pregna-5,20(22)-diene-3β-yl laurate | 478622-95-6

• 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: pregna-5,20(22)-diene-3β-yl laurate
• 英文别名: [(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-prop-1-en-2-yl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] dodecanoate
• CAS: 478622-95-6
• 化学式: C₃₄H₅₆O₂
• 分子量: 496.817
• InChiKey: FQJNKLSVOQALQM-ZDKXLEIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pregna-5,20(22)-diene-3β-yl laurate 在 hydroxylamine-O-sulfonic acid 作用下， 生成 22-amino-5-pregnen-3β-yl laurate
  参考文献：
  名称：

  Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia

  摘要：

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00193-2
• 作为产物：
  描述：

  孕烯醇酮 在 吡啶 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 甲醇 、 叔丁醇 为溶剂， 生成 pregna-5,20(22)-diene-3β-yl laurate
  参考文献：
  名称：

  Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia

  摘要：

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00193-2

文献信息

• Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia
  作者：Gang Zheng、Hui Li、Kathy Yang、Dana Blessington、Kai Licha、Sissel Lund-Katz、Britton Chance、Jerry D. Glickson

  DOI：10.1016/s0960-894x(02)00193-2

  日期：2002.6

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.