2-(2-aminoethoxy)ethyl-2,3,4,6-tetraacetyl-α-D-mannopyranoside | 1117726-04-1

• 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: 2-(2-aminoethoxy)ethyl-2,3,4,6-tetraacetyl-α-D-mannopyranoside
• 英文别名: 2-(2-aminoethoxy)ethyl O-2',3',4',6'-tetraacetyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[2-(2-aminoethoxy)ethoxy]oxan-2-yl]methyl acetate
• CAS: 1117726-04-1
• 化学式: C₁₈H₂₉NO₁₁
• 分子量: 435.428
• InChiKey: LMJFYJRRDSFQIQ-ZBRFXRBCSA-N

物化性质

• 沸点：
  502.2±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(2-aminoethoxy)ethyl-2,3,4,6-tetraacetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 2-(2-Aminoethoxy)ethyl α-D-mannopyranoside
  参考文献：
  名称：

  寡糖-喜树碱偶联物作为潜在的抗肿瘤药：设计，合成和生物学评估。

  摘要：

  合成了三十种新颖的20（S）-O-连接的喜树碱（CPT）糖缀合物。他们表现出更有效的体外细胞毒性过伊立替康，但非常弱的直接拓扑异构酶I在100.0观察（TOPO I）抑制μ M.寡糖类型，PEG接头的长度和乙酰基作用于细胞毒性，选择性，水溶性明显影响，并新合成的CPT糖缀合物的稳定性。结构40与CPT相比，博来霉素（BLM）二糖与引入的酯部分中的二甘醇相连，具有更高的抗肿瘤活性和独特的选择性。静脉内动物急性毒性（160 mg / kg）未检测到毒性。总的来说，将具有靶向肿瘤的寡糖附着到CPT的20（S）-OH上可以为当前的Topo I毒药带来的艰巨问题提供解决方案。

  DOI：

  10.1016/j.ejmech.2020.112509
• 作为产物：
  描述：

  2-(2-Azidoethoxy)ethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 以79%的产率得到2-(2-aminoethoxy)ethyl-2,3,4,6-tetraacetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Inhibition binding studies of glycodendrimer/lectin interactions using surface plasmon resonance

  摘要：

  Understanding protein/carbohydrate interactions is essential for elucidating biological pathways and cellular mechanisms but is often difficult due to the prevalence of multivalent interactions. Here, we evaluate the multivalent glycodendrimer framework as a means to describe the inhibition potency of multivalent mannose-functionalized dendrimers using surface plasmon resonance (SPR). Using highly robust, mannose-functionalized dithiol self-assembled monolayers on gold surfaces, we found that glycodendrimers were efficient inhibitors of protein/carbohydrate interactions. IC50 values ranging from 260 nM to 13 nM were obtained for mannose-functionalized dendrimers with Concanavalin A. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.038

文献信息

• A Strategy for the Targeting of Photosensitizers. Synthesis, Characterization, and Photobiological Property of Porphyrins Bearing Glycodendrimeric Moieties
  作者：Séverine Ballut、Delphine Naud-Martin、Bernard Loock、Philippe Maillard

  DOI：10.1021/jo102185d

  日期：2011.4.1

  This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, respectively. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting.
• Graft Copolymer Polyelectrolyte Complexes for Drug Delivery
  申请人：Rutgers, The State University of New Jersey

  公开号：US20160199502A1

  公开（公告）日：2016-07-14

  Graft copolymer polyelectrolyte complexes are disclosed for the efficient delivery of anionic, cationic or polyelectrolyte therapeutic agents into biological cells, and for maintaining the biological activity of these molecules while in serum and other aqueous environments are provided. Such complexes comprise (1) an anionic graft copolymer containing an anionic polymer backbone, with pendent carboxylic acid groups and pendant chains containing amphipathic or hydrophilic polymers covalently bonded to a portion of the pendant carboxylic acid groups, (2) one or more anionic, cationic or polyelectrolyte therapeutic agents, and (3) optionally a liposome optionally containing an additional therapeutic agent. Also disclosed are functional nanoparticles containing the complexes.
• US9789194B2
  申请人：——

  公开号：US9789194B2

  公开（公告）日：2017-10-17