Brevetoxin B
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| Category | Mycotoxins |
| Catalog number | BBF-00589 |
| CAS | 79580-28-2 |
| Molecular Weight | 895.08 |
| Molecular Formula | C50H70O14 |
| Purity | ≥95% |
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Description
Brevetoxin B is a polyacyl toxoid produced by Ptychodiscus brevis (Gymnodiniuin bervis). It has a strong effect of activating cell membrane sodium channels, and Tetrodotoxin can counteract its activity.
Specification
| Synonyms | PbTx-2 |
| Storage | Stable in freeze-dried state; keep in dark and cold place; in solution, keep at -20 °C. |
| IUPAC Name | 2-[[(1R,3S,5R,7S,9R,11S,12S,14R,16R,18S,20R,21Z,24S,26R,28S,30R,31R,33S,35R,37S,42R,44S,46R,48S)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-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-14-yl]methyl]prop-2-enal |
| Canonical SMILES | CC1CC2C(CC3(C(O2)CC4C(O3)C(=CC(=O)O4)C)C)OC5C1OC6CC7C(CC8C(O7)(CC=CC9C(O8)CC1C(O9)CC2C(O1)(C(CC(O2)CC(=C)C=O)O)C)C)(OC6(CC5)C)C |
| InChI | InChI=1S/C50H70O14/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/h9-10,16,24,26,28-42,44-45,52H,1,11-15,17-23H2,2-8H3/b10-9-/t26-,28-,29-,30+,31+,32+,33+,34-,35+,36-,37+,38-,39+,40-,41-,42-,44-,45-,46+,47-,48+,49+,50+/m1/s1 |
| InChI Key | LYTCVQQGCSNFJU-FGRVLNGBSA-N |
| Source | Brevetoxin-B, produced by the red tide organism, Gymnodium breVe Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. |
Properties
| Appearance | Lyophilized solid |
| Melting Point | 295-297°C |
| Density | 1.188 g/cm3 |
| Solubility | Soluble in chloroform, hexane |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Brevetoxins are neurotoxins that bind to voltage-gated sodium channels in nerve cells, leading to disruption of normal neurological processes and causing the illness clinically described as neurotoxic shellfish poisoning (NSP). Brevetoxins bind to site 5 on the alpha-subunit of voltage sensitive sodium channels (VSSCs), which serve as key proteins in the structure of the cell membrane. |
Reference Reading
1. Total synthesis of brevetoxin-B
Nobuyuki Hori, Koji Kawamura, Hiroko Matsukura, Goh Matsuo, Tadashi Nakata J Am Chem Soc . 2004 Nov 10;126(44):14374-6. doi: 10.1021/ja0449269.
Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.
2. Semisynthesis of radiolabeled amino acid and lipid brevetoxin metabolites and their blood elimination kinetics in C57BL/6 mice
Noah Muha, Christopher O Miles, John S Ramsdell, Tod A Leighfield Chem Res Toxicol . 2013 Jun 17;26(6):868-77. doi: 10.1021/tx4000057.
Brevetoxin B (BTX-B), produced by dinoflagellates of the species Karenia, is a highly reactive molecule, due in part to an α,β-unsaturated aldehyde group at the terminal side chain, leading to the production of metabolites in shellfish by reduction, oxidation, and conjugation. We have investigated in mice the blood elimination of three common bioactive brevetoxin metabolites found in shellfish, which have been semisynthesized from BTX-B in radioactive forms. BTX-B was reduced at C42 to yield [(3)H] dihydro-BTX-B. [(3)H] S-desoxy-BTX-B2 (cysteine brevetoxin B) was semisynthesized from BTX-B by the conjugation of cysteine at the C50 olefinic group then [(3)H] radiolabeled by C42 aldehyde reduction. [(14)C] N-Palmitoyl-S-desoxy-BTX-B2 was prepared using S-desoxy-BTX-B2 as the starting material with addition of the [(14)C] radiolabeled fatty acid via cysteine-amide linkage. The elimination of intravenously administered [(3)H] S-desoxy-BTX-B2, [(14)C] N-palmitoyl-S-desoxy-BTX-B2, or [(3)H] dihydro-BTX-B was measured in blood collected from C57BL/6 mice over a 48 h period. Each brevetoxin metabolite tested exhibited biexponential elimination kinetics and fit a two-compartment model of elimination that was applied to generate toxicokinetic parameters. The rate of transfer between the central compartment (i.e., blood) and the peripheral compartment (e.g., tissue) for each brevetoxin differed substantially, with dihydro-BTX-B exchanging rapidly with the peripheral compartment, S-desoxy-BTX-B2 eliminating rapidly from the central compartment, and N-palmitoyl-S-desoxy-BTX-B2 eliminating slowly from the central compartment. Toxicokinetic parameters were analyzed in the context of the unique structure of each brevetoxin metabolite resulting from a reduction, amino acid conjugation, or fatty acid addition to BTX-B.
3. Brevetoxin-B of Gymnodinium breve toxin-induced contractions of smooth muscles due to the transmitter release from nerves
S Shibata, Y Ishida Pharmacology . 1985;31(4):237-40. doi: 10.1159/000138120.
Brevetoxin-B (BTX-B), a Gymnodinium breve toxin, isolated from the dinoflagellate, produced contraction of guinea pig ileum and rabbit aorta. Atropine (10(-6) M) and phentolamine (10(-6) M) abolished the BTX-B (10(-7) or 10(-6)-induced contraction of the ileum or aorta, respectively. Tetrodotoxin and saxitoxin (both 5 x 10(-7) M) also abolished the responses to BTX-B in the both tissues. Results suggest that BTX-B produces smooth muscle contractions through the tetrodotoxin- and saxitoxin-sensitive release of transmitters from autonomic nerves.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C50H70O14
Molecular Weight (Monoisotopic Mass): 894.4766 Da
Molecular Weight (Avergae Mass): 895.0824 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C50H70O14
Molecular Weight (Monoisotopic Mass): 894.4766 Da
Molecular Weight (Avergae Mass): 895.0824 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
