microcystin-LA

• 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: microcystin-LA
• 英文别名: MC-LA；(2R)-5-[[3-[[(2R)-1-[[(2S)-1-[[(1R,2S)-3-[[2-[[(2S,3S,8S,9S)-1-amino-9-methoxy-2,6,8-trimethyl-1-oxo-10-phenyldeca-4,6-dien-3-yl]amino]-2-oxoethyl]amino]-1-carboxy-2-methyl-3-oxopropyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-oxoprop-1-en-2-yl]-methylamino]-2-methyl-5-oxopentanoic acid
• 化学式: C₄₆H₆₉N₇O₁₂
• 分子量: 912.094
• InChiKey: CYAJEMFRSQGFIG-ISWIILBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  65
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  293
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 microcystin-LA 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 MC-LA-AM2
  参考文献：
  名称：

  Acyloxymethyl Esterification of Nodularin-R and Microcystin-LA Produces Inactive Protoxins that Become Reactivated and Produce Apoptosis inside Intact Cells

  摘要：

  We report the esterification of the carboxyl groups of the cyclic peptide toxins nodularin-R. and microcystin-LA to produce stable diacetoxymethyl and dipropionyloxymethyl ester derivatives. The derivatives had no activity but were reactivated upon esterase treatment. When injected into cells, the acyloxymethyl moieties were cleaved off and apoptosis induced. Linking the acyloxymethyl-ester moiety of these potent toxins to carriers destined for endocytosis paves the way for selective apoptosis induction in target (e.g., cancer) cells.

  DOI：

  10.1021/jm900502e