In vivo seizure induction and affinity studies of domoic acid and isodomoic acids-D, -E and -F

Neuropharmacology

Volumn 59, Issue 3, 2010, Pages 129-138

  Sawant, P M ^a   Tyndall, J D A ^b   Holland, P T ^c   Peake, B M ^b   Mountfort, D O ^c   Kerr, D S ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b UNIVERSITY OF OTAGO   (New Zealand)

^c CAWTHRON INSTITUTE   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMPA RECEPTOR; DOMOIC ACID; ISODOMOIC ACID A; ISODOMOIC ACID B; ISODOMOIC ACID C; ISODOMOIC ACID D; ISODOMOIC ACID E; ISODOMOIC ACID F; ISODOMOIC ACID G; ISODOMOIC ACID H; UNCLASSIFIED DRUG; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; GLUK2 KAINATE RECEPTOR; KAINIC ACID; KAINIC ACID RECEPTOR; NEUROMUSCULAR DEPOLARIZING AGENT; PROTEIN BINDING; TRITIUM;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; DRUG PURIFICATION; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG STRUCTURE; DRUG TOLERABILITY; MALE; MOLECULAR MODEL; NEUROPROTECTION; NONHUMAN; PRIORITY JOURNAL; RAT; SEIZURE; ANALOGS AND DERIVATIVES; ANALYSIS OF VARIANCE; ANIMAL; BINDING COMPETITION; CHEMICAL STRUCTURE; CHEMICALLY INDUCED; CHEMISTRY; CONFORMATION; DISEASE MODEL; DOSE RESPONSE; DRUG EFFECTS; DRUG TOLERANCE; HIPPOCAMPUS; ISOMERISM; SPRAGUE DAWLEY RAT; SYNAPTOSOME; TOXICITY; ULTRASTRUCTURE;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANALYSIS OF VARIANCE; ANIMALS; BINDING, COMPETITIVE; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG TOLERANCE; HIPPOCAMPUS; ISOMERISM; KAINIC ACID; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEUROMUSCULAR DEPOLARIZING AGENTS; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, KAINIC ACID; SEIZURES; SYNAPTOSOMES; TRITIUM;

EID: 77954141831     PISSN: 00283908     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2010.03.019     Document Type: Article

References (73)

1. Armstrong N., Gouaux E. Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core. Neuron 2000, 28:165-181.
2. Bejarano A.C., VanDolah F.M., Gulland F.M., Rowles T.K., Schwacke L.H. Production and toxicity of the marine biotoxin domoic acid and its effects on wildlife: a review. Hum. Ecol. Risk Assess. 2008, 14:544-567.
3. Berman F.W., LePage K.T., Murray T.F. Domoic acid neurotoxicity in cultured cerebellar granule neurons is controlled preferentially by the NMDA receptor Ca(+) influx pathway. Brain Res. 2002, 924:20-29.
4. Blondeau N., Plamondon H., Richelme C., Heurteaux C., Lazdunski M. K(ATP) channel openers, adenosine agonists and epileptic preconditioning are stress signals inducing hippocampal neuroprotection. Neuroscience 2000, 100:465-474.
5. Blondeau N., Widmann C., Lazdunski M., Heurteaux C. Activation of the nuclear factor-kappaB is a key event in brain tolerance. J. Neurosci. 2001, 21:4668-4677.
6. Bouillon R.C., Knierim T.L., Kieber R.J., Skrabal S.A., Wright J.L.C. Photodegradation of the algal toxin domoic acid in natural water matrices. Limnol. Oceanogr. 2006, 51:321-330.
7. Bouillon R., Kieber R.J., Skrabal S.A., Wright J.L.C. Photochemistry and identification of photodegradation products of the marine toxin domoic acid. Marine Chem. 2008, 110:18-27.
8. Bragin A., Azizyan A., Almajano J., Wilson C.L., Engel J. Analysis of chronic seizure onsets after intrahippocampal kainic acid injection in freely moving rats. Epilepsia 2005, 46:1592-1598.
9. Carcache L.M., Rodriguez J., Rein K.S. The structural basis for kainoid selectivity at AMPA receptors revealed by low-mode docking calculations. Bioorg. Med. Chem. 2003, 11:551-559.
10. Cendes F., Andermann F., Carpenter S., Zatorre R.J., Cashman N.R. Temporal lobe epilepsy caused by domoic acid intoxication: evidence for glutamate receptor-mediated excitotoxicity in humans. Ann. Neurol. 1995, 37:123-126.
11. Cheng Y., Prusoff W.H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharm. 1973, 22:3099-3108.
12. Clayden J., Read B., Hebditch K.R. Chemistry of domoic acid, isodomoic acids, and their analogues. Tetrahedron 2005, 61:5713-5724.
13. Clements J.D., Feltz A., Sahara Y., Westbrook G.L. Activation kinetics of AMPA receptor channels reveal the number of functional agonist binding sites. J. Neurosci. 1998, 18:119-127.
14. 3H]-kainic acid binding to brain membranes: a re-evaluation of ligand potency and selectivity. J. Pharm. Toxicol. Methods 2000, 42:121-125.
15. Dakshinamurti K., Sharma S.K., Sundaram M. Domoic acid induced seizure activity in rats. Neurosci. Lett. 1991, 127:193-197.
16. Dave K.R., Saul I., Pradoa R., Busto R., Perez-Pinzon M.A. Remote organ ischemic preconditioning protect brain from ischemic damage following asphyxial cardiac arrest. Neurosci. Lett. 2006, 404:170-175.
17. El Bahh B., Auvergne R., Leré C., Brana C., Le Gal La Salle G., Rougier A. Decreased epileptic susceptibility correlates with neuropeptide Y overexpression in a model of tolerance to excitotoxicity. Brain Res. 2001, 894:209-217.
18. Fay A.M., Corbeil C.R., Brown P., Moitessier N., Bowie D. Functional characterisation and in silico docking of full and partial GluK2 kainate receptor agonists. Mol. Pharmacol. 2009, 75:1096-1107.
19. Hald H., Naur P., Pickering D.S., Sprogøe D., Madsen U., Timmermann D.B., Ahring P.K., Liljefors T., Schousboe A., Egebjerg J., Gajhede M., Kastrup J.S. Partial agonism and antagonism of the ionotropic glutamate receptor iGLuR5: structures of the ligand-binding core in complex with domoic acid and 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid. J. Biol. Chem. 2007, 282:25726-25736.
20. Hampson D.R., Manalo J.L. The activation of glutamate receptors by kainic acid and domoic acid. Nat. Toxin. 1998, 6:153-158.
21. Hampson D.R., Huang X.P., Wells J.W., Walter J.A., Wright J.L. Interaction of domoic acid and several derivatives with kainic acid and AMPA binding sites in rat brain. Euro. J. Pharmacol. 1992, 218:1-8.
22. Hawkins L.M., Beaver K.M., Jane D.E., Taylor P.M., Sunter D.C., Roberts P.J. Characterization of the pharmacology and regional distribution of (S)-[3H]-5-fluorowillardiine binding in rat brain. Br. J. Pharmacol. 1995, 116:2033-2039.
23. Hawkinson J.E., Espitia S.A. Effects of thiocyanate and AMPA receptor ligands on (S)-5-fluorowillardiine, (S)-AMPA and (R, S)-AMPA binding. Euro. J. Pharmacol. 1997, 329:213-221.
24. Hesp B.R., Wrightson T., Mullaney I., Kerr D.S. Kainate receptor agonists and antagonists mediate tolerance to kainic acid and reduce high-affinity GTPase activity in young, but not aged, rat hippocampus. J. Neurochem. 2004, 90:70-79.
25. Hesp B.R., Clarkson A., Sawant P.M., Kerr D.S. Domoic acid preconditioning and seizure induction in young and aged rats. Epilepsy Res. 2007, 76:103-112.
26. + channels in cerebral ischemic preconditioning. Proc. Natl. Acad. Sci. USA 1995, 92:4666-4670.
27. Holland P.T., Selwood A.I., Mountfort D.O., Wilkins A.L., McNabb P., Rhodes L.L., Doucette G.J., Mikulski C.M., King K.L. Isodomoic acid C, an unusual amnesic shellfish poisoning toxin from Pseudo-nitzschia australis. Chem. Res. Toxicol. 2005, 18:814-816.
28. Honoré T., Nielsen M. Complex structure of quisqualate-sensitive glutamate receptors in rat cortex. Neurosci. Lett. 1985, 54:27-32.
29. Jin R., Banke T.G., Mayer M.L., Traynelis S.F., Gouaux E. Structural basis for partial agonist action at ionotropic glutamate receptors. Nat. Neurosci. 2003, 6:803-810.
30. 3H]-kainate binding. Euro. J. Pharmacol. 1993, 246:195-204.
31. Kelly M.E., McIntyre D.C. Hippocampal kindling protects several structures from the neuronal damage resulting from kainic acid-induced status epilepticus. Brain Res. 1994, 634:245-256.
32. Kerr D.S., Crawford N. Age-related changes in AMPA and KA receptor pharmacology. Proc. 19th Int. Australasian Winter Conf. Brain Res. 2001, 19:25.
33. Kerr D.S., Razak A., Crawford N. Age-related changes in tolerance to the marine algal excitotoxin domoic acid. Neuropharmacol 2002, 43:357-366.
34. Kessler M., Suzuki E., Montgomery K., Arai A.C. Physiological significance of high- and low-affinity agonist binding to neuronal and recombinant AMPA receptors. Neurochem. Int. 2008, 52:1383-1393.
35. A receptorá. Neurosci. Lett. 2005, 384:87-92.
36. Larm J.A., Beart P.M., Cheung N.S. Neurotoxin domoic acid produces cytotoxicity via kainate- and AMPA-sensitive receptors in cultured cortical neurons. Neurochem. Int. 1997, 31:677-682.
37. Lere C., El Bahh B., Le Gal La Salle G., Rougier A. A model of lepileptic tolerance for investigating neuroprotection, epileptic susceptibility and gene expression-related plastic changes. Brain Res. Protoc. 2002, 9:49-56.
38. Lerma J., Paternain A.V., Naranjo J.R., Mellstrom B. Functional kainite selective glutamate receptors in cultured hippocampal neurons. Proc. Natl. Acad. Sci. USA 1993, 90:11688-11692.
39. Maeda M., Kodama T., Tanaka T., Ohfune Y., Nomoto K., Nishimura K., Fujita T. Insecticidal and neuromuscular activities of domoic acid and its related compounds. J. Pestic. Sci. 1984, 9:27-32.
40. Maeda M., Kodama K., Tanaka T., Yoshizumi Y., Takemoto T., Nomoto K., Fujita T. Structures of isodomoic acids A, B and C, novel insecticidal amino acids from the red alga Chondria armata. Chem. Pharmaceut. Bull. 1986, 34:4892-4895.
41. Mayer M.L. Crystal structures of the GluR5 and GluR6 ligand binding cores: molecular mechanisms underlying kainate receptor selectivity. Neuron 2005, 45:539-552.
42. Nanao M.H., Green T., Stern-Bach Y., Heinemann S.F., Choe S. Structure of the kainate receptor subunit GluR6 agonist-binding domain complexed with domoic acid. Proc. Natl. Acad. Sci. USA 2005, 102:1708-1713.
43. Nicholls A., MacCuish N.E., MacCuish J.D. Variable selection and model validation of 2D and 3D molecular descriptors. J. Comput. Aid. Mol. Des 2004, 18:451-474.
44. Nielsen E.O., Johansen T.H., Watjen F., Drejer J. Characterization of the binding of [3H]NS 257, a novel competitive AMPA receptor antagonist, to rat brain membranes and brain sections. J. Neurochem. 1995, 65:1264-1273.
45. Perez-Pinzon M.A. Neuroprotective effects of ischemic preconditioning in brain mitochondria following cerebral ischemia. J. Bioenerg. Biomembranes 2004, 36:323-327.
46. ATP channels. J. Cerebr. Blood Flow Met. 1999, 19:1296-1308.
47. Pulido O.M. Domoic acid toxicologic pathology: a review. Marine Drugs 2008, 6:180-219.
48. Qiu S., Currás-Collazo M.C. Histopathological and molecular changes produced by hippocampal microinjection of domoic acid. Neurotox. Teratol. 2006, 28:354-362.
49. Qiu S., Pak C.W., Curras-Collazo M.C. Sequential involvement of distinct glutamate receptors in domoic acid-induced neurotoxicity in rat mixed cortical cultures: effect of multiple dose/duration paradigms, chronological age, and repeated exposure. Toxicol. Sci. 2006, 89:243-256.
50. Quinn G.P., Keough M.J. Experimental Design and Data Analysis for Biologists 2002, Cambridge Univ Press, Cambridge.
51. Renard A., Crépel F., Audinat E. Evidence for two types of non-NMDA receptors in rat cerbellar purkinje cells maintained in slice cultures. Neuropharmacol 1995, 34:335-346.
52. Reshef A., Sperling O., Zoref-Shani E. Preconditioning of primary rat neuronal cultures against ischemic injury: characterization of the letime window of protection. Brain Res. 1996, 741:252-257.
53. Rhodes L.L., Holland P.T., Adamson J.E., McNabb P., Selwood A.I. Production of a new isomer of domoic acid by New Zealand isolates of the diatom Pseudo-nitzschia australis. Molluscan Shellfish Safety 2003, 43-48. Xunta de Galicia IOC of UNESCO, Santiago de Compostela, Spain. A. Villalba (Ed.).
54. Rush T.S., Grant J.A., Mosyak L., Nicholls A. A shape-based 3-D scaffold hopping method and its application to a bacterial protein-protein interaction. J. Med. Chem. 2005, 48:1489-1495.
55. Sakai R., Swanson G.T., Shimamoto K., Green T., Contractor A., Ghetti A., Tamura-Horikawa Y., Oiwa C., Kamiya H. Pharmacological properties of the potent epileptogenic amino acid dysiherbaine, a novel glutamate receptor agonist isolated from the marine sponge Dysidea herbacea. J. Pharmacol. Exp. Ther. 2001, 296:655-663.
56. Saleh M.C., Connell B.J., Saleh T.M. Ischemic tolerance following low dose NMDA involves modulation of cellular stress proteins. Brain Res. 2009, 1247:212-220.
57. Sasahira M., Lowry T., Simon R.P., Greenberg D.A. Epileptic tolerance: prior seizures protect against seizure-induced neuronal injury. Neurosci. Lett. 1995, 185:95-98.
58. Sawant P.M., Weare B.A., Holland P., Selwood A., King K.L., Mikulski C.M., Doucett G.J., Mountfort D.O., Kerr D.S. Isodomoic acids A and C exhibit low KA receptor affinity and reduced in vitro potency in hippocampal region CA1. Toxicon 2007, 50:627-638.
59. Sawant P.M., Holland P.T., Mountfort D.O., Kerr D.S. In vivo seizure induction and pharmacological preconditioning by domoic acid and isodomoic acids A, B and C. Neuropharmacol 2008, 55:1412-1418.
60. Sawant, P.M., Mountfort, D.O., Kerr, D.S., Spectral analysis of electrocorticographic activity during pharmacological preconditioning and seizure induction by intrahippocampal domoic acid. Hippocampus, in press.
61. Scallet A.C., Kowalke P.K., Rountree R.L., Thorn B.T., Binienda Z.K. Electroencephalographic, behavioral and c-fos responses to acute domoic acid exposure. Neurotox. Teratol. 2004, 26:331-342.
62. Schurr A., Payne R.S., Tseng M.T., Gozal E., Gozal D. Excitotoxic preconditioning elicited by both glutamate and hypoxia and abolished by lactate transport inhibition in rat hippocampal slices. Neurosci. Lett. 2001, 307:151-154.
63. 3H]-AMPA to rat brain synaptic plasma membranes. Brit. J. Pharmacol. 1992, 105:83-86.
64. Sommer B., Burnashev N., Verdoorn T.A., Keinanen K., Sakmann B., Seeburg P.H. A glutamate receptor channel with high affinity for domoate and kainate. EMBO J. 1992, 11:1651-1656.
65. Strain S.M., Tasker R.A. Hippocampal damage produced by systemic injections of domoic acid in mice. Neuroscience 1991, 44:343-352.
66. Tanimoto, T.T. 1957, IBM Internal Report 17th Nov. 1957.
67. Walter J.A., Falk M., Wright J.L.C. Chemistry of the shellfish toxin domoic acid: characterization of related compounds. Can. J. Chem. 1994, 72:430-436.
68. Wright J.L.C., Falk M., McInnes A.G., Walter J.A. Identification of isodomoic acid D and two new geometrical isomers of domoic acid in toxic mussels. Can. J. Chem. 1990, 68:22-25.
69. Wright J.L.C., Bird C.J., DeFreitas A.S.W., Hampson D., McDonald J., Quilliam M.A. Chemistry, biology and toxicology of domoic acid and its somers. Proceedings of a Symposium, Domoic Acid Toxicity 1990, 21-26. Canada Diseases Weekly Report, Ottawa, Ontario, Canada. I. Hynie, E.C.D. Todd (Eds.).
70. Xi D., Ramsdell J.S. Glutamate receptors and calcium entry mechanisms for domoic acid in hippocampal neurons. Neuroreport 1996, 7:1115-1120.
71. Young A.B., Fagg G.E. Excitatory amino acid receptors in the brain: membrane binding and autoradiographic approaches. Trends Pharmacol. Sci. 1990, 11:126-133.
72. Zaman L., Arakawa O., Shimosu A., Onoue Y., Nishio S., Shida Y., Noguchi T. Two new isomers of domoic acid from a red alga, Chondria armata. Toxicon 1997, 35:205-212.
73. Zhang Y., Nayeem N., Green T. Mutations to the kainate receptor subunit GluR6 binding pocket that selectively affect domoate binding. Mol. Pharmacol. 2008, 74:1163-1169.