cholest-5-en-3β-oxyethane-N,N-dimethylamine | 7694-43-1

• 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: cholest-5-en-3β-oxyethane-N,N-dimethylamine
• 英文别名: cholest-5-en-3β-oxyethan-N,N-dimethylamine；2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-N,N-dimethylethan-1-amine；Cholesteryl-N,N-Dimethylethanolamine；2-[[(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]oxy]-N,N-dimethylethanamine
• CAS: 7694-43-1
• 化学式: C₃₁H₅₅NO
• 分子量: 457.784
• InChiKey: UHNXOFNYRNSBID-BWVDWJPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cholest-5-en-3β-oxyethane-N,N-dimethylamine 、 1,12-二溴十二烷 以 甲醇 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Gene Delivery Efficacies of Novel Cholesterol-Based Gemini Cationic Lipids and Their Serum Compatibility:  A Structure−Activity Investigation

  摘要：

  Five cholesterol-based gemini cationic lipids, which differ in the length of the spacer [-(CH2)(n)-] chain between the head groups, have been synthesized. These lipids are useful as nonviral gene delivery agents, and all cholesterol-based gemini lipids (2a-2e) are better transfecting agents than their monomeric lipid counterpart 1. Transfection efficiency of all the gemini lipids except lipid 2a [-(CH2)(3)-] was maintained even when the serum was present during the transfection conditions as compared to the monomeric lipid 1, with which a dramatic decrease in transfection efficiency was observed. With the increase in spacer chain length from propanediyl [-(CH2)(3)-] to pentanediyl [-(CH2)(5)-], transfection efficiency increased both in the absence and presence of serum. However, transfection efficiency decreased with further increase in the length from the pentanediyl [-(CH2)(5)-] to the dodecanediyl [-(CH2)(12)-] spacer. Among these gemini lipids 2c showed the highest transfection activity, which was also greater than that of the commercially available formulation.

  DOI：

  10.1021/jm0611253
• 作为产物：
  描述：

  胆固醇 在 吡啶 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 40.0h， 生成 cholest-5-en-3β-oxyethane-N,N-dimethylamine
  参考文献：
  名称：

  Co-liposomes comprising a lipidated multivalent RGD-peptide and a cationic gemini cholesterol induce selective gene transfection in αvβ3 and αvβ5 integrin receptor-rich cancer cells

  摘要：

  通过基于阳离子双胆固醇脂质体的棕榈酰化-RGD4介导的基因转移和细胞靶向。

  DOI：

  10.1039/c4tb00701h

文献信息

• Efficacious redox-responsive gene delivery in serum by ferrocenylated monomeric and dimeric cationic cholesterols
  作者：Gururaja Vulugundam、Krishan Kumar、Paturu Kondaiah、Santanu Bhattacharya

  DOI：10.1039/c4ob02513j

  日期：——

  New redox-active monomeric and dimeric ferrocenylated cationic cholesterols for gene transfection.

  新的氧化还原活性单聚体和二聶基阳离子类固醇用于基因转染。
• [EN] MRNAS ENCODING IMMUNE MODULATING POLYPEPTIDES AND USES THEREOF<br/>[FR] ARNM CODANT DES POLYPEPTIDES DE MODULATION IMMUNITAIRE ET LEURS UTILISATIONS
  申请人：MODERNA TX INC

  公开号：WO2021076805A1

  公开（公告）日：2021-04-22

  The disclosure features lipid nanoparticle (LNP) compositions comprising immune modulating polypeptides and uses thereof. The LNP compositions of the present disclosure comprise mRNA therapeutics encoding immune modulating polypeptides, e.g., interleukin 2 (IL- 2) and/or granulocyte macrophage colony stimulating factor (GM-CSF). The LNP compositions of the present disclosure can stimulate T regulatory cells, e.g., increase the level and/or activity of T regulatory cells in vivo or ex vivo.

  披露了包含免疫调节多肽的脂质纳米粒子（LNP）组合物及其用途。本公开的LNP组合物包括编码免疫调节多肽的mRNA治疗药物，例如白细胞介素2（IL-2）和/或粒细胞巨噬细胞集落刺激因子（GM-CSF）。本公开的LNP组合物可以刺激T调节细胞，例如在体内或体外增加T调节细胞的水平和/或活性。
• STEROL ANALOGS AND USES THEREOF
  申请人：ModernaTX, Inc.

  公开号：US20220402965A1

  公开（公告）日：2022-12-22

  The invention relates to compositions and methods for the preparation, manufacture, and therapeutic use of compositions comprising mRNA and a lipid nanoparticle comprising a compound of the invention and an ionizable lipid.

  本发明涉及包含mRNA和脂质纳米粒子的组合物的制备、制造和治疗用途的方法和组合物，所述脂质纳米粒子包括本发明的化合物和可离子化脂质。
• COMPOSITIONS AND METHODS FOR DELIVERY OF AGENTS TO IMMUNE CELLS
  申请人：ModernaTX, Inc.

  公开号：US20190314291A1

  公开（公告）日：2019-10-17

  The disclosure features immune cell delivery lipid nanoparticle (LNP) compositions that allow for enhanced delivery of agents, e.g., nucleic acids, such as therapeutic and/or prophylactic RNAs, to immune cells, in particular T cells, as well as B cells, dendritic cells and monocytes. The LNPs comprise an effective amount of an immune cell delivery potentiating lipid such that delivery of an agent by an immune cell delivery LNP is enhanced as compared to an LNP lacking the immune cell delivery potentiating agent. Methods of using the immune cell delivery LNPs for delivery of agents, e.g., nucleic acid delivery, for protein expression, for modulating immune cell activity and modulating immune responses are also disclosed.
• LIPID NANOPARTICLE FORMULATION
  申请人：ModernaTX, Inc.

  公开号：US20200129445A1

  公开（公告）日：2020-04-30

  The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include an ionizable lipid, a phospholipid, a first sterol or a tocopherol, and optionally a second sterol different from the first sterol. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.