Chemistry of Natural Compounds

, Volume 18, Issue 4, pp 375–388 | Cite as

Supercytostatics and supercytotoxins

  • A. A. Semenov
Article
  • 30 Downloads

Abstract

Natural compounds are considered which in concentrations of 5·10−8 M inhibit the proliferation of culturable malignant mammalian cells. It is proposed to call them supercytostatics and supercytotoxins. Their cytotoxic activities are based on various biochemical mechanisms. Among the supercytostatics there are mitotic poisons, inhibitors of protein and nucleic acid synthesis, and membrane and cytoplasmic enzymes. However, in many cases there are grounds for assuming that the critical cell targets do not coincide with the observed biochemical effects of the supercytostatics. In spite of their diverse chemical structures, the majority of substances contain similar structural fragments which may be complementary to unknown receptors participating in the regulation of cell proliferation.

Keywords

Colchicine Taxol Triptolide Dicarbonyl Cucurbitacin 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    H. Stahelin, Planta Med.,22, 336 (1972).PubMedGoogle Scholar
  2. 2.
    W. J. Gensler, C. D. Murthy, and M. H. Trammell, J. Med. Chem.,20, 635 (1977).PubMedGoogle Scholar
  3. 3.
    H. C. Wulf and G. Wettenmark, Arch. Dermatol. Res.,260, 87 (1977).PubMedGoogle Scholar
  4. 4.
    D. K. White and F. D. Greene, J. Am. Chem. Soc.,100, 6757 (1978).Google Scholar
  5. 5.
    S. M. Kupchan, Y. Komoda, A. R. Branfman, R. G. Dailey, and V. A. Zimmerly, J. Am. Chem. Soc.,96, 3706 (1974).Google Scholar
  6. 6.
    M. C. Wani, H. L. Taylor, and M. E. Wall, Chem. Commun., 390 (1973).Google Scholar
  7. 7.
    D. Werner, K. H. Dönges, Planta Med.,22, 306 (1972).PubMedGoogle Scholar
  8. 8.
    K. De Kalyan, G. T. Shiau, and R. E. Harmon, J. Prakt. Chem.,318, 523 (1976).Google Scholar
  9. 9.
    M. Bobek, R. L. Whistler, and A. Bloch, J. Med. Chem.,15, 168 (1972).PubMedGoogle Scholar
  10. 10.
    H. Stahelin, Eur. J. Cancer,6, 303 (1970).PubMedGoogle Scholar
  11. 11.
    J. J. Hoffmann, D. J. Lutzbetak, S. J. Torrance, and J. R. Cole, Phytochemistry,17, 1448 (1978).Google Scholar
  12. 12.
    A. W. Wood, R. L. Chang, W. Levin, and R. E. Lehr, Proc. Natl. Acad. Sci., USA,74, 2746 (1977).PubMedPubMedCentralGoogle Scholar
  13. 13.
    S. P. Gunasekera, G. A. Cordell, and N. R. Farnsworth, Phytochem.,19, 1213 (1980).Google Scholar
  14. 14.
    M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, and A. T. McPhail, J. Am. Chem. Soc.,93, 2325 (1971).PubMedGoogle Scholar
  15. 15.
    S. M. Kupchan and R. L. Baxter, Science,187, 652 (1975).PubMedGoogle Scholar
  16. 16.
    J. Nyborg and T. Lacour, Nature (London),257, 824 (1975).PubMedGoogle Scholar
  17. 17.
    S. M. Kupchan, J. G. Sweeny, R. L. Baxter, T. Murae, V. A. Zimmerly, and R. R. Sickles, J. Am. Chem. Soc.,97, 672 (1975).PubMedGoogle Scholar
  18. 18.
    S. M. Kupchan, Y. Shizuri, W. C. Samner, H. R. Haynes, A. P. Leighton, and B. R. Sickles, J. Org. Chem.,41, 3850 (1976).PubMedGoogle Scholar
  19. 19.
    S. M. Kupchan, Y. Shizuri, T. Murae, J. G. Sweeny, H. R. Haynes, M. S. Shen, J. C. Barrick, and R. F. Bryan, J. Am. Chem. Soc.,98, 5719 (1976).PubMedGoogle Scholar
  20. 20.
    S. M. Kupchan, R. W. Britton, J. A. Lacadie, M. F. Ziegler, and K. W. Sigel, J. Org. Chem.,40, 648 (1975).PubMedGoogle Scholar
  21. 21.
    S. M. Kupchan, D. R. Streelman, J. Org. Chem.,41, 3481 (1976).PubMedGoogle Scholar
  22. 22.
    S. M. Kupchan and J. A. Lacadie, J. Org. Chem.,40, 654 (1975).PubMedGoogle Scholar
  23. 23.
    S. M. Kupchan, W. A. Court, R. G. Dailey, C. J. Dilmore, and R. F. Bryan, J. Am. Chem. Soc.,94, 7194 (1972).PubMedGoogle Scholar
  24. 24.
    J. W. Loder and R. H. Nearn, Tetrahedron Lett., 2497 (1975).Google Scholar
  25. 25.
    S. M. Kupchan, D. R. Streelman, B. B. Jarvis, R. G. Dailey, and A. T. Sneder, J. Org. Chem.,42, 4221 (1977).PubMedGoogle Scholar
  26. 26.
    H. Minato, T. Katayama, and K. Tori, Tetrahedron Lett., 2579 (1975).Google Scholar
  27. 27.
    J. Konopa, A. Matuszkiewicz, M. Hrabowska, and K. Onoszka, Arzneim-Forsch.,91, 1741 (1974).Google Scholar
  28. 28.
    J. Polonsky, Z. Varon, B. Arnoux, and C. Packard, J. Am. Chem. Soc.,100, 7731 (1978).Google Scholar
  29. 29.
    S. M. Kupchan, R. J. Hemingway, and J. C. Hemingway, J. Org. Chem.,34, 3894 (1969).PubMedGoogle Scholar
  30. 30.
    S. M. Kupchan and I. Ognyanov, Tetrahedron Lett., 1709 (1969).Google Scholar
  31. 31.
    S. M. Kupchan, J. L. Moniot, C. W. Sigel, and R. J. Hemingway, J. Org. Chem.,36, 2611 (1971).PubMedGoogle Scholar
  32. 32.
    S. M. Kupchan, J. R. Knox, J. E. Kelsey, and J. A. S. Renauld, Science146, 1685 (1964).PubMedGoogle Scholar
  33. 33.
    A. Closse and R. Huguenin, Helv. Chim. Acta,57, 533 (1974).PubMedGoogle Scholar
  34. 34.
    S. D. Jolad, J. J. Hoffman, S. J. Torrance, R. M. Wiedhopf, J. R. Cole, S. K. Arora, R. B. Bates, R. L. Gargiulo, and G. R. Kriek, J. Am. Chem. Soc.,99, 8040 (1977).Google Scholar
  35. 35.
    J. Meinhofer, H. Maeda, C. B. Glaser, J. Czombos, and K. Kuromitsu, Science,178, 875 (1972).Google Scholar
  36. 36.
    L. S. Kappen, M. A. Napier, and I. H. Goldberg, Proc. Natl. Acad. Sci. USA,77, 1970 (1980).PubMedPubMedCentralGoogle Scholar
  37. 37.
    J. Elting and R. Montgomery, Biochem. Biophys. Res. Commun.,71, 871 (1976).PubMedGoogle Scholar
  38. 38.
    K. Hora, M. Ishiguro, G. Fumatsu, and M. Fumatsu, Agr. Biol. Chem.,39, 1639 (1975).Google Scholar
  39. 39.
    S. Nanno, M. Ishiguro, G. Funatsu, and M. Funatsu, Agr. Biol. Chem.,39, 1645 (1975).Google Scholar
  40. 40.
    S. S. Li, C. H. Wei, J. J. Lin, and T. C. Tung, Biochem. Biophys. Res. Commun.,65, 1191 (1975).PubMedGoogle Scholar
  41. 41.
    J. C. Robins, R. Hyman, V. Stalling, and G. L. Nicolson, J. Natl. Cancer Inst.,58, 1027 (1977).Google Scholar
  42. 42.
    Wha Bin Im, Chao-Kuo Chiang, and R. Montgomery, J. Biol. Chem.,253, 3259 (1978).PubMedGoogle Scholar
  43. 43.
    K. Refsnes, T. Haylett, K. Sandvig, and S. Olsnes, Biochem. Biophys. Res. Commun.,79, 1176 (1977).PubMedGoogle Scholar
  44. 44.
    V. I. Gel'fand and V. A. Rozenblat, in: Biological Chemistry, Vol. II (Advances of Science and Technology, VINITI) [in Russian], Moscow (1977), p. 78.Google Scholar
  45. 45.
    G. L. Nicolson, Biochim. Biophys. Acta,457, 57 (1976).PubMedGoogle Scholar
  46. 46.
    V. V. Kiselev, Khim. Prir. Soedin.,3 (1977).Google Scholar
  47. 47.
    L. Wilson, Ann. N. Y. Acad. Sci.,253, 213 (1975).PubMedGoogle Scholar
  48. 48.
    F. Cortese, B. Bhattacharyya, and J. Wolf, Fed. Proc.,35, 483 (1976).Google Scholar
  49. 49.
    J. K. Kelleher, Mol. Pharmacol.,13, 232 (1977).PubMedGoogle Scholar
  50. 50.
    M. H. Zweig and C. F. Chignell, Biochem. Pharmacol.,22, 2141 (1973).PubMedGoogle Scholar
  51. 51.
    L. Wilson, K. M. Kreswell, and D. Chin., Biochem.,14, 5585 (1975).Google Scholar
  52. 52.
    M. K. Wolpert-DeFilippes, R. H. Adamson, R. L. Cysyk, and D. G. Johns, Biochem. Pharmacol.,24, 751 (1975).PubMedGoogle Scholar
  53. 53.
    M. K. Wolpert-DeFilippes, V. H. Bono, R. L. Dion, and D. G. Johns, Biochem. Pharmacol.,24, 1735 (1975).PubMedGoogle Scholar
  54. 54.
    S. Remillard, L. I. Rebhun, G. A. Howie, and S. M. Kupchan, Science,189, 1002 (1975).PubMedGoogle Scholar
  55. 55.
    F. Mandelbaum-Shavit, M. K. Wolpert-DeFilippes, and D. G. Johns, Biochem. Biophys. Res. Commun.,72, 47 (1976).PubMedGoogle Scholar
  56. 56.
    B. Bhattacharyya and J. Wolf, FEBS Lett.,75, 159 (1977).PubMedGoogle Scholar
  57. 57.
    P. B. Schiff, J. Fant, and S. B. Horwitz, Nature (London),277, 665 (1979).PubMedGoogle Scholar
  58. 58.
    P. B. Schiff, and S. B. Horwitz, Proc. Natl. Acad. Sci. USA,77, 1561 (1981).Google Scholar
  59. 59.
    B. F. Issel, A. W. Prestayko, R. L. Comis, and S. T. Crooke, Cancer Treat. Rev.,6, 239 (1979).Google Scholar
  60. 60.
    M. T. Kuo and T. S. A. Sami, Biochim. Biophys. Acta,518, 186 (1978).PubMedGoogle Scholar
  61. 61.
    K. Edo, K. Shigery, F. Kitame, N. Ishida, Y. Koide, G. Kusano, and S. Nozoe, J. Antibiot.,33, 347 (1980).PubMedGoogle Scholar
  62. 62.
    T. H. Sawyer, K. Guetzow, M. O. J. Olson, H. Busch, A. W. Prestayko, and S. T. Crooke, Biochem. Biophys. Res. Commun,86, 1133 (1979).PubMedGoogle Scholar
  63. 63.
    A. G. Schultz, Chem. Rev.,73, 385 (1973).PubMedGoogle Scholar
  64. 64.
    S. A. Eigebaly, I. H. Hall, K.-H. Lee, Y. Sumida, Y. Imakura, R. Y. Wu, J. Pharm. Sci.,68, 887 (1979).PubMedGoogle Scholar
  65. 65.
    E. F. Gale, P. E. Reynolds, E. Cundliffe, H. Richmond, and M. J. Waring, The Molecular Basis of Antibiotic Action, Wiley, London (1972).Google Scholar
  66. 66.
    B. Brdar and E. Reich., Period. Biol.,78, 51 (1976).Google Scholar
  67. 67.
    S. Iapalucci-Espinosa, S. Cereghini, and M. T. Fraze de Fernandez, Biochemistry,16, 3 (1977).Google Scholar
  68. 68.
    J. Konopa, J. Zelinski, A. Matuszkiewicz, M. Hrabowska, in: Advances in Antimicrobial and Antineoplastic Chemotherapy, Vol. 2, Prague, 163 (1972).Google Scholar
  69. 69.
    A. P. Grollman, C. Grunfeld, C. F. Brewer, and D. M. Markus, Cancer Chemother. Rep., Part 1,58, 491 (1974).PubMedGoogle Scholar
  70. 70.
    G. L. Nicolson, M. Lacorbière, and T. R. Hunter, Cancer Res.,35, 144 (1975).PubMedGoogle Scholar
  71. 71.
    K. Onozaki, H. Hayatsu, and T. Ukita, Biochim. Biophys. Acta,407, 99 (1975).PubMedGoogle Scholar
  72. 72.
    A. M. Pappenheimer, Ann. Rev. Biochem.,46, 69 (1977).PubMedGoogle Scholar
  73. 73.
    R. A. Tobey, D. J. Orlicky, L. L. Deaven, L. B. Rall, and R. J. Kissane, Cancer Res.,38, 4415 (1978).PubMedGoogle Scholar
  74. 74.
    L. L. Liao, A. P. Grollman, and S. B. Horwitz, Biochim. Biophys. Acta,454, 273 (1976).PubMedGoogle Scholar
  75. 75.
    C. J. Carter and M. Cannon, Biochem. J.,166, 399 (1977).PubMedPubMedCentralGoogle Scholar
  76. 76.
    L. L. Liao, S. M. Kupchan, and S. B. Horwitz, Mol. Pharmacol.,12, 167 (1976).PubMedGoogle Scholar
  77. 77.
    M. Fresno, A. Gonzales, D. Vazquez, and A. Jimenez, Biochim. Biophys. Acta,518, 104 (1978).PubMedGoogle Scholar
  78. 78.
    K. J. Bucher, Diss. Abstr. Int., B,37, 2816 (1976).Google Scholar
  79. 79.
    S. M. Kupchan, An. Acad. Brazil. Ciênc., Suppl.,42, 25 (1970).Google Scholar
  80. 80.
    N. B. Glick, in: Metabolic Inhibitors, Vol. 3, Academic Press, New York (1972), p. 232.Google Scholar
  81. 81.
    T. Tobin, T. Akera, S. L. Brody, and T. M. Brody, Biochem. Soc. Transact.2, 1375 (1974).Google Scholar
  82. 82.
    E. Fujita and Y. Nagao, Bioorg. Chem.,6, 287 (1977).Google Scholar
  83. 83.
    I. H. Goldberg, Cancer Chemother. Rep., Part 1,58, 479 (1974).PubMedGoogle Scholar
  84. 84.
    G. R. Donaldson, M. R. Atkinson, and A. W. Murray, Biochem. Biophys. Res. Commun.,31, 104 (1968).PubMedGoogle Scholar
  85. 85.
    I. H. Hall, J. Pharm. Sci.,67, 1232 (1978).PubMedGoogle Scholar
  86. 86.
    I. H. Hall, K. H. Lee, S. A. Eigebaly, J. Pharm. Sci.,67, 552 (1978).PubMedGoogle Scholar
  87. 87.
    T. S. A. Sami, and H. Lazarus, Peptides Proceedings of the Fifth American Peptide Symposium (1977), p. 221; Chem. Abstr.,89, 170 (1978).Google Scholar
  88. 88.
    M. Satake, T. Ebina, N. Ishida, Gann,70, 545 (1979).PubMedGoogle Scholar
  89. 89.
    G. L. Nicolson, Biochim. Biophys. Acta,458, 1 (1977).Google Scholar
  90. 90.
    N. P. Korolev, Usp. Sov. Biol.,86, 463 (1978).Google Scholar
  91. 91.
    A. Mittinen and I. Virtanen, Protides of Biological Fluids. Proceedings of the 26th Colloquium, 1978, Pergamon, Oxford (1979), p. 511.Google Scholar
  92. 92.
    B. R. Brinkley and G. M. Fuller, Texas Rep. Biol. Med.,36, 26 (1978).Google Scholar
  93. 93.
    G. Parry and S. N. Hawkes, Proc. Natl. Acad. Sci. USA,75, 3703 (1978).PubMedPubMedCentralGoogle Scholar
  94. 94.
    B. M. Spigelman, M. A. Lopata, and M. W. Kirschner, Cell,16, 239 (1979).Google Scholar
  95. 95.
    E. Wang, J. A. Connoly, V. I. Kalnins, and P. W. Choppin, Proc. Natl. Acad. Sci. USA,76, 5719 (1979).PubMedPubMedCentralGoogle Scholar
  96. 96.
    M. E. Stearnes and D. L. Brown, Proc. Natl. Acad. Sci. USA,76, 5745 (1979).Google Scholar
  97. 97.
    J. A. Snyder and J. R. McIntosh, Annu. Rev. Biochem.,45, 699 (1976).PubMedGoogle Scholar
  98. 98.
    B. R. Telzer, and L. Rosenbaum, J. Cell. Biol.,81, 484 (1979).PubMedGoogle Scholar
  99. 99.
    E. C. Raff, Int. Rev. Cytol.,59, 1 (1979).PubMedGoogle Scholar
  100. 100.
    T. T. Puck, Proc. Natl. Acad. Sci. USA,74, 4491 (1977).PubMedPubMedCentralGoogle Scholar
  101. 101.
    R. Simantov and L. Sax, FEBS Lett.,90, 69 (1978).PubMedGoogle Scholar
  102. 102.
    D. A. McClain and G. L. Edelman, Proc. Natl. Acad. Sci. USA,77, 2748 (1980).PubMedPubMedCentralGoogle Scholar
  103. 103.
    T. Kurokawa, M. Kurokawa, and S. Ishibashi, Biochim. Biophys. Acta, 583, 467 (1979).PubMedGoogle Scholar
  104. 104.
    P. R. Walker and J. F. Whitfield, Proc. Natl. Acad. Sci., USA,75, 1394 (1978).PubMedPubMedCentralGoogle Scholar
  105. 105.
    M. Freidkin, A. Legg, E. Rosengurt, Proc. Natl. Acad. Sci. USA,76, 3909 (1979).Google Scholar
  106. 106.
    H. Madoc-Jones and F. Mauro, J. Cell. Physiol.,72, 185 (1969).Google Scholar
  107. 107.
    M. Segawa and K. Kondo, Experientia,34, 996 (1978).Google Scholar
  108. 108.
    A. M. Chiriffe and E. P. Studzinski, Proc. Soc. Exp. Biol. Med.,157, 206 (1978).Google Scholar
  109. 109.
    B. H. Toh and G. C. Hard, Nature (London),269, 695 (1977).PubMedGoogle Scholar
  110. 110.
    D. B. Rifkin, R. M. Crowe, and R. Pollack, Cell,18, 361 (1979).PubMedGoogle Scholar
  111. 111.
    J. Wehland, W. Herzog, and K. Weber, J. Mol. Biol.,111, 329 (1977).PubMedGoogle Scholar
  112. 112.
    J. Polonsky, J. Varenne, T. Prange, and C. Pascard, Tetrahedron Lett.,21, 1853 (1980).Google Scholar
  113. 113.
    G. H. Stout, W. G. Balkenhol, M. Poling, and G. L. Hickernel, J. Am. Chem. Soc.,92, 1070 (1970).Google Scholar
  114. 114.
    A. Szent-György, Proc. Natl. Acad. Sci. USA,74, 2844 (1977).Google Scholar
  115. 115.
    C. W. J. Chang, Chem. Educat.,50, 260 (1973).Google Scholar
  116. 116.
    J. E. Casida, M. Eto, A. D. Mascioni, J. L. Engel, D. S. Mildbrath, and J. G. Verkade, Toxicol. Appl. Pharmacol.,36, 261 (1976).PubMedGoogle Scholar
  117. 117.
    D. E. Wright, Tetrahedron,35, 1207 (1979).Google Scholar
  118. 118.
    S. M. Kupchan and R. M. Schubert, Science,185, 791 (1974).PubMedGoogle Scholar
  119. 119.
    S. M. Kupchan, G. Tsou, J. Org. Chem.,38, 1055 (1973).Google Scholar
  120. 120.
    S. M. Kupchan, J. A. Lacadie, G. A. Gowie, and B. R. Sickles, J. Med. Chem.,19, 1130 (1976).PubMedGoogle Scholar
  121. 121.
    S. M. Kupchan, A. R. Branfman, and A. T. Sneden, J. Am. Chem. Soc.,97, 5294 (1975).PubMedGoogle Scholar
  122. 122.
    C. Paoletti, C. Lesca, S. Cros, C. Malvy, and C. Auclair, Biochem. Pharmacol.,28, 345 (1979).PubMedGoogle Scholar
  123. 123.
    R. W. Miller, R. G. Powell, C. R. Smith, E. Arnold, and J. Clardy, J. Org. Chem.,46, 1469 (1981).Google Scholar
  124. 124.
    T. Ebina, K. Ohtsuki, M. Seto, and N. Ishida, Eur. J. Cancer,11, 155 (1975).PubMedGoogle Scholar
  125. 125.
    K. Linnainmaa, M. Sorsa, and T. Ilus, Hereditas,90, 151 (1979).PubMedGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • A. A. Semenov

There are no affiliations available

Personalised recommendations