N-[1,3-dihydroxy-2-(hydroxymethyl)prop-2-yl]-6-[(benzyloxy)carbonylamino]hexanamide | 68636-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[1,3-dihydroxy-2-(hydroxymethyl)prop-2-yl]-6-[(benzyloxy)carbonylamino]hexanamide
• 英文别名: [6-(benzyloxycarbonamido)hexanamido]-tris(hydroxymethyl)-methane；Cbz-AHT；benzyl N-[6-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-6-oxohexyl]carbamate
• CAS: 68636-70-4
• 化学式: C₁₈H₂₈N₂O₆
• 分子量: 368.43
• InChiKey: FFFAZXRIHUVBJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  128
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[1,3-dihydroxy-2-(hydroxymethyl)prop-2-yl]-6-[(benzyloxy)carbonylamino]hexanamide 在 palladium 10% on activated carbon 、 甲酸铵 、 sodium methylate 、 mercury(II) cyanide 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 生成 Man3-AHT
  参考文献：
  名称：

  Mannosylated Polyion Complexes for In Vivo Gene Delivery into CD11c⁺ Dendritic Cells

  摘要：

  Dendritic cells (DCs) possess unique abilities in initiating primary immune responses and thus represent prime targets for DNA-based vaccinations. Here, we describe the design and synthesis of mannosylated polyion complexes (PICs) composed of cationic polyethylenimine (PEI) and hydrophilic polyethylene glycol (PEG) segments, and bearing mono- and trivalent mannose as a ligand for targeting mannose receptor (MR/CD206)-positive DCs. Amino-terminated mannose (Man)-containing ligands in mono- and trivalent presentations (Man- and Man(3)-, respectively) were prepared and conjugated to PEG via an N-hydroxysuccinimide (NHS)-activated terminal. Thiolated PEI was conjugated to the mannosylated PEG via the maleimide (MAL)-activated terminal. The resulting positively charged diblock copolymers bearing mannoses (Man-PEG-b-PEI and Man3-PEG-b-PEI) were self-assembled with DNA to form PICs with lower surface charge than did their PEI building block and mean hydrodynamic diameters in the range of 100-450 nm, depending on the N/P ratio. Man3-PEG-b-PEI demonstrated a 3-4-fold greater transfection efficiency in MR-positive dendritic cell lines (THP-1, DC2.4), relative to Man-PEG-b-PEI, exhibited low cytotoxicity when compared with PEI, and showed low transfection efficiency in nondendritic HeLa cells. In preliminary in vivo experiments, Man-PEG-b-PEI/DNA and Man3-PEG-b-PEI/DNA demonstrated 2-3-fold higher gene delivery efficiency into CD11c+ DCs collected from inguinal lymph nodes of C57/BL6 mice, when compared to PEI/DNA complexes, as shown by GFP expression measurements, 24 h post subcutaneous injection. The results indicate that the mannosylated PICs are a safe and effective gene delivery system, showing in vivo specificity toward CD11c(+) DCs.

  DOI：

  10.1021/mp5005492
• 作为产物：
  描述：

  6-氨基己酸 在 sodium hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 N-[1,3-dihydroxy-2-(hydroxymethyl)prop-2-yl]-6-[(benzyloxy)carbonylamino]hexanamide
  参考文献：
  名称：

  将膦酰基乙酸酯靶向肝脏：膦酰基乙酸酯-三乳糖苷结合物的合成† •

  摘要：

  作为继续研究向人肝递送药物的一部分，已合成了膦酰乙酸酯-三乳糖苷结合物（12），总产率为23％。该缀合物的合成的短短取决于溴乙酰胺8与亚磷酸三（三甲基甲硅烷基）酯的成功Michaelis-Arbuzov反应。

  DOI：

  10.1560/8qka-dfyf-fj70-e1cx

文献信息

• Mannose-Decorated Multicomponent Supramolecular Polymers Trigger Effective Uptake into Antigen-Presenting Cells
  作者：David Straßburger、Natascha Stergiou、Moritz Urschbach、Hajime Yurugi、Daniel Spitzer、Dieter Schollmeyer、Edgar Schmitt、Pol Besenius

  DOI：10.1002/cbic.201800114

  日期：2018.5.4

  macrophage targets: A modular route is presented to prepare multifunctional supramolecular polymers based on self‐assembled dendritic peptide amphiphiles decorated with mannosides to effectively target antigen‐presenting cells, such as macrophages. The multicomponent co‐assembly protocol is a powerful platform for the development of fully synthetic multifunctional vaccines.

  自组装巨噬细胞靶标：提出了一种模块化路线，该方法基于以甘露糖苷修饰的自组装树突状肽两亲物为基础，以有效靶向抗原呈递细胞（例如巨噬细胞）来制备多功能超分子聚合物。多组分共装配协议是开发完全合成的多功能疫苗的强大平台。
• Vecteurs synthétiques de faible poids moléculaire spécifiques de récepteurs à sucre, conjugués en comportant et procédés de préparation
  申请人：IRE-CELLTARG S.A.

  公开号：EP0363275A1

  公开（公告）日：1990-04-11

  La présente invention a pour objet un vecteur synthétique consistant dans un composé chimique de faible poids moléculaire, en particulier inférieur à 5000, présentant une affinité pour les cellules exposant à leur membrane plasmique des récepteurs reconnaissant spécifiquement des résidus sucrés consistant en des cycles glycosidiques de saccharides, caractérisé en ce qu'il présente une structure chimique de base sur laquelle sont fixés plusieurs cycles glycosidiques de saccharides espacés de telle manière que chaque site de reconnaissance de ces résidus sucrés du recepteur soit susceptible d'être occupé. la présente invention a également pour objet l'utilisation de ces vecteurs comme agent d'imagerie ou des conjugués de ce type de vecteur avec un médicament, notamment choisi parmi les substances antitumorales, antivirales et antiparasitaires, ainsi que des procédés de préparation desdits vecteurs.

  本发明的目的是一种合成载体，它由低分子量的化合物组成，特别是分子量小于 5000 的化合物，这种化合物对细胞的质膜受体具有亲和力，细胞的质膜受体专门识别由糖的糖苷环组成的糖残基，其特征在于它有一个基本的化学结构，在这个结构上连接着几个糖的糖苷环，这些糖苷环的间隔方式使受体的这些糖残基的每个识别位点都能被占据。 本发明的另一个目的是将这些载体用作成像剂，或将这类载体与药物（特别是从抗肿瘤、抗病毒和抗寄生虫物质中选择）共轭，以及制备上述载体的工艺。
• Synthesis of some cluster glycosides suitable for attachment to proteins or solid matrices
  作者：Chuan Lee Yuan

  DOI：10.1016/s0008-6215(00)84141-5

  日期：1978.12
• MARY, ANNE;FALMAGNE, JEAN-BERNARD;TROUET, ANDRE
  作者：MARY, ANNE、FALMAGNE, JEAN-BERNARD、TROUET, ANDRE

  DOI：——

  日期：——
• Mannosylated Polyion Complexes for <i>In Vivo</i> Gene Delivery into CD11c⁺ Dendritic Cells
  作者：Lior Raviv、Michal Jaron-Mendelson、Ayelet David

  DOI：10.1021/mp5005492

  日期：2015.2.2

  Dendritic cells (DCs) possess unique abilities in initiating primary immune responses and thus represent prime targets for DNA-based vaccinations. Here, we describe the design and synthesis of mannosylated polyion complexes (PICs) composed of cationic polyethylenimine (PEI) and hydrophilic polyethylene glycol (PEG) segments, and bearing mono- and trivalent mannose as a ligand for targeting mannose receptor (MR/CD206)-positive DCs. Amino-terminated mannose (Man)-containing ligands in mono- and trivalent presentations (Man- and Man(3)-, respectively) were prepared and conjugated to PEG via an N-hydroxysuccinimide (NHS)-activated terminal. Thiolated PEI was conjugated to the mannosylated PEG via the maleimide (MAL)-activated terminal. The resulting positively charged diblock copolymers bearing mannoses (Man-PEG-b-PEI and Man3-PEG-b-PEI) were self-assembled with DNA to form PICs with lower surface charge than did their PEI building block and mean hydrodynamic diameters in the range of 100-450 nm, depending on the N/P ratio. Man3-PEG-b-PEI demonstrated a 3-4-fold greater transfection efficiency in MR-positive dendritic cell lines (THP-1, DC2.4), relative to Man-PEG-b-PEI, exhibited low cytotoxicity when compared with PEI, and showed low transfection efficiency in nondendritic HeLa cells. In preliminary in vivo experiments, Man-PEG-b-PEI/DNA and Man3-PEG-b-PEI/DNA demonstrated 2-3-fold higher gene delivery efficiency into CD11c+ DCs collected from inguinal lymph nodes of C57/BL6 mice, when compared to PEI/DNA complexes, as shown by GFP expression measurements, 24 h post subcutaneous injection. The results indicate that the mannosylated PICs are a safe and effective gene delivery system, showing in vivo specificity toward CD11c(+) DCs.