8-bromo-3,6-dioxaoctyl α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-bromo-3,6-dioxaoctyl α-L-rhamnopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]-6-methyloxane-3,4,5-triol
• 化学式: C₁₂H₂₃BrO₇
• 分子量: 359.214
• InChiKey: PQISYIREFYOTMW-PREPNJAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  L-鼠李糖 在 四溴化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 生成 8-bromo-3,6-dioxaoctyl α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: application to liposomal targeting of keratinocytes and skin

  摘要：

  The usefulness of vesicles to cargo material depends on the design of new ligands able to incorporate easily inside the bilayer and also to direct the vesicles to the targeted site. Therefore, the synthesis of two new rhamnose-bearing surfactants is described. The hydrophobic part consists of cholesterol (in compound 3) and citrylidene phloroglucinol (in compound 6). The ability of these two rhamnolipids to incorporate into a DPPC membrane and to form aggregates is investigated, respectively, by differential scanning calorimetry and by surface tension measurements. Those two new surfactants were incorporated in fluorescent liposomes to study their interactions with keratinocytes and skin sections. Intraliposomal delivery to keratinocytes was observed in both cases, even if the kinetics of delivery were different according to the rhamnosurfactant used. Skin sections were stained by both liposomal formulations, and different interactions between the liposomes and skin cells according to the surfactant used were noted. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.009

文献信息

• Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: application to liposomal targeting of keratinocytes and skin
  作者：Véronique Barragan-Montero、Jean-Yves Winum、Jean-Pierre Molès、Emmanuelle Juan、Caroline Clavel、Jean-Louis Montero

  DOI：10.1016/j.ejmech.2005.04.009

  日期：2005.10

  The usefulness of vesicles to cargo material depends on the design of new ligands able to incorporate easily inside the bilayer and also to direct the vesicles to the targeted site. Therefore, the synthesis of two new rhamnose-bearing surfactants is described. The hydrophobic part consists of cholesterol (in compound 3) and citrylidene phloroglucinol (in compound 6). The ability of these two rhamnolipids to incorporate into a DPPC membrane and to form aggregates is investigated, respectively, by differential scanning calorimetry and by surface tension measurements. Those two new surfactants were incorporated in fluorescent liposomes to study their interactions with keratinocytes and skin sections. Intraliposomal delivery to keratinocytes was observed in both cases, even if the kinetics of delivery were different according to the rhamnosurfactant used. Skin sections were stained by both liposomal formulations, and different interactions between the liposomes and skin cells according to the surfactant used were noted. (c) 2005 Elsevier SAS. All rights reserved.