微囊藻毒素(LR亚型) | 101043-37-2

• 物质功能分类: 分析化学 - 标准品 - 分析标准品
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: 微囊藻毒素(LR亚型)
• 中文别名: 微囊藻毒素LR；微囊藻毒素
• 英文名称: microcystin-LR
• 英文别名: cyclo-D-alanine-L-leucine-erythro-β-methyl-D-isoaspartic acid-L-arginine-4E,6E-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid-D-isoglutamic acid-N-methyldehydroalanine；cyclo(D-Ala-L-Leu-D-MeAsp-L-Arg-Adda-D-Glu-Mdha)；microcystin–leucine–arginine；microcystin leucine-arginine；microcystin-leucine arginine；(5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• CAS: 101043-37-2
• 化学式: C₄₉H₇₄N₁₀O₁₂
• 分子量: 995.186
• InChiKey: ZYZCGGRZINLQBL-GWRQVWKTSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)
• 闪点：
  11 °C
• 溶解度：
  乙醇：1 mg/mL
• 颜色/状态：
  Solid, clear film
• 解离常数：
  pKa1 2.09; pKa2 = 2.19; pKa3 = 12.48
• 稳定性/保质期：

  在常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  71
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  343
• 氢给体数：
  10
• 氢受体数：
  13

ADMET

代谢

微囊藻素（MC）-LR-GSH、MC-LR-Cys和MC-LR在太湖杂食性鱼类的组织分布进行了研究。MC-LR和MC-LR-Cys在肝脏、肾脏和肌肉中被检测到。肝脏和肾脏中MC-LR的浓度分别为0.052微克/克干重和0.067微克/克干重。MC-LR-Cys似乎是一个重要的代谢物，肝脏和肾脏的平均含量分别为1.104微克/克干重和0.724微克/克干重，肝脏和肾脏中MC-LR-Cys/MC-LR的比例高达21.4和10.8。肝脏中MC-LR-Cys/MC-LR比例较高，以及MC-LR-Cys与MC-LR浓度之间存在显著相关性，这表明对于杂食性鱼类来说，肝脏在通过形成MC-LR-Cys来解毒MC-LR方面更为活跃。此外，肾脏中MC-LR-Cys的积累和排泄/代谢之间可能存在一种平衡。MC-LR-Cys可以直接在肾脏形成，或者从肝脏或其他组织转运而来，而肾脏中的MC-LR-Cys可能会解离为MC-LR或被排出。尽管在肌肉中很少检测到MC-LR及其代谢物，但有必要研究食用肌肉中有毒代谢物的分布。

Tissue distribution of microcystin (MC)-LR-GSH, MC-LR-Cys and MC-LR of omnivorous fish in Lake Taihu was investigated. MC-LR and MC-LR-Cys were detected in liver, kidney and muscle. The concentration of MC-LR in liver and kidney was 0.052 ug g-1 DW and 0.067 ug g-1 DW, respectively. MC-LR-Cys appeared to be an important metabolite with average contents of 1.104 ug g-1 DW and 0.724 ug g-1 DW in liver and kidney, and the MC-LR-Cys/MC-LR ratio in liver and kidney reaching as high as 21.4 and 10.8. High MC-LR-Cys/MC-LR ratio and a significant correlation between MC-LR-Cys and MC-LR concentration in liver, suggest that liver is more active in detoxification of MC-LR by formation of MC-LR-Cys for omnivorous fish. Furthermore, there might be a balance between the accumulation and depuration/metabolism of MC-LR-Cys in kidney. The MC-LR-Cys can be formed in kidney directly, or transported from liver or other tissues, while the MC-LR-Cys in kidney might be dissociated to MC-LR or excreted. Although MC-LR and its metabolites were scarcely detected in muscle, it is necessary to investigate the distribution of toxic metabolites in edible muscle.

来源:Hazardous Substances Data Bank (HSDB)

代谢

肝脏在微囊藻毒素的解毒过程中扮演着重要角色。在尿液、粪便和肝细胞溶质组分中观察到了解毒产物，但这些产物的结构尚未被鉴定。微囊藻毒素-LR的解毒产物比母体毒素更具水溶性。

The liver plays a large role in the detoxification of microcystins. Detoxification products were seen in urine, feces, and liver cytosolic fractions, but these products have not been structurally identified. The detoxification products of microcystin-LR are more water soluble than the parent toxin.

来源:Hazardous Substances Data Bank (HSDB)

代谢

谷胱甘肽（GSH）在抗氧化防御和对微囊藻毒素-LR（MC-LR）的解毒代谢中发挥关键作用。然而，哺乳动物中MC-LR的解毒过程仍然在很大程度上是未知的。本文首次定量分析了SD大鼠在MC-LR暴露后肝脏中MC-LR及其GSH途径代谢物（MC-LR-GSH和MC-LR-Cys）的变化。在大鼠接受0.25和0.5半数致死量（LD50）的MC-LR腹腔注射（i.p.）之前，用或不用GSH合成的抑制剂丁硫氨酸-(S,R)-亚磺酰亚胺（BSO）预处理。实验期间，MC-LR-GSH的含量相对较低；然而，在0.5 LD50组中，MC-LR-Cys与MC-LR的比例高达6.65。这些结果表明，MC-LR-GSH可以有效地转化为MC-LR-Cys，这一代谢规律与之前报道的