cholesterol-3-(carboxyaminopropan-3-ol) | 200337-33-3

• 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: cholesterol-3-(carboxyaminopropan-3-ol)
• 英文别名: cholesteryl 3-hydroxypropylcarbamate；[(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-(3-hydroxypropyl)carbamate
• CAS: 200337-33-3
• 化学式: C₃₁H₅₃NO₃
• 分子量: 487.767
• InChiKey: LOQBFXSUAYISNO-GTPODGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cholesterol-3-(carboxyaminopropan-3-ol) 在 三乙胺 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers

  摘要：

  一系列新的阳离子脂质合成细节涉及具有两种不同脂肪链的脂质。转染效率表明将一种萜烯基链与月桂基链或油酸基链结合是有趣的。

  DOI：

  10.1039/c3ob42270d
• 作为产物：
  描述：

  胆固醇甲酰氯 、 3-氨基-1-丙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cholesterol-3-(carboxyaminopropan-3-ol)
  参考文献：
  名称：

  Carrier-free cellular uptake and the gene-silencing activity of the lipophilic siRNAs is strongly affected by the length of the linker between siRNA and lipophilic group

  摘要：

  通过与分子结合，这些分子可以通过自然运输机制进入细胞，从而增强siRNA的细胞摄取。在此，我们研究了通过不同长度的亚甲基连接子将疏水性残基（胆固醇、石胆酸、油醇和石胆酸油胺）连接到正义链的5′端，制备的耐核酸酶的抗MDR1 siRNA的无载体细胞摄取。我们开发了一种方便的H-磷酸盐和磷酰胺方法的组合，用于合成siRNA的5′-疏水性偶联物。发现当在微摩尔浓度范围内使用时，疏水性siRNA能够有效地渗透到HEK293、HepG2细胞和KB-8-5癌细胞中。摄取效率取决于疏水性部分类型、部分与siRNA之间的连接子长度以及细胞类型。在所有测试的偶联物中，含有6到10个碳原子的连接子连接的胆固醇化siRNA显示出最佳的摄取和基因沉默特性：连接子缩短会降低siRNA偶联物的细胞摄取效率，而连接子延长有助于摄取，但会延迟基因沉默效应并降低沉默效率。

  DOI：

  10.1093/nar/gkr1002

文献信息

• DUPLEX OLIGONUCLEOTIDE COMPLEXES AND METHODS FOR GENE SILENCING BY RNA INTERFERENCE
  申请人：Yamada Christina

  公开号：US20080085869A1

  公开（公告）日：2008-04-10

  Provided herein are duplex oligonucleotide complexes which can be administered to a cell, tissue or organism to silence a target gene without the aid of a transfection reagent(s). The duplex oligonucleotide complexes of the disclosure include a conjugate moiety that facilitates delivery to a cell, tissue or organism.

  本文提供了一种双链寡核苷酸复合物，可以被输送到细胞、组织或生物体中，以沉默目标基因，而无需转染试剂的帮助。本公开的双链寡核苷酸复合物包括一个共轭基团，有助于将其输送到细胞、组织或生物体中。
• TRIPARTITE OLIGONUCLEOTIDE COMPLEXES AND METHODS FOR GENE SILENCING BY RNA INTERFERENCE
  申请人：Yamada Christina

  公开号：US20100093085A1

  公开（公告）日：2010-04-15

  Provided herein are tripartite oligonucleotide complexes which can be administered to a cell, tissue or organism to silence a target gene. The tripartite oligonucleotide complexes of the disclosure may include a conjugate moiety that facilitates delivery to a cell, tissue or organism without the aid of a transfection reagent

  本文提供了三分体寡核苷酸复合物，可用于静默目标基因的细胞、组织或生物的治疗。本文所述的三分体寡核苷酸复合物可能包括一个共轭基团，以便在不需要转染试剂的情况下促进其递送到细胞、组织或生物中。
• Duplex Oligonucleotide Complexes and Methods for Gene Silencing by RNA Interference
  申请人：Yamada Christina

  公开号：US20120322855A1

  公开（公告）日：2012-12-20

  Provided herein are duplex oligonucleotide complexes which can be administered to a cell, tissue or organism to silence a target gene without the aid of a transfection reagent(s). The duplex oligonucleotide complexes of the disclosure include a conjugate moiety that facilitates delivery to a cell, tissue or organism.

  本文提供了一种双链寡核苷酸复合物，可以在不使用转染试剂的情况下被输送到细胞、组织或生物体中，以沉默目标基因。本文所述的双链寡核苷酸复合物包括一个共轭基团，可以促进其输送到细胞、组织或生物体中。
• POLYCATIONIC STEROL DERIVATIVES AS TRANSFECTION AGENTS
  申请人：IC-VEC LIMITED

  公开号：EP0918790B1

  公开（公告）日：2004-01-28
• Polyamine Analogues of 3β-[N-(N′,N′-Dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) as Agents for Gene Delivery
  作者：Robert G. Cooper、Christopher J. Etheridge、Luisa Stewart、John Marshall、Samantha Rudginsky、Seng H. Cheng、Andrew D. Miller

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

  日期：1998.1

  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.