dicetyl chlorophosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dicetyl chlorophosphate
• 英文别名: chlorophosphoric acid dihexadecyl ester；Chlorophosphorsaeure-dihexadecylester；Phosphorsaeure-di-n-hexadecylester-chlorid；Phosphorsaeure-dicetylester-chlorid；1-[Chloro(hexadecoxy)phosphoryl]oxyhexadecane；1-[chloro(hexadecoxy)phosphoryl]oxyhexadecane
• 化学式: C₃₂H₆₆ClO₃P
• 分子量: 565.301
• InChiKey: AJMJIPMRAKDFQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  37
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dicetyl chlorophosphate 在 barium dihydroxide 作用下， 生成 phosphoric acid dihexadecyl ester; barium salt
  参考文献：
  名称：

  Plimmer; Burch, Journal of the Chemical Society, 1929, p. 298

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(hexadecyl) phosphonate 在 四氯化碳 作用下， 生成 dicetyl chlorophosphate
  参考文献：
  名称：

  New amphiphilic N-phosphoryl oligopeptides designed for gene delivery

  摘要：

  Gene therapy is a potent tool for the treatment of cancer and other gene defect diseases, which involves using DNA that encodes a functional, therapeutic gene to replace a mutated gene. However, the DNA transfection efficiency is restricted by its negative charges and low susceptibility to endonucleases which prevent them penetrating tissue and cellular membranes. Both viral and non-viral vectors have been used for gene delivery, but the former are limited by their immunogenicity, while the latter are less efficient than their viral counterpart. Cationic amphiphilic lipopeptides whose structures can be easily modified and transformed have been used as non-viral vectors in gene delivery system due to their low cytotoxicity and high transfection efficiency. In this study, a series of cationic amphiphilic N-phosphoryl oligopeptides with varied lengths of hydrophobic tails and oligopeptide headgroups (C12-K6, C14-K6, C16-K6, Chol-K6 and C12-H6) were synthesized and used as gene delivery vectors. The affinities, abilities to condense pDNA and transfection efficiencies of the K6-lipopeptides were better than those of the H6-lipopeptides. In addition, the hydrophobic chains of the lipopeptides also affected their transfection efficiencies. The K6-lipopeptide with a hydrophobic chain of twelve carbons (C12-K6) showed the highest transfection efficiency in all these synthetic lipopeptides. At an optimal P/N ratio of 20, C12-K6 showed comparable pDNA transfection efficiency to PEI-25k, a well-defined gene delivery vector, but the cytotoxicity of C12-K6 was much lower. With acceptable gene transfection efficiency and low cytotoxicity, this cationic amphiphilic lipopeptide will have promising applications in gene therapy. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2014.04.007

文献信息

• Rigorous control of vesicle-forming lipid pKa by fluorine-conjugated bioisosteres for gene-silencing with siRNA
  作者：Ayaka Okamoto、Hiroyuki Koide、Naoki Morita、Yusuke Hirai、Yuji Kawato、Hiromichi Egami、Yoshitaka Hamashima、Tomohiro Asai、Takehisa Dewa、Naoto Oku

  DOI：10.1016/j.jconrel.2018.12.044

  日期：2019.2

  While the influence of pK(a) provided by amine-containing materials in siRNA delivery vectors for use in genesilencing has been widely studied, there are little reports in which amine pK(a) is controlled rigorously by using bioisosteres and its effect on gene-silencing. Here, we report that amine pK(a) could be rigorously controlled by replacement of hydrogen atom(s) with fluorine atom(s). A series of mono- and di-amine lipids with a different number of fluorine atoms were synthesized. The pK(a) of the polyamine lipids was shifted to a lower value with an increase in the number of fluorine atoms. The optimal pK(a) for high gene-silencing efficiency varied according to the number of amine residues in the polyamine lipid. Whereas the endosomal escape ability of mono-amine lipid-containing lipid vesicles (LVs) depended on the pK(a), that of all tested di-amine lipid-containing LVs showed equal membrane-destabilizing activity. LVs showing moderately weak interactions with siRNA facilitated cytoplasmic release of siRNA, resulting in strong gene-silencing. These findings indicate that appropriate amine pK(a) engineering depending on the number of amines is important for the induction of effective RNA interference.
• Plimmer; Burch, Journal of the Chemical Society, 1929, p. 298
  作者：Plimmer、Burch

  DOI：——

  日期：——
• New amphiphilic N-phosphoryl oligopeptides designed for gene delivery
  作者：Yunfei Sun、Long Chen、Fude Sun、Xibo Tian、Shi-Zhong Luo

  DOI：10.1016/j.ijpharm.2014.04.007

  日期：2014.7

  Gene therapy is a potent tool for the treatment of cancer and other gene defect diseases, which involves using DNA that encodes a functional, therapeutic gene to replace a mutated gene. However, the DNA transfection efficiency is restricted by its negative charges and low susceptibility to endonucleases which prevent them penetrating tissue and cellular membranes. Both viral and non-viral vectors have been used for gene delivery, but the former are limited by their immunogenicity, while the latter are less efficient than their viral counterpart. Cationic amphiphilic lipopeptides whose structures can be easily modified and transformed have been used as non-viral vectors in gene delivery system due to their low cytotoxicity and high transfection efficiency. In this study, a series of cationic amphiphilic N-phosphoryl oligopeptides with varied lengths of hydrophobic tails and oligopeptide headgroups (C12-K6, C14-K6, C16-K6, Chol-K6 and C12-H6) were synthesized and used as gene delivery vectors. The affinities, abilities to condense pDNA and transfection efficiencies of the K6-lipopeptides were better than those of the H6-lipopeptides. In addition, the hydrophobic chains of the lipopeptides also affected their transfection efficiencies. The K6-lipopeptide with a hydrophobic chain of twelve carbons (C12-K6) showed the highest transfection efficiency in all these synthetic lipopeptides. At an optimal P/N ratio of 20, C12-K6 showed comparable pDNA transfection efficiency to PEI-25k, a well-defined gene delivery vector, but the cytotoxicity of C12-K6 was much lower. With acceptable gene transfection efficiency and low cytotoxicity, this cationic amphiphilic lipopeptide will have promising applications in gene therapy. (C) 2014 Elsevier B.V. All rights reserved.