Natural and derivative brevetoxins: Historical background, multiplicity, and effects

Environmental Health Perspectives

Volumn 113, Issue 5, 2005, Pages 621-625

  Baden, Daniel G ^a   Bourdelais, Andrea J ^a   Jacocks, Henry ^a   Michelliza, Sophie ^a   Naar, Jerome ^a  

^a UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

Author keywords

Brevenal; Brevetoxin; Florida red tide; Immunotoxicant; Karenia brevis; Neurotoxin; PbTx; Polyether; Pulmonary toxicant

Indexed keywords

BREVETOXIN; POLYETHER; THIOBUTABARBITAL;

ARTICLE; CHEMICAL MODIFICATION; DINOFLAGELLATE; ENVIRONMENTAL EXPOSURE; HUMAN; HYPOTHESIS; LETHALITY; MEDICAL RESEARCH; NONHUMAN; PRIORITY JOURNAL; RED TIDE; SYMPTOM; TOXIN STRUCTURE;

ANIMALS; DINOFLAGELLIDA; EUTROPHICATION; FLORIDA; HUMANS; INHALATION EXPOSURE; MARINE TOXINS; OXOCINS; PUBLIC HEALTH; RESPIRATORY TRACT DISEASES; RISK ASSESSMENT; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPENTAL;

DINOPHYCEAE; KARENIA BREVIS;

EID: 19044370182     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.7499     Document Type: Article

References (42)

1. Abraham WM, Bourdelais AJ, Ahmed A, Sereberiakov I, Baden DG. 2005. Effects of inhaled brevetoxins in allergic airways: toxin-allergen interactions and pharmacologic intervention. Environ Health Perspect 113:632-637.
2. Backer LC, Kirkpatrick B, Fleming LE, Chang YS, Pierce R, Bean JA, et al. 2005. Occupational exposure to aerosolized brevetoxins during Florida red tide events: effects on a healthy worker population. Environ Health Perspect 113:644-649.
3. Baden DG, 1977. Metabolism and Toxinology of Florida's Red Tide Dinoflagellate Gymnodinium breve [PhD Thesis]. Miami, FL:University of Miami.
4. Baden DG. 1983 Marine food-borne dinoflagellate toxins. Int Rev Cytol 82:99-150.
5. Baden, DG. 1989. Biochemistry of the brevetoxins: potent activators of voltage-sensitive sodium channels. FASEB J 3:1807-1817.
6. Baden DG, Adams DJ. 2000. Brevetoxins: chemistry, mechanism of action, and methods of detection. In: Seafood and Freshwater Toxins (Botana LM, ed). New York:Marcel Dekker, 505-532.
7. Baden DG, Mende TJ. 1981. Toxicity of two toxins isolated from Ptychodiscus brevis. Toxicon 20:457-461.
8. Baden DG, Mende TJ, Walling J, Schultz DR. 1984. Specific antibodies directed against toxins of Ptychodiscus brevis. Toxicon 22:783-789.
9. Baden DG, Rein KS, Gawley RE, Jeglitsch G, Adams DJ. 1996. Marine toxins: scientific approaches, synthetic transformations, and molecular mechanisms. In: Harmful and Toxic Algal Blooms (Yasumoto T, Oshima Y, and Fukuyo Y, eds). Paris:Intergovernmental Oceanographic Commission of UNESCO, 473-476.
10. Baden DG, Tomas CM. 1988. Variations in major toxin composition for six clones of Ptychodiscus brevis. Toxicon 26:961-963.
11. Benson JM, Hahn FF, March TH, McDonald JD, Gomez AP, Sopori MJ, et al. 2005. Inhalation toxicity of brevetoxin 3 in rats exposed for twenty-two days. Environ Health Perspect 113:626-631.
12. Bourdelais, AJ, Baden DG. 2004. Toxic brevetoxin complexes are in aqueous solutions [Abstract]. Toxicologist 78(1-S):807.
13. Bourdelais AJ, Campbell S, Jacocks H, Naar J, Wright JLC, Carsi J, et al. 2004. Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays. Cell Mol Neurobiol 24:553-563.
14. Bourdelais AJ, Campbell SK, Kubanek J, Wright JLC, Baden DG. In press. Florida's red tide dinoflagellate Karenia brevis may modulate its potency by producing a non-toxic competitive antagonist. In: Harmful Algae 2002. Xth International Conference on Harmful Algae (Steidinger KA, Landsberg JH, Tomas CM, Vargo GA, eds). Paris: International Oceanographic Commission of UNESCO and Florida Fish and Wildlife Conservation Commission.
15. Bourdelais AJ, Jacocks HM, Wright JLC, Bigwarfe PM, Baden DG. 2005. A new polyether ladder compound produced by the dinoflagellate Karenia brevis. J Nat Prod 68:2-6.
16. Catterall WA, Risk M. 1981. Toxin T46 from Gymnodinium breve (formerly Ptychodiscus brevis) enhances activation of voltage-sensitive sodium channels by veratridine. Mol Pharmacol 19:345-348.
17. Cheng YS, Zhou Y, Irvin CM, Pierce RH, Naar J, Backer LC, et al. 2005. Characterization of marine aerosol for assessment of human exposure to brevetoxins. Environ Health Perspect 113:638-643.
18. Chou HN, Shimizu Y, VanDuyne G, Clardy J. 1985. Isolation and structure of two new polycyclic ethers from Gymnodinium breve Davis (= Ptychodiscus brevis). Tetrahedron Lett 26:2865-2868.
19. Fleming LE, Kirkpatrick B, Backer LC, Bean JA, Wanner A, Dalpra D, et al. 2005. Initial evaluation of the effects of aerosolized Florida red tide toxins (brevetoxins) in persons with asthma. Environ Health Perspect 113:650-657.
20. Galtsoff PS. 1948. Red tide. Spec. Sci Rep US Fish Wildl Serv 46:1-44.
21. Gawley RE, Rein KS, Jeglitsch G, Adams DJ, Theodorakis EA, Tiebes J, et al. 1995. The relationship of brevetoxins "length" and A-ring functionality to binding and activity in neuronal sodium channels. Chem Biol 2:533-541.
22. Gawley RE, Rein KS, Kinoshita M, Baden DG. 1992. Binding of brevetoxins and ciguatoxin to the voltage-sensitive sodium channel and conformational analysis of brevetoxin B. Toxicon 30:780-785.
23. Ingle RM. 1954. Irritant gas associated with red tide. Mar Lab Univ Miami Spec Serv Bull 9:1-4.
24. Jeglitsch G, Rein KS, Baden DG, Adams DJ. 1998. Brevetoxin-3 (PbTx-3) and its derivatives modulate single tetrodotoxin-sensitive sodium channels in rat sensory neurons. J Pharmacol Exp Ther 284:516-525.
25. Lin YY, Risk M, Ray SM, Van Engen D, Clardy J, Golik J, et al. 1981. Isolation and structure of brevetoxin B from "red tide" dionoflagellate Gymnodinium breve (Ptychodiscus brevis). J Am Chem Soc 103:6773-6776.
26. Martin DF, Chatterjee AB. 1969. Isolation and characterization of a toxin from the Florida red tide organism. Nature 221:9.
27. McFarren EF, Tanabe H, Silva FJ, Wilson WB, Campbell JE, Lewis KH. 1965. The occurrence of a ciguatera-like poisons in oysters, clams, and Gymnodinium breve cultures. Toxicon 3:111-123.
28. Nicoloau KC, Rutjes FPJT, Theodorakis EA, Tiebes J, Sato M, Untersteller E. 1995. Total synthesis of brevetoxin B. 2. Completion. J Am Chem Soc 117:1173-1174.
29. Nicoloau KC, Yang Z, Shi GQ, Gunzner JL, Agrios KA, Gartner P. 1998. Total synthesis of brevotoxin A. Nature 392:264-269.
30. Poli MA, Mende TJ, Baden DG. 1986. Brevetoxins, unique activators of voltage sensitive sodium channels, bind to specific sites in rat brain synaptosomes. Mol Pharmacol 30:129-135.
31. Purkerson SL, Baden DG, Fieber LA. 1999. Brevetoxin modulates neuronal sodium channels in two cell lines derived from rat brain. Neurotoxicology 20:909-920.
32. Purkerson-Parker SL, Fieber L, Rein KS, Podana T, Baden DG. 2000. Brevetoxin derivatives that inhibit toxin activity. Chem Biol 7:385-393.
33. Rein KS, Baden DG, Gawley RE. 1994a. Conformational analysis of the sodium channel modulator brevetoxin a, comparison with brevetoxin B conformations, and an hypothesis about the common pharmacophore of the "site 5" toxins. J Org Chem 59:2101-2106.
34. Rein KS, Lynn B, Baden DG, Gawley RE. 1994b. Brevotoxin B: chemical modifications, synaptosome binding, toxicity, and an unexpected conformational effect. J Org Chem 59:2107-2113.
35. Shimizu Y, Chou HN, Bando H, VanDuyne G, Clardy JC. 1986. Structure of brevetoxin A (gb-1), the most potent toxin in the Florida red tide organism (Gymnodinium breve). J Am Chem Soc 108:514-515.
36. Shimizu Y, Gupta S, Prasad AVK. 1990. Biosynthesis of dinoflagellate toxins. In: Toxic Marine Phytoplankton (Graneli E, Sundstrom B, Edler L, Anderson DM eds). New York: Elsevier, 62-76.
37. Steidinger KA, Baden DG. 1984. Toxic marine dinoflagellates. In: Dinoflagellates (Spector DL, ed). New York:Academic Press, 201-299.
38. Sudaranam S, Duke-Virca G, March DJ, Srinivasan S. 1992. An approach to computer aided inhibitor design: application to cathepsin I. J Comput Aided Mol Des 6:223-233.
39. Taylor R. 1994. Evolutions: the voltage-gated sodium channel. J NIH Res 6:112.
40. Trainer VL, Baden DG, Catterall WA. 1994. Identification of the peptide components of the brevetoxin receptor site of rat brain sodium channels. J Biol Chem 269:19904-19909.
41. Woodcock AH. 1948. Note concerning human respiratory irritation associated with high concentrations of plankton and mass mortalities of marine organisms. J Mar Res 7:56-62.
42. Zobell CE. 1942. Microorganisms in marine air. Aerobiology (AAAS) 17:55-68.