cholesteryl ricinoleate | 40445-74-7

• 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: cholesteryl ricinoleate
• 英文别名: [(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] (Z)-12-hydroxyoctadec-9-enoate
• CAS: 40445-74-7
• 化学式: C₄₅H₇₈O₃
• 分子量: 667.113
• InChiKey: SECMIXNUMRJSQR-NQHZIXQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cholesteryl ricinoleate 在 4-二甲氨基吡啶 作用下， 以 乙醚 、 苯 为溶剂， 反应 66.0h， 生成 12-<<<carbonyl>oxy>oleoyl>cholesterol
  参考文献：
  名称：

  Selective delivery of cytotoxic compounds to cells by the LDL pathway

  摘要：

  Cancer cells need cholesterol to make new membrane. They get it either by de novo synthesis or from low-density lipoprotein (LDL), or both. Some types of cancer have very high LDL requirements. LDL particles, which circulate in the blood, contain a cholesteryl ester core surrounded by a phospholipid coat containing apoproteins that are recognized by LDL receptors on cell surfaces. After attachment to cells, LDL is endocytosed into lysosomes, where the core is exposed and hydrolyzed. A technique is known whereby LDL can be isolated, its core removed and replaced by a compatible lipophilic substance, and then reconstituted into intact LDL particles that are recognized and internalized by cells in the normal manner. A series of cytotoxic compounds has been synthesized, designed to be compatible with reconstituted LDL, and directed against cancers that copiously internalize LDL. They were evaluated by measuring the toxicity of reconstituted LDL toward test cells bearing LDL receptors. Selectivity was determined by comparison, either with mutant cells with few LDL receptors or with reconstituted methylated LDL (which is not recognized by LDL receptors) on normal cells. Two compounds, 19 and 25, were found that reconstitute well, kill or arrest the test cells at reasonably low concentrations, and are completely selective, suggesting that they are delivered to cells exclusively via the LDL pathway.

  DOI：

  10.1021/jm00374a017

文献信息

• Preparation and spectral properties of lipophilic fluorescein derivatives: application to plasma low-density lipoprotein
  作者：J. R. Falck、Monty Krieger、J. L. Goldstein、M. S. Brown

  DOI：10.1021/ja00414a087

  日期：1981.12
• Selective delivery of cytotoxic compounds to cells by the LDL pathway
  作者：Raymond A. Firestone、Judith M. Pisano、J. R. Falck、Michael M. McPhaul、Monty Krieger

  DOI：10.1021/jm00374a017

  日期：1984.8

  Cancer cells need cholesterol to make new membrane. They get it either by de novo synthesis or from low-density lipoprotein (LDL), or both. Some types of cancer have very high LDL requirements. LDL particles, which circulate in the blood, contain a cholesteryl ester core surrounded by a phospholipid coat containing apoproteins that are recognized by LDL receptors on cell surfaces. After attachment to cells, LDL is endocytosed into lysosomes, where the core is exposed and hydrolyzed. A technique is known whereby LDL can be isolated, its core removed and replaced by a compatible lipophilic substance, and then reconstituted into intact LDL particles that are recognized and internalized by cells in the normal manner. A series of cytotoxic compounds has been synthesized, designed to be compatible with reconstituted LDL, and directed against cancers that copiously internalize LDL. They were evaluated by measuring the toxicity of reconstituted LDL toward test cells bearing LDL receptors. Selectivity was determined by comparison, either with mutant cells with few LDL receptors or with reconstituted methylated LDL (which is not recognized by LDL receptors) on normal cells. Two compounds, 19 and 25, were found that reconstitute well, kill or arrest the test cells at reasonably low concentrations, and are completely selective, suggesting that they are delivered to cells exclusively via the LDL pathway.