[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(2-oxoethyl)carbamate | 200337-34-4

• 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: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(2-oxoethyl)carbamate
• CAS: 200337-34-4
• 化学式: C₃₀H₄₉NO₃
• 分子量: 471.724
• InChiKey: MBKFLAJSXYJTQT-NXUCFJMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(2-oxoethyl)carbamate 在 palladium on activated charcoal sodium tetrahydroborate 、 环己烯 、 三甲基膦 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-aminoethylamino)ethyl]carbamate
  参考文献：
  名称：

  Polyamine Analogues of 3β-[N-(N′,N′-Dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) as Agents for Gene Delivery

  摘要：

  Cationic liposomes are rapidly proving very effective at mediating the delivery of genes to cells in vitro. Moreover, the use of cationic liposomes for gene delivery in vivo is now under consideration. In previous work, we were able to demonstrate that cationic liposomes, formulated from 3 beta-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) and the neutral phospholipid, dioleoyl L-alpha-phosphatidylethanolamine (DOPE), were able to transfect the lungs of mice in vivo. However, it rapidly became apparent that substantial improvements in the gene delivery efficiency, by approximately two orders of magnitude, would be needed for human lung transfection to be possible. In the following paper we describe the synthesis of a range of polyamine analogues of DC-Chol, which were formulated into cationic liposomes with DOPE and evaluated for efficiency of gene delivery in vitro and in vivo in mice. We report that cationic liposomes formulated from DOPE and the novel pentamine N-15-cholesteryloxycarbonyl-3,7,12-triazapentadecane-1,15-diamine (CTAP) were 100 times more efficient than DC-Chol/DOPE liposomes at gene delivery in vivo (500 times more effective than DNA alone). Therefore, we believe that CTAP/DOPE cationic liposomes should have clinical applications in human gene therapy approaches to the treatment of lung disorders as well as to other clinical conditions.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<137::aid-chem137>3.0.co;2-2
• 作为产物：
  描述：

  N¹-cholesteryloxycarbonyl-1-amino-2-hydroxyethane 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(2-oxoethyl)carbamate
  参考文献：
  名称：

  Polyamine Analogues of 3β-[N-(N′,N′-Dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) as Agents for Gene Delivery

  摘要：

  Cationic liposomes are rapidly proving very effective at mediating the delivery of genes to cells in vitro. Moreover, the use of cationic liposomes for gene delivery in vivo is now under consideration. In previous work, we were able to demonstrate that cationic liposomes, formulated from 3 beta-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) and the neutral phospholipid, dioleoyl L-alpha-phosphatidylethanolamine (DOPE), were able to transfect the lungs of mice in vivo. However, it rapidly became apparent that substantial improvements in the gene delivery efficiency, by approximately two orders of magnitude, would be needed for human lung transfection to be possible. In the following paper we describe the synthesis of a range of polyamine analogues of DC-Chol, which were formulated into cationic liposomes with DOPE and evaluated for efficiency of gene delivery in vitro and in vivo in mice. We report that cationic liposomes formulated from DOPE and the novel pentamine N-15-cholesteryloxycarbonyl-3,7,12-triazapentadecane-1,15-diamine (CTAP) were 100 times more efficient than DC-Chol/DOPE liposomes at gene delivery in vivo (500 times more effective than DNA alone). Therefore, we believe that CTAP/DOPE cationic liposomes should have clinical applications in human gene therapy approaches to the treatment of lung disorders as well as to other clinical conditions.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<137::aid-chem137>3.0.co;2-2

文献信息

• [EN] COMPOSITION COMPRISING A COMBINATION OF DERIVATISED CATIONIC LIPOSOMES AND ACTIVE AGENT<br/>[FR] COMPOSITION COMPRENANT UNE COMBINAISON DE LIPOSOMES CATIONIQUES DERIVES ET D'AGENT ACTIF
  申请人：IMPERIAL COLLEGE INNOVATIONS LIMITED

  公开号：WO1999054344A1

  公开（公告）日：1999-10-28

  (EN) There is provided use of a combination of a derivatised cationic liposome and an agent of interest in the preparation of a composition for delivering the agent of interest to a site that is distal to the site of administration of the composition, wherein the derivatised cationic liposome comprises a cationic liposome forming entity and a head group and/or a ligand, and wherein the head group and/or ligand increases macrophage uptake of the cationic liposome.(FR) L'invention concerne l'utilisation d'une combinaison d'un liposome cationique dérivé et d'un agent intéressant lors de la préparation d'une composition pour introduire l'agent intéressant dans un site distal par rapport au site d'administration de la composition, le liposome cationique dérivé comprenant une entité de formation de liposome cationique et un groupe de tête et/ou un ligand, le groupe de tête et/ou ligand augmentant l'apport macrophage du liposome cationique.