Publications on Conotoxins from B.M. Olivera and colleagues - (Olivera BM, Cruz LJ, Gray WR, (Emeritus), Hillyard DR, Jacobsen R, McIntosh JM, Yoshikami D., and others)
***** Complete list of Olivera's Publications 1964-2004 ***** ***** List of J. Michael McIntosh's Publications 1982-2000 ***** Selected References on Cone shell toxins - most recent listed first : See also recent papers listed in "What's new for 1999; 2000 and 2001 Links to Baldomero Olivera's research within the Bioscience Program and Molecular Biology (Neurobiology). Prof. Baldomero Olivera is scientific founder of Cognetix Inc and both Prof. Olivera and Dr Lourdes Cruz are members of The Board of GeneSeas Asia Inc.
Maillo, M., M.B. Aguilar, E. Lopez-Vera, A.G. Craig, G. Bulaj, B.M. Olivera and E.P. Heimer de la Cortera (2001) Conorfamide, a Conus venom peptide belonging to the RFamide family of neuropeptides. Toxicon, 40: 401-407.
Espiritu DJ, Watkins M, Dia-Monje V, Cartier GE, Cruz LJ, Olivera BM. (2001) Venomous cone snails: molecular phylogeny and the generation of toxin diversity. Toxicon, 39: 1899-1916.
Espiritu, J.D., L.J. Cruz, G.E. Cartier and B.M. Olivera (2001) Venomous gastropods: Conus, conoideans and other neogastropod families. Bollettino Malacologico, in press.
Baldomero M Olivera, Lourdes J Cruz and Doju Yoshikami (1999) Effects of Conus peptides on the behavior of mice [Review article] Current Opinion in Neurobiology 9:772-777.
Craig, A. G., Norberg, T., Griffin, D., Hoeger, C., Akhtar, M., Schmidt, K., Low, W., Dykert, J., Richelson, E., Navarro, V., Mazella, J., Watkins, M., Hillyard, D., Imperial, J., Cruz, L. J., Olivera, B. M. (1999). "Contulakin-G, an O-Glycosylated Invertebrate Neurotensin" J. Biol. Chem. 274: 13752-13759. Shon, K., Olivera, B.M., Watkins, M., Jacobsen, R.B.,
Gray, W.R, Floresca, C.Z., Cruz, L.J., Hillyard, D.R., Brink, A., Terlau,
H., Yoshikami, D. (1998) m
-CTX PIIIA, a new peptide for discriminating among tetrodotoxin-sensitive
Na channel subtypes. J. Neurosci 18: 4473-4481.
Bandyopadhyay, P.K., Colledge, C.J., Walker, C.S.,
Zhou, L., Hillyard, D.R., Olivera, B.M. (1998) Conantokin-G precursor and
its role in g -carboxylation
by a vitamin K-dependent carboxylase from a Conus snail. J.Biol.Chem.
273: 5447-5450.
Jacobsen, R., Yoshikami, D., D., Ellison, M., Martinez,
J., Gray, W.R., Cartier, G.E., Shon, K.J., Groebe, D.R., Abramson, S.N.,
Olivera, B.M. and McIntosh, J.M. (1997) Differential targeting of nicotinic
acetylcholine receptors by novel alphaA-conotoxins J Biol Chem 272
(36) 22531-22537.
Shon, K-J., Grilley, M., Jacobsen, R., Cartier, E.,
Hopkins, C., Gray, W.R., Watkins, M., Hillyard, D.R., Rivier, J., Torres,
J., Yoshikami, D., and Olivera, B.M. (1997) A noncompetitive peptide inhibitor
of the nicotinic acetylcholine receptor from Conus purpurascens
venom. Biochemistry 36: 9581-9587.
Stanley, T.B., Stafford, D.W., Olivera, B.M. and
Bandyopadhyay, P.K. (1997) Identification of a vitamin K-dependent carboxylase
in the venom duct of a Conus snail. FEBS Letters 407 85-88. [Abstract:
Peptides from the venom ducts of cone snails (genus Conus) contain gamma-carboxyglutamate
residues. The gamma-glutamyl carboxylase responsible for this post-translational
modification is localized in the microsomal fraction, strictly dependent
on vitamin K, activated by ammonium sulfate, and is associated with endogenous
substrate. The K(m) of the enzyme for vitamin K is comparable to that for
the bovine carboxylase. However, a propeptide containing substrate related
to the blood coagulation protein factor IX, a highly efficient substrate
for the bovine enzyme, was poorly carboxylated by the Conus enzyme, suggesting
differences in gamma-carboxylase recognition signal sequences and/or structural
requirements at the carboxylation site.]
Tavazoie, S.F., Tavazoie, M.F., McIntosh, J.M., Olivera,
B.M and Yoshikami, D., (1997) Differential block of nicotinic synapses on
B versus C neurones in sympathetic ganglia of frog by a-conotoxins MII
and ImI. Brit. J. Pharmacol. 120: 995-1000.
Han KH, Hwang KJ, Kim SM, Kim SK, Gray WR, Olivera
BM, Rivier J, Shon KJ (1997) NMR structure determination of a novel conotoxin,
[Pro 7,13] alpha A-conotoxin PIVA. Biochemistry 36: 1669-1677 [Abstract:
A high-resolution solution conformation of a novel conotoxin, [Pro 7,13]
alpha A-conotoxin PIVA, GCCGSYPNAACHPCSCKDROSYCGQ-NH2, has been determined
by two-dimensional 1H NMR methods and distance geometry calculations. The
total of 324 NOE-derived interproton distance restraints including 33 long-range
NOE restraints as well as 11 phi and 7 chi 1 torsion angle restraints was
used for computation of structures. Back-calculation from the experimental
NOE spectrum has provided 49 new NOE restraints and yielded the final R-factors
of Ra = 0.641 and Rb = 0.157. The final RMSD values are 0.90 and 1.16 A
for the backbone and the heavy atoms, respectively. The C-terminal half
of the molecule involving the residues 12-24 is extremely well-defined
with a backbone RMSD value of 0.56 A, whereas the N-terminal 3-11 disulfide
loop is relatively flexible, possessing a backbone RMSD value of 1.09 A.
The [Pro 7,13] alpha A-conotoxin PIVA does not contain any significant
secondary structure although the 21S-24G nearly completes one turn of a
3(10) helix. The overall protein fold is largely maintained by the three
disulfide bridges of 2-16, 3-11, and 14-23. The presence of the three disulfide
bridges imposes geometric constraints that force the molecule to form six
continuous bends involving the following residues: 3C-5S, 7P-10A, 12H-14C,
15S-17K, 17K-19R, and 21S-25Q. The overall shape of the [Pro 7,13] alpha
A-conotoxin PIVA can be described as an "iron". Residues 15S-19R form a
loop that protrudes out of the "bottom plate" formed by the rest of the
protein and constitute the handle of the iron. The N-terminal tip of the
molecule is relatively immobile due to attractive electrostatic interactions
between the gamma-hydroxyl group of 20 Hyp and the phenolic hydroxyl group
of 22Y. The flexible 3-11 disulfide loop consists mostly of hydrophobic
residues, while the best-defined 14-23 disulfide loop contains the highly
charged hydrophilic 15S-19R "handle" domain exposed to the exterior of
the protein. Binding to nicotinic acetylcholine receptor can be mediated
through two different types of interactions: one involving the aromatic
hydrophobic residues such as 6Y and 12H and the other involving the positively
charged hydrophilic side chain of the 19R. The side chain of the 19R in
the [Pro 7, 13] alpha A-conotoxin PIVA and that of the 9R of the alpha-conotoxin
G1, and also the side chains of the 12H and 6Y in the former and those
of 10H and 11Y in the latter can be aligned to point to the same direction
when the corresponding backbone atoms are superimposed to an RMSD value
of 2.5 A.]
Craig, A., Fischer,W., Rivier,J.E. McIntosh J.M.and
Gray,W.R. "Mass spectrometric scanning methods applied to Conus venom"
Techniques in Protein Chemistry (in press)
Read a popular
account of "Toto" Olivera's recent research in the Salt Lake Tribune,
describing envenomation by the piscivorous Purple Cone, C. purpurascens,
complete with photos of the mollusc immobilizing a Clown Fish.
Alternatively,
read the scientific account in Nature below: Terlau, H., Shon, K-J., Grilley, M., Stocker, M.,
Stuhmer, W. and Olivera, B.M. (1996) Strategy for rapid immobilization
of prey by a fish-hunting marine snail. Nature 381: 148-151.
Cartier, G.E., Yoshikami, D., Gray, W.R., Luo, S.,
Olivera, B.M. and McIntosh, M. (1996) A new a-conotoxin which targets a3b2
nicotinic acetylcholine receptor. J. Biol. Chem. 271: 7522-7528.
Martinez, J.S., Olivera, B.M., Gray, W.R., Craig,
A.G., Groebe, D.R., Abramson, S.N. and McIntosh, J.M. (1995) a-conotoxin
EI, a new nicotinic acetylcholine receptor antagonist with novel selectivity.
Biochemistry 34: 14519-14526.
Masson, A., Shon, K-J., Oliver, B.M., Spira, M.E.
(1995) Alterations of voltage-activated sodium current by a novel conotoxin
from the venom of Conus gloriamaris. J. Neurophysiology 73: 1295-1302.
Olivera
BM., Hillyard DR., Marsh M. and Yoshikami, D. (1995) Combinatorial peptide
libraries in drug design: lessons from venomous cone snails. Trends Biotechnol
13: 422-426.
Hopkins C., Grilley M., Miller C., Shon KJ., Cruz
LJ., Gray
WR., Dykert J., Rivier J., Yoshikami, D. and Olivera
BM (1995) A new family of Conus peptides targeted to the nicotinic
acetylcholine receptor. J Biol Chem 270: 22361-22367.
McIntosh JM., Hasson A., Spira ME., Gray WR., Li
W., Marsh M., Hillyard DR and Olivera BM (1995) A new family of conotoxins
that blocks voltage-gated sodium channels. J Biol Chem 270: 16796-16802
Shon KJ., Grilley MM., Marsh M., Yoshikami, D.,
Hall AR., Kurz B., Gray WR., Imperial JS., Hillyard DR and Olivera BM (1995)
Purification, characterization, synthesis, and cloning of the lockjaw peptide
from Conus purpurascens venom. Biochemistry 34: 4913-8.
McIntosh JM., Ghomashchi F., Gelb MH., Dooley DJ.,
Stoehr SJ., Giordani AB., Naisbitt SR and Olivera BM (1995) Conodipine-M,
a novel phospholipase A2 isolated from the venom of the marine snail Conus
magus. J Biol Chem 270: 3518-26.
Shon, K-J., Hasson, A., Spira, M.E., Cruz L.J., Gray,
W.R. and Olivera B.M. (1994) Delta-Conotoxin GmVIA, a novel peptide from
the venom of Conus gloriamaris. Biochemistry 33: 11420-11425
Filloux, F., Karras, J., Imperial, J.S., Gray W.R.
and Olivera B.M. (1994) The distribution of omega-conotoxin MVIIC[nle]
binding sites in rat brain measured by autoradiography" Neuroscience Letters,
178:2 263-266
Olivera BM., Miljanich GP., Ramachandran J and
Adams ME (1994) Calcium channel diversity and neurotransmitter release:
the omega-conotoxins and omega-agatoxins. Annu Rev Biochem 63: 823-67.
Shon KJ., Hasson A., Spira ME., Cruz LJ., Gray
WR and Olivera BM (1994) Delta-conotoxin GmVIA, a novel peptide from the
venom of Conus gloriamaris. Biochemistry 33: 11420-5.
Adams ME and Olivera BM (1994) Neurotoxins: overview
of an emerging research technology. Trends Neurosci 17: 151-5.
McIntosh JM., Yoshikami, D., Mahe E., Nielsen DB.,
Rivier JE., Gray WR and Olivera BM (1994) A nicotinic acetylcholine receptor
ligand of unique specificity, alpha-conotoxin ImI. J Biol Chem 269: 16733-16739.
Monje VD., Haack JA., Naisbitt SR., Miljanich
G., Ramachandran J., Nasdasdi L., Olivera BM., Hillyard DR and Gray WR
(1993) A new Conus peptide ligand for Ca channel subtypes. Neuropharmacology
32: 1141-9.
Haack JA., Kinser P., Yoshikami, D. and Olivera BM
(1993) Biotinylated derivatives of omega-conotoxins GVIA and MVIID: probes
for neuronal calcium channels. Neuropharmacology 32: 1151-9.
Salzet M., Bulet P., Van Dorsselaer A and Malecha
J (1993) Isolation, structural characterization and biological function
of a lysine-conopressin in the central nervous system of the pharyngobdellid
leech Erpobdella octoculata. Eur J Biochem 217: 897-903.
Myers, R.A., Cruz, L.J., Rivier, J.E. and Olivera,
B.M. (1993) Conus peptides as chemical probes for receptors and ion channels.
Chem. Rev. 93: 1923-1936. [Review]
Ramilo CA., Zafaralla GC., Nadasdi L., Hammerland
LG., Yoshikami, D., Gray WR., Kristipati R., Ramachandran J., Miljanich
G., Olivera BM and Cruz, LJ (1992) Novel alpha- and omega-conotoxins from
Conus striatus venom. Biochemistry 31: 9919-9926.
Hammerland LG, Olivera BM, and Yoshikami D.
(1992) Conantokin-G selectively inhibits N-methyl-D-aspartate-induced currents in Xenopus oocytes injected with mouse brain mRNA. Eur J Pharmacol. 226: 239-244.
Santos AD., Imperial JS., Chaudhary T., Beavis RC.,
Chait BT., Hunsperger JP., Olivera BM., Adams ME. and Hillyard DR (1992)
Heterodimeric structure of the spider toxin omega-agatoxin IA revealed
by precursor analysis and mass spectrometry. J Biol Chem 267: 20701-5.
Hillyard DR, Monje VD, Mintz IM, Bean BP, Nadasdi
L, Ramachandran J, Miljanich G, Azimi-Zoonooz A, McIntosh JM, Cruz, LJ,
Imperial JS, Olivera BM (1992) A new Conus peptide ligand for mammalian
presynaptic Ca2+ channels. Neuron 9:69-77
Olivera BM., Imperial JS., Cruz LJ., Bindokas VP.,
Venema VJ and Adams ME (1991) Calcium channel-targeted polypeptide toxins.
Ann N Y Acad Sci 635: 114-22.
Olivera BM., Rivier J., Scott JK., Hillyard DR
and Cruz LJ (1991) Conotoxins. J Biol Chem 266: 22067-70.
Myers RA., Zafaralla GC., Gray WR., Abbott J., Cruz
LJ and Olivera BM (1991) alpha-Conotoxins, small peptide probes of nicotinic
acetylcholine receptors. Biochemistry 30: 9370-9377.
Lev-Ram, V., Olivera, B.M., Levitan, I.B., Corpuz,
G.P., Ramilo, C.A., Hillyard, D.R. and Cruz, L.J. (1991) Molluscan
Conus venoms: A source of toxin probes for molluscan neuroboiology. In:
Molluscan Neurobiology. Edited by K.S. Kits, H.H. Boer and J. Joose.
Proceedings of the 3rd Symposium on Molluscan Neurobiology, Amsterdam,
the Netherlands, Aug 20-24 1990, North-Holland, Amsterdam / Oxford / New
York, 1991 [Abstract: The approximately 50 different species
of molluscivorous Conus marine snails use their venoms to prey on other
molluscs. Although the physiological characterization of these venoms has
just been initiated, extensive biochemical work has revealed that the venoms
are very complex, with many disulfide rich peptides present in a single
venom. Preliminary evidence that these components are likely to affect
receptors and ion channels in molluscan neurons is described here.
The molluscivorous Conus are therefore a potentially rich source of specifically
targeted ligands for the receptors and ion channels that are responsible
for molluscan nervous system function. We anticipate that these will
become standard tools in molluscan neurobiology]
Mena EE., Gullak MF., Pagnozzi MJ., Richter KE.,
Rivier J., Cruz LJ and Olivera BM (1990) Conantokin-G: a novel peptide
antagonist to the N-methyl-D-aspartic acid. (NMDA) receptor. Neurosci Lett
118: 241-244.
Olivera BM., Gray WR., Zeikus R., McIntosh JM., Varga
J., Rivier J., de Santos V and Cruz LJ (1985) Peptide neurotoxins from
fish-hunting cone snails. Science 230: 1338-43.
Olivera BM., Cruz LJ., de
Santos V., LeCheminant GW., Griffin D., Zeikus R., McIntosh JM., Galyean
R., Varga J., Gray WR., and Rivier, J. (1987) Neuronal calcium channel
antagonists. Discrimination between calcium channel subtypes using omega-conotoxin
from Conus magus venom. Biochemistry 26: 2086-90.
Biological Activity : Omega-CgTx MVII A and Omega-CgTx GVI A (from Conus geographus) are both neuronal Ca2+ channels blockers and appear to compete for the same sites in mammalian brain, but they seem to present some differences in their receptor binding characteristics; in particular the high affinity binding of Omega-CgTx MVII A has narrower specificity in amphibian brain. Molecular Weight : 2,639.2 Solubility in : well in water and saline Purity min. : typically 97 % (HPLC) Storage recommendations : Stable in freeze dried state. In solution, keep at -20°C. Source
Olivera BM., Rivier J., Clark C., Ramilo CA.,
Corpuz GP., Abogadie FC., Mena EE., Woodward SR., Hillyard DR and Cruz
LJ (1990) Diversity of Conus neuropeptides. Science 249: 257-63.
Haack JA., Rivier J., Parks TN., Mena EE., Cruz LJ
and Olivera BM (1990) Conantokin-T. A gamma-carboxyglutamate containing
peptide with N-methyl-d-aspartate antagonist activity. J Biol Chem 265:
6025-9. Source
Woodward SR., Cruz LJ., Olivera BM and Hillyard DR
(1990) Constant and hypervariable regions in conotoxin propeptides. EMBO
J 9: 1015-20.
Yoshikami, D., Bagabaldo Z and Olivera BM (1989) The
inhibitory effects of omega-conotoxins on Ca channels and synapses. Ann
N Y Acad Sci 560: 230-48.
Hillyard DR., Olivera BM., Woodward S., Corpuz GP.,
Gray WR., Ramilo CA and Cruz LJ (1989) A molluscivorous Conus toxin: conserved
frameworks in conotoxins. Biochemistry 28: 358-61.
Zafaralla GC., Ramilo C., Gray WR., Karlstrom R.,
Olivera BM and Cruz LJ (1988) Phylogenetic specificity of cholinergic ligands:
alpha-conotoxin SI. Biochemistry 27: 7102-7105.
Gray, WR., Olivera, BM and Cruz, LJ (1988) Peptide
toxins from venomous Conus snails. Ann. Rev. Biochem. 57: 665 -
Rivier J., Galyean R., Simon L., Cruz LJ., Olivera
BM and Gray WR (1987) Total synthesis and further characterization of the
gamma-carboxyglutamate-containing "sleeper" peptide from Conus geographus
venom. Biochemistry 26: 8508-12.
Cruz LJ., de Santos V., Zafaralla GC., Ramilo CA.,
Zeikus R., Gray WR and Olivera BM (1987) Invertebrate vasopressin/oxytocin
homologs. Characterization of peptides from Conus geographus and Conus
straitus venoms. J Biol Chem 262: 15821-4.
EARLIER 1981-1986
Olivera BM., Gray WR., Zeikus R., McIntosh JM., Varga
J., Rivier J., de Santos V and Cruz LJ (1985) Peptide neurotoxins from
fish-hunting cone snails. Science 230: 1338-43.
Cruz LJ., Gray WR., Olivera BM., Zeikus RD., Kerr
L., Yoshikami, D. and Moczydlowski E (1985) Conus geographus toxins that
discriminate between neuronal and muscle sodium channels. J Biol Chem 260:
9280-9288.
McIntosh JM., Olivera BM., Cruz LJ and Gray WR (1984)
Gamma-carboxyglutamate in a neuroactive toxin. J Biol Chem 259: 14343-6.
Olivera BM., McIntosh JM., Cruz LJ., Luque FA and
Gray WR (1984) Purification and sequence of a presynaptic peptide toxin
from Conus geographus venom. Biochemistry 23: 5087-5090.
Gray WR., Luque FA., Galyean R., Atherton E., Sheppard
RC., Stone BL., Reyes A., Alford J., McIntosh M., Olivera BM., et al(1984)
Conotoxin GI: disulfide bridges, synthesis, and preparation of iodinated
derivatives. Biochemistry 23: 2796-802.
Gray WR., Rivier JE., Galyean R., Cruz LJ and Olivera
BM (1983) Conotoxin MI. Disulfide bonding and conformational states. J
Biol Chem 258: 12247-51.
McIntosh M., Cruz LJ., Hunkapiller MW., Gray WR and
Olivera BM (1982) Isolation and structure of a peptide toxin from the marine
snail Conus magus. Arch Biochem Biophys 218: 329-34.
Gray WR., Luque A., Olivera BM., Barrett J and Cruz
LJ (1981) Peptide toxins from Conus geographus venom. J Biol Chem 256:
4734-40.
Cruz, L.Z., Gray, W.R. and Olivera, B.M. (1978) Purification
and properties of a myotoxin from Conus geographus. Archs. Biochem.
Biophys. 190: 539-548
BGL December 2001
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