The Vinca Alkaloids

  • W. A. Creasey
Part of the Antibiotics book series (ANTIBIOTICS, volume 5 / 2)

Abstract

The vinca alkaloids are antineoplastic indole derivatives (Fig. 1) that are isolated from the leaves of the periwinkle plant, Vinca rosea L., or more correctly, Catharanthus roseus G. Don. This plant is of Madagascan origin, although its distribution is now pantropical (Stearn, 1975). Even in varieties selected for the highest alkaloid content, the concentrations of these antitumor agents are very low, as much as 1 kg of dried leaves being needed to obtain 3 mg of vincristine, for example.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Abraham, D.J.: Structure elucidation and chemistry of the bis catharanthus alkaloids. In: The catharanthus alkaloids, botany, chemistry, pharmacology, and clinical use. Taylor, W.I., Farnsworth, N.R. (eds.), p. 125. New York: Marcel Dekker 1975Google Scholar
  2. Adelmann, M.R., Borisy, G.G., Shelanski, M.L., Weisenberg, R.C., Taylor, E.W.: Cytoplasmic filaments and tubules. Fed. Proc. 27, 1186–1193 (1968)Google Scholar
  3. Agustin, B.M., Creasey, W.A.: Effects of vinca alkaloids on the synthesis of RNA in mouse brain. Nature (London) 215, 965–966 (1967)Google Scholar
  4. Aisenberg, A.C.: Suppression of immune response by “vincristine” and “vinblastine”. Nature (London) 200, 484 (1963)Google Scholar
  5. Anderson, P.J., Song, S.K., Slotwiner, P.: The fine structure of spheromembranous degeneration of skeletal muscle induced by vincristine. J. Neuropathol. Exp. Neurol. 26, 15–24 (1967)PubMedGoogle Scholar
  6. Armstrong, J.G.: New derivatives of the Vinca rosea alkaloids. Acta Genet. Med. (Roma) 17, 193–196 (1968)Google Scholar
  7. Armstrong, J.G., Dyke, R.W., Fouts, P.J., Hawthorne, J.J., Jansen, C.J. Jr., Peabody, A.M.: Initial clinical experience with vinglycinate sulfate, a molecular modification of vinblastine. Cancer Res. 27, 221–227 (1967)PubMedGoogle Scholar
  8. Beer, C.T.: The leukopenic action of extracts of Vinca rosea. A.R. Br. Emp. Cancer Campaign 33, 487–488 (1955)Google Scholar
  9. Beer, C.T., Richards, J.R.: The metabolism of Vinca alkaloids part II. The fate of tritiated vinblastine in rats. Lloydia 27, 352–360 (1964)Google Scholar
  10. Behnke, O., Forer, A.: Evidence for four classes of microtubules in individual cells. J. Cell Sci. 2, 169–192 (1967)PubMedGoogle Scholar
  11. Bennett, T., Gardiner, S.M.: The effects of intravenous injections of vinblastine or vincristine on the response of the rat heart to nerve stimulation and to drugs. Br. J. Pharmacol. 53, 444 P (1975)Google Scholar
  12. Bensch, K.G., Malawista, S.E.: Microtubule crystals in mammalian cells. J. Cell. Biol. 40, 95–107 (1969)PubMedGoogle Scholar
  13. Bensch, K.G., Marantz, R., Wisniewski, H., Shelanski, M.: Induction in vitro of microtubular crystals by vinca alkaloids. Science 165, 495–496 (1969)PubMedGoogle Scholar
  14. Bhattacharyya, B., Wolff, J.: Tubulin aggregation and disaggregation: mediation by two distinct vinblastine binding sites. Proc. Natl. Acad. Sci. USA 73, 2375–2378 (1976)PubMedGoogle Scholar
  15. Bleyer, W.A., Frisby, S.A., Oliverio, V.T.: Uptake of vincristine by murine leukemia cells. Biochem. Pharmacol. 24, 633–639 (1975)PubMedGoogle Scholar
  16. Blum, R.H., Dawson, D.M.: Vindesine (V) — phase I study of a vinca alkaloid. Proc. Am. Assoc. Cancer Res. 17, 108 (1976)Google Scholar
  17. Bodey, G.P., Freireich, E.J.: Initial clinical studies of vindesine (desacetylvinblastine amide sulfate). Proc. Am. Assoc. Cancer Res. 17, 128 (1976)Google Scholar
  18. Borisy, G.G., Marcum, J.M., Olmsted, J.B., Murphy, D.B., Johnson, K.A.: Purification of tubulin and associated high molecular weight proteins from porcine brain and characterization of microtubule assembly in vitro. Ann. N.Y. Acad. Sci. 253, 107–132 (1975)PubMedGoogle Scholar
  19. Bradley, W.G., Lassman, L.P., Pearce, G.W., Walton, J.N.: The neuromyopathy of vincristine in man. Clinical, electrophysiological and pathological studies. J. Neurol. Sci. 10, 107–131 (1970)PubMedGoogle Scholar
  20. Bryan, J.: Definition of three classes of binding sites in isolated microtubule crystals. Biochemistry 11, 2611–2616(1972)PubMedGoogle Scholar
  21. Burnside, B.: The form and arrangement of microtubules: an historical, primarily morphological review. Ann. N.Y. Acad. Sci. 253, 14–26 (1975)PubMedGoogle Scholar
  22. Capponi, A.M., Vallotton, M.B.: Renin release by rat kidney slices incubated in vitro. Role of sodium and of alpha- and beta-adrenergic receptors and effect of vincristine. Circ. Res. 39, 200–203 (1976)PubMedGoogle Scholar
  23. Casey, E.B., Fullerton, P.M., Jelliffe, A.W.: Vincristine neurotoxicity: a clinical and electrophysiological study of eighteen patients. Clin. Sci. 38, 23P–24P (1970)PubMedGoogle Scholar
  24. Castle, M.C., Margileth, D.A., Oliverio, V.T.: Distribution and excretion of [3H] vincristine in the rat and the dog. Cancer Res. 36, 3684–3689 (1976)PubMedGoogle Scholar
  25. Chung, L.W.K., Gabourel, J.D.: Adrenal steroid release by vinblastine sulfate and its contributions to vinblastine sulfate effects on rat thymus. Biochem. Pharmacol. 20, 1749–1756 (1971)PubMedGoogle Scholar
  26. Clarkson, B.: Clinical applications of cell cycle kinetics. In: Handbook of experimental pharmacology, Part I. Sartorelli, A.C., Johns, D.G. (eds.), Vol. 38, pp. 156–193. Berlin, Heidelberg, New York: Springer 1974Google Scholar
  27. Cline, M.J.: Effect of vincristine on synthesis of ribonucleic acid and protein in leukaemic leucocytes. Br. J. Haematol. 14, 21–29 (1968)PubMedGoogle Scholar
  28. Cohlan, S.Q., Kitay, D.: The teratogenic effect of vincaleukoblastine in the pregnant rat. J. Pediatr. 66, 541–544 (1965)PubMedGoogle Scholar
  29. Costa, M., Filogamo, G.: Effetti della colchicina nella fibre adrenergiche dei plessi nervosi intestinali. Boll. Soc. Ital. Biol. Sper. 46, 865–867 (1970)PubMedGoogle Scholar
  30. Creasey, W.A.: Tumor-inhibitory effects of combinations of the vinca alkaloids with actinomycin D. Biochem. Pharmacol. 15, 367–375 (1966)PubMedGoogle Scholar
  31. Creasey, W.A.: Modifications in biochemical pathways produced by the vinca alkaloids. Cancer Chemother. Rep. 52, 501–507 (1968)PubMedGoogle Scholar
  32. Creasey, W.A.: Biochemical effects of the vinca alkaloids-IV. Studies with vinleurosine. Biochem. Pharmacol. 18, 227–232 (1969)PubMedGoogle Scholar
  33. Creasey, W.A.: The vinca alkaloids. Biochem. Pharmacol. Suppl. 2, 23, 217–223 (1974)Google Scholar
  34. Creasey, W.A.: Vinca alkaloids and colchicine. In: Handbook of experimental pharmacology, part II. Sartorelli, A.C., Johns, D.G. (eds.), Vol. 38, pp. 670–694. Berlin, Heidelberg, New York: Springer 1975 aGoogle Scholar
  35. Creasey, W.A.: Biochemistry of dimeric Catharanthus alkaloids. In: The catharanthus alkaloids, botany, chemistry, pharmacology and clinical use. Taylor, W.I., Farnsworth, N.R. (eds.), pp. 209–236. New York: Marcel Dekker 1975bGoogle Scholar
  36. Creasey, W.A.: Pharmacological considerations in combination chemotherapy. Pharmacol. Ther. A1, 307–325 (1977a)Google Scholar
  37. Creasey, W.A.: Plant alkaloids. In: Cancer: a comprehensive treatise. Becker, F.F. (ed.), Vol. 5, pp. 379–425. New York: Plenum Press 1977bGoogle Scholar
  38. Creasey, W.A., Markiw, M.E.: Biochemical effects of the vinca alkaloids-I. Effects of vinblastine on nucleic acid synthesis in mouse tumor cells. Biochem. Pharmacol. 13, 135–142 (1964 a)PubMedGoogle Scholar
  39. Creasey, W.A., Markiw, M.E.: Biochemical effects of the vinca alkaloids-II. A comparison of the effects of colchicine, vinblastine and vincristine on the synthesis of ribonucleic acids in Ehrlich ascites carcinoma cells. Biochim. Biophys. Acta 87, 601–609 (1964 b)PubMedGoogle Scholar
  40. Creasey, W.A., Markiw, M.E.: Biochemical effects of the vinca alkaloids-III. The synthesis of ribonucleic acid and the incorporation of amino acids in Ehrlich ascites cells in vitro. Biochem. Biophys. Acta 103, 635–645 (1965)PubMedGoogle Scholar
  41. Creasey, W.A., Bensch, K.G., Malawista, S.E.: Colchicine, vinblastine and griseofulvin. Pharmacological studies with human leukocytes. Biochem. Pharmacol. 20, 1579–1588 (1971)Google Scholar
  42. Creasey, W.A., Scott, A.I., Wei, C.C., Kutcher, J., Schwartz, A., Marsh, J.C.: Pharmacological studies with vinblastine in the dog. Cancer Res. 35, 1116–1120 (1975)PubMedGoogle Scholar
  43. Culpeper, N.: The Complete herbal, 1653. Reprinted for Imperial Chemical Industries. Birmingham: Kynoch Press 1953Google Scholar
  44. Currie, V., Wong, P., Tan, R., Tan, C., Krakoff, I: Preliminary clinical studies of desacetyl vinblastine amide sulfate (DVA), a new vinca alkaloid. Proc. Am. Assoc. Cancer Res. 17, 174 (1976)Google Scholar
  45. Cutts, J.H.: Changes in mitosis in ascites tumors and normal bone marrow induced by vincaleukoblastine in vitro. Can. Cancer Conf. 4, 363–372 (1961)Google Scholar
  46. Cutts, J.H., Beer, C.T., Noble, R.L.: Effects on hematopoiesis in rats of extracts of Vinca rosea. Rev. Can. Biol. 16, 487 (1957)Google Scholar
  47. Cutts, J.H., Beer, C.T., Noble, R.L.: Biological properties of vincaleukoblastine, an alkaloid in Vincarosea Linn., with reference to its antitumor action. Cancer Res. 20, 1023–1031 (1960)PubMedGoogle Scholar
  48. Dahlström, A., Heiwall, P.O., Häggendal, J., Saunders, N.R.: Effect of antimitotic drugs on the intraaxonal transport of neurotransmitters in rat adrenergic and cholinergic nerves. Ann. N.Y. Acad. Sci. 253, 507–516 (1975)PubMedGoogle Scholar
  49. De Conti, R.C., Creasey, W.A.: Clinical aspects of the dimeric Catharanthus alkaloids. In: The catharanthus alkaloids, botany, chemistry, pharmacology and clinical use. Taylor, W.I., Farnsworth, N.R. (eds.), pp. 237–278. New York: Marcel Dekker 1975Google Scholar
  50. De Harven, E.: Action de la colchicine et de certaines hormones corticosurrénaliennes sur les mitoses des follicules pileux du rat. Rev. Belge Pathol. 25, 277 (1956)Google Scholar
  51. Dixon, G.J., Dulmadge, E.A., Mulligan, L.T., Mellett, L.B.: Cell culture bioassay for vincristine sulfate in sera from mice, rats, dogs, and monkeys. Cancer Res. 29, 1810–1813 (1969)PubMedGoogle Scholar
  52. Donigian, D.W., Owellen, R.J.: Interaction of vinblastine, vincristine and colchicine with serum proteins. Biochem. Pharmacol. 22, 2113–2119 (1973)PubMedGoogle Scholar
  53. Donoso, J.A., Green, L.S., Heller-Bettinger, I.E., Samson, F.E.: Action of the Vinca alkaloids vincristine, vinblastine, and desacetyl vinblastine, amide on axonal fibrillar organelles in vitro. Cancer Res. 37, 1401–1407 (1977)PubMedGoogle Scholar
  54. Dustin, P., Jr.: New aspects of the pharmacology of antimitotic agents. Pharmacol. Rev. 15, 449–480 (1963)PubMedGoogle Scholar
  55. Ecknauer, R.: Intestinal absorption of glucose immediately after vincristine administration in rats. Experientia 32, 709–711 (1976)PubMedGoogle Scholar
  56. Eli Lilly & Co.: Compound 99094, desacetyl vinblastine amide sulfate, an investigational new drug. Information for clinical investigators. Indianapolis: Eli Lilly & Co. 1975Google Scholar
  57. Engelborghs, Y., Heremans, K.A.H., De Maeyer, L.C.M., Hoebeke, J.: Effect of temperature and pressure on polymerization equilibrium of neuronal microtubules. Nature (London) 259, 686–688 (1976)Google Scholar
  58. Estridge, M.: Polypeptides similar to the a and β subunits of tubulin are exposed on the neuronal surface. Nature (London) 268, 60–63 (1977)Google Scholar
  59. Farnsworth, N.R., Blomster, R.N., Buckley, J.P.: Catharanthus alkaloids XIII. Antineoplastic and hypotensive activity of alkaloid fractions and certain alkaloids from Catharanthus lanceus. J. Pharm. Sci. 56, 23–27 (1967)PubMedGoogle Scholar
  60. Farnsworth, N.R., Svoboda, G.H., Blomster, R.N.: Antiviral activity of selected Catharanthus alkaloids. J. Pharm. Sci. 57, 2174–2175 (1968)PubMedGoogle Scholar
  61. Ferm, V.H.: Congenital malformations in hamster embryos after treatment with vinblastine and vincristine. Science 141, 426 (1963)PubMedGoogle Scholar
  62. Fine, R.E.: Heterogeneity of tubulin. Nature New Biol. 233, 283–284 (1971)PubMedGoogle Scholar
  63. Fine, R.N., Clarke, R.R., Shore, N.A.: Hyponatremia and vincristine therapy. Syndrome possibly resulting from inappropriate antidiuretic hormone secretion. Am. J. Dis. Child. 112, 256–259 (1966)PubMedGoogle Scholar
  64. Frei, E., III, Gottlieb, J.A.: Combination chemotherapy: Clinical considerations. In: Handbook of experimental pharmacology, part I. Sartorelli, A.C., Johns, D.G. (eds.), Vol. 38, pp. 449–467. Berlin, Heidelberg, New York: Springer 1974Google Scholar
  65. Gailani, S.D., Armstrong, J.G., Carbone, P.P., Tan, C., Holland, J.F.: Clinical trial of vinleurosine sulfate (NSC-90636): a new drug derived from Vinca rosea Linn. Cancer Chemother. Rep. 50, 95–103 (1966)PubMedGoogle Scholar
  66. Garcia, F.A.: A botany symposium on medicinal plants. In: Proc. 8th Pacific Sci. Congr. of the Natl. Res. Council of the Philippines, IV[A, 182 (1954)Google Scholar
  67. Gelfand, E.W., Morris, S.A., Resch, K.: Antibody-dependent cytotoxicity: modulation by the cytochalasins and microtubule-disruptive agents. J. Immunol. 114, 919–924 (1975)PubMedGoogle Scholar
  68. George, P., Journey, L.J., Goldstein, M.N.: Effect of vincristine on the fine structure of HeLa cells during mitosis. J. Natl. Cancer Inst. 35, 355–375 (1965)PubMedGoogle Scholar
  69. Gillespie, E., Levine, R.J., Malawista, S.E.: Histamine release from rat peritoneal mast cells: inhibition by colchicine and potentiation by deuterium oxide. J. Pharmacol. Exp. Ther. 164, 158–165 (1968)PubMedGoogle Scholar
  70. Goldfinger, S.E., Howell, R.R., Seegmiller, J.E.: Suppression of metabolic accompaniment of phagocytosis by colchicine. Arthritis Rheum. 8, 1112–1122 (1965)PubMedGoogle Scholar
  71. Goldin, A., Venditti, J.M., Mantel, N.: Combination chemotherapy; Basic considerations. In: Handbook of experimental pharmacology, Part I. Sartorelli, A.C., Johns, D.G. (eds.), Vol. 38, pp. 411–448. Berlin, Heidelberg, New York: Springer 1974Google Scholar
  72. Gottschalk, P.G., Dyck, P.J., Kiely, J.M.: Vinca alkaloid neuropathy: nerve biopsy studies in rats and in man. Neurology 18, 875–882 (1968)PubMedGoogle Scholar
  73. Graff, G.L.A., Guening, C., Hildebrand, J.: Action du sulfate de vincristine sur le gastrocnémien de rat I. Mis en evidence de deux compartements, metaboliquement distincts, pour le phosphate inorganique; effets sur les phosphates organiques acidosolubles et les phospholipides. C.R. Soc. Biol. 161, 2645–2651 (1967)Google Scholar
  74. Hancock, B.W., Naysmith, A.: Vincristine-induced autonomie neuropathy. Br. Med. J. 3, 207 (1975)PubMedGoogle Scholar
  75. Hebden, H.F., Hadfield, J.R., Beer, C.T.: The binding of vinblastine by platelets in the rat. Cancer Res. 30, 1417–1424(1970)PubMedGoogle Scholar
  76. Hodes, M.E., Rohn, R.J., Bond, W.H., Yardey, J.: Clinical trials with leurosine methiodide, an alkaloid from Vinca rosea Linn. Cancer Chemother. Rep. 28, 53–55 (1963)PubMedGoogle Scholar
  77. Hunter, J.C.: Effects of vincaleukoblastine sulfate on metabolism of thioguanine-resistant L1210 leukemia cells. Biochem. Pharmacol. 12, 283–291 (1963)PubMedGoogle Scholar
  78. Hwang, Y.F., Hamilton, H.E., Sheets, R.F.: Vinblastine-induced thrombocytosis. Lancet 1969 II, 1075–1076Google Scholar
  79. Johnson, I.S.: Observations on antiviral screening. Ann. N.Y. Acad. Sci. 130, 52–55 (1965)PubMedGoogle Scholar
  80. Johnson, I.S., Wright, H.F., Svoboda, G.H.: Experimental basis for clinical evaluation of anti-tumor principles derived from Vinca rosea Linn. J. Lab. Clin. Med. 54, 830 (1959)Google Scholar
  81. Johnson, I.S., Armstrong, J.G., Gorman, M., Burnett, J.P. Jr.: The vinca alkaloids: A new class of oncolytic agents. Cancer Res. 23, 1390–1427 (1963)PubMedGoogle Scholar
  82. Johnson, I.S., Hargrove, W.W., Harris, P.N., Wright, H.F., Boder, G.B.: Preclinical studies with vinglycinate, one of a series of chemically derived analogs of vinblastine. Cancer Res. 26, 2431–2436 (1966)PubMedGoogle Scholar
  83. Jones, R.G.W., Richards, J.F., Beer, C.T.: Biochemical studies with the vinca alkaloids II. Effect of vinblastine on the biosynthesis of nucleic acids and their precursors in rat thymus cells. Cancer Res. 26, 882–887 (1966)PubMedGoogle Scholar
  84. Journey, L.J., Burdman, J., George, P.: Ultrastructural studies on tissue culture cells treated with vincristine (NSC-67574). Cancer Chemother. Rep. 52, 509–517 (1968)PubMedGoogle Scholar
  85. Kingsbury, E.W., Voelz, H.: Induction of helical arrays of ribosomes by vinblastine sulfate in Escherichia coli. Science 166, 768–769 (1969)PubMedGoogle Scholar
  86. Kirschner, M.W., Suter, M., Weingarten, M., Littman, D.: The role of rings in the assembly of microtubules in vitro. Ann. N.Y. Acad. Sci. 253, 90–106 (1975)PubMedGoogle Scholar
  87. Klevecz, R.R., Forrest, G.L.: Regulation of tubulin expression through the cell cycle. Ann. N.Y. Acad. Sci. 253, 292–303 (1975)PubMedGoogle Scholar
  88. Kotorii, K., Mori, H., Yoshida, M.: A peculiar crystalline structure in neurons of rabbits treated with vincristine. Kurume Med. J. 18, 57–63 (1971)PubMedGoogle Scholar
  89. Krakoff, I.H.: Discussion of conference on gout and purine metabolism. Arthritis Rheum. 8, 760 (1965)Google Scholar
  90. Krishan, A.: Time lapse and ultrastructure studies on the reversal of mitotic arrest induced by vinblastine sulfate in Earle’s L. cells. J. Natl. Cancer Inst. 41, 581–595 (1968)Google Scholar
  91. Krishan, A., Frei, E. III: Morphological basis for the cytolytic effect of vinblastine and vincristine on cultured human leukemic lymphoblasts. Cancer Res. 35, 497–501 (1975)PubMedGoogle Scholar
  92. Krishan, A., Hsu, D.: Vinblastine-induced ribosomal complexes. Effect of some metabolic inhibitors on their formation and structure. J. Cell Biol. 49, 927–932 (1971)PubMedGoogle Scholar
  93. Krowke, R., Zimmerman, B., Merker, H.J.: Biochemical and electron microscopic studies of rat embryos in in vivo culture. Naunyn Schmiedebergs Arch. Pharmakol. 266, 382–383 (1970)PubMedGoogle Scholar
  94. Kutney, J.P., Gregonis, D.E., Imhof, R., Itoh, I., Jahngen, E.: Absolute sterochemistry of the bisindole alkaloids of the vinblastine type. Circular dichroism studies. J. Am. Chem. Soc. 97, 5013–5015(1975a)PubMedGoogle Scholar
  95. Kutney, J.P., Beck, J., Bylsma, F., Cook, J., Cretney, W.J., Fuji, K., Imhof, R., Tresurywala, A.M.: Total synthesis of indole and dihydroindole alkaloids. VIII. Studies on the synthesis of bisindole alkaloids in the vinblastine-vincristine series. The chloroindolenine approach. Helv. Chim. Acta 58, 1690–1719 (1975b)PubMedGoogle Scholar
  96. Lacy, P.E., Howell, S.L., Young, D.A., Fink, C.J.: New hypothesis on insulin secretion. Nature (London) 219, 1177–1179 (1968)Google Scholar
  97. Langlois, N., Gueritte, F., Langlois, Y., Potier, P.: Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids. J. Am. Chem. Soc. 98, 7017 (1976)PubMedGoogle Scholar
  98. Luyckx, A., Van Lancker, J.L.: Metabolic effects of vinblastine. II. The effect of vinblastine on deoxyribonucleic acid and ribonucleic acid synthesis of regenerating liver. Lab. Invest. 15, 1301–1303 (1966)PubMedGoogle Scholar
  99. Madoc-Jones, H., Mauro, F.: Interphase action of vinblastine and vincristine: differences in their lethal action through the mitotic cycle of cultured mammalian cells. J. Cell Physiol. 72, 185–196 (1968)PubMedGoogle Scholar
  100. Malawista, S.E., Sato, H.: Vinblastine produces uniaxial, birefringent crystals in starfish oocytes. J. Cell Biol. 42, 596–599 (1969)PubMedGoogle Scholar
  101. Malawista, S.E., Sato, H., Bensch, K.G.: Vinblastine and griseofulvin reversibly disrupt the living mitotic spindle. Science 160, 770–772 (1968)PubMedGoogle Scholar
  102. Malawista, S.E., Sato, H., Creasey, W.A.: Dissociation of the mitotic spindle in oocytes exposed to griseofulvin and vinblastine. Exp. Cell Res. 99, 193–197 (1976)Google Scholar
  103. Mandelkow, E.M., Mandelkow, E., Unwin, N., Cohen, C.: Tubulin hoops. Nature (London) 265, 655–657 (1977)Google Scholar
  104. Marantz, R., Shelanski, M.: Structure of microtubule crystals induced by vinblastine in vitro. J. Cell Biol. 44, 234–238 (1970)PubMedGoogle Scholar
  105. Mathé, G., Schneider, M., Band, P., Amiel, J.L., Schwarzenberg, L., Cattan, A., Schlumberger, J.R.: Leurosine sulfate (NSC-90636) in treatment of Hodgkin’s disease, acute lymphoblastic leukemia, and lymphoblastic lymphosarcoma. Cancer Chemother. Rep. 49, 47–49 (1965)PubMedGoogle Scholar
  106. McIntosh, J.R., Cande, Z., Snyder, J., Vanderslice, K.: Studies on the mechanism of mitosis. Ann. N.Y. Acad. Sci. 253, 407–427 (1975)Google Scholar
  107. McLeod, J.G., Penny, R.: Vincristine neuropathy: an electrophysiological and histological study. J. Neurol. Neurosurg. Psychiatr. 32, 297–304 (1969)PubMedGoogle Scholar
  108. Miller, J.C., Gutowski, G.E., Poore, G.A., Boder, G.B.: Alkaloids of Vinca rosea L. (Catharanthus roseus G. Don). 38. 4′-Dehydrated derivatives. J. Med. Chem. 20, 409–413 (1977)PubMedGoogle Scholar
  109. Nelson, R.L., Root, M.A., Dyke, R.W., Ahmadzai, S.: Pharmacokinetics of desacetyl vinblastine amide (Vindesine) in man. Proc. Am. Assoc. Cancer Res. 17, 30 (1976)Google Scholar
  110. Neuss, N.A., Barnes, J., Huckstep, L.L.: Vinca alkaloids XXXV. Desacetoxy-vinblastine a new minor alkaloid from Vincarosea L. (Catharanthus roseus G. Don). Experientia 38, 18–20 (1975)Google Scholar
  111. Noble, R.L., Beer, C.T., Cutts, J.H.: Further biological activities of vincaleukoblastine — an alkaloid from Vinca rosea (L). Biochem. Pharmacol. 1, 347–348 (1958)Google Scholar
  112. Noble, R.L., Beer, C.T., McIntyre, R.W.: Biological effects of dihydrovinblastine. Cancer 20, 885–890 (1967)PubMedGoogle Scholar
  113. Nomura, Y., Segawa, T.: Influences of colchicine and vinblastine on the uptake of 5-hydroxytryptamine and norepinephrine by rat brain synaptosomes and small vesicle fractions. J. Neurochem. 24, 1257–1259 (1975)PubMedGoogle Scholar
  114. Obrecht, P., Fusening, N.E.: Die Wirkung von Vincaleukoblastin (Velbe®) auf die Glykolyse von Tumorzellen. Eur. J. Cancer 2, 109–115 (1966)PubMedGoogle Scholar
  115. Ochs, S., Worth, R.: Comparison of the block of fast axoplasmic transport in mammalian nerve by vincristine, vinblastine and desacetyl vinblastine amide (DVA). Proc. Am. Assoc. Cancer Res. 16, 70 (1975)Google Scholar
  116. Olmsted, J.B., Borisy, G.G.: Microtubules. Annu. Rev. Biochem. 42, 507–540 (1973)PubMedGoogle Scholar
  117. Olmsted, J.B., Carlson, K., Klebe, R., Ruddle, F., Rosenbaum, J.L.: Isolation of microtubule protein from cultured mouse neuroblastoma cells. Proc. Natl. Acad. Sci. USA 65, 129–136 (1970)PubMedGoogle Scholar
  118. Orci, L., Lemarchand, Y., Singh, A., Assimacopoulos-Jennet, F., Rouiller, C.H., Jeanrenaud, B.: Role of microtubules in lipoprotein secretion by the liver. Nature (London) 244, 30–32 (1973)Google Scholar
  119. Owellen, R.J., Donigian, D.W.: [3H] Vincristine. Preparation and preliminary pharmacology. J. Med. Chem. 15, 894–898 (1972)PubMedGoogle Scholar
  120. Owellen, R.J., Hartke, C.A.: The pharmacokinetics of 4-acetyl tritium vinblastine in two patients. Cancer Res. 35, 975–980 (1975)PubMedGoogle Scholar
  121. Owellen, R.J., Hartke, C.A., Dickerson, R.M., Hains, F.O.: Inhibition of tubulin-microtubule polymerization by drugs of the Vinca alkaloid class. Cancer Res. 36, 1499–1502 (1976)PubMedGoogle Scholar
  122. Owellen, R.J., Hartke, C.A., Hains, F.O.: Pharmacokinetics and metabolism of vinblastine in humans. Cancer Res. 37, 2597–2602 (1977a)PubMedGoogle Scholar
  123. Owellen, R.J., Root, M.A., Hains, F.O.: Pharmacokinetics of vindesine and vincristine in humans. Cancer Res. 37, 2603–2607 (1977b)PubMedGoogle Scholar
  124. Palmer, C.G., Warren, A.K., Simpson, P.J.: A comparison of the cytologic effects of leurosine methiodide and vinblastine in tissue culture. Cancer Chemother. Rep. 31, 1–2 (1963)PubMedGoogle Scholar
  125. Peckolt, T.: Heil- und Nutzpflanzen Braziliens. Ber. Dtsch. Pharm. Ges. 20, 36–58 (1910)Google Scholar
  126. Richards, J.F., Jones, R.G.W., Beer, C.T.: Biochemical studies with the vinca alkaloids I. Effect on nucleic acid formation by isolated cell suspensions. Cancer Res. 26, 876–881 (1966)PubMedGoogle Scholar
  127. Robertson, J.H., McCarthy, G.M.: Periwinkle alkaloids and the platelet count. Lancet 1969II, 353–355Google Scholar
  128. Roodman, G.D., Hutton, J.J., Bollum, F.J.: DNA polymerase activities during erythropoiesis. Effects of erythropoietin, vinblastine, colcemid, and daunomycin. Exp. Cell Res. 91, 269–278 (1975)PubMedGoogle Scholar
  129. Rosenbaum, J.L., Carlson, K.: Cilia regeneration in Tetrahymema and its inhibition by colchicine. J. Cell Biol. 40, 415–425 (1969)PubMedGoogle Scholar
  130. Sandler, S.G., Tobin, W., Henderson, E.S.: Vincristine-induced neuropathy. A clinical study of fifty leukemia patients. Neurology 19, 367–374 (1969)PubMedGoogle Scholar
  131. Sartorelli, A.C., Creasey, W.A.: Combination chemotherapy. In: Cancer medicine. Holland, J.F., Frei, E. III (eds.), pp. 707–717. Philadelphia: Lea and Febiger 1973Google Scholar
  132. Schmitt, H., Josephs, R., Reisler, E.: A search for in vivo factors in regulation of microtubule assembly. Nature (London) 265, 653–655 (1977)Google Scholar
  133. Schochet, S.S., Lampert, P.W., Earle, K.M.: Neuronal changes induced by intrathecal vincristine sulfate. J. Neuropathol. Exp. Neurol. 27, 645–658 (1968)PubMedGoogle Scholar
  134. Sharma, R.K., Nagcháudhuri, J.: A study of amino acid absorption from small intestines of vinblastine-treated rats with altered mucosal morphology. Indian J. Med. Res. 64, 1225–1234 (1976)PubMedGoogle Scholar
  135. Slater, L.M., Wainer, R.A., Serpick, A.A.: Vincristine neurotoxicity with hyponatremia. Cancer 23, 122–125 (1969)PubMedGoogle Scholar
  136. Slotnick, I.J., Dougherty, M., James, D.H. Jr.: Vincristine inhibition of DNA synthesis in Tetrahymena pyriformis. Cancer Res. 26, 673–675 (1966)PubMedGoogle Scholar
  137. Smith, D.S., Järlfors, V., Cameron, B.F.: Morphological evidence for the participation of microtubules in axonal transport. Ann. N.Y. Acad. Sci. 253, 472–506 (1975)PubMedGoogle Scholar
  138. Soifer, D., Laszlo, A., Mack, K., Scotto, J., Siconolfi, L.: The association of a cyclic AMP-dependent protein kinase activity with microtubule protein. Ann. N.Y. Acad. Sci. 253, 598–610 (1975)PubMedGoogle Scholar
  139. Stearn, W.T.: Synopsis of the genus Catharanthus (Apocynaceae). In: The catharanthus alkaloids, botany, chemistry, pharmacology, and clinical use. Taylor, W.I., Farnsworth, N.R. (eds.), pp. 9–44. New York: Marcel Dekker 1975Google Scholar
  140. Stein, O., Sanger, L., Stein, Y.: Colchicine-induced inhibition of lipoprotein and protein secretion into the serum and lack of interference with secretion of biliary phospholipids and cholesterol by rat liver in vivo. J. Cell Biol. 62, 90–103 (1974)PubMedGoogle Scholar
  141. Stuart, M.J., Cuaso, C., Miler, M., Oski, F.A.: Syndrome of recurrent increased secretion of antidiuretic hormone following multiple doses of vincristine. Blood 45, 315–320 (1975)PubMedGoogle Scholar
  142. Svoboda, G.H.: A note on several alkaloids from Vinca rosea Linn. I. Leurosine, virosine and perivine. J. Am. Pharm. Ass. 47, 834 (1958)Google Scholar
  143. Svoboda, G.H.: Alkaloids of Vinca rosea Linn. IX. Extraction and characterization of leurosidine and leurocristine. Lloydia 24, 173–178 (1961)Google Scholar
  144. Svoboda, G.H., Barnes, A.J. Jr.: Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don) XXIV. Vinaspine, vincathicine, rovidine, desacetyl VLB and vinaphamine. J. Pharm. Sci. 53, 1227–1231 (1964)PubMedGoogle Scholar
  145. Svoboda, G.H., Blake, D.A.: The phytochemistry and pharmacology of Catharanthus roseus. In: The catharanthus alkaloids, botany, chemistry, pharmacology, and clinical use. Taylor, W.I., Farnsworth, N.R. (eds.), pp. 45–83. New York: Marcel Dekker 1975Google Scholar
  146. Swerdlow, B., Creasey, W.A.: Binding of vinblastine in vitro to ribosomes of sarcoma 180 cells. Biochem. Pharmacol. 24, 1243–1245 (1975)PubMedGoogle Scholar
  147. Tafur, S., Jones, W.E., Dorman, D.E., Logsdon, E.E., Svoboda, G.H.: Alkaloids of Vinca rosea L. (Catharanthus roseus G. Don) XXXVI. Isolation and characterization of new dimeric alkaloids. J. Pharm. Sci. 64, 1953 (1975)PubMedGoogle Scholar
  148. Teplitz, R.L., Mazie, J.C., Gerson, I., Barr, K.J.: The effects of microtubular binding agents on secretion of IgM antibody. Exp. Cell Res. 90, 392–400 (1975)PubMedGoogle Scholar
  149. Tobin, W.E., Sandler, S.G.: Depression of muscle spindle function with vincristine. Nature (London) 212, 90–91 (1966)Google Scholar
  150. Tobin, W.E., Sandler, S.G.: Neurophysiologic alterations induced by vincristine (NSC-67574). Cancer Chemother. Rep. 52, 519–526 (1968)PubMedGoogle Scholar
  151. Todd, G.C., Gibson, W.R., Griffing, W.J., Morton, D.M.: The preclinical study of desacetyl vinblastine amide (DVA). Proc. Am. Assoc. Cancer Res. 16, 70 (1975)Google Scholar
  152. Ueda, M., Sawadi, M., Kawakami, M., Minesita, T., Takeda, H.: Pressure mechanism of vincristine sulfate. Jpn. J. Pharmacol. 19, 324–325 (1969)PubMedGoogle Scholar
  153. Uy, Q.L., Moen, T.H., Johns, R.J., Owens, A.H. Jr.: Vincristine neurotoxicity in rodents. Johns Hopkins Med. J. 121, 349–360 (1967)PubMedGoogle Scholar
  154. Van Lancker, J.L., Flangas, A.L., Allen, J.: Metabolic effects of vinblastine. I. The effect of vinblastine on nucleic acid synthesis in spleen and bone marrow. Lab. Invest. 15, 1291–1300 (1966)PubMedGoogle Scholar
  155. Vasiliev, J.M., Gelfand, I.M., Guelstein, V.I.: Initiation of DNA synthesis in cell cultures by colcemid. Proc. Natl. Acad. Sci. USA 68, 977–979 (1971)PubMedGoogle Scholar
  156. Venditti, J.M., Abbott, B.J.: Studies on oncolytic agents from natural sources. Correlations of activity against animal tumors and clinical effectiveness. Lloydia 30, 332–348 (1967)Google Scholar
  157. Wagner, E.K., Roizman, B.: Effect of the vinca alkaloids on RNA synthesis in human cells in vitro. Science 162, 569–570 (1968)PubMedGoogle Scholar
  158. Warnecke, P., Seeber, S.: Angriffspunkte von Vinca-Alkaloiden im Protein und Nucleinsäurestoffwechsel. Z. Krebsforsch. 71, 361–367 (1968)PubMedGoogle Scholar
  159. Watt, J.M., Breyer-Brandwijk, M.G.: Medicinal and poisonous plants of Southern and Eastern Africa. p. 85. London: E. & S. Livingston 1962Google Scholar
  160. White, C.T.: Queensl. Agric. J. 23, 143 (1925). Quoted in: Svoboda, G.H., Blake, D.A.: The phytochemistry and pharmacology of Catharanthus roseus. In: The catharanthus alkaloids. Taylor, W.I., Farnsworth, N.R. (eds.), p. 47. New York: Marcel Dekker 1975Google Scholar
  161. Williams, J.A., Lee, M.: Microtubules and pancreatic amylase release by mouse pancreas in vitro. J. Cell Biol. 71, 795–806 (1976)PubMedGoogle Scholar
  162. Wilson, L.: Action of drugs on microtubules. Life Sci. 17, 303–309 (1975a)PubMedGoogle Scholar
  163. Wilson, L.: Microtubules as drug receptors: pharmacological properties of microtubule protein. Ann. N.Y. Acad. Sci. 253, 213–231 (1975b)PubMedGoogle Scholar
  164. Wilson, L., Bryan, J., Ruby, A., Mazia, D.: Precipitation of proteins by vinblastine and calcium ions. Proc. Natl. Acad. Sci. USA 66, 807–814 (1970)PubMedGoogle Scholar
  165. Wolff, J., Bhattacharyya, B.: Microtubules and thyroid hormone mobilization. Ann. N.Y. Acad. Sci. 253, 763–770 (1975)PubMedGoogle Scholar
  166. Yasin, R., Hughes, B.P., Parker, J.A.: The effect of vincristine on the calcium transport and phospholipid composition of rat skeletal muscle microsomes. Lab. Invest. 29, 207–215 (1973)PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin · Heidelberg 1979

Authors and Affiliations

  • W. A. Creasey

There are no affiliations available

Personalised recommendations