3β-[2-(4-dimethylaminopyridinio)acetoxy]lup-20-en-28-oic acid bromide | 1246175-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-[2-(4-dimethylaminopyridinio)acetoxy]lup-20-en-28-oic acid bromide
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[2-[4-(dimethylamino)pyridin-1-ium-1-yl]acetyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid;bromide
• CAS: 1246175-12-1
• 化学式: Br*C₃₉H₅₉N₂O₄
• 分子量: 699.812
• InChiKey: YCWIAWWADFMRKG-AOOLBFPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-二甲氨基吡啶 、 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-bromoacetyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid 以 N,N-二甲基乙酰胺 为溶剂， 生成 3β-[2-(4-dimethylaminopyridinio)acetoxy]lup-20-en-28-oic acid bromide
  参考文献：
  名称：

  Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function

  摘要：

  Development of mitochondrially-targeted drugs is receiving increasing attention because of the central roles these organelles play in energy production, reactive oxygen generation, and regulation of cell death pathways. Previous studies have demonstrated that both natural and synthetic triterpenoids can disrupt mitochondrial structure and function. In this study, we tested the ability of a number of dimethylaminopyridine (DMAP) derivatives of lupane triterpenoids to target mitochochondria in two human melanoma cell lines and an untransformed normal fibroblast line. These compounds induced a striking fragmentation and depolarization of the mitochondrial network, along with an inhibition of cell proliferation. A range of potencies among these compounds was noted, which was correlated with the number, position, and orientation of the DMAP groups. Overall, the extent of proliferation inhibition mirrored the effectiveness of mitochondrial disruption. Thus, DMAP derivatives of lupane triterpenoids can be potent mitochondrial perturbants that appear to suppress cell growth primarily via their mitochondrial effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.075

文献信息

• Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function
  作者：Jon Holy、Oksana Kolomitsyna、Dmytro Krasutsky、Paulo J. Oliveira、Edward Perkins、Pavel A. Krasutsky

  DOI：10.1016/j.bmc.2010.06.075

  日期：2010.8

  Development of mitochondrially-targeted drugs is receiving increasing attention because of the central roles these organelles play in energy production, reactive oxygen generation, and regulation of cell death pathways. Previous studies have demonstrated that both natural and synthetic triterpenoids can disrupt mitochondrial structure and function. In this study, we tested the ability of a number of dimethylaminopyridine (DMAP) derivatives of lupane triterpenoids to target mitochochondria in two human melanoma cell lines and an untransformed normal fibroblast line. These compounds induced a striking fragmentation and depolarization of the mitochondrial network, along with an inhibition of cell proliferation. A range of potencies among these compounds was noted, which was correlated with the number, position, and orientation of the DMAP groups. Overall, the extent of proliferation inhibition mirrored the effectiveness of mitochondrial disruption. Thus, DMAP derivatives of lupane triterpenoids can be potent mitochondrial perturbants that appear to suppress cell growth primarily via their mitochondrial effects. (C) 2010 Elsevier Ltd. All rights reserved.