Brevetoxin 3

Name: Brevetoxin 3
SKU: B6918
Availability: InStock

Product ID B6918

Cas No. 85079-48-7

Purity ≥95%

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Description

Brevetoxins are lipid-soluble polyether neurotoxins initially produced by the dinoflagellate Karenia brevis. Brevetoxins act as agonists, binding the neurotoxin site 5 on SCN4A/Nav1.4 and SCN5A/Nav1.5 voltage-gated Na+ channels in skeletal muscle and cardiac tissue, producing a channel opening effect; this activity results in bronchoconstriction and airway inflammation in vivo. Stimulation of the voltage-gated Na+ channels also induces NMDA receptor-mediated release of L-glutamate and L-aspartate in neurons. Brevetoxin 3 is a type B brevetoxin and a metabolite of brevetoxin 2.

Product Info

Cas No.	85079-48-7
Purity	≥95%
Formula	C₅₀H₇₂O₁₄
Formula Wt.	897.20
IUPAC Name	(21Z)-12-hydroxy-14-[2-(hydroxymethyl)prop-2-enyl]-1,3,11,24,31,41,44-heptamethyl-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.03,26.05,24.07,20.09,18.011,16.030,48.033,46.035,44.037,42]pentaconta-21,40-dien-39-one
Synonym	PbTx-3
Melting Point	291-293°C. (dec.)
Solubility	Soluble in acetone, ethyl acetate, ethanol, and methanol.
Appearance	White Film

Shipping and Storage

Store Temp	-20°C
Ship Temp	Ambient

Downloads

MSDS	B6918 MSDS PDF
Info Sheet	B6918 Info Sheet PDF

References

Zaias J, Fleming LE, Baden DG, et al. Repeated exposure to aerosolized brevetoxin-3 induces prolonged airway hyperresponsiveness and lung inflammation in sheep. Inhal Toxicol. 2011 Mar;23(4):205-11. PMID: 21456953.

Liberona JL, Cárdenas JC, Reyes R, et al. Sodium-dependent action potentials induced by brevetoxin-3 trigger both IP3 increase and intracellular Ca2+ release in rat skeletal myotubes. Cell Calcium. 2008 Sep;44(3):289-97. PMID: 18276006.

Cao Z, George J, Baden DG, et al. Brevetoxin-induced phosphorylation of Pyk2 and Src in murine neocortical neurons involves distinct signaling pathways. Brain Res. 2007 Dec 12;1184:17-27. PMID: 17963734.

Radwan FF, Ramsdell JS. Characterization of in vitro oxidative and conjugative metabolic pathways for brevetoxin (PbTx-2). Toxicol Sci. 2006 Jan;89(1):57-65. PMID: 16221966.

Colman JR, Ramsdell JS. The type B brevetoxin (PbTx-3) adversely affects development, cardiovascular function, and survival in Medaka (Oryzias latipes) embryos. Environ Health Perspect. 2003 Dec;111(16):1920-5. PMID: 14644667.

Bottein Dechraoui MY, Ramsdell JS. Type B brevetoxins show tissue selectivity for voltage-gated sodium channels: comparison of brain, skeletal muscle and cardiac sodium channels. Toxicon. 2003 Jun;41(7):919-27. PMID: 12782093.

Berman FW, Murray TF. Brevetoxins cause acute excitotoxicity in primary cultures of rat cerebellar granule neurons. J Pharmacol Exp Ther. 1999 Jul;290(1):439-44. PMID: 10381810.

Jeglitsch G, Rein K, Baden DG, et al. Brevetoxin-3 (PbTx-3) and its derivatives modulate single tetrodotoxin-sensitive sodium channels in rat sensory neurons. J Pharmacol Exp Ther. 1998 Feb;284(2):516-25. PMID: 9454792.

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Brevetoxin 3

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