N-cholesteryloxycarbonyl-2,3-dihydroxypropylamine | 170962-96-6

• 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: N-cholesteryloxycarbonyl-2,3-dihydroxypropylamine
• 英文别名: cholesterol 2,3-dihydroxypropylcarbamate；[(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-(2,3-dihydroxypropyl)carbamate
• CAS: 170962-96-6
• 化学式: C₃₁H₅₃NO₄
• 分子量: 503.766
• InChiKey: RQMKMWQXWZNOAC-OXTUKQHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  36
• 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：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-cholesteryloxycarbonyl-2,3-dihydroxypropylamine 在 吡啶 、 N-甲基咪唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Structure-Activity Relationships of Cytotoxic Cholesterol-Modified DNA Duplexes

  摘要：

  Short DNA duplexes with cholesterol linked at the 3'-terminus of each strand have unique, selective cytotoxic properties. The structural requirements for biological activity were explored through chemical synthesis of analogs and testing in cultured hepatoma cells. Effects of modifications to the sequence, backbone, 3'-sterol, 3'-linker, and 5'-terminus were evaluated. Self-complementary 3'-modified oligodeoxynucleotide (ODN) 10-mers were prepared from solid supports bearing the modification and linker of interest. Any changes to the normal phosphodiester backbone were poorly tolerated. The presence of cholesterol or a closely related sterol was an absolute requirement for activity. The length and position of attachment of the linker to cholesterol was important, with longer linkers showing reduced activity. Large, lipophilic groups at the 5'-terminus gave reduced cytotoxicity and poor solubility properties. The short length and unique structure of these ODNs allowed efficient automated synthesis on a 400 mu mol scale and simplified purification.

  DOI：

  10.1021/jm00022a025
• 作为产物：
  描述：

  胆固醇 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 N-cholesteryloxycarbonyl-2,3-dihydroxypropylamine
  参考文献：
  名称：

  Structure-Activity Relationships of Cytotoxic Cholesterol-Modified DNA Duplexes

  摘要：

  Short DNA duplexes with cholesterol linked at the 3'-terminus of each strand have unique, selective cytotoxic properties. The structural requirements for biological activity were explored through chemical synthesis of analogs and testing in cultured hepatoma cells. Effects of modifications to the sequence, backbone, 3'-sterol, 3'-linker, and 5'-terminus were evaluated. Self-complementary 3'-modified oligodeoxynucleotide (ODN) 10-mers were prepared from solid supports bearing the modification and linker of interest. Any changes to the normal phosphodiester backbone were poorly tolerated. The presence of cholesterol or a closely related sterol was an absolute requirement for activity. The length and position of attachment of the linker to cholesterol was important, with longer linkers showing reduced activity. Large, lipophilic groups at the 5'-terminus gave reduced cytotoxicity and poor solubility properties. The short length and unique structure of these ODNs allowed efficient automated synthesis on a 400 mu mol scale and simplified purification.

  DOI：

  10.1021/jm00022a025

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。
• Duplex oligonucleotide complexes and methods for gene silencing by RNA interference
  申请人：Dharmacon, Inc.

  公开号：US08252755B2

  公开（公告）日：2012-08-28

  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，可以在不需要转染试剂的情况下被施用于细胞、组织或生物体，以沉默目标基因。该公开的双链寡核苷酸复合物包括一个共轭基团，可促进其输送到细胞、组织或生物体。
• Composition comprenant une dispersion aqueuse de vésicules lipidiques à base de carbamates à chaîne cholestéryle, utilisation notamment en cosmétique et nouveaux composés
  申请人：L'OREAL

  公开号：EP0890577A1

  公开（公告）日：1999-01-13

  L'invention concerne une composition, notamment cosmétique ou dermatologique, contenant une dispersion aqueuse de vésicules comprenant une membrane de lipidique caractérisée par le fait que la membrane lipidique comprend au moins un carbamate de formule (I) suivante : formule dans laquelle R1 désigne un atome d'hydrogène ou un radical alkyle, et R2 désigne un radical alkyle, sous réserve que le groupement (R1)(R2)N- comporte au moins deux groupements hydroxyle. L'invention concerne aussi certains composés nouveaux de formule (I).

  本发明涉及一种组合物，特别是一种化妆品或皮肤病组合物，该组合物含有一种包含脂质膜的囊泡的水分散液，其特征在于脂质膜包含至少一种下式(I)的氨基甲酸酯： 式中 R1 表示氢原子或烷基，R2 表示烷基，但(R1)(R2)N-基团至少含有两个羟基。 本发明还涉及某些新的式（I）化合物。