PbTx-6 | 97938-23-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 短裸甲藻毒素及其衍生物
• 英文名称: PbTx-6
• 英文别名: 2-[[(1R,3S,5R,6R,8S,10R,12S,17R,19S,21R,23S,26R,28S,30R,32S,34R,36S,37S,39R,41R,43S,45S,46S,48S,50S)-37-hydroxy-6,16,19,26,28,36,50-heptamethyl-14-oxo-4,9,13,18,22,27,31,35,40,44,47,51-dodecaoxadodecacyclo[26.23.0.03,26.05,23.08,21.010,19.012,17.030,50.032,45.034,43.036,41.046,48]henpentacont-15-en-39-yl]methyl]prop-2-enal
• CAS: 97938-23-3
• 化学式: C₅₀H₇₀O₁₅
• 分子量: 911.097
• InChiKey: XXPMBLWPRXRSBN-IRJZHXJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  65
• 可旋转键数：
  3
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  brevetoxin-2 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 以95%的产率得到PbTx-6
  参考文献：
  名称：

  [EN] POLYETHER BREVETOXIN DERIVATIVES AS A TREATMENT FOR NEUROTOXIC SHELLFISH POISONING AND CIGUATERA FISH POISONING
  [FR] DERIVES DE POLYETHER BREVETOXINE POUR LE TRAITEMENT D'EMPOISONNEMENTS NEUROTOXIQUES PAR LES CRUSTACES ET DE LA CIGUATERA

  摘要：

  本发明涉及衍生自布雷维毒素或PbTx的化合物、包含该化合物的药物配方以及将该化合物用于治疗神经毒性贝类中毒或雪卡鱼毒中毒的方法，其中该化合物具有一般式（I）和（III）：其中R、R1、R2、R3、A、n和Y对于每种化合物在此定义。

  公开号：

  WO2005027903A1

文献信息

• [EN] POLYETHER BREVETOXIN DERIVATIVES AS A TREATMENT FOR NEUROTOXIC SHELLFISH POISONING AND CIGUATERA FISH POISONING<br/>[FR] DERIVES DE POLYETHER BREVETOXINE POUR LE TRAITEMENT D'EMPOISONNEMENTS NEUROTOXIQUES PAR LES CRUSTACES ET DE LA CIGUATERA
  申请人：UNIVESITY OF NORTH CAROLINA AT

  公开号：WO2005027903A1

  公开（公告）日：2005-03-31

  Disclosed are compounds that are derivatives of brevetoxin, or PbTx, pharmaceutical formulations comprising the compounds, and methods of administering the compounds to a subject for the treatment of neurotoxic shellfish poisoning or ciguatera fish poisoning, wherein the compounds have general Formulas (I) and (III): wherein R, R1, R2, R3, A, n, and Y are as defined herein for each compound.

  本发明涉及衍生自布雷维毒素或PbTx的化合物、包含该化合物的药物配方以及将该化合物用于治疗神经毒性贝类中毒或雪卡鱼毒中毒的方法，其中该化合物具有一般式（I）和（III）：其中R、R1、R2、R3、A、n和Y对于每种化合物在此定义。
• Brevetoxin B: Chemical Modifications, Synaptosome Binding, Toxicity, and an Unexpected Conformational Effect
  作者：Kathleen S. Rein、Bert Lynn、Robert E. Gawley、Daniel G. Baden

  DOI：10.1021/jo00087a028

  日期：1994.4

  Five naturally occurring brevetoxins and seven synthetically modified brevetoxins were examined for their affinity for site 5 of the voltage-gated sodium channel and their toxicity to mosquito fish, Gambusia affinis. All but three of the toxins studied still retained some affinity for their receptor site (IC50's in the range of 1-100 nM). Compound 7, having all three carbon-carbon double bonds reduced, is almost 3 orders of magnitude less strongly bound than 4, which has only two carbon-carbon bonds reduced. This large effect resulting from H-ring reduction was unexpected, due to the similarity of this region of the molecule to the corresponding region of brevetoxin-A, which has a fully saturated eight-membered G-ring and is the most strongly bound toxin of those studied. Conformational analysis revealed that the unsaturated H-ring of brevetoxin B favors the boat-chair conformation as does the saturated G-ring of brevetoxin A. Upon reduction, the H-ring of brevetoxin B shifts to a crown conformation. This subtle change in conformational preference induces a significant change in the gross shape of the molecule, which we believe is responsible for the loss of binding affinity and toxicity.