L-lysine-dicholamide | 625448-62-6

• 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: L-lysine-dicholamide
• 英文别名: N₁,N₂-lysine dicholeamide；lysine dicholamide；(2S)-2,6-bis[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]hexanoic acid
• CAS: 625448-62-6
• 化学式: C₅₄H₉₀N₂O₁₀
• 分子量: 927.316
• InChiKey: IXQWQEUBYPLYKR-YWTYNQARSA-N

物化性质

• 沸点：
  1051.7±65.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  66
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  217
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  L-lysine-dicholamide 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (S)-6-{(S)-2,6-Bis-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexanoylamino}-2-tert-butoxycarbonylamino-hexanoic acid
  参考文献：
  名称：

  Poly(choloyl)-Based Amphiphiles as Pore-Forming Agents:  Transport-Active Monomers by Design

  摘要：

  This paper describes the design and synthesis of a family of pore-forming amphiphiles. Two of these amphiphiles, which are derived from cholic acid, lysine, and p-phenylenediamine, can produce pores in lipid bilayers as individual molecules. In sharp contrast, analogous amphiphiles that do not contain a rigid 1,4-phenylenediamide moiety favor the formation of dimer-based pores. Kinetic evidence in support of monomer- and dimer-based pores has been obtained from Na+ transport measurements across bilayers made from 1-palmitoyl-2-oleoyl-2-sn-glycero-3-phosphocholine (POPC). Structure-activity studies that have been carried out with pore-forming, dimer-based amphiphiles have also revealed a significant activity dependence on their overall compactness. The practical potential of pore-forming amphiphiles with controllable supramolecular properties is briefly discussed.

  DOI：

  10.1021/ja053527q
• 作为产物：
  描述：

  L-赖氨酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以75%的产率得到L-lysine-dicholamide
  参考文献：
  名称：

  [EN] SULFATED MOLECULAR UMBRELLAS CONTAINING 6-200 CHOLANIC ACID (DERIVATIVE) UNITS AS ANTI-HIV AND ANTI-HSV AGENTS
  [FR] PARAPLUIES MOLECULAIRES SULFATES EN TANT QU'AGENTS ANTI-VIH ET ANTI-VHS

  摘要：

  公开号：

  WO2006034369A3

文献信息

• REDUCED TOXICITY MOLECULAR CONJUGATES OF ANTI-FUNGAL AGENTS
  申请人：Lehigh University

  公开号：US20170042923A1

  公开（公告）日：2017-02-16

  Compositions, compounds and methods are described for addressing both toxicity of membrane disruptive anti-microbial agents as well as poor transport of such agents across the blood-brain-barrier (BBB) via the use of molecular appendages including one or more facial amphiphiles. These molecules have in vitro anti-fungal activity that is very similar to that of the native drug but with hemolytic activity and toxicity towards mammalian cells that is greatly reduced.

  描述了用于解决膜破坏型抗微生物药物的毒性以及这些药物在穿越血脑屏障（BBB）时的运输不良的构成物、化合物和方法，通过使用包括一个或多个脸部两性分子在内的分子附件。这些分子在体外具有与原始药物非常相似的抗真菌活性，但对哺乳动物细胞的溶血活性和毒性大大降低。
• Mehiri, Mohamed; Chen, Wen-Hua; Janout, Vaclav, Journal of the American Chemical Society, 2009, vol. 131, p. 1338 - 1339
  作者：Mehiri, Mohamed、Chen, Wen-Hua、Janout, Vaclav、Regen, Steven L.

  DOI：——

  日期：——