Lyngbyatoxin | 70497-14-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Lyngbyatoxin
• 英文别名: 5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-9-methyl-10-propan-2-yl-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one
• CAS: 70497-14-2
• 化学式: C₂₇H₃₉N₃O₂
• 分子量: 437.6
• InChiKey: KISDGNGREAJPQR-UHFFFAOYSA-N

物化性质

• 沸点：
  665.1±55.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.4
• 氢给体数：
  3
• 氢受体数：
  3

ADMET

毒理性

• 毒性总结

石房蛤毒素A是一种肿瘤促进剂。石房蛤毒素A和相关化合物能与蛋白激酶C（PKC）同工酶的富含半胱氨酸的C1结构域（C1A和C1B）结合并激活它们，这可能导致肿瘤形成（A15358）。在癌细胞中，PKC同工酶通过增加或减少参与各种细胞信号通路，参与细胞增殖、存活、侵袭、迁移、凋亡、血管生成以及对抗癌药物的抗性（L2138）。石房蛤毒素A还能诱导鸟氨酸脱羧酶（A3219）。由鸟氨酸脱羧酶（ODC）催化的鸟氨酸脱羧反应是合成多胺的第一步和承诺步骤，特别是腐胺、精脒和精胺。ODC在多种癌症中上调。ODC促进癌变的机制复杂，并不完全清楚。除了对DNA稳定性的直接影响外，多胺还上调间隙连接基因并下调紧密连接基因。间隙连接基因参与致癌细胞间的通信，而紧密连接基因作为肿瘤抑制因子。（维基百科）

Lyngbyatoxin A is a tumor promoter. Lyngbyatoxin A and related compounds bind to the cysteine-rich C1 domains (C1A and C1B) of protein kinase C (PKC) isozymes to activate them, possibly leading to tumor formation (A15358). In cancer cells, PKC isozymes are involved in cell proliferation, survival, invasion, migration, apoptosis, angiogenesis, and anticancer drug resistance through their increased or decreased participation in various cellular signaling pathways (L2138). Lyngbyatoxin A also induces ornithine decarboxylase (A3219). The ornithine decarboxylation reaction catalyzed by ornithine decarboxylase (ODC) is the first and committed step in the synthesis of polyamines, particularly putrescine, spermidine and spermine. ODC is upregulated in a wide variety of cancers. The mechanism by which ODC promotes carcinogenesis is complex and not entirely known. Along with their direct effect on DNA stability, polyamines also upregulate gap junction genes and downregulate tight junction genes. Gap junction genes are involved in communication between carcinogenic cells and tight junction genes act as tumor suppressors. (Wikipedia)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

未列入国际癌症研究机构(IARC)的清单。

Not listed by IARC.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

Lyngbyatoxin A 被认为是导致“游泳者痒”的原因之一，具有高度炎症效应（A15358）。Lyngbyatoxin A 是一种强效刺激物和起疱剂，同时也是致癌物。在较低浓度下，它更常见地引起较轻的症状，被称为海藻皮炎。（维基百科）

Lyngbyatoxin A is known as the causative agent of 'swimmer’s itch' with its highly inflammatory effect (A15358). Lyngbyatoxin A is a potent irritant and vesicant, as well as a carcinogen. Low concentrations more commonly encountered cause milder symptoms, known as seaweed dermatitis. (Wikipedia)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

皮肤接触；摄入

Dermal; ingestion

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

皮肤炎症，起水泡。

Inflammation of the skin, blistering.

来源:Toxin and Toxin Target Database (T3DB)