43
Views
20
CrossRef citations to date
0
Altmetric
Research Article

Biologically Active Alkaloids from Poison Frogs (Dendrobatidae)

Pages 33-86 | Published online: 28 Sep 2008

References

  • Adams H. J., Mastri A. R., Doherty D., Jr., Charron D. Spinal anesthesia with batrachotoxin in sheep and microscopic examination of spinal cords and roots. Pharmacol. Res. Comm. 1978; 10: 719–728
  • Adler M., Oliveira A. C., Albuquerque E. X., Mansour N. A., Eldefrawi A. T. Reaction of tetraethylammonium with the open and closed conformations of the acetylcholine receptor ionic channel complex. J. Gen. Physiol. 1979a; 74: 129–152
  • Adler M., Oliveira A. C., Eldefrawi M. E., Eldefrawi A. T., Albuquerque E. X. Tetraethylammonium: Voltage-dependent action on endplate conductance and inhibition of ligand binding to postsynaptic proteins. Proc. Nat. Acad. Sci. (USA) 1979b; 76: 531–535
  • Albuquerque E. X. The mode of action of batrachotoxin. Federat. Proc. 1972; 31: 1133–1138
  • Albuquerque E. X., Daly J. W. Batrachotoxin, a selective probe for channels modulating sodium conductances in electrogenic membranes. Receptors and Recognition 1, P. Cuatracasas. series B, Chapman and Hall, London 1977; 297–338
  • Albuquerque E. X., Gage P. W. Differential effects of perhydrohistrionicotoxin on neurally and iontophoretically evoked endplate currents. Proc. Nat. Acad. Sci. (USA) 1978; 75: 1596–1599
  • Albuquerque E. X., Oliveira A. C. Physiological studies on the ionic channel of nicotinic neuromuscular synapses. Adv. Cytopharmacol. 1979; 3: 197–211
  • Albuquerque E. X., Warnick J. E. Pharmacology of batrachotoxin. IV. Interaction with tetrodotoxin on innervated and chronically denervated rat skeletal muscle. J. Pharmacol. Exp. Therapeut. 1972a; 180: 683–697
  • Albuquerque E. X., Adler M., Spivak C. E., Aguayo L. Mechanism of nicotinic channel activation and blockade. Ann. N.Y. Acad. Sci. 1980a; 358: 204–238
  • Albuquerque E. X., Barnard E. A., Chiu T. H., Lapa A. J., Dolly J. O., Jansson S.-E., Daly J., Witkop B. Acetylcholine receptor and ion conductance modulator sites at the murine neuromuscular junction: Evidence from specific toxin reactions. Proc. Nat. Acad. Sci. (USA) 1973a; 70: 949–953
  • Albuquerque E. X., Brookes N., Onur R., Warnick J. E. Kinetics of interaction of batrachotoxin and tetrodotoxin on rat diaphragm muscle. Mol. Pharmacol. 1976; 12: 82–91
  • Albuquerque E. X., Daly J. W., Witkop B. Batrachotoxin: Chemistry and pharmacology. Science 1971a; 172: 995–1002
  • Albuquerque E. X., Eldefrawi A. T., Eldefrawi M. E., Mansour N. A., Tsai M.-C. Amantadine: Neuromuscular blockade by suppression of ionic conductance of the acetylcholine receptor. Science 1978; 199: 788–790
  • Albuquerque E. X., Gage P. W., Oliveira A. C. Differential effect of perhydrohistrionicotoxin on ‘intrinsic’ and ‘extrinsic’ end-plate responses. J. Physiol. 1979; 297: 423–442
  • Albuquerque E. X., Kuba K., Daly J. Effect of histrionicotoxin on the ionic conductance modulator of the cholinergic receptor: A quantitative analysis of the end-plate current. J. Pharmacol. Exp. Therapeut. 1974a; 189: 513–524
  • Albuquerque E. X., Kuba K., Lapa A. J., Daly J. W., Witkop B. Acetylcholine receptor and ionic conductance modulator of innervated and denervated muscle membranes. Effect of histrionicotoxins. Exploratory Concepts in Muscular Dystrophy, A. T. Molhorat. Excerpta Medica, Amsterdam 1974b; Vol. II: 585–600
  • Albuquerque E. X., Sasa M., Avner B. P., Daly J. W. Possible site of action of batrachotoxin. Nature New Biology 1971b; 234: 93–94
  • Albuquerque E. X., Sasa M., Sarvey J. M. Batrachotoxin has no effect on the electrogenic membranes of lobster and crayfish muscles. Life Sci. 1972b; 11: 357–363
  • Albuquerque E. X., Seyama I., Narahashi T. Characterization of batrachotoxin-induced depolarization of the squid giant axons. J. Pharmacol. Exp. Therapeut. 1973b; 184: 308–314
  • Albuquerque E. X., Tsai M.-C., Aronstam R. S., Eldefrawi A. T., Eldefrawi M. E. Sites of action of phencyclidine. II. Interaction with the ionic channel of the nicotinic receptor. Mol. Pharmacol. 1980b; 18: 167–178
  • Albuquerque E. X., Tsai M.-C., Aronstram R. S., Witkop B., Eldefrawi A. T., Eledefrawi M. E. Phencyclidine interactions with the ionic channel of the acetylcholine receptor and electrogenic membrane. Proc. Nat. Acad. Sci. (USA) 1980c; 77: 1224–1228
  • Albuquerque E. X., Warnick J. E., Guth L. Spinal cord regeneration and paraplegia. Prog. Clin. Biol. Res. 1980d; 39: 41–62
  • Albuquerque E. X., Warnick J. E., Sansone F. M. The pharmacology of batrachotoxin. II. Effect on electrical properties of the mammalian nerve and skeletal muscle membranes. J. Pharmacol. Exp. Therapeut. 1971c; 176: 511–528
  • Albuquerque E. X, Warnick J. E., Maleque M. A., Kauffman F. C., Tamburini R., Nimit Y., Daly J. W. The pharmacology of pumiliotoxin-B. I. Interaction with calcium sites in the sarcoplasmic reticulum of skeletal muscle. Mol. Pharmacol. 1981a; 19: 411–424
  • Albuquerque E. X., Warnick J. E., Sansone F. M., Daly J. The pharmacology of batrachotoxin. V. A comparative study of membrane properties and the effects of batrachotoxin on sartorius muscles of the frogs Phyllobates, aurotaenia, Rana, pipiens. J. Pharmacol. Exp. Therapeut. 1973c; 184: 315–329
  • Albuquerque E. X., Warnick J. E., Tamburini R., Kaufman F. C., Daly J. W. Interaction of pumiliotoxin-B with calcium sites in the sarcoplasmic reticulum and nerve terminal of normal and dystrophic muscle. Exploratory Concepts in Muscular Dystrophy. Excerpta Medica, Amsterdam 1981b, in press
  • Anwyl R., Narahashi T. Inhibition of the acetylcholine receptor by histrionicotoxin. Brit. J. Pharmacol. 1980; 68: 611–616
  • Aratani M., Dunkerton L. V., Fukuyama T., Kishi Y., Kakoi H., Sugiura S., Inoue S. Synthetic studies on histrionicotoxins. I. A stereocontrolled synthesis of (±)-perhydrohistrionico-toxin. J. Org. Chem. 1975; 40: 2009–2011
  • Aronstam R. S. Interactions of tricyclic antidepressants with a synaptic ion channel. Life Sci. 1981; 28: 59–64
  • Aronstam R. S., Eldefrawi A. T., Eldefrawi M. E. Similarities in the binding sites of the muscarinic receptor and the ionic channel of the nicotinic receptor. Biochem. Pharmacol. 1980; 29: 1311–1314
  • Aronstam R. S., Eidefrawi A. T., Pessah I. N., Daly J. W., Albuquerque E. X., Eldefrawi M. E. Regulation of [3H]perhydro-histrionicotoxin binding to Torpedo, ocellata electroplax by effectors of the acetylcholine receptor. J. Biol. Chem. 1981; 256: 2843–2851
  • Bartels-Bernal E., Rosenberry T. L., Daly J. W. Effect of batrachotoxin on the electroplax of electric eel: Evidence for voltage-dependent interaction with sodium channels. Proc, Nat. Acad. Sci. (USA) 1977; 74: 951–955
  • Bartels de Bernal E. M.I., Llano Diaz E. Algunos efectos de la batracotoxina sobre las electroplacas de la anguila electrica y su antagonismo con anesthesicos locales. Acta Med. Valle 1975; 6: 74–80
  • Blanchard S. G., Raftery M. A. Identification of the polypeptide chains in Torpedo, californica electroplax membranes that interact with a local anesthetic analog. Proc. Nat. Acad. Sci. (USA) 1979; 76: 81–85
  • Blanchard S. G., Elliott J., Raftery M. A. Interaction of local anesthetics with Torpedo, californica membrane-bound acetylcholine receptor. Biochemistry 1979; 18: 5880–5885
  • Boegman R. J., Albuquerque E. X. Axonal transport in rats rendered paraplegic following a single subarachnoid injection of either batrachotoxin or 6-aminonicotinamide into the spinal cord. J. Neurobiol. 1980; 11: 283–290
  • Boegman R. J., Oliver T. W. Neural influence on muscle hydrolase activity. Life Sci. 1980; 27: 1339–1344
  • Boegman R. J., Riopelle R. J. The role of axonal transport and impulse conduction on the uptake and retrograde transport of nerve growth factor and bovine serum albumin in peripheral nerve. J. Neurobiol. 1980a; 11: 497–501
  • Boegman R. J., Riopelle R. J. Batrachotoxin blocks slow and retrograde axonal transport in vivo. Neurosci. Lett. 1980b; 18: 143–147
  • Boegman R. J., Deshpande S. S., Albuquerque E. X. Consequences of axonal transport blockade induced by batrachotoxin on mammalian neuromuscular junction I. Early pre-and post-synaptic changes. Brain Res. 1980; 187: 183–196
  • Brown G. B., Daly J. W. Interaction of batrachotoxinin-A benzoate with voltage sensitive sodium channels. The effects of pH. Cell. Mol. Neurobiol. 1982, in press
  • Brown G. B., Tieszen S. C., Daly J. W., Warnick J. E., Albuquerque E. X. Batrachotoxin-A 20-α-benzoate: A new radioactive ligand for voltage sensitive sodium channels. Cell. Mol. Neurobiol. 1981; 1: 19–40
  • Brown J. H. Calcium-dependent blockade of cardiac cyclic AMP accumulation by batrachotoxin and veratridine. Mol. Pharmacol. 1981; 20: 113–117
  • Burgermeister W., Catterall W. A., Witkop B. Histrionicotoxin enhances agonist-induced desensitization of acetylcholine receptor. Proc. Nat. Acad. Sci. (USA) 1977; 74: 5754–5758
  • Burgermeister W., Klein W. L., Nirenberg M., Witkop B. Comparative binding studies with cholinergic ligands and histrionicotoxin at muscarinic receptors of neural cell lines. Mol. Pharmacol. 1978; 14: 751–767
  • Catterall W. A. Inhibition of voltage-sensitive sodium channels in neuroblastoma cells by antiarrhythmic drugs. Mol. Pharmacol. 1981; 20: 356–362
  • Catterall W. A. Activation of the action potential Na+ ionophore by neurotoxins: An allosteric model. J. Biol. Chem. 1977a; 252: 8669–8676
  • Catterall W. A. Activation of the action potential Na+ ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin. J. Biol. Chem. 1975a; 250: 4053–4059
  • Catterall W. A. Cooperative activation of action potential Na+ ionophore by neurotoxins. Proc. Nat. Acad. Sci. (USA) 1975b; 72: 1782–1786
  • Catterall W. A. Activation and inhibition of the action potential Na+ ionophore of cultured rat muscle cells by neurotoxins. Biochem. Biophys. Res. Comm. 1976a; 68: 136–142
  • Catterall W. A. Purification of a toxic protein from scorpion venom which activates the action potential Na+ ionophore. J. Biol. Chem. 1976b; 251: 5528–5536
  • Catterall W. A. Membrane potential-dependent binding of scorpion toxin to the action potential Na+ ionophore. Studies with a toxin derivative prepared by lactoperoxidase-catalyzed iodination. J. Biol. Chem. 1977b; 252: 8660–8668
  • Catterall W. A. Neurotoxins as allosteric modifiers of voltage-sensitive sodium channels. Adv. Cytopharmacol. 1979; 3: 305–316
  • Catterall W. A. Pharmacologic properties of voltage-sensitive sodium channels in chick muscle fibers developing in vitro. Dev. Biol. 1980a; 78: 222–230
  • Catterall W. A. Neurotoxins that act on voltage-sensitive sodium channels in excitable membranes. Ann. Rev. Pharmacol. Toxicol. 1980b; 20: 15–44
  • Catterall W. A., Beneski D. A. Interaction of polypeptide neurotoxins with a receptor site associated with voltage-sensitive sodium channels. J. Supramol. Struct. 1980; 14: 295–304
  • Catterall W. A., Beress L. Sea anemone toxin and scorpion toxin share a common receptor site associated with the action potential sodium ionophore. J. Biol. Chem. 1978; 253: 7393–7396
  • Catterall W. A., Ray R. Interactions of neurotoxins with the action potential Na+ ionophore. J. Supramol. Struct. 1976; 5: 397–407
  • Catterall W. A., Risk M. Toxin T46 from Ptychodiscus, brevis (formerly Gymnodinium, breve) enhanced activation of voltage sensitive sodium channels by veratridine. Mol. Pharmacol. 1981; 19: 345–348
  • Catterall W. A., Morrow C. S., Hartshorne R. P. Neurotoxin binding to receptor sites associated with voltage-sensitive sodium channels in intact, lysed, and detergent-solubilized brain membranes. J. Biol. Chem. 1979; 254: 11379–11388
  • Catterall W. A., Ray R., Morrow C. S. Membrane potential dependent binding of scorpion toxin to action potential Na ionophore. Proc. Nat. Acad. Sci. (USA) 1976; 73: 2682–2686
  • Catterall W. A., Morrow C. S., Brown G. B., Daly J. W. Binding of batrachotoxinin A 20-α-benzoate to a receptor site associated with sodium channels in synaptic nerve ending particles. J. Biol. Chem. 1981, in press
  • Colquhoun D., Henderson R., Ritchie J. M. The binding of labelled tetrodotoxin to non-myelinated nerve fibres. J. Physiol (London) 1972; 227: 95–126
  • Conn P. J., Rogers D. C. Gonadotropin release from pituitary cultures following activation of endogenous ion channels. Endocrinology 1980; 107: 2133–2134
  • Corey E. J., Arnett J. F., Widiger G. N. A simple total synthesis of (±)-perhydrohistrionicotoxin. J. Amer. Chem. Soc. 1975a; 97: 430–431
  • Corey E. J., Ueda Y., Ruden R. A. Synthetic route to neurotoxins in the 2,7-epi-histrionicotoxin series. Tetrahedron Letters, 1975b: 4347–4350
  • Creveling C. R., McNeal E. T., McCulloh D. H., Daly J. W. Membrane potentials in cell-free preparations from guinea pig cerebral cortex: Effect of depolarizing agents and cyclic nucleotides. J. Neurochemistry 1980; 35: 922–932
  • Creveling C. R., McNeal E., Daly J. W., Brown G. B. Depolarization of brain vesicle preparations and binding of batra-chotoxins: Blockage by local anesthetics. Mol. Pharmacol. 1982, submitted
  • Daly J. W. Alkaloids of neotropical poison frogs (Dendrobatidae). Prog. Chem. Nat. Products, W. Herz. Springer Verlag, New York 1982; Volume 43, in press
  • Daly J. W., Myers C. W. Toxicity of Panamanian poison frogs (Dendrobates): Some biological and chemical aspects. Science 1967; 156: 970–973
  • Daly J., Witkop B. Batrachotoxin, an extremely active cardio-and neurotoxin from the Colombian arrow poison frog. Clinical Toxicology 1971; 4: 331–342
  • Daly J., Albuquerque E. X., Kauffman F. C., Oesch F. Effects of bactrachotoxin on electroplax Na+-K+-ATPase and levels of ATP in rat muscle. J. Neurochem. 1972; 19: 2829–2833
  • Daly J. W., Brown G. B., Mensah-Dwumah M., Myers C. W. Classification of skin alkaloids from neotropical poison-dart frogs (Dendrobatidae). Toxicon 1978; 16: 163–188
  • Daly J. W., Karle I., Myers C. W., Tokuyama T., Waters J. A., Witkop B. Histrionicotoxins: Roentgen-ray analysis of the novel allenic and acetylenic spiroalkaloids isolated from a Colombian frog, Dendrobates, histrionicus. Proc. Nat. Acad. Sci. (USA) 1971; 68: 1870–1875
  • Daly J. W., McNeal E., Partington C., Neuwirth M., Creveling C. R. Accumulations of cyclic AMP in adenine-labeled cell-free preparations from guinea pig cerebral cortex: Role of α-adrenergic and H1-histaminergic receptors. J. Neurochem. 1980a; 35: 326–337
  • Daly J. W., Myers C. W., Warnick J. E., Albuquerque E. X. Levels of batrachotoxin and lack of sensitivity to its action in poison-dart frogs (Phyllobates). Science 1980b; 208: 1383–1385
  • Daly J. W., Tokuyama T., Fujiwara T., Highet R. J., Karle I. L. A new class of indolizidine alkaloids from the poison frog, Dendrobates, tricolor. X-ray analysis of 8-hydroxy-8-methyl-6-(2′-methylhexylidene)-1-azabicyclo [4.3.0]nonane. J. Amer. Chem. Soc. 1980c; 102: 830–836
  • Daly J. W., Witkop B., Tokuyama T., Nishikawa T., Karle I. L. Gephyrotoxins, histrionicotoxins and pumiliotoxins from the neotropical frog Dendrobates, histrionicus. Helv. Chim. Acta 1977; 60: 1128–1140
  • Dolly J. O., Albuquerque E. X., Sarvey J. M., Mallick B., Barnard E. A. Binding of perhydrohistrionicotoxin to the postsynaptic membrane of skeletal muscle in relation to its blockade of acetylcholine-induced depolarization. Mol. Pharmacol. 1977; 13: 1–14
  • Eldefrawi M. E., Eldefrawi A. T. Biochemical studies on the ionic channel of Torpedo acetylcholine receptor. Adv. Cytopharmacol. 1979; 3: 213–223
  • Eldefrawi M. E., Eldefrawi A. T. Coupling between the nicotinic acetylcholine receptor site and the ionic channel site. Ann. New York Acad. Sci. 1980; 358: 239–252
  • Eldefrawi A. T., Bakry N. M., Eldefrawi M. E., Tsai M.-C., Albuquerque E. X. Nereistoxin interaction with the acetylcholine receptor-ionic channel complex. Mol. Pharmacol. 1980a; 17: 172–179
  • Eldefrawi A. T., Eldefrawi M. E., Albuquerque E. X., Oliveira A. C., Mansour N., Adler M., Daly J. W., Brown G. B., Burgermeister W., Witkop B. Perhydrohistrionicotoxin A potential ligand for the ion conductance modulator of the acetylcholine receptor. Proc. Nat. Acad. Sci. (USA) 1977; 74: 2172–2176
  • Eldefrawi M. E., Aronstam R. S., Bakry N. M., Eldefrawi A. T., Albuquerque E. X. Activation, inactivation, and desensitization of acetylcholine receptor channel complex detected by binding of perhydrohistrionicotoxin. Proc. Nat. Acad. Sci. (USA) 1980b; 77: 2309–2313
  • Eldefrawi M. E., Copio D. S., Hudson C. S., Rash J., Mansour N. A., Eldefrawi A. T., Albuquerque E. X. Effects of antibodies to Torpedo acetylcholine receptor on the acetylcholine receptor-ionic channel complex of Torpedo electroplax and rabbit intercostal muscle. Exp. Neurol. 1979; 64: 428–444
  • Eldefrawi M. E., Eldefrawi A. T., Aronstam R. S., Maleque M. A., Warnick J. E., Albuquerque E. X. [H-3]phencyclidine-a probe of the ionic channel of the nicotinic receptor. Proc. Nat. Acad. Sci. USA 1980c; 77: 7458–7462
  • Eldefrawi M. E., Eldefrawi A. T., Mansour N. A., Daly J. W., Witkop B., Albuquerque E. X. Acetylcholine receptor and ionic channel of Torpedo electroplax: Binding of perhydro-histrionicotoxin to membrane and solubilized preparations. Biochemistry 1978; 17: 5474–5484
  • Eldefrawi M. E., Shaker N., Mansour N. A., Warnick J. E., Albuquerque E. X. Detection of nicotinic cholinergic transmission in Malapterurus, electricus electroplax. Life Science 1981a; 29: 1033–1037
  • Eldefrawi M. E., Warnick J. E., Schofield G. G., Albuquerque E. X., Eldefrawi A. T. Interaction of imipramine with the ionic channel of the acetylcholine receptor of motor enplate and electric organ. Biochem. Pharmacol. 1981b; 30: 1391–1394
  • Elliott J., Raftery M. A. Interactions of perhydrohistrioni-cotoxin with postsynaptic membranes. Biochem. Biophys. Res. Comm. 1977; 77: 1347–1353
  • Elliott J., Raftery M. A. Binding of perhydrohistrionicotoxin to intact and detergent-solubilized membranes enriched in nicotinic acetylcholine receptor. Biochemistry 1979; 18: 1868–1874
  • Elliott J., Dunn S. M.J., Blanchard S. G., Raftery M. A. Specific binding of perhydrohistrionicotoxin to Torpedo acetylcholine receptor. Proc. Nat. Acad. Sci. (USA) 1979; 76: 2576–2579
  • Forman D. S., Shain W. G., Jr. Batrachotoxin blocks saltatory organelle movement in electrically excitable neuroblastoma cells. Brain Res. 1981; 211: 242–247
  • Frelin C., Vigne P., Ponzio G., Romey G., Tourneur Y., Husson H. P., Lazdunski M. The interaction of ervatamine and epiervatamine with the action potential Na+ ionophore. Mol. Pharmacol. 1981; 20: 107–112
  • Garcia J. H., Deshpande S. S., Pence R. S., Albuquerque E. X. Spinal myelopathy induced by subarachnoid batrachotoxin: Ultrastructure and electrophysiology. Brain Res. 1978; 140: 75–87
  • Garrison D. L., Albuquerque E. X., Warnick J. E., Daly J. W., Witkop B. Antagonism of carbamylcholine-induced depolarization by batrachotoxin and veratridine. Mol. Pharmacol. 1978; 14: 111–121
  • Gill D. L., Grollman E. F., Kohn L. D. Calcium transport mechanisms in membrane vesicles from guinea pig brain synaptosomes. J. Biol. Chem. 1981; 256: 184–192
  • Glavinovic M., Henry J. L., Kato G., Krnjevic K., Puil E. Histrionicotoxin: Effects on some central and peripheral excitable cells. Canad. J. Physiol. Pharmacol. 1974; 52: 1220–1226
  • Heidmann T., Changeux J.-P. Structural and functional properties of the acetylcholine receptor protein in its purified and membrane-bound states. Ann. Rev. Biochem. 1978; 47: 317–357
  • Henderson R., Strichartz G. Ion fluxes through the sodium channels of garfish olfactory nerve membranes. J. Physiol. (London) 1974; 238: 329–342
  • Hery F., Simonnet G., Bourgoin S., Soubrie P., Artaud F., Hamon M., Glowinski J. Effect of nerve activity on the in vivo release of [3H]serotonin continuously formed from L-[3H]tryptophan in the caudate nucleus of the cat. Brain Res. 1979; 169: 317–334
  • Hogan P. M., Albuquerque E. X. The pharmacology of batrachotoxin. III. Effect on the heart Purkinje fibers. J. Pharmacol. Exp. Therapeut. 1971; 176: 529–537
  • Holz R. W., Coyle J. T. The effects of various salts, temperature, and the alkaloids veratridine and batrachotoxin on the uptake of [3H]dopamine into synaptosomes from rat striatum. Mol. Pharmacol. 1974; 10: 746–758
  • Honerjaeger P., Reiter M. Batrachotoxin: Activity-dependent prolongation of the cardiac action potential and positive inotropic effect. Brit. J. Pharmacol. 1976; 58: 415P
  • Honerjaeger P., Reiter M. The cardiotoxic effect of batrachotoxin. Naunyn-Schmiedeberg's Arch. Pharmacol. 1977; 299: 239–252
  • Huang L.-Y. M., Catterall W. A., Ehrenstein G. Comparison of ionic selectivity of batrachotoxin-activated channels with different tetrodotoxin dissociation constants. J. Gen. Physiol. 1979; 73: 839–854
  • Huang L.-Y. M., Ehrenstein G. Local anesthetics QX 572 and benzocaine act at separate sites on the batrachotoxin-activated sodium channel. J. Physiol. 1981; 77: 137–154
  • Huang L.-Y. M., Ehrenstein G., Catterall W. A. Interaction between batrachotoxin and yohimbine. Biophys. J. 1978; 23: 219–231
  • Huang M., Daly J. W. Interrelationships among levels of ATP, adenosine and cyclic AMP in incubated slices of guinea pig cerebral cortex: Effect of depolarizing agents, psychotropic drugs and metabolic inhibitors. J. Neurochem. 1974; 23: 393–404
  • Huang M., Shimizu H., Daly J. W. Accumulation of cyclic adenosine monophosphate in incubated slices of brain tissue. 2. Effect of depolarizing agents, membrane stabilizers, phosphodiesterase inhibitors and adenosine analogs. J. Med. Chem. 1972; 15: 462–466
  • Ibuka T., Masaki N., Saji I., Tanaka K., Inubushi Y. Synthesis of dl-pumiliotoxin C hydrochloride and its crystal structure. Chem. Pharm. Bull. (Japan) 1975; 23: 2779–2790
  • Jacques Y., Romey G., Lazdunski M. Toxin-induced K+ efflux through the Na+ channel of neuroblastoma cells. Eur. J. Biochem. 1980; 111: 265–273
  • Jansson S.-E., Albuquerque E. X., Daly J. The pharmacology of batrachotoxin. VI. Effects on the mammalian motor nerve terminal. J. Pharmacol. Exp. Therapeut. 1974; 189: 525–537
  • Johnson D. F., Daly J. W. Biosynthesis of cholesterol and cholesterol acetate in dendrobatid arrow poison frogs. Biochem. Pharmacol. 1971; 20: 2555–2559
  • Kato G., Changeux J.-P. Studies on the effect of histrionicotoxin on the monocellular electroplax from Electrophorus, electricus and on the binding of [3H]acetylcholine to membrane fragments from Torpedo, marmorata. Mol. Pharmacol. 1976; 12: 92–100
  • Kato G., Glavinovic M., Henry J., Krnjevic K., Puil E., Tattrie B. Actions of histrionicotoxin on acetylcholine receptors. Croatica Chemica Acta 1975; 47: 439–447
  • Kayaalp S. O., Albuquerque E. X., Warnick J. E. Ganglionic and cardiac actions of batrachotoxin. Eur. J. Pharmacol. 1970; 12: 10–18
  • Khodorov B. Some aspects of the pharmacology of sodium channels in nerve membrane. Process of inactivation. Biochem. Pharmacol. 1979; 28: 1451–1459
  • Khodorov B. I. Chemicals as tools to study nerve fiber sodium channels: Effects of batrachotoxin and some local anesthetics. Membrane Transport Processes, D. C. Tosteson, Y. A. Duchinnikov, R. Latorre. Raven Press, New York 1978; Vol. II: 153–174
  • Khodorov B. I. Pharmacologic analysis of sodium channel inactivation in a nerve fiber membrane. Neirofiziologiya 1980; 12: 317–331
  • Khodorov B. I., Revenko S. V. Further analysis of the mechanisms of action of batrachotoxin on the membrane of myelinated nerve. Neuroscience 1979; 4: 1315–1330
  • Khodorov B. I., Peganov E. M., Revenko S. V., Shishkova L. D. Sodium currents in voltage clamped nerve fiber of frog under the combined action of batrachotoxin and procaine. Brain Res. 1975; 84: 541–546
  • Kilpatrick D. L., Slepetis R., Kirshner N. Inhibition of catecholamine secretion from adrenal medulla cells by neuro-toxins and cholinergic antagonists. J. Neurochem. 1981a; 37: 125–131
  • Kilpatrick D. L., Slepetis R., Kirshner N. Ion channels and membrane potential in stimulus-secretion coupling in adrenal medulla cells. J. Neurochem. 1981b; 36: 1245–1255
  • Krodel E. K., Beckman R. A., Cohen J. B. Identification of a local anesthetic binding site in nicotinic post-synaptic membranes isolated from Torpedo, marmorata electric tissue. Mol. Pharmacol. 1979; 15: 294–312
  • Krueger B. K., Blaustein M. P. Sodium channels in presynaptic nerve terminals. J. Gen. Physiol. 1980; 76: 287–313
  • Kumara-Siri M. H. Batrachotoxin inhibits axonal transport without affecting membrane potential in single neurons of Aplysia, californica. J. Neurobiol. 1979; 10: 509–512
  • Lapa A. J., Albuquerque E. X., Sarvey J. M., Daly J., Witkop B. Effects of histrionicotoxin on the chemosensitive and electrical properties of skeletal muscle. Exp. Neurol. 1975; 47: 558–578
  • Lawrence J. C., Catterall W. A. Textrodotoxin-insensitive sodium channels. Binding of polypeptide neurotoxins in primary cultures of rat muscle cells. J. Biol. Chem. 1981a; 256: 6223–6229
  • Lawrence J. C., Catterall W. A. Tetrodotoxin-insensitive sodium channels. Ion flux studies of neurotoxin action in a clonal rat muscle cell line. J. Biol. Chem. 1981b; 256: 6213–6222
  • Lazdunski M., Balerna M., Barhanin J., Chicheportiche R., Fosset M., Frelin C., Jacques Y., Lombet A., Pouyssegur J., Renaud J. F., Romey G., Schweitz H., Vincent J. P. Molecular aspects of the structure and mechanism of the voltage-dependent sodium channel. Ann. New York Acad. Sci. 1980a; 358: 169–182
  • Lazdunski M., Balerna M., Barhanin J., Chicheportiche R., Fosset M., Frelin C., Jacques Y., Lombet A., Pouyssequr J., Renaud J. F., Romey G., Schweitz H., Vincent J. P. The voltage-dependent sodium channel as a drug receptor. Neurotransmitters and their Receptors, U. Z. Littauer, Y. Dudai, I. Silman, V. I. Teichberg, Z. Vogel. John Wiley & Sons, New York 1980b; 511–530
  • Lester H. A. Analysis of sodium and potassium redistribution during sustained permeability increases at the innervated face of Electrophorus electroplaques. J. Gen. Physiol. 1978; 72: 847–862
  • Macdonald T. L. Indolizidine alkaloid synthesis. Preparation of the pharaoh ant trail pheromone and gephyrotoxin 223 stereoisomers. J. Organ. Chem. (USA) 1980; 45: 193–195
  • Marki F., Witkop B. The venom of the Colombian arrow poison frog Phyllobates, bicolor. Experientia 1963; 19: 329–338
  • Masukawa L. M., Albuquerque E. X. Voltage-and time-dependent action of histrionicotoxin on the endplate current of the frog muscle. J. Gen. Physiol. 1978; 72: 351–367
  • Matthews J. C., Albuquerque E. X., Eldefrawi M. E. Influence of batrachotoxin, veratridine, grayanotoxin I and tetrodotoxin on uptake of Na-22 by rat brain membrane preparations. Life Sci. 1979; 25: 1651–1658
  • Matthews J. C., Warnick J. E., Albuquerque E. X., Eldefrawi M. E. Characterization of the electrogenic sodium channel from rat brain membranes using neurotoxin-dependent 22Na+ uptake. Membrane Biochem. 1981, in press
  • Max S. R., Deshpande S. S., Albuquerque E. X. Neural regulation of muscle acetylcholinesterase: Effects of batrachotoxin and 6-aminonicotinamide. Brain Res. 1977; 130: 101–107
  • McCarthy K. D., Harden T. K. Identification of two benzodiazepine binding sites on cells cultured from rat cerebral cortex. J. Pharmacol. Exp. Therapeut. 1981; 216: 183–191
  • McNeal E. T., Creveling C. R., Daly J. W. Cyclic AMP-generating systems in cell-free preparations from guinea pig cerebral cortex: Loss of adenosine and amine responsiveness due to low levels of endogenous adenosine. J. Neurochem. 1980; 35: 338–342
  • Mensah-Dwumah M., Daly J. W. Pharmacological activity of alkaloids from poison-dart frogs (Dendrobatidae). Toxicon 1978; 16: 189–194
  • Mezey K. Venenos de flecha de Colombia. Acad. Colombiana de Ciencias Exactas fisicas y naturales (Bogota) Revista 1947a; 7: 319–323
  • Mezey K. “Fiu-Fiú”. Estudio toxicològica y farmacodinamico de un veneno de flechas y dardos, obtenido de la secreciòn cutànea de una “Rana del Choco” (Dendrobates sp.) [Cèsar Uribe-Piedrahita]. Bogota, Colombia 1947b
  • Moore G. R.W., Boegman R. J., Robertson D. M., Riopelle R. J. Batrachotoxin induced axonal necrosis in peripheral nerves. Brain Res. 1981; 207: 481–485
  • Myers C. W., Daly J. W. Preliminary evaluation of skin toxins and vocalizations in taxonomic and evolutionary studies of poison-dart frogs (Dendrobatidae). Bull. Amer. Museum Natural History 1976; 157: 173–262
  • Myers C. W., Daly J. W. A name for the poison frog of Cordillera Azul, eastern Peru, with notes on its biology and skin toxins (Dendrobatidae). American Museum Novitates No. 2674, 1979: 1–24
  • Myers C. W., Daly J. W. Taxonomy and ecology of Dendrobates, bombetesA new Andean poison frog with new skin toxins. American Museum Novitates 1980; 1–23, No. 2692
  • Myers C. W., Daly J. W., Malkin B. A dangerously toxic new frog (Phyllobates) used by Embera Indians of western Colombia, with discussion of blowgun fabrication and dart poisoning. Bull. Amer. Museum Natural History 1978; 161: 307–366
  • Narahashi T. Toxic chemicals as probes of nerve membrane function. Adv. Exp. Med. Biol. 1977; 84: 407–445
  • Narahashi T., Albuquerque E. X., Deguchi T. Effects of batrachotoxin on membrane potential and conductance of squid giant axons. J. Gen. Physiol. 1971a; 58: 54–70
  • Narahashi T., Deguchi T., Albuquerque E. X. Effects of batrachotoxin on nerve membrane potential and conductances. Nature New Biology 1971b; 229: 221–222
  • Neubig R. R., Krodel E. K., Boyd N. D., Cohen J. B. Acetyl-choline and local anesthetic binding to Torpedo nicotinic postsynaptic membranes after removal of nonreceptor peptides. Proc. Nat. Acad. Sci. (USA) 1979; 76: 690–694
  • Neuwirth M., Daly J. W., Myers C. W., Tice L. W. Morphology of the granular secretory glands in skin of poison-dart frogs (Dendrobatidae). Tissue & Cell 1979; 11: 755–771
  • Nimitkitpaisan Y., Daly J. W., Jessup P. J., Overman L. E., Eldefrawi A. T., Eldefrawi M. E., Warnick J. W., Albuquerque E. X. Pumiliotoxin-C and synthetic analogs: A new class of nicotinic antagonists. Trans. Am. Soc. Neurochem. 1980; 11: 233
  • Ochs S., Worth R. Batrachotoxin block of fast axoplasmic transport in mammalian nerve fibers. Science 1975; 187: 1087–1089
  • Otten U., Thoenen H. Role of membrane depolarization in transsynaptic induction of tyrosine hydroxylase in organ cultures of sympathetic ganglia. Neurosci. Lett. 1976; 2: 93–96
  • Oswald R., Changeux J.-P. Ultraviolet light-induced labeling by noncompetitive blockers of the acetylcholine receptor from Torpedo, marmorata. Proc. Nat. Acad. Sci. (USA) 1981, in press
  • Peganov E. M., Revenko S. V., Khodorov B. I., Shishkova L. D. Batrachotoxin and aconitine, modifiers of rapid sodium channels in the nerve fiber membrane. Mol. Biol. (Kiev) 1976; 15: 42–56
  • Ponzio G., Jacques Y., Frelin C., Chicheportiche R., Lazdunski M. An in vitro system to study the action potential sodium channel. FEBS Lett. 1980; 121: 265–269
  • Posada Arango A. El veneno de rana de los indios del Chocò. “Estudios cientificos del doctor Andrès Posado con algunos otros escritos suyos sobre diversos temas”, C. A. Molina. Imprenta Oficial, MedellìnColombia 1909; 78–88
  • Ramos S., Grollman E. F., Lazo P. S., Dyer S. A., Habig W. H., Hardegree M. C., Kaback H. R., Kohn L. D. Effect of tetanus toxin on the accumulation of the permeant lipophilic cation tetraphenylphosphonium by guinea pig brain synaptosomes. Proc. Nat. Acad. Sci. (USA) 1979; 76: 4783–4787
  • Ray R., Catterall W. A. Membrane potential dependent binding of scorpion toxin to the action of potential sodium ionophore. Studies with a 3-(4-hydroxy-3-[125I]iodophenyl) propionyl derivative. J. Neurochem. 1978; 31: 397–407
  • Ray R., Morrow C. S., Catterall W. A. Binding of scorpion toxin to receptor sites associated with voltage-sensitive sodium channels in synaptic nerve ending particles. J. Biol. Chem. 1978; 253: 7307–7313
  • Revenko S. V. Effect of electrical stimulation of nodes of Ranvier on the rate of sodium channel modification by batrachotoxin under conditions of potential fixation. Neiro-fiziologiya 1977; 9: 546–549
  • Revenko S. V., Khodorov B. I. Effect of batrachotoxin on the selectivity of sodium channels in myelinated nerve fibre membrane. Neirofiziologiya 1977; 9: 313–316
  • Roseen J. S., Fuhrman F. A. Comparison of the effects of atelopidtoxin with those of tetrodotoxin, saxitoxin and batrachotoxin on beating of cultured chick heart cells. Toxicon 1971; 9: 411–415
  • Santesson C. G. An arrow poison with cardiac effect from the New World. “Comparative Ethnographical Studies. 9”, E. Nordenskiold. Elanders Boktryckeri, Goteborg 1931; 157–187
  • Santesson C. G. Froschgift aus Columbia. Naunyn-Schmiedeberg's Arch. Pharmacol. 1936; 181: 180
  • Schimerlik M. I., Quast U., Raftery M. A. Ligand-induced changes in membrane-bound acetylcholine receptor observed by ethidium fluroescence. 3. Stopped-flow studies with histri-onicotoxin. Biochemistry 1979; 18: 1902–1906
  • Shimizu H., Daly J. W. Effect of depolarizing agents on accumulation of cyclic adenosine 3′,5′-monophosphate in cerebral cortical slices. Eur. J. Pharmacol. 1972; 17: 240–252
  • Shimizu H., Creveling C. R., Daly J. Stimulated formation of adenosine 3′,5′-cyclic phosphate in cerebral cortex: Synergism between electrical activity and biogenic amines. Proc. Nat. Acad. Sci. (USA) 1970a; 65: 1033–1040
  • Shimizu H., Creveling C. R., Daly J. W. Cyclic adenosine 3′,5′-monophosphate formation in brain slices: Stimulation by batrachotoxin, ouabain, veratridine, and potassium ions. Mol. Pharmacol. 1970b; 6: 184–188
  • Shimizu H., Creveling C. R., Daly J. W. Effect of membrane depolarization and biogenic amines on the formation of cyclic AMP in incubated brain slices. Adv. Biochem. Psychopharmacol. 1970c; 3: 135–154
  • Shotzberger G. S., Albuquerque E. X., Daly J. W. The effects of batrachotoxin on cat papillary muscle. J. Pharmacol. Exp. Therapeut. 1976; 196: 433–444
  • Simpson L. L. Pharmacological studies on the subcellular site of action of botulinum toxin type A. J. Pharmacol. Exp. Therapeut. 1978; 206: 661–669
  • Sobel A., Heidmann T., Changeux J.-P. Purification of a protein binding quinacrine and histrionicotoxin from membrane fragments rich in acetylcholine receptor from Torpedo-marmorata. Compt. Rendus Acad. Sci. Paris 1977; 285D: 1255–1258
  • Sobel A., Heidmann T., Hofler J., Changeux J.-P. Distinct protein components from Torpedo, marmorata membranes carry the acetylcholine receptor site and the binding site for local anesthetics and histrionicotoxin. Proc. Nat. Acad. Sci. (USA) 1978; 75: 510–514
  • Spande T. F., Daly J. W., Hart D. H., Tsai Y.-M., Macdonald T. L. The structure of gephyrotoxin 223AB. Experientia 1981, in press
  • Spivak C. E., Maleque M. A., Oliveira A. C., Masukawa L., Tokuyama T., Daly J. W., Albuquerque E. X. Actions of histrionicotoxins at the ion channel of the nicotinic acetylcholine receptor and the voltage sensitive ion channels of muscle membranes. Mol. Pharmacol. 1981, in press
  • Takahashi K., Witkop B., Brossi A., Maleque A. C., Albuquerque E. X. Total synthesis and electrophysiological properties of natural (-)perhydrohistrionicotoxin, its unnatural (+)-antipode and their desamyl analogs. Helv. Chim. Acta 1982, submitted
  • Tamburini R., Albuquerque E. X., Daly J. W., Kauffman F. C. Inhibition of calcium-dependent ATPase from sarcoplasmic reticulum by a new class of indolizidine alkaloids pumilio-toxins A, B and 251D. J. Neurochem. 1981; 37: 775–780
  • Tamkun M. M., Catterall W. A. Ion flux studies of voltage-sensitive sodium channels in synaptic nerve-ending particles. Mol. Pharmacol. 1981; 19: 78–86
  • Tang C. M., Strichartz G. R., Orkand R. K. Sodium channels in axons and glial cells of the optic nerve of Necturus, maculosa. J. Gen. Physiol. 1979; 74: 629–642
  • Tiedt T. N., Albuquerque E. X., Bakry N. M., Eldefrawi M. E., Eldefrawi A. T. Voltage-and time-dependent actions of piperocaine on the ion channel of the acetylcholine receptor. Mol. Pharmacol. 1979; 16: 909–921
  • Tokuyama T., Daly J., Witkop B. The structure of batracho-toxin, a steroidal alkaloid from the Colombian arrow poison frog, Phyllobates, aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs. J. Amer. Chem. Soc. 1969; 91: 3931–3938
  • Tokuyama T., Daly J., Witkop B., Karle I. L., Karle J. The structure of batrachotoxinin A, a novel steroidal alkaloid from the Colombian arrow poison frog. J. Amer. Chem. Soc. 1968; 90: 1917–1918
  • Tokuyama T., Daly J. W. Steroidal alkaloids (batrachotoxins and 4-hydroxybatrachotoxins), indole alkaloids (calycanthine and chimonanthine) and a piperidinyldipyridine alkaloid (noranabasamine) in skin extracts from the Colombian poisondart frog Phyllobates, terribilis (Dendrobatidae). Tetrahedron Letters 1982, in preparation
  • Tsai M.-C., Mansour N. A., Eldefrawi A. T., Eldefrawi M. E., Albuquerque E. X. Mechanism of action of amantadine on neuromuscular transmission. Mol. Pharmacol. 1978; 14: 787–803
  • Tsai M.-C., Oliveira A. C., Albuquerque E. X., Eldefrawi M. E., Eldefrawi A. T. Mode of action of quinacrine on the acetyl-choline receptor ionic channel complex. Mol. Pharmacol. 1979; 16: 382–392
  • Vincent J. P., Balerna M., Barhanin J., Fosset M., Lazdunski M. Binding of sea anemone toxin to receptor sites associated with gating system of sodium channel in synaptic nerve endings in vitro. Proc. Nat. Acad. Sci. (USA) 1980; 77: 1646–1650
  • Von Braun J., Gmelin W., Petzold A. “Uber Bz-Tetrahydro-chinoline und ihre Derivate (IV)”. Ber. Deutschen Chemischen Gesellshaften 1924; 57: 382–391
  • Wagner H. R., Davis J. N. β-Adrenergic receptor regulation by agonists and membrane depolarization in rat brain slices. Proc. Nat. Acad. Sci. USA 1979; 76: 2057–2061
  • Wan K. K., Boegman R. J. Changes in rat muscle sarcoplasmic reticulum following neural application of batrachotoxin or tetrodotoxin. Exp. Neurol. 1980a; 70: 475–486
  • Wan K. K., Boegman R. J. Calcium uptake by muscle sarcoplasmic reticulum following neural application of batrachotoxin or tetrodotoxin. FEBS Lett. 1980b; 112: 163–167
  • Warnick J. E., Albuquerque E. X. Models of paraplegia in animals: Trophic relationships. Federat. Proc. 1978; 37: 2811–2817
  • Warnick J. E., Albuquerque E. X., Lapa A. J., Daly J., Witkop B. Actions of neurotoxins on the acetylcholine receptor-ionic conductance modulator unit and on sodium channels. Proc. Sixth Int. Congr. Pharmacol. 1976; 1: 67–76
  • Warnick J. E., Albuquerque E. X., Onur R., Jansson S.-E., Daly J., Tokuyama T., Witkop B. The pharmacology of batrachotoxin. VII. Structure-activity relationships and the effects of pH. J. Pharmacol. Exp. Therapeut. 1975; 193: 232–245
  • Warnick J. E., Albuquerque E. X., Sansone F. M. The pharmacology of batrachotoxin. I. Effects on the contractile mechanism and on neuromuscular transmission of mammalian skeletal muscle. J. Pharmacol. Exp. Therapeut. 1971; 176: 497–510
  • Wennogle L. P., Oswald R., Saitoh T., Changeux J.-P. Dissection of the 66000-Dalton subunit of the acetylcholine receptor. Biochemistry 1981; 20: 2492–2496
  • West G. J., Catterall W. A. Selection of variant neuroblastoma clones with missing or altered sodium channels. Proc. Nat. Acad. Sci. (USA) 1979; 76: 4136–4140
  • Witzemann V., Raftery M. Ligand binding sites and subunit interactions of Torpedo, californica acetylcholine receptor. Biochemistry 1978; 17: 3598–3604
  • Wu W. C.-S., Raftery M. A. Functional properties of acetylcholine receptor monomeric and dimeric forms in reconstituted membranes. Biochem. Biophys. Res. Commun. 1981; 99: 436–444

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.