75, 5178–5180 (1978); J. Y. Choe, A. B. Combs, and K. Folkera, Res. Commun. Chem. Pathol. Pharmacol.,23, 199–202 (1979).Google Scholar
  62. 62.
    Y. Shimichi, F. Kitade, K. Okada, at al., Chemotherapy (Tokyo),27, 675–680 (1979).Google Scholar
  63. 63.
    K. Okada, S. Yamada, Y. Kawashima, et al., Cancer Res.,40, 1663–1667 (1980).Google Scholar
  64. 64.
    T. Murase, K. Obato, and T. Ozawa, Ganto Kagaku Ryoho,5, 395–400 (1978). Cited in Chem. Abstr.,90, No. N16157a (1979).Google Scholar
  65. 65.
    E. P. Cortes, M. Gupta, G. Chou, et al., in: Biomedical and Clinical Aspects of Coenzyme Q (K. Folkere and Y. Yamamura, eds.), Amsterdam (1977), pp. 267–278.Google Scholar
  66. 66.
    T. Kishii, K. Fujii, S. Motoyama, et al., J. Molec. Med.,3, 185–193 (1978).Google Scholar
  67. 67.
    H. Tokugawa, H. Ohira, I. Tanaka, et al., in: Biomedical and Clinical Aspects of Coenzime Q, Amsterdam (1980), pp. 109–122.Google Scholar
  68. 68.
    P. J. Quinn, H. Baum, E. J. Harris, et al., ibid., pp. 435–436.Google Scholar
  69. 69.
    A. F. Wagner, R. J. Stopkie, and K. Folkers, Arch. Biochem. Biophys.,107, 184–186 (1964).Google Scholar
  70. 70.
    T. M. Farley, J. Scholloer, and K. Folkers, Biochem. Biophys. Res. Commun.,24, 299–303 (1966).Google Scholar
  71. 71.
    J. L. G. Nilsson, T. M. Farley, J. Scholler, et al., Arch. Biochem. Biophys.,123, 422–426 (1968).Google Scholar
  72. 72.
    M. H. Godinez, E. L. Trumpower, P. C. Carpenter, et al., ibid.,140, 39–46 (1970).Google Scholar
  73. 73.
    N. K. Monakhov, E. A. Obol'nikova, L. G. Igdal, et al., Vopr. Med, Khim., No. 3, 276–284 (1974).Google Scholar
  74. 74.
    K. Folkers, G. Littaru, L. Ho, et al., Int. J. Vitam. Nutr. Res.,40, 380–390 (1970).Google Scholar
  75. 75.
    G. Lenaz, C. D. Daves, and K. Folkers, Arch, Biochem. Biophys.,123, 539–550 (1968).Google Scholar
  76. 76.
    F. S. Skelton and K. Folkers, Int. J. Vitam. Nutr. Res.,40, 153–158 (1970).Google Scholar
  77. 77.
    K. Folkers, G. P. Littaru, R. Nakamura, et al., ibid.,42, 139–163 (1972).Google Scholar
  78. 78.
    G. P. Littaru, D. Jones, and J. Scholler, et al., ibid. 127–138.Google Scholar
  79. 79.
    J. K. Smith, H. W. Moore, and K. Folkers, Proc. Soc. Exp. Biol. Med. (N.Y.),118, 782–786 (1965).Google Scholar
  80. 80.
    T. M. Farley, G. D. Daves, J. Scholler, et al., Int. J. Vitam. Nutr. Res.,38, 355–361 (1968).Google Scholar
  81. 81.
    J. Scholler, T. M. Farley, and K. Folkers, Int. Z. Vitaminforsch.,38, 369–375 (1968); J. Scholler, D. Jones, G. P. Littaru, et al., Biochem. Biophys. Res. Commun.,41, 1298–1305 (1970); G. P. Littaru, D. Jones, J. Scholler, et al., ibid., 1306–1313.Google Scholar
  82. 82.
    A. S. Majaj and K. Folkers, Int. J. Vitam. Nutr. Res.,38, 182–195 (1968); O. Sovik, J. H. Strömme, and K. Folkers, Acta Poediat. Scand. (Uppsala),60, 428–432 (1971); K. Folkers, R. Nakamura, G. P. Littaru, et al., Proc. Natl. Acad. Sci. USA,71, 1098–2102 (1974).Google Scholar
  83. 83.
    M. Sugimoto, T. Ideta, K. Imanashi, et al., in: Biomedical and Clinical Aspects of Coenzyme Q (K. Folkers and Y. Yamamura, eds.), Amsterdam (1977), pp. 243–249.Google Scholar
  84. 84.
    T. Miyata, Japanese Patent No. 77-99220 (1977); Chem. Abstr.,88, N27814x (1978).Google Scholar
  85. 85.
    A. Tsunemitsu and T. Matsumura, J. Dent. Res.,46, 1382–1384 (1967).Google Scholar
  86. 86.
    G. P. Littaru, R. Nakamura, H. Lester, et al., Proc. Natl. Acad. Sci. USA,68, 2332–2335 (1971); R. Nakamura, G. P. Littaru, K. Folkers, et al., Int. J. Vitam. Nutr. Res.,43, 84–88 (1973).Google Scholar
  87. 87.
    R. Nakamura, G. P. Littaru, K. Folkers, et al., Proc. Natl. Acad. Sci. USA,71, 1456–1460 (1974).Google Scholar
  88. 88.
    T. Matsumura, A. Tsunemitsu, M. Kani, et al., Shin-yaku to Rinsho (New Drugs and Clinics),17, 935–941 (1968); T. Matsumura, S. Sahi, R. Nakamura, et al., Int. J. Vitam. Nutr. Res.,43, 537–548 (1973); K. Folkers, T. Watanabe, R. M. Arnold, et al., J. Med.,8, 333–348 (1977).Google Scholar
  89. 89.
    E. G. Bliznakov, A. Casey, and E. Premuzie, Experientia,26, 953–954 (1970).Google Scholar
  90. 90.
    E. G. Bliznakov, Proc. Natl. Acad. Sci. USA,70, 390–394 (1973).Google Scholar
  91. 91.
    I. Imada, I. Azuma, S. Kishimoto, et al., Int. Arch. Allergy,43, 898–907 (1972).Google Scholar
  92. 92.
    I. Imada, M. Watanabe, N. Matusumoto, et al., Biochemistry,9, 2870–2878 (1970); K. Sugimura, I. Azuma, Y. Yamamura, et al., Int. J. Vitam. Nutr. Res.,46, 192–203 (1976); K. Sugimura, I. Azuma, Y. Yamamura, et al., ibid, 464–471.Google Scholar
  93. 93.
    M. Watanabe, M. Toyoda, I. Imada, et al., Chem. Pharm. Bull.,22, 176–182 (1974).Google Scholar
  94. 94.
    E. G. Bliznakov, T. Watenabe, S. Saji, et al., J. Med.,9, 337–346 (1978).Google Scholar
  95. 95.
    E. G. Bliznakov, Adv. Exp. Med. Biol.,121A, 361–369 (1980).Google Scholar
  96. 96.
    E. G. Bliznakov, Biomedicine,26, 73–76 (1977).Google Scholar
  97. 97.
    E. G. Bliznakov, in: The Reticuloendothelial System and Immune Phenomena (R. R. Di Luzio, ed.), New York (1971), pp. 315–324.Google Scholar
  98. 98.
    K. Kato, K. Yokota, Y. Tsutsui, et al., German (FRG) Patent No. (1973); Chem. Abstr.,79, N45797n (1973).Google Scholar
  99. 99.
    E. G. Bliznakov and A. D. Adler, Pathol. Microbiol.38, 393–340 (1972).Google Scholar
  100. 100.
    J. Scholler, T. M. Farley, and K. Folkers, Int. J. Vitam. Nutr. Res.,38, 362–368 (1968).Google Scholar
  101. 101.
    K. Yamada, Y. Tatsukawa, M. Takenaka, et al., in: Biomedical and Clinical Aspects of Coenzyme Q, Amsterdam (1980), pp. 123–132. Y. Tatsukawa, Y. Dohi, K. Yamada, et al., Life Sci.,24, 1309–1314 (1979).Google Scholar
  102. 102.
    Y. Kohli, T. Maekawa, and S. Yorioka, et al., Kyoto-furtitsu Ika Doigaku Zasshi,88, 1229–1233 (1979). Cited in Chem. Abstr.,93, N665r (1980); Y. Kohli, Y. Suto, and T. Kodama, Jpn. J. Exp. Med.,51, 105–108 (1981).Google Scholar
  103. 103.
    F. Nagahama, Jpn. Patent No. 77-99221 (1977); Chem. Abstr.,88, N27813w (1978).Google Scholar
  104. 104.
    T. Murase, K. Obata, and T. Ozawa, Japanese Patent No. 79-129132 (1979); Chem. Abstr.,92, N153145a (1980).Google Scholar
  105. 105.
    T. Kamimura, Japanese Patent No. 77-99223 (1977); Chem. Abstr.,88, N27816z (1978).Google Scholar
  106. 106.
    S. Kimura and A. Isobe Japanese Patent No. 79–89036 (1979); Chem. Abstr.,92, N64756h (1980).Google Scholar
  107. 107.
    T. Nemoto, Japanese Patent No. 78-20432 (1978); Chem. Abstr.,89, N48910m (1978).Google Scholar
  108. 108.
    T. Sugano, Japanese Patent No. 77-99219 (1977).Google Scholar
  109. 109.
    T. Morimotsu, T. Hagiwara, M. Ide, et al., Heart Res.,3, 155–166 (1980).Google Scholar
  110. 110.
    E. G. Novoselova, N. I. Perepelkina, I. K. Kolomiitseva, et al., Radiobiologiya,19, No. 4, 572–576 (1979).Google Scholar
  111. 111.
    I. K. Kolomiitseva, E. G. Novoselova, and E. A. Obol'nikova, Dokl. Akad. Nauk SSSR,251, No. 1, 240–242 (1980).Google Scholar
  112. 112.
    Y. Shigeta, K. Izumi, and H. Abe, J. Vitaminol.,12, 293–298 (1966).Google Scholar
  113. 113.
    S. S. M. Katazawa, T. Ozawa, K. Suzuki, et al., Experientia,36, 1002–1003 (1980).Google Scholar
  114. 114.
    B. Chipperfield and J. R. Chipperfield, Clin. Chim. Acta,31, 459–465 (1971).Google Scholar
  115. 115.
    K. Folkers, T. H. Porter, J. R. Bertino, et al., Res. Commun. Chem. Pathol. Pharmacol.,19, 485–490 (1978); T. H. Porter, Ch. S. Tsai, T. Kishi, et al., Acta Pharm. Suec.,15, 97–104 (1978); T. H. Porter, T. Kishi, H. Kishi, et al., Bioorg. Chem.,7, 333–350 (1978); K. Folkers and T. H. Porter, Biochem. Biophys. Res. Commun.,83, 353–356 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • L. M. Kogan
    • 1
  • E. A. Obol'nikova
    • 1
  • G. I. Samokhvalov
    • 1
  1. 1.Vitamin Scientific-Industrial CombineMoscow

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