octadec-4-yn-1-ol | 97569-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octadec-4-yn-1-ol
• 英文别名: 4-Octadecynol
• CAS: 97569-59-0
• 化学式: C₁₈H₃₄O
• 分子量: 266.467
• InChiKey: LIUDYJTXXSGHNP-UHFFFAOYSA-N

物化性质

• 沸点：
  376.0±25.0 °C(Predicted)
• 密度：
  0.869±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  octadec-4-yn-1-ol 在 Jones's reagent 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 、 二甲基亚砜 、 丙酮 为溶剂， 反应 9.0h， 生成 di(octadec-4-ynoyl)phosphatidylcholine
  参考文献：
  名称：

  A dialkynoyl analogue of DOPE improves gene transfer of lower-charged, cationic lipoplexes

  摘要：

  带正电荷的基因递送载体，如阳离子脂质体，通常通过将阳离子脂质和中性脂质以1:1的摩尔比例混合制备，存在一个根本性缺陷：一方面，正电荷促进细胞摄取；另一方面，正电荷导致其在体内与带负电的血清成分发生聚集。本文报道了一种更相稳定的两性离子且具有融合性的脂质DOPE的类似物，能够在几乎不明显降低转染活性的情况下，将脂质体中的阳离子脂质成分从50%降低到9%。这种电荷的减少可能增加体内稳定性，同时仍保持高细胞摄取率和转基因表达。

  DOI：

  10.1039/b514532e
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 36.25h， 生成 octadec-4-yn-1-ol
  参考文献：
  名称：

  A dialkynoyl analogue of DOPE improves gene transfer of lower-charged, cationic lipoplexes

  摘要：

  带正电荷的基因递送载体，如阳离子脂质体，通常通过将阳离子脂质和中性脂质以1:1的摩尔比例混合制备，存在一个根本性缺陷：一方面，正电荷促进细胞摄取；另一方面，正电荷导致其在体内与带负电的血清成分发生聚集。本文报道了一种更相稳定的两性离子且具有融合性的脂质DOPE的类似物，能够在几乎不明显降低转染活性的情况下，将脂质体中的阳离子脂质成分从50%降低到9%。这种电荷的减少可能增加体内稳定性，同时仍保持高细胞摄取率和转基因表达。

  DOI：

  10.1039/b514532e

文献信息

• Properties of unusual phospholipids IV: Chemoenzymatic synthesis of phospholipids bearing acetylenic fatty acids
  作者：Sandra Pisch、Uwe T. Bornscheuer、Hartmut H. Meyer、Rolf D. Schmid

  DOI：10.1016/s0040-4020(97)01043-0

  日期：1997.10

  were studied in this transphosphatidylation reaction. Under optimized conditions (40 °C, organic solvent: buffer ratio 1:1.5 (v/v), pH 5.6), the conversion of phosphatidylcholine to the corresponding phospholipids with the head groups glycerol, ethanolamine and L-serine reached 99% at 40°C in 1 h. The quantitative analysis of the transphosphatidylation reactions was performed by TLC-FID.

  以高收率（56％和57％）合成14-octycynoic（1）和4-octadecynoic（2）酸，并在sn 1-和sn 2-位置掺入甘油磷脂酰胆碱。这些磷脂酰胆碱的头基在双相系统中使用磷脂酶D（PLD）进行交换。抗生素链霉菌（Streptomyces sp。）的PLD 。在该转磷脂酰化反应中研究了花生，卷心菜。在最佳条件下（40°C，有机溶剂：缓冲液比例1：1.5（v / v），pH 5.6），磷脂酰胆碱转化为具有甘油，乙醇胺和L头基的相应磷脂-丝氨酸在40°C下在1小时内达到99％。通过TLC-FID进行转磷脂酰化反应的定量分析。
• In Vivo Studies of Dialkynoyl Analogues of DOTAP Demonstrate Improved Gene Transfer Efficiency of Cationic Liposomes in Mouse Lung
  作者：Steven Fletcher、Ayesha Ahmad、Eric Perouzel、Andrew Heron、Andrew D. Miller、Michael R. Jorgensen

  DOI：10.1021/jm0507227

  日期：2006.1.1

  A novel set of dialkynoyl analogues of the cationic, gene delivery lipid DOTAP (1) was synthesized. Structure-activity studies demonstrate that replacement of the cis-double bonds of DOTAP with triple bonds in varying positions alters both the physical properties of the resultant cationic liposome-DNA complexes and their biological functionalities, both in vitro and in vivo. Particularly, in vivo studies demonstrate that pDNA transfection of mouse lung endothelial cells with lead analogue DS(14-yne)TAP (4):cholesterol lipoplexes exhibits double the transfection level with less associated toxicity relative to the well-established DOTAP:cholesterol system. In fact, 4:cholesterol delivers up to 3 times the dose of pDNA in mice than can be tolerated by DOTAP, leading to nearly 3 times greater marker-gene expression. X-ray diffraction studies suggest that lipoplexes containing analogue 4 display increased stability at physiological temperatures. Our results thus suggest that analogue 4 is a potentially strong candidate for the gene therapy of lung tumors.
• Concise synthesis of (+)-serinolamide A
  作者：Ya-Ru Gao、Shi-Huan Guo、Zhuan-Xiang Zhang、Shuai Mao、Yan-Lei Zhang、Yong-Qiang Wang

  DOI：10.1016/j.tetlet.2013.09.084

  日期：2013.11

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.
• A dialkynoyl analogue of DOPE improves gene transfer of lower-charged, cationic lipoplexes
  作者：Steven Fletcher、Ayesha Ahmad、Eric Perouzel、Michael R. Jorgensen、Andrew D. Miller

  DOI：10.1039/b514532e

  日期：——

  Positively-charged gene delivery agents, such as cationic liposomes, typically prepared by mixing a cationic lipid and a neutral lipid in a 1 : 1 molar ratio, exhibit a fundamental flaw: on the one hand, the charge encourages cell uptake; on the other hand, the charge leads to aggregation in vivo with anionic serum components. We herein report a more phase-stable analogue of the zwitterionic and fusogenic lipid DOPE that allows for the reduction of the cationic lipid component of the liposome from 50 to 9 mol% with almost no apparent loss in transfection activity. This reduction in charge may induce important in vivo stability whilst still imparting high cell uptake and transgene expression.

  带正电荷的基因递送载体，如阳离子脂质体，通常通过将阳离子脂质和中性脂质以1:1的摩尔比例混合制备，存在一个根本性缺陷：一方面，正电荷促进细胞摄取；另一方面，正电荷导致其在体内与带负电的血清成分发生聚集。本文报道了一种更相稳定的两性离子且具有融合性的脂质DOPE的类似物，能够在几乎不明显降低转染活性的情况下，将脂质体中的阳离子脂质成分从50%降低到9%。这种电荷的减少可能增加体内稳定性，同时仍保持高细胞摄取率和转基因表达。