1-glyceryl cholesterol | 121076-41-3

• 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: 1-glyceryl cholesterol
• 英文别名: 3-[[(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]propane-1,2-diol
• CAS: 121076-41-3
• 化学式: C₃₀H₅₂O₃
• 分子量: 460.741
• InChiKey: DRMIQDFEIJAEOL-LLACCSHGSA-N

物化性质

• 沸点：
  577.2±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-glyceryl cholesterol 、 三苯基氯甲烷 以 吡啶 为溶剂， 反应 18.0h， 生成 三苯基甲醇 、 1-cholesteryl-3-trityl glycerol
  参考文献：
  名称：

  Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties

  摘要：

  We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37 degrees C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.

  DOI：

  10.1021/ja8065557
• 作为产物：
  描述：

  3-(2,3-isopropylidene-1-glyceryl)cholesterol 在 盐酸 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-glyceryl cholesterol
  参考文献：
  名称：

  Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties

  摘要：

  We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37 degrees C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.

  DOI：

  10.1021/ja8065557

文献信息

• 새로운 스테로이드 기반 양친매성 화합물 및 이의 활용
  申请人：Industry-University Cooperation Foundation Hanyang University ERICA Campus 한양대학교 에리카산학협력단(120120008551) Corp. No ▼ 131471-0017977BRN ▼134-82-10205

  公开号：KR20190119543A

  公开（公告）日：2019-10-22

  본 발명은 새롭게 개발한 스테로이드 기반의 양친매성 화합물, 이의 제조방법 및 이를 이용하여 막단백질을 추출, 용해화, 안정화, 결정화 또는 분석하는 방법에 관한 것이다. 또한, 이 화합물은 기존의 화합물보다 다양한 구조와 특성을 지닌 막단백질들을 세포막에서 효율적으로 추출하고 이를 수용액에서 장기간 안정적으로 보관할 수 있고, 이를 통해 그 기능분석 및 구조 분석에 활용될 수 있다. 막단백질 구조 및 기능 분석은 신약 개발에 밀접한 관계가 있는 만큼 현 생물학 및 화학에서 가장 관심을 갖고 있는 분야 중 하나이다.

  This invention relates to a newly developed steroid-based amphiphilic compound, its manufacturing method, and a method for extracting, solubilizing, stabilizing, crystallizing, or analyzing membrane proteins using it. Moreover, this compound can efficiently extract membrane proteins with diverse structures and characteristics from cell membranes compared to conventional compounds, enabling long-term stable storage in solution, which can be utilized for functional and structural analysis. The analysis of membrane protein structure and function is closely related to drug development and is therefore one of the most prominent areas of interest in current biology and chemistry.
• MICROENCAPSULATION AND ELECTROSTATIC PROCESSING METHOD
  申请人：NASA/Johnson Space Center

  公开号：EP1079918A1

  公开（公告）日：2001-03-07
• [EN] MICROENCAPSULATION AND ELECTROSTATIC PROCESSING METHOD<br/>[FR] PROCEDE DE MICROENCAPSULATION ET DE TRAITEMENT ELECTROSTATIQUE
  申请人：NASA/JOHNSON SPACE CENTER

  公开号：WO1999059714A1

  公开（公告）日：1999-11-25

  (EN) Methods are provided for forming spherical multilamellar microcapsules having alternating hydrophilic and hydrophobic liquid layers, surrounded by flexible, semi-permeable hydrophobic or hydrophilic outer membranes which can be tailored specifically to control the diffusion rate. The methods of the invention rely on low shear mixing and liquid-liquid diffusion process and are particularly well suited for forming microcapsules containing both hydrophilic and hydrophobic drugs. These methods can be carried out in the absence of gravity and do not rely on density-driven phase separation, mechanical mixing or solvent evaporation phases. The methods include the process of forming, washing and filtering microcapsules. In addition, the methods contemplate coating microcapsules with ancillary coatings using an electrostatic field and free fluid electrophoresis of the microcapsules. The microcapsules produced by such methods are particularly useful in the delivery of pharmaceutical compositions.(FR) L'invention concerne des procédés pour former des microcapsules multilamellaires présentant des couches liquides alternatives hydrophiles et hydrophobes entourées de membranes externes souples, semi-perméables, hydrophiles ou hydrophobes, qui peuvent être adaptés de manière spécifique pour réguler la vitesse de diffusion. Les procédés de l'invention font intervenir un mélange à faible cisaillement et un processus de diffusion liquide-liquide et conviennent particulièrement pour la formation de microcapsules contenant des médicaments tant hydrophiles qu'hydrophobes. Ces procédés peuvent être réalisés en l'absence de gravité et ne sont pas tributaires d'une séparation de phase axée sur la densité, ou de phases d'agitation mécanique ou d'évaporation des solvants. Ces procédés consistent à former, laver et filtrer des microcapsules. Ils consistent en outre à enrober des microcapsules avec des enrobages accessoires mettant en oeuvre un champ électrostatique et une électrophorèse à fluide libre des microcapsules. Les microcapsules ainsi produits conviennent particulièrement pour l'administration de compositions pharmaceutiques.
• Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties
  作者：Zhaohua Huang、Francis C. Szoka

  DOI：10.1021/ja8065557

  日期：2008.11.19

  We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37 degrees C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.