N-(allyloxycarbonyl)-12-aminododecanoic acid | 139270-93-2

• 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: N-(allyloxycarbonyl)-12-aminododecanoic acid
• 英文别名: 12-Allyloxycarbonylaminododecanoic acid；12-(prop-2-enoxycarbonylamino)dodecanoic acid
• CAS: 139270-93-2
• 化学式: C₁₆H₂₉NO₄
• 分子量: 299.411
• InChiKey: RGNUHQFIOFDEHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(allyloxycarbonyl)-12-aminododecanoic acid 在 四(三苯基膦)钯 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二乙胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 [5-(12-aminododecanoyl)amino-pentyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection

  摘要：

  We report on the synthesis of various acridine(Acr)-spacer-nuclear localization signal (NLS) peptide conjugates and explore whether their use as NLS-labeling agent of plasmidic DNA could improve gene nuclear import and expression into cells when mediated by synthetic DNA complexes. As the conditions of successful use of the NLS properties to enhance gene transfer are not clear, and with the aim of detecting and defining the requirements of NLS-enhanced transfection, we investigated gene delivery and expression into various cell lines with various DNA complexes (lipoplexes or polyplexes) that were formulated for various N/P ratios from various preformed Acr-spacer-NLS/DNA complexes (1: 1, 5:1 and 10: 1 molar ratio). For the in vitro transfection assays, the lipoplexes and polyplexes were formulated from the preformed Acr-spacer-NLS/DNA complexes and dioctadecylamidoglycylspermine (DOGS)/dioleylphosphatidylethanolamine (DOPE) 1:1 mol and branched polyethyleneimine (PEI) 25 kDa, respectively, which are very efficient in vitro gene transfer systems. We show by fluorescence experiments that part of the acridine-NLS-conjugates remains intercalated within the plasmid for most of the N/P lipoplexes and polyplexes investigated. We show that, as several other studies performed with NLS-conjugates that are not covalently linked to DNA, the expression of the transgene is in most cases not improved upon complexation of plasmidic DNA with NLS-intercalating conjugates prior to its formulation as lipoplexes or polyplexes. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.015
• 作为产物：
  描述：

  氯甲酸烯丙酯 、 12-氨基十二酸 在 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 以54%的产率得到N-(allyloxycarbonyl)-12-aminododecanoic acid
  参考文献：
  名称：

  Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection

  摘要：

  We report on the synthesis of various acridine(Acr)-spacer-nuclear localization signal (NLS) peptide conjugates and explore whether their use as NLS-labeling agent of plasmidic DNA could improve gene nuclear import and expression into cells when mediated by synthetic DNA complexes. As the conditions of successful use of the NLS properties to enhance gene transfer are not clear, and with the aim of detecting and defining the requirements of NLS-enhanced transfection, we investigated gene delivery and expression into various cell lines with various DNA complexes (lipoplexes or polyplexes) that were formulated for various N/P ratios from various preformed Acr-spacer-NLS/DNA complexes (1: 1, 5:1 and 10: 1 molar ratio). For the in vitro transfection assays, the lipoplexes and polyplexes were formulated from the preformed Acr-spacer-NLS/DNA complexes and dioctadecylamidoglycylspermine (DOGS)/dioleylphosphatidylethanolamine (DOPE) 1:1 mol and branched polyethyleneimine (PEI) 25 kDa, respectively, which are very efficient in vitro gene transfer systems. We show by fluorescence experiments that part of the acridine-NLS-conjugates remains intercalated within the plasmid for most of the N/P lipoplexes and polyplexes investigated. We show that, as several other studies performed with NLS-conjugates that are not covalently linked to DNA, the expression of the transgene is in most cases not improved upon complexation of plasmidic DNA with NLS-intercalating conjugates prior to its formulation as lipoplexes or polyplexes. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.015

文献信息

• Radicicol derivatives, their preparation and their anti-tumor activity
  申请人：Sankyo Company, Limited

  公开号：US05597846A1

  公开（公告）日：1997-01-28

  A compound of the formula ##STR1## in which: R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen atoms and groups of formula R.sup.3 --CO--, wherein R.sup.3 represents a group selected from the group consisting of unsubstituted alkyl groups having from 9 to 20 carbon atoms; substituted alkyl groups having from 10 to 20 carbon atoms; unsubstituted alkenyl groups having from 9 to 20 carbon atoms; substituted alkenyl group having from 10 to 20 carbon atoms; unsubstituted alkynyl groups having from 8 to 10 carbon atoms; and substituted alkynyl groups having from 8 to 10 carbon atoms wherein R.sup.1 and R.sup.2 are not both hydrogen atoms or acetyl groups. The compounds have antitumor activity.

  该化合物的化学式为##STR1## 其中：R.sup.1和R.sup.2分别选自氢原子和R.sup.3 --CO--的公式组成的群，其中R.sup.3代表从未取代的烷基基团，碳原子数为9至20个；取代的烷基基团，碳原子数为10至20个；从未取代的烯基基团，碳原子数为9至20个；取代的烯基基团，碳原子数为10至20个；从未取代的炔基基团，碳原子数为8至10个；取代的炔基基团，碳原子数为8至10个，其中R.sup.1和R.sup.2不同时为氢原子或乙酰基团。该化合物具有抗肿瘤活性。
• Radicicol derivatives, their preparation and their anti-tumour activity
  申请人：Sankyo Company Limited

  公开号：EP0460950A1

  公开（公告）日：1991-12-11

  Radiacol derivatives in which one or both hydroxy groups are acylated have valuable anti-tumor activity or may be used as chemical intermediates.

  其中一个或两个羟基被酰化的萝卜醇衍生物具有宝贵的抗肿瘤活性，或可用作化学中间体。
• US5597846A
  申请人：——

  公开号：US5597846A

  公开（公告）日：1997-01-28
• US5650430A
  申请人：——

  公开号：US5650430A

  公开（公告）日：1997-07-22
• [EN] RADICICOL DERIVATIVES, THEIR PREPARATION AND THEIR ANTI-TUMOR ACTIVITY
  申请人：SANKYO COMPANY LIMITED

  公开号：WO1991018905A1

  公开（公告）日：1991-12-12

  (EN) Radicicol derivatives in which one or both hydroxy groups are acylated have valuable anti-tumor activity or may be used as chemical intermediates.(FR) Les dérivés radicicoles, dans lesquels au moins l'un des deux groupes hydroxy est acylé, présentent une précieuse activité antitumorale ou peuvent servir de produits chimiques intermédiaires.