Skip to main content

The Vinca Alkaloids

  • Chapter

Part of the Antibiotics book series (1512,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.

Keywords

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.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • 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 1975

    Google Scholar 

  • 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 

  • Agustin, B.M., Creasey, W.A.: Effects of vinca alkaloids on the synthesis of RNA in mouse brain. Nature (London) 215, 965–966 (1967)

    CAS  Google Scholar 

  • Aisenberg, A.C.: Suppression of immune response by “vincristine” and “vinblastine”. Nature (London) 200, 484 (1963)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Armstrong, J.G.: New derivatives of the Vinca rosea alkaloids. Acta Genet. Med. (Roma) 17, 193–196 (1968)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Beer, C.T.: The leukopenic action of extracts of Vinca rosea. A.R. Br. Emp. Cancer Campaign 33, 487–488 (1955)

    Google Scholar 

  • 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)

    CAS  Google Scholar 

  • Behnke, O., Forer, A.: Evidence for four classes of microtubules in individual cells. J. Cell Sci. 2, 169–192 (1967)

    PubMed  CAS  Google Scholar 

  • 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 

  • Bensch, K.G., Malawista, S.E.: Microtubule crystals in mammalian cells. J. Cell. Biol. 40, 95–107 (1969)

    PubMed  CAS  Google Scholar 

  • Bensch, K.G., Marantz, R., Wisniewski, H., Shelanski, M.: Induction in vitro of microtubular crystals by vinca alkaloids. Science 165, 495–496 (1969)

    PubMed  CAS  Google Scholar 

  • Bhattacharyya, B., Wolff, J.: Tubulin aggregation and disaggregation: mediation by two distinct vinblastine binding sites. Proc. Natl. Acad. Sci. USA 73, 2375–2378 (1976)

    PubMed  CAS  Google Scholar 

  • Bleyer, W.A., Frisby, S.A., Oliverio, V.T.: Uptake of vincristine by murine leukemia cells. Biochem. Pharmacol. 24, 633–639 (1975)

    PubMed  CAS  Google Scholar 

  • 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 

  • Bodey, G.P., Freireich, E.J.: Initial clinical studies of vindesine (desacetylvinblastine amide sulfate). Proc. Am. Assoc. Cancer Res. 17, 128 (1976)

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Bryan, J.: Definition of three classes of binding sites in isolated microtubule crystals. Biochemistry 11, 2611–2616(1972)

    PubMed  CAS  Google Scholar 

  • Burnside, B.: The form and arrangement of microtubules: an historical, primarily morphological review. Ann. N.Y. Acad. Sci. 253, 14–26 (1975)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 1974

    Google Scholar 

  • Cline, M.J.: Effect of vincristine on synthesis of ribonucleic acid and protein in leukaemic leucocytes. Br. J. Haematol. 14, 21–29 (1968)

    PubMed  CAS  Google Scholar 

  • Cohlan, S.Q., Kitay, D.: The teratogenic effect of vincaleukoblastine in the pregnant rat. J. Pediatr. 66, 541–544 (1965)

    PubMed  CAS  Google Scholar 

  • Costa, M., Filogamo, G.: Effetti della colchicina nella fibre adrenergiche dei plessi nervosi intestinali. Boll. Soc. Ital. Biol. Sper. 46, 865–867 (1970)

    PubMed  CAS  Google Scholar 

  • Creasey, W.A.: Tumor-inhibitory effects of combinations of the vinca alkaloids with actinomycin D. Biochem. Pharmacol. 15, 367–375 (1966)

    PubMed  CAS  Google Scholar 

  • Creasey, W.A.: Modifications in biochemical pathways produced by the vinca alkaloids. Cancer Chemother. Rep. 52, 501–507 (1968)

    PubMed  CAS  Google Scholar 

  • Creasey, W.A.: Biochemical effects of the vinca alkaloids-IV. Studies with vinleurosine. Biochem. Pharmacol. 18, 227–232 (1969)

    PubMed  CAS  Google Scholar 

  • Creasey, W.A.: The vinca alkaloids. Biochem. Pharmacol. Suppl. 2, 23, 217–223 (1974)

    Google Scholar 

  • 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 a

    Google Scholar 

  • 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 1975b

    Google Scholar 

  • Creasey, W.A.: Pharmacological considerations in combination chemotherapy. Pharmacol. Ther. A1, 307–325 (1977a)

    Google Scholar 

  • Creasey, W.A.: Plant alkaloids. In: Cancer: a comprehensive treatise. Becker, F.F. (ed.), Vol. 5, pp. 379–425. New York: Plenum Press 1977b

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Creasey, W.A., Bensch, K.G., Malawista, S.E.: Colchicine, vinblastine and griseofulvin. Pharmacological studies with human leukocytes. Biochem. Pharmacol. 20, 1579–1588 (1971)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Culpeper, N.: The Complete herbal, 1653. Reprinted for Imperial Chemical Industries. Birmingham: Kynoch Press 1953

    Google Scholar 

  • 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 

  • 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 

  • 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 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  Google Scholar 

  • 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 1975

    Google Scholar 

  • 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 

  • 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)

    PubMed  CAS  Google Scholar 

  • Donigian, D.W., Owellen, R.J.: Interaction of vinblastine, vincristine and colchicine with serum proteins. Biochem. Pharmacol. 22, 2113–2119 (1973)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Dustin, P., Jr.: New aspects of the pharmacology of antimitotic agents. Pharmacol. Rev. 15, 449–480 (1963)

    PubMed  CAS  Google Scholar 

  • Ecknauer, R.: Intestinal absorption of glucose immediately after vincristine administration in rats. Experientia 32, 709–711 (1976)

    PubMed  CAS  Google Scholar 

  • Eli Lilly & Co.: Compound 99094, desacetyl vinblastine amide sulfate, an investigational new drug. Information for clinical investigators. Indianapolis: Eli Lilly & Co. 1975

    Google Scholar 

  • 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)

    CAS  Google Scholar 

  • Estridge, M.: Polypeptides similar to the a and β subunits of tubulin are exposed on the neuronal surface. Nature (London) 268, 60–63 (1977)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Farnsworth, N.R., Svoboda, G.H., Blomster, R.N.: Antiviral activity of selected Catharanthus alkaloids. J. Pharm. Sci. 57, 2174–2175 (1968)

    PubMed  CAS  Google Scholar 

  • Ferm, V.H.: Congenital malformations in hamster embryos after treatment with vinblastine and vincristine. Science 141, 426 (1963)

    PubMed  CAS  Google Scholar 

  • Fine, R.E.: Heterogeneity of tubulin. Nature New Biol. 233, 283–284 (1971)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 1974

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Goldfinger, S.E., Howell, R.R., Seegmiller, J.E.: Suppression of metabolic accompaniment of phagocytosis by colchicine. Arthritis Rheum. 8, 1112–1122 (1965)

    PubMed  CAS  Google Scholar 

  • 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 1974

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    CAS  Google Scholar 

  • Hancock, B.W., Naysmith, A.: Vincristine-induced autonomie neuropathy. Br. Med. J. 3, 207 (1975)

    PubMed  CAS  Google Scholar 

  • Hebden, H.F., Hadfield, J.R., Beer, C.T.: The binding of vinblastine by platelets in the rat. Cancer Res. 30, 1417–1424(1970)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Hunter, J.C.: Effects of vincaleukoblastine sulfate on metabolism of thioguanine-resistant L1210 leukemia cells. Biochem. Pharmacol. 12, 283–291 (1963)

    PubMed  CAS  Google Scholar 

  • Hwang, Y.F., Hamilton, H.E., Sheets, R.F.: Vinblastine-induced thrombocytosis. Lancet 1969 II, 1075–1076

    Google Scholar 

  • Johnson, I.S.: Observations on antiviral screening. Ann. N.Y. Acad. Sci. 130, 52–55 (1965)

    PubMed  CAS  Google Scholar 

  • 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 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Kingsbury, E.W., Voelz, H.: Induction of helical arrays of ribosomes by vinblastine sulfate in Escherichia coli. Science 166, 768–769 (1969)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Klevecz, R.R., Forrest, G.L.: Regulation of tubulin expression through the cell cycle. Ann. N.Y. Acad. Sci. 253, 292–303 (1975)

    PubMed  CAS  Google Scholar 

  • Kotorii, K., Mori, H., Yoshida, M.: A peculiar crystalline structure in neurons of rabbits treated with vincristine. Kurume Med. J. 18, 57–63 (1971)

    PubMed  CAS  Google Scholar 

  • Krakoff, I.H.: Discussion of conference on gout and purine metabolism. Arthritis Rheum. 8, 760 (1965)

    Google Scholar 

  • 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)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Lacy, P.E., Howell, S.L., Young, D.A., Fink, C.J.: New hypothesis on insulin secretion. Nature (London) 219, 1177–1179 (1968)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Malawista, S.E., Sato, H.: Vinblastine produces uniaxial, birefringent crystals in starfish oocytes. J. Cell Biol. 42, 596–599 (1969)

    PubMed  CAS  Google Scholar 

  • Malawista, S.E., Sato, H., Bensch, K.G.: Vinblastine and griseofulvin reversibly disrupt the living mitotic spindle. Science 160, 770–772 (1968)

    PubMed  CAS  Google Scholar 

  • 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)

    CAS  Google Scholar 

  • Mandelkow, E.M., Mandelkow, E., Unwin, N., Cohen, C.: Tubulin hoops. Nature (London) 265, 655–657 (1977)

    CAS  Google Scholar 

  • Marantz, R., Shelanski, M.: Structure of microtubule crystals induced by vinblastine in vitro. J. Cell Biol. 44, 234–238 (1970)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  Google Scholar 

  • 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 

  • McLeod, J.G., Penny, R.: Vincristine neuropathy: an electrophysiological and histological study. J. Neurol. Neurosurg. Psychiatr. 32, 297–304 (1969)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 

  • 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 

  • 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 

  • Noble, R.L., Beer, C.T., McIntyre, R.W.: Biological effects of dihydrovinblastine. Cancer 20, 885–890 (1967)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Obrecht, P., Fusening, N.E.: Die Wirkung von Vincaleukoblastin (Velbe®) auf die Glykolyse von Tumorzellen. Eur. J. Cancer 2, 109–115 (1966)

    PubMed  CAS  Google Scholar 

  • 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 

  • Olmsted, J.B., Borisy, G.G.: Microtubules. Annu. Rev. Biochem. 42, 507–540 (1973)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    CAS  Google Scholar 

  • Owellen, R.J., Donigian, D.W.: [3H] Vincristine. Preparation and preliminary pharmacology. J. Med. Chem. 15, 894–898 (1972)

    PubMed  CAS  Google Scholar 

  • Owellen, R.J., Hartke, C.A.: The pharmacokinetics of 4-acetyl tritium vinblastine in two patients. Cancer Res. 35, 975–980 (1975)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Owellen, R.J., Hartke, C.A., Hains, F.O.: Pharmacokinetics and metabolism of vinblastine in humans. Cancer Res. 37, 2597–2602 (1977a)

    PubMed  CAS  Google Scholar 

  • Owellen, R.J., Root, M.A., Hains, F.O.: Pharmacokinetics of vindesine and vincristine in humans. Cancer Res. 37, 2603–2607 (1977b)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Peckolt, T.: Heil- und Nutzpflanzen Braziliens. Ber. Dtsch. Pharm. Ges. 20, 36–58 (1910)

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Robertson, J.H., McCarthy, G.M.: Periwinkle alkaloids and the platelet count. Lancet 1969II, 353–355

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Rosenbaum, J.L., Carlson, K.: Cilia regeneration in Tetrahymema and its inhibition by colchicine. J. Cell Biol. 40, 415–425 (1969)

    PubMed  CAS  Google Scholar 

  • Sandler, S.G., Tobin, W., Henderson, E.S.: Vincristine-induced neuropathy. A clinical study of fifty leukemia patients. Neurology 19, 367–374 (1969)

    PubMed  CAS  Google Scholar 

  • 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 1973

    Google Scholar 

  • Schmitt, H., Josephs, R., Reisler, E.: A search for in vivo factors in regulation of microtubule assembly. Nature (London) 265, 653–655 (1977)

    CAS  Google Scholar 

  • Schochet, S.S., Lampert, P.W., Earle, K.M.: Neuronal changes induced by intrathecal vincristine sulfate. J. Neuropathol. Exp. Neurol. 27, 645–658 (1968)

    PubMed  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Slater, L.M., Wainer, R.A., Serpick, A.A.: Vincristine neurotoxicity with hyponatremia. Cancer 23, 122–125 (1969)

    PubMed  CAS  Google Scholar 

  • Slotnick, I.J., Dougherty, M., James, D.H. Jr.: Vincristine inhibition of DNA synthesis in Tetrahymena pyriformis. Cancer Res. 26, 673–675 (1966)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 1975

    Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Svoboda, G.H.: A note on several alkaloids from Vinca rosea Linn. I. Leurosine, virosine and perivine. J. Am. Pharm. Ass. 47, 834 (1958)

    CAS  Google Scholar 

  • Svoboda, G.H.: Alkaloids of Vinca rosea Linn. IX. Extraction and characterization of leurosidine and leurocristine. Lloydia 24, 173–178 (1961)

    CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 1975

    Google Scholar 

  • Swerdlow, B., Creasey, W.A.: Binding of vinblastine in vitro to ribosomes of sarcoma 180 cells. Biochem. Pharmacol. 24, 1243–1245 (1975)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Tobin, W.E., Sandler, S.G.: Depression of muscle spindle function with vincristine. Nature (London) 212, 90–91 (1966)

    CAS  Google Scholar 

  • Tobin, W.E., Sandler, S.G.: Neurophysiologic alterations induced by vincristine (NSC-67574). Cancer Chemother. Rep. 52, 519–526 (1968)

    PubMed  CAS  Google Scholar 

  • 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 

  • Ueda, M., Sawadi, M., Kawakami, M., Minesita, T., Takeda, H.: Pressure mechanism of vincristine sulfate. Jpn. J. Pharmacol. 19, 324–325 (1969)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • 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 

  • Wagner, E.K., Roizman, B.: Effect of the vinca alkaloids on RNA synthesis in human cells in vitro. Science 162, 569–570 (1968)

    PubMed  CAS  Google Scholar 

  • Warnecke, P., Seeber, S.: Angriffspunkte von Vinca-Alkaloiden im Protein und Nucleinsäurestoffwechsel. Z. Krebsforsch. 71, 361–367 (1968)

    PubMed  CAS  Google Scholar 

  • Watt, J.M., Breyer-Brandwijk, M.G.: Medicinal and poisonous plants of Southern and Eastern Africa. p. 85. London: E. & S. Livingston 1962

    Google Scholar 

  • 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 1975

    Google Scholar 

  • Williams, J.A., Lee, M.: Microtubules and pancreatic amylase release by mouse pancreas in vitro. J. Cell Biol. 71, 795–806 (1976)

    PubMed  CAS  Google Scholar 

  • Wilson, L.: Action of drugs on microtubules. Life Sci. 17, 303–309 (1975a)

    PubMed  CAS  Google Scholar 

  • Wilson, L.: Microtubules as drug receptors: pharmacological properties of microtubule protein. Ann. N.Y. Acad. Sci. 253, 213–231 (1975b)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

  • Wolff, J., Bhattacharyya, B.: Microtubules and thyroid hormone mobilization. Ann. N.Y. Acad. Sci. 253, 763–770 (1975)

    PubMed  CAS  Google Scholar 

  • 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)

    PubMed  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1979 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Creasey, W.A. (1979). The Vinca Alkaloids. 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_21

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-46407-2_21

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46409-6

  • Online ISBN: 978-3-642-46407-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics