[2-[[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethyl]-trimethylazanium;chloride | 1443441-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [2-[[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethyl]-trimethylazanium;chloride
• CAS: 1443441-81-3
• 化学式: C₃₀H₅₂NO₄*Cl
• 分子量: 526.2
• InChiKey: HXNLXICFISMATH-IXIBQILOSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  石胆酸 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 108.0h， 生成 [2-[[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethyl]-trimethylazanium;chloride
  参考文献：
  名称：

  Deciphering the role of charge, hydration, and hydrophobicity for cytotoxic activities and membrane interactions of bile acid based facial amphiphiles

  摘要：

  We synthesized four cationic bile add based facial amphiphiles featuring trimethyl ammonium head groups. We evaluated the role of these amphiphiles for cytotoxic activities against colon cancer cells and their membrane interactions by varying charge, hydration and hydrophobicity. The singly charged cationic Lithocholic add based amphiphile (LCA-TMA(1)) is most cytotoxic, whereas the triply charged cationic Cholic add based amphiphile (CA-TMA(3)) is least cytotoxic. Light microscopy and Annexin-FITC assay revealed that these facial amphiphiles caused late apoptosis. In addition, we studied the interactions of these amphiphiles with model membrane systems by Prodan-based hydration, DPH-based anisotropy, and differential scanning calorimetry. LCA-TMA(1) is most hydrophobic with a hard charge causing efficient dehydration and maximum perturbations of membranes thereby facilitating translocation and high cytotoxicity against colon cancer cells. In contrast, the highly hydrated and multiple charged CA-TMA(3) caused least membrane perturbations leading to low translocation and less cytotoxicity. As expected, Chenodeoxycholic add and Deoxycholic add based amphiphiles (CDCA-TMA(2), DCA-TMA(2)) featuring two charged head groups showed intermediate behavior. Thus, we deciphered that charge, hydration, and hydrophobicity of these amphiphiles govern membrane interactions, translocation, and resulting cytoxicity against colon cancer cells. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbamem.2013.04.003

文献信息

• Bile acid amphiphiles with tunable head groups as highly selective antitubercular agents
  作者：Sandhya Bansal、Manish Singh、Saqib Kidwai、Priyanshu Bhargava、Ashima Singh、Vedagopuram Sreekanth、Ramandeep Singh、Avinash Bajaj

  DOI：10.1039/c4md00303a

  日期：——

  Hard-charged amphiphiles are highly selective against mycobacteria, whereas soft-charged amphiphiles are active against Gram-positive and Gram-negative bacteria.

  硬电荷两性分子对分枝杆菌具有高度选择性，而软电荷两性分子对革兰氏阳性和革兰氏阴性细菌具有活性。