Brevetoxin derivatives that inhibit toxin activity

Chemistry and Biology

Volumn 7, Issue 6, 2000, Pages 385-393

  Purkerson Parker, Sherry L ^a   Fieber, Lynne A ^b   Rein, Kathleen S ^c   Podona, Tchao ^c   Baden, Daniel G ^d  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b UNIVERSITY OF MIAMI   (United States)

^c FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^d UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

Author keywords

Brevetoxin antagonists; Brevetoxins; Marine neurotoxins; Sodium channel

Indexed keywords

ANIMALIA;

EID: 0034044128     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(00)00119-8     Document Type: Article

References (24)

1. Poli M.A., Mende T.J., Baden D.G. Brevetoxins, unique activators of voltage-sensitive sodium channels, bind to specific sites in rat brain synaptosomes. Mol. Pharmacol. 30:1986;129-135.
2. Martin D.F., Martin B.B. Red tide terror: effects of red tide and related toxins. J. Chem. Ed. 53:1976;614-617.
3. Bossart G.D., Baden D.G., Ewing R.Y., Roberts B., Wright S.D. Brevetoxicosis in manatees (Trichechus manatus latirostrius) from the 1996 epizootic: gross, histologic, and immunohistochemical features. Toxicol. Pathol. 26:1998;277-282.
4. Sims J.K.A. Theoretical discourse on the pharmacology of toxic marine ingestions. Ann. Emerg. Med. 16:1987;1006-1014.
5. Jeglitsch G.A., Rein K.S., Baden D.G., Adams D.J. Brevetoxin-3 (PbTx-3) and its derivatives modulate single tetrodotoxin-sensitive sodium channels in rat sensory neurons. J. Pharmacol. Exp. Ther. 284:1998;516-524.
6. Purkerson S.L., Baden D.G., Fieber L.A. Brevetoxin modulates neuronal sodium channels in two cell lines derived from rat brain. Neurotoxicology. 20:2000;909-920.
7. Schreibmayer W., Jeglitsch G.A. The sodium channel activator brevetoxin-3 uncovers a multiplicity of different open states of the cardiac sodium channel. Biochem. Biophys. Acta. 1104:1992;223-242.
8. Westerfield M., Moore J.W., Kim Y.S., Padilla G.M. How Gymnodinium breve red tide toxin(s) produces repetitive firing in squid axions. Am. J. Physiol. 232:1977;C23-C29.
9. Atchison W.D., Luke V.S., Narahashi T., Vogel S.M. Nerve membrane sodium channels as the target site of brevetoxins at neuromuscular junctions. Br. J. Pharmacol. 89:1986;731-738.
10. Wu C.H., Huang J.M.C., Vogel S.M., Luke V.S., Atchison W.D., Narahashi T. Actions of Ptychodiscus brevis toxins on nerve and muscle membranes. Toxicon. 23:1985;481-487.
11. Catterall W.A. Cellular and molecular biology of voltage-gated sodium channels. Physiol. Rev. 72:1992;S15-S46.
12. Trainer V.L., Thomsen W.J., Catterall W.A., Baden D.G. Photoaffinity labeling of the brevetoxin receptor on sodium channels in rat brain synaptosomes. Mol. Pharmacol. 40:1991;988-994.
13. Matile S., Nakanishi K. Selective cation movement across lipid bilayers containing brevetoxin B. Angew. Chem. Int. Ed. Engl. 35:1996;757-759.
14. Gawley R.E., Baden D.G.et al. The relationship of brevetoxin 'length' and A-ring functionality to binding and activity in neuronal sodium channels. Chem. Biol. 2:1995;533-541.
15. Rein K.S., Lynn B., Gawley R.E., Baden D.G. Brevetoxin B: chemical modification, synaptosome binding, and toxicity, an unexpected conformational effect. J. Org. Chem. 59:1994;2107-2113.
16. Rein K.S., Baden D.G., Gawley R.E. Conformational analysis of the sodium channel modulator brevetoxin A, comparison with brevetoxin B conformations, and a hypothesis about the common pharmacophore of the 'site 5' toxins. J. Org. Chem. 59:1994;2101-2106.
17. Baden D.G., Rein K.S., Gawley R.E., Jeglitsch G., Adams D.J. Is the A-ring lactone of brevetoxin PbTx-3 required for sodium channel orphan receptor binding and activity? Natural Toxins. 2:1993;212-221.
18. Baden D.G., Rein K.S., Gawley R.E., Jeglitsch G., Adams D.J. Marine toxins: scientific approaches, synthetic transformations, and molecular mechanisms. Yasumoto T., Oshima Y., Fukuyo Y. Harmful and Toxic Algal Blooms. 1996;473-476 International Oceanographic Commission UNESCO, Paris.
19. Matile S., Berova N., Nakanishi K. Exciton coupled circular dichroic studies of self-assembled brevetoxin-porphyrin conjugates in lipid bilayers and polar solvents. Chem. Biol. 3:1996;379-392.
20. Dodd R.P., Hardey J.A., Oakley A.E., Edwardson J.A., Perry E.K., Delaunoy J.P. A rapid method for preparing synaptosomes: comparison with alternative procedures. J. Brain. Res. 226:1981;107-118.
21. 50) of an enzyme reaction. Biochem. Pharmacol. 22:1973;3099-3108.
22. Mohamadi F., Still W.C. MacroModel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11:1990;440-450.
23. Dib-Hajj S.D., Hinson A.W., Black J.A., Waxman S.G. Sodium channel mRNA in the B104 neuroblastoma cell line. FEBS Lett. 384:1996;78-82.
24. Penner, R. (1995). Practical guide to patch clamping. In Single-Channel Recording. (2nd edn), pp. 3-30, Plenum Press, London.