Brevetoxin A

Brevetoxin A is a neurotoxin produced by the dinoflagellate K. brevis. It has been found in water samples collected during red tide blooms. Brevetoxin A is an activator of voltage-gated sodium channels (Nav) that binds to neurotoxin site 5 on the alpha subunit of the channel. Brevetoxins reduce the activation potential required to open the channel, increase the mean open time of the channel, and slow inactivation of the channel. It increases intracellular calcium levels in primary rat cerebellar granule cells (EC50 = 19.6 nM). Brevetoxin A induces the release of lactate dehydrogenase (LDH), L-glutamate, and L-aspartate from primary rat cerebellar granule neurons (EC50s = 8.65, 7.57, and 7.91 nM, respectively). It is lethal to fish (LC100 = 4 ng/ml in guppies) and mice (LD50 = 0.5 mg/kg, i.p.).. SMILES: C[C@@]12C[C@@](O[C@@]([C@@H](C3)O)([H])[C@](O[C@H]3CC(C=O)=C)([H])C4)([H])[C@]4([H])O[C@@]1([H])CCC[C@]5([H])[C@@](/C=C\C[C@]6([H])[C@@](C/C=C\C[C@](O[C@](C[C@](O[C@](CC7=O)([H])[C@@](O7)([H])C[C@@H]8C)([H])[C@@]9(C8)C)([H])[C@@](O9)([H])C%10)([H])[C@@]([C@@H]%10C)([H])O6)([H])O5)([H])O2. InChi Code: InChI=1S/C49H70O13/c1-26-17-36-39(22-45(52)58-36)57-44-21-38-40(62-48(44,4)23-26)18-28(3)46-35(55-38)11-7-6-10-31-32(59-46)12-8-14-34-33(54-31)13-9-15-43-49(5,61-34)24-42-37(56-43)20-41-47(60-42)30(51)19-29(53-41)16-27(2)25-50/h6-8,14,25-26,28-44,46-47,51H,2,9-13,15-24H2,1,3-5H3/b7-6-,14-8-/t26-,28+,29-,30+,31-,32+,33+,34-,35+,36+,37+,38-,39-,40+,41-,42-,43-,44+,46-,47+,48-,49+/m0/s1. InChi Key: MGVIMUPHKPHTKF-CHBIFOJISA-N