rac-2,3-bis(octadecyloxy)propane-1-thiol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-2,3-bis(octadecyloxy)propane-1-thiol
• 英文别名: 3-mercapto-1,2-bis-O-(octadecyl)propane；2,3-dioctadecoxypropane-1-thiol
• 化学式: C₃₉H₈₀O₂S
• 分子量: 613.129
• InChiKey: VQFSALLSVRLNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.84
• 重原子数：
  42.0
• 可旋转键数：
  38.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  rac-2,3-bis(octadecyloxy)propane-1-thiol 在 PTAD 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 20.0~70.0 ℃ 、200.0 kPa 条件下， 反应 190.5h， 生成 2-((2,3-bis(octadecyloxy)propyl)disulfanyl)-N,N-dimethyl-N-(2-O-biotinyl-tetraethylenglykol-1-yl)-ethanammonium tosylate
  参考文献：
  名称：

  Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems

  摘要：

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.089
• 作为产物：
  描述：

  硬脂醇 在 吡啶 、 氢氧化钾 、 四丁基硫酸氢铵 、 sodium 、 叔丁醇 作用下， 以 乙醚 为溶剂， 反应 108.0h， 生成 rac-2,3-bis(octadecyloxy)propane-1-thiol
  参考文献：
  名称：

  Lipopolycationic Telomers for Gene Transfer: Synthesis and Evaluation of Their in Vitro Transfection Efficiency

  摘要：

  We report on the synthesis of a series of lipopolyamine telomers I-14,n, I-18,n, and II-18,n and on their in vitro gene-transfer capability. Their structure consists of a polyamine polar moiety, including n primary amine functions (from 1 to 70), connected to a hydrophobic moiety, including two hydrocarbon C14 or C18 chains, through a mercaptopropanoyl or mercaptoglyceryl unit and an amide or ether function. They were obtained by telomerization of N-(2-[(BOC)aminoethyl]})acrylamide with N,N-ditetradecyl- and N,N-dioctadecylpropanamide-3-thiol and rac-1,2-dioctadecyloxypropane-3-thiol, respectively, then BOC deprotection. For NIP ratios (N = number of telomer amine equivalents; P = number of DNA phosphates) from 0.8 to 10, these lipopolyamines condensed DNA, with or without the use of DOPE, forming lipopolyplexes or teloplexes of mean sizes less than zoo nm. Some trends, structure-activity and structure-toxicity relationships, were established to achieve both highest in vitro transfection levels and cell viability. Thus, DNA formulations based on telomers I-14,20 and I-18,20 and for NIP ratios lower than 5 led to the most efficient teloplex formulations for plasmid delivery to lung epithelial A549 cells.

  DOI：

  10.1021/jm9911579

文献信息

• Reduction-Sensitive Liposomes from a Multifunctional Lipid Conjugate and Natural Phospholipids: Reduction and Release Kinetics and Cellular Uptake
  作者：Björn Goldenbogen、Nicolai Brodersen、Andrea Gramatica、Martin Loew、Jürgen Liebscher、Andreas Herrmann、Holger Egger、Bastian Budde、Anna Arbuzova

  DOI：10.1021/la201160y

  日期：2011.9.6

  organization leading to the release of entrapped molecules. Upon nonspecific uptake of vesicles by macrophages, calcein release from reduction-sensitive liposomes consisting of the disulfide conjugate and phospholipids was more efficient than from reduction-insensitive liposomes composed only of phospholipids. The binding of streptavidin to the conjugates did not interfere with either the subsequent reduction

  靶向和可触发的递送系统的开发与抗癌治疗具有高度相关性。我们在这里报告的还原敏感性脂质体由新型的多功能脂质样共轭物，包含二硫键和生物素部分，以及天然磷脂组成。使用丹磺酰基标记的缀合物1，研究了将二硫键缀合物掺入囊泡及其还原的动力学，并利用了丹磺酰基荧光环境敏感性和从丹磺酰基转移至若丹明标记的磷脂的Förster共振能量转移。二硫键的裂解（例如，通过三（2-羧乙基）膦（TCEP），二硫苏糖醇（DTT），l-半胱氨酸或谷胱甘肽（GSH））去除了结合物的亲水头基，从而改变了膜的结构，导致被包裹分子的释放。在巨噬细胞非特异性摄取囊泡时，钙黄绿素从由二硫化物缀合物和磷脂组成的还原敏感性脂质体释放的钙黄绿素比仅由磷脂组成的还原敏感性脂质体的释放更为有效。链霉亲和素与结合物的结合既不干扰结合物的二硫键的随后还原，也不干扰所捕获分子的释放。过度表达HER2受体的乳腺癌细胞系BT-474表现出高摄取负载有生物
• Synthesis of inositol phospholipids with thiophosphoester bonds
  作者：Maria A. Alisi、Mario Brufani、Luigi Filocamo、Gianluca Gostoli、Stefano Maiorana、Maria C. Cesta、Enrico Ferrari、Sperandina Lappa、Piergiuseppe Pagella

  DOI：10.1016/0040-4039(93)88048-n

  日期：1992.12

  The synthesis of phosphatidylinositol (PI) analogues (+/-)1-O-(1-O-octadecanoyl-2-O-acetyl-rac-3-thioglycerylphosphoryl)-myo-inositol (7), (+/-)1-O-(1,2-di-O-octadecyl-rac-3-thiogly-cerylphosphoryl)-myo-inositol (14a), (+/-)1-O-(1,2-di-O-octyl-rac-3-thioglycerylphosphoryl)-myo-inositol (14b) and (+/-)1-O-(1-O-octadecyl-2-O-methyl-rac-3-thioglycerylphosphoryl)-myo-inositol (14c) designed to show a novel mode of PI-phospholipase C (PI-PLC) inhibition, is described.
• Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems
  作者：Nicolai Brodersen、Anna Arbuzova、Andreas Herrmann、Holger Egger、Jürgen Liebscher

  DOI：10.1016/j.tet.2011.07.089

  日期：2011.10

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.
• Lipopolycationic Telomers for Gene Transfer: Synthesis and Evaluation of Their in Vitro Transfection Efficiency
  作者：Géraldine Verderone、Nathalie Van Craynest、Otmane Boussif、Catherine Santaella、Rainer Bischoff、Hanno V. J. Kolbe、Pierre Vierling

  DOI：10.1021/jm9911579

  日期：2000.4.6

  We report on the synthesis of a series of lipopolyamine telomers I-14,n, I-18,n, and II-18,n and on their in vitro gene-transfer capability. Their structure consists of a polyamine polar moiety, including n primary amine functions (from 1 to 70), connected to a hydrophobic moiety, including two hydrocarbon C14 or C18 chains, through a mercaptopropanoyl or mercaptoglyceryl unit and an amide or ether function. They were obtained by telomerization of N-(2-[(BOC)aminoethyl]})acrylamide with N,N-ditetradecyl- and N,N-dioctadecylpropanamide-3-thiol and rac-1,2-dioctadecyloxypropane-3-thiol, respectively, then BOC deprotection. For NIP ratios (N = number of telomer amine equivalents; P = number of DNA phosphates) from 0.8 to 10, these lipopolyamines condensed DNA, with or without the use of DOPE, forming lipopolyplexes or teloplexes of mean sizes less than zoo nm. Some trends, structure-activity and structure-toxicity relationships, were established to achieve both highest in vitro transfection levels and cell viability. Thus, DNA formulations based on telomers I-14,20 and I-18,20 and for NIP ratios lower than 5 led to the most efficient teloplex formulations for plasmid delivery to lung epithelial A549 cells.