Conotoxins and their potential pharmaceutical applications

Drug Development Research

Volumn 46, Issue 3-4, 1999, Pages 219-234

  Adams, David J ^a   Alewood, Paul F ^b   Craik, David J ^b   Drinkwater, Roger D ^a   Lewis, Richard J ^a,b  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b Ctr for Drug Design and Development   (Australia)

Author keywords

Acetylcholine; Crystal structure; Gene cloning NMR spectroscopy; Ion channels; Nicotinic receptor; Peptide; Sodium channel; Synaptic transmission

Indexed keywords

CONOTOXIN; NICOTINIC RECEPTOR; OMEGA CONOTOXIN; OMEGA CONOTOXIN MVIIA;

ANALGESIC ACTIVITY; ARTICLE; CALCIUM TRANSPORT; CHRONIC PAIN; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG TARGETING; HUMAN; NEUROTRANSMISSION; NONHUMAN; POTASSIUM TRANSPORT; SODIUM TRANSPORT; STRUCTURE ACTIVITY RELATION; TOXIN STRUCTURE;

EID: 0033066629     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2299(199903/04)46:3/4<219::AID-DDR7>3.0.CO;2-S     Document Type: Article

References (66)

1. Alewood PF. 1998. Conotoxins as molecular templates for drug design. In: Ramage R, Epton R, editors. Peptides. Bodwin, UK: Mayflower Scientific, p 183-186.
2. Alewood PF, Alewood D, Miranda L, Love S, Meutermans W, Wilson D. 1997. Rapid in situ neutralization protocols for Boc and Imoc solid phase chemistries. Methods Enzymol 289:14-29.
3. Bingham J-P, Jones A, Lewis RJ, Andrews PR, Alewood PE 1996. Conus venom peptides (conopeptides): inter-species, intra-species and within individual variation revealed by ionspray mass spectrometry. In: Lazarovici P et al., editors. Biochemical aspects of marine pharmacology. Alaken Inc., Colorado, p 13-27.
4. Cartier GE, Yoshikami D, Gray WR, Luo S, Olivera BM, McIntosh JM. 1996. A new α-conotoxin which targets α3β2 nicotinic acetylcholine receptors. J Biol Chem 271:7522-7528.
5. Chen L-Q, Chahine M, Kallen RG, Barchi RL, Horn R. 1992. Chimeric study of sodium channels from rat skeletal and cardiac muscle. FEBS Lett 309:253-257.
6. Colledge CJ, Hunsperger JP, Imperial JS, Hillyard DR. 1992. Precursor structure of ω-conotoxin GVIA from a cDNA clone. Toxicon 30:111-1116.
7. Colquhoun LM, Patrick JW. 1997. Pharmacology of neuronal nicotinic acetylcholine receptor subtypes. Adv Pharmacol 39:191-220.
8. Cornet B, Bonmatin J-M, Hetru C, Hoffman JA, Ptak M, Vovelle E 1995. Refined three-dimensional solution structure of insect defensin A. Structure 3:435-448.
9. Cruz LJ. 1996. Primary structural motifs of Conus peptides. In: Singh BR, Tu AT, editors. Natural toxins II. New York: Plenum Press. p 155-167.
10. Cruz LJ, Gray WR, Olivera BM, Zeikus RD, Kerr L, Yoshikami D, Moczydlowski E. 1985. Conus geographus toxins that discriminate between neuronal and muscle sodium channels. J Biol Chem 260:9280-9288.
11. + conduction and selectivity. Science 280:69-77.
12. Fainzilber M, Hasson A, Oren R, Burlingame AL, Gordon D, Spira ME, Zlotkin E. 1994. New mollusc-specific alpha-conotoxins block Aplysia neuronal acetylcholine receptors. Biochemistry 33:9523-9529.
13. Gray WR. 1993. Disulfide structures of highly bridged peptides: a new strategy for analysis. Protein Sci 2:1732-1748.
14. Gray WR, Luque A, Olivera BM, Barrett J, Cruz LJ. 1981. Peptide toxins from Conus geographus venom. J Biol Chem 256: 4734-4740.
15. Gehrmann J, Alewood PF, Craik DJ. 1998. Structure determination of the three disulfide bond isomers of α-conotoxin GI: a model for the role of disulfide bonds in structural stability. J Mol Biol 278:401-415.
16. Groebe DR, Dumm JM, Levitan ES, Abramson SN. 1995. α-Conotoxins selectively inhibit one of the two acetylcholine binding sites of nicotinic receptors. Mol Pharmacol 48:105-111.
17. Guddat LW, Martin JL, Shan L, Edmundson AB, Gray WR. 1996. Three-dimensional structure of the α-conotoxin GI at 1.2 Å resolution. Biochemistry 35:11329-11335.
18. Hann RM, Pagon OR, Eterovic VA. 1994. The α-conotoxins GI and MI distinguish between the nicotinic acetylcholine receptor agonist sites while SI does not. Biochemistry 33:14058-14063.
19. Harvey SC, McIntosh JM, Cartier GE, Maddox FN, Luetje CW. 1997. Determinants of specificity for α-conotoxin MII on α3β2 neuronal nicotinic receptors. Mol Pharmacol 51:336-342.
20. Hill JM, Alewood PF, Craik DJ. 1996. Three-dimensional solution structure of μ-conotoxin GIIIB, a specific blocker of skeletal muscle sodium channels. Biochemistry 35:8824-8835.
21. Hill JM, Alewood PF, Craik DJ. 1997. Solution structure of the sodium channel antagonist conotoxin GS: a new molecular caliper for probing sodium channel geometry. Structure 5:571-583.
22. Hill JM, Oomen CJ, Miranda LP, Bingham J-P Alewood PF, Craik DJ. 1998. Three-dimensional solution structure of α-conotoxin MII by NMR spectroscopy: effects of solution environment on helicity. Biochemistry 37:15621-15630.
23. Hogg RC, Lewis RJ, Adams DJ. 1999. α-Conotoxin analogue, PnIA[A10L], and α-bungarotoxin block the same component of nicotinic ACh-induced current in rat parasymapthetic neurons. Proc Aust Neurosci Soc 10:152.
24. Hopkins C, Grilley M, Miller C, Shon K-J, Cruz LJ, Gray WR, Dykert J, Rivier J, Yoshikami D, Olivera BM. 1995. A new family of Conus peptides targed to the nicotinic acetylcholine receptor. J Biol Chem 270:22361-22367.
25. Hu S-H, Gehrmann J, Guddat LW, Alewood PE Craik DJ, Martin JL. 1996. The 1.1 Å crystal structure of the neuronal acetylcholine receptor antagonist, α-conotoxin PnIA from Conus pennaceus. Structure 4:417-423.
26. Hu S-H, Gehrmann J, Alewood PE Craik DJ, Martin JL. 1997. Crystal structure at 1.1 Å resolution of α-conotoxin PnIB: comparison with α-conotoxins PnIA and GI. Biochemistry 36:11323-11330.
27. 15]EpI, a novel α-conotoxin from Conus episcopatus, solved by direct methods. Biochemistry 37:11425-11433.
28. Jacobsen R, Yoshikami D, Ellison M, Martinez J, Gray WR, Cartier GE, Shon K-J, Groebe DR, Abramson SN, Olivera BM, McIntosh JM. 1997. Differential targeting of nicotinic acetylcholine receptors by novel αA-conotoxins. J Biol Chem 272:22531-22537.
29. Jan LY, Jan YN. 1997. Cloned potassium channels from eukaryotes and prokaryotes. Annu Rev Neurosci 20:91-123.
30. Johnson DS, Martinez J, Elgoyhen AB, Heinemann SE Mclntosh JM. 1995. α-Conotoxin Im1 exhibits subtype-specific nicotinic acetylcholine receptor blockade: preferential inhibition of homomeric α7 and α9 receptors. Mol Pharmacol 48:194-199.
31. Jones A, Bingham J-P, Gehrmann J, Bond T, Loughnan M, Atkins A, Lewis RJ, Alewood PF. 1996. Isolation and characterisation of conopeptides by high-performance liquid chromatography combined with mass spectrometry and tandem mass spectrometry. Rapid Commun Mass Spectrom 10:138-143.
32. 3H]dopamine release from rat striatal synaptosomes and slices. J Neurochem 70:1069-1076.
33. Kulak JM, Nguyen TA, Olivera BM, McIntosh JM. 1997. α-Conotoxin MII blocks nicotine-stimulated dopamine release in rat striatal synaptosomes. J Neurosci 17:5263-5270.
34. Lewis RJ, Bingham J-P, Jones A, Alewood PF. 1994. Analysis of Conus venoms by ionspray mass spectrometry. Australasian Biotech 4:298-300.
35. Loughnan M, Bond T, Atkins A, Cuevas J, Adams DJ, Broxton NM, Livett BG, Down JG, Jones A, Alewood PE Lewis RJ. 1998. α-Conotoxin EpI, a novel sulfated peptide from Conus episcopatus that selectively targets neuronal nicotinic acetylcholine receptors. J Biol Chem 273:15667-15674.
36. Luo S, Kulak JM, Cartier GE, Jacobsen RB, Yoshikami D, Olivera BM, McIntosh JM. 1998. α-Conotoxin AuIB selectively blocks α3β4 nicotinic acetylcholine receptors and nicotine-evoked norepinephrine release. J Neurosci 18:8571-8579.
37. Martinez JS, Olivera BM, Gray WR, Craig AG, Groebe DR, Abramson SN, McIntosh JM. 1995. α-Conotoxin EI, a new nicotinic acetylcholine receptor antagonist with novel selectivity. Biochemistry 34:14519-14526.
38. McGehee DS, Role LW. 1995. Physiological diversity of nicotinic acetylcholine receptors expressed by vertebrate neurons. Annu Rev Physiol 57:521-546.
39. McIntosh JM, Cruz LJ, Hunkapiller MW, Gray WR, Olivera BM. 1982. Isolation and structure of a peptide toxin from the marine snail Conus magus. Arch Biochem Biophys 218:329-334.
40. Mclntosh JM, Yoshikami D, Mahe E, Nielsen DB, Rivier JE, Gray WR, Olivera, BM. 1994. A nicotinic acetylcholine receptor ligand of unique specificity, α-eonotoxin Iml. J Biol Chem 269:16733-16739.
41. +-channel blocking peptides. Neuron 15:5-10.
42. 3H]saxitoxin and μ-conotoxins. Proc Natl Acad Sci USA 83:5321-5325.
43. Myers RA, Zafaralla GC, Gray WR, Abbott J, Cruz LJ, Olivera BM. 1991. α-Conotoxins, small peptide probes of nicotinic acetylcholine receptors. Biochemistry 30:9370-9377.
44. Myers RA, Cruz LJ, Rivier JE, Olivera BM. 1993. Conus peptides as chemical probes for receptors and ion channels. Chem Rev 93:1923-1936.
45. Nakao M, Nishiuchi Y, Nakata M, Watanabe TX, Kimura T, Sakakibara S. 1995. Synthesis and disulfide structure determination of conotoxin GS, a γ-carboxyglutamic acid-containing neurotonic peptide. Lett Pept Sci 2:17-26.
46. Narasimhan L, Singh J, Humblet C, Guruprasad K, Blundell T. 1994. Snail and spider toxins share a similar tertiary structure and 'cystine motif.' Nat Struct Biol 1:850-852.
47. Nielsen KJ, Thomas L, Lewis RJ, Alewood PF, Craik DJ. 1996. A consensus structure for ω-conotoxins with different selectivities for voltage-sensitive calcium channel subtypes: comparison of MVIIA, SVIB and SNX-202. J Mol Biol 263:297-310.
48. Noda M, Shimizu S, Tanabe T, Takai T, Kayano T, Ikeda T, Takahashi H, Nakayama H, Kanaoka Y, Minamino N, Kangawa K, Matsuo H, Raftery MA, Hirose T, Inayama S, Hayashida H, Miyata T, Numa S. 1984. Primary structure of Electrophorus electricus sodium channel deduced from cDNA sequence. Nature 312:121-127.
49. 3H]saxitoxin binding to skeletal muscle sodium channels by geographutoxin II, a polypeptide channel blocker. J Biol Chem 261:6149-6152.
50. Olivera BM, Rivier J, Clark C, Ramilo C, Corpuz GP, Abogadie FC, Mena EE, Woodward SR, Hillyard DR, Cruz LJ. 1990. Diversity of Conus neuropeptides. Science 249:257-263.
51. Olivera BM, Miljanich G, Ramachandran J, Adams ME. 1994. Calcium channel diversity and neurotransmitter release: the ω-conotoxins and ω-agatoxins. Annu Rev Biochem 63:823-867.
52. Pallaghy PK, Nielsen KJ, Craik DJ, Norton RS. 1994. A common structural motif incorporating a cystine knot and a triple-stranded β-sheet in toxic and inhibitory polypeptides. Protein Sci 3:1833-1839.
53. Picciotto MR, Zoli M, Rimondini R, Léna C, Marubio LM, Pich EM, Fuxe K, Changeux J-P. 1998. Acetylcholine receptors containing the β2 subunit are involved in the reinforcing properties of nicotine. Nature 391:173-177.
54. Poth K, Nutter TJ, Cuevas J, Parker MJ, Adams DJ, Luetje CW. 1997. Heterogeneity of nicotinic receptor class and subunit mRNA expression among individual parasympathetic neurons from rat intracardiac ganglia. J Neurosci 17:586-596.
55. Ramilo CA, Zafaralla GC, Nadasdi L, Hammerland LG, Yoshikami D, Gray WR, Kristipati R, Ramachandran J, Miljanich G, Olivera BM, Cruz LJ. 1992. Novel α-and ω-conotoxins from Conus striatus venom. Biochemistry 31:9919-9926.
56. Sangameswaran L, Delgado SG, Fish LM, Koch BD, Jakeman LB, Stewart GR, Sze P, Hunter JC, Eglen RM, Herman RC. 1996. Structure and function of a novel voltage-gated, tetrodotoxin-resistant sodium channel specific to sensory neurons. J Biol Chem 271:5953-5956.
57. Sato S, Nakamura H, Ohizumi Y, Kobayashi J, Hirata Y. 1983. The amino acid sequences of homologous hydroxvproline-containing myotoxins from the marine snail Conus geographus venom. FEBS Lett 155:277-280.
58. Scanlon MJ, Naranjo D, Thomas L, Alewood, PF, Lewis RJ, Craik DJ. 1997. The structure of novel potassium channel toxin, κ-conotoxin PVIIA, from the venom of Conus purpurascens: implications for the mechanism of channel block. Structure 5:1585-1597.
59. Schnölzer M, Alewood P, Jones A, Alewood D, Kent SBH. 1992. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Int J Pept Protein Res 40:180-193.
60. Shon K-J, Olivera BM, Watkins M, Jacobsen RB, Gray WR, Floresca CZ, Cruz LJ, Hillyard DR, Brink A, Terlau H, Yoshikami D. 1998. μ-Conotoxin PIIIA, a new peptide for discriminating among tetrodotoxin-sensitive Na channel subtypes. J Neurosci 18:4473-4481.
61. Skjaerbaek N, Nielsen KJ, Lewis RJ, Alewood P, Craik DJ. 1997. Determination of the solution structures of conantokin-G and conantokin-T by CD and NMR spectroscopy. J Biol Chem 272:2291-2299.
62. Terlau H, Shon K-J, Grilley M, Stocker M, Stühmer W, Olivera BM. 1996. Strategy for rapid immobilisation of prey by a fish-hunting marine snail. Nature 381:148-151.
63. Unwin N. 1998. The nicotinic acetylcholine receptor of the Torpedo electric ray. J Struct Biol 121:181-190.
64. Watson MJ, Lewis RJ, Adams DJ. 1998. Effects of synthetic μ-conotoxins on voltage-dependent sodium currents in rat sensory neurones. Proc Aust Physiol Pharmacol Soc 29:326P.
65. Yanagawa Y, Abe T, Satake M, Odani S, Suzuki J, Ishikawa K. 1988. A novel sodium channel inhibitor from Conus geographus: purification, structure, and pharmacological properties. Biochemistry 27:6256-6262.
66. Zafaralla GC, Ramilo C, Gray WR, Karlstrom R, Olivera BM, Cruz LJ. 1988. Phylogenetic specificity of cholinergic ligands: α-conotoxin SI. Biochemistry 27:7102-7105.