203734-M

Brevetoxin PbTx-3, Ptychodiscus brevis

Lipid-soluble polyether marine toxin produced by the red tide dinoflagellate, Ptychodiscus brevis, found along the Gulf Coast of Florida.

• Synonym(s): Brevetoxin PbTx-3, Ptychodiscus brevis, Pumiliotoxin, Dihydrobrevetoxin B
• Empirical Formula (Hill Notation): C₅₀H₇₂O₁₄
• CAS Number: 85079-48-7
• Molecular Weight: 897.10
• MDL number: MFCD00214096
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• description: RTECS - XW5885000
• assay: >95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• solubility: ethanol: 10 mg/mL; DMSO: 30 mg/mL; acetonitrile: 30 mg/mL; chloroform: 30 mg/mL; methanol: 30 mg/mL; water: sparingly soluble
• Storage temp.: −20°C
• SMILES string: O1C2(C(OC8(C(OC9C(OC%10C(OC%11(C(OC(CC%11O)CC(=C)CO)C%10)C)C9)\C=C/C8)C2)C)CC3OC4C(OC5C(OC6C(OC7C(OC(=O)C=C7C)C6)(C5)C)CC4C)CCC31C)C
• InChI: 1S/C50H72O14/c1-25(24-51)14-28-17-37(52)50(8)41(54-28)19-33-34(61-50)18-32-29(55-33)10-9-12-46(4)42(58-32)23-49(7)40(62-46)21-39-47(5,64-49)13-11-30-44(60-39)26(2)15-31-36(56-30)22-48(6)38(57-31)20-35-45(63-48)27(3)16-43(53)59-35/h9-10,16,26,28-42,44-45,51-52H,1,11-15,17-24H2,2-8H3/b10-9-
• InChI key: BKMHDYJRAAJTAD-KTKRTIGZSA-N

Description

General description

Lipid-soluble polyether marine toxin produced by the red tide dinoflagellate, Ptychodiscus brevis, found along the Gulf Coast of Florida. Voltage-dependent Na⁺ channel activator that causes contractile paralysis in animal models by binding to a unique site on these channels. The excitatory action of brevetoxins on nerve and muscle membranes is responsible for a wide spectrum of the toxic effects, including massive transmitter release from nerve endings, muscle fasciculations, and ventricular fibrillation. The toxin does not bind to either tetrodotoxin or aconitine/veratridine sites.

Biochem/physiol Actions

Primary Target
Voltage-dependent Na+ channel activator

Warning

Toxicity: Highly Toxic (H)

Reconstitution

Following reconstitution, aliquot, purge with inert gas and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C. Store stock solutions in glass vials; brevetoxin will stick to plastic. Use PTFE or silicon pipette tips.

Other Notes

Baden, D.G., et al. 1994. Nat. Toxins2, 212.
Rein, K., et al. 1994. J. Org. Chem.59, 2107.
Edwards, R.A., et al. 1992. Mol. Brain Res.14, 64.
Trainer, V.L. 1991. Mol. Pharmacol.40, 988.
Tsai, M.C., and Chen, M.L. 1991. Br. J. Pharmacol.103, 1126.
Trainer, V.L., et al. 1990. ACS Symposium Series418, 166.
Baden, D.G., et al. 1988. Toxicon26, 97.
Poli, M.A., et al. 1986. Mol. Pharmacol.30, 129.
Shimizu, Y., et al. 1986. J. Am. Chem. Soc.108, 514.
Baden, D.G., et al. 1982. Toxicon19, 455.
Catterfall, W.A., and Risk, M. 1981. Mol. Pharmacol.19, 345.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H300,H410
• pcodes: P264 - P273 - P301 + P310 - P391 - P405 - P501
• Hazard Classifications: Acute Tox. 1 Oral - Aquatic Acute 1 - Aquatic Chronic 1
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable