carboxymethyl-β-cyclodextrin | 139053-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carboxymethyl-β-cyclodextrin
• 英文别名: heptakis-(6-O-carboxymethyl)-cyclomaltoheptaose；carboxymethyl-β-CD；carboxymethyl ether β-cyclodextrin；2-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-10,15,20,25,30,35-hexakis(carboxymethoxymethyl)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]acetic acid
• CAS: 139053-41-1
• 化学式: C₅₆H₈₄O₄₉
• 分子量: 1541.25
• InChiKey: WROHVVIPQXODQM-YWBSARSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.1
• 重原子数：
  105
• 可旋转键数：
  28
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  738
• 氢给体数：
  21
• 氢受体数：
  49

反应信息

• 作为反应物：
  描述：

  carboxymethyl-β-cyclodextrin 、 gadolinium(III) chloride hexahydrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 18.0h， 生成 heptakis-(6-O-carboxymethyl)-cyclomaltoheptaose gadolinium
  参考文献：
  名称：

  MRI probes based on C6-peracetate β-cyclodextrins: Synthesis, gadolinium complexation and in vivo relaxivity studies

  摘要：

  The initial synthesis of two p-cyclodextrin derivatives bearing seven carboxylate ligands was optimized in order to improve the production of contrast agents. A speciation study using potentiometric analysis was performed on a gadolinium(III) complex. The in vivo myocardic activity was evaluated on mice. This study highlights the best efficiency for the cyclodextrin derivative having free hydroxyl groups and validated the biomedical potential of the flexible cyclodextrin scaffold as a cardiac MRI probe. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.03.013
• 作为产物：
  描述：

  heptakis-(6-O-ethoxycarboxyethyl)-cyclomaltoheptaose 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以63%的产率得到carboxymethyl-β-cyclodextrin
  参考文献：
  名称：

  MRI probes based on C6-peracetate β-cyclodextrins: Synthesis, gadolinium complexation and in vivo relaxivity studies

  摘要：

  The initial synthesis of two p-cyclodextrin derivatives bearing seven carboxylate ligands was optimized in order to improve the production of contrast agents. A speciation study using potentiometric analysis was performed on a gadolinium(III) complex. The in vivo myocardic activity was evaluated on mice. This study highlights the best efficiency for the cyclodextrin derivative having free hydroxyl groups and validated the biomedical potential of the flexible cyclodextrin scaffold as a cardiac MRI probe. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.03.013

文献信息

• Chiral Separation of Uncharged Pomalidomide Enantiomers Using Carboxymethyl-β-Cyclodextrin: A Validated Capillary Electrophoretic Method
  作者：Zoltán-István Szabó、Levente Szőcs、Daniela-Lucia Muntean、Béla NoszáL、Gergő Tóth

  DOI：10.1002/chir.22563

  日期：2016.3

  effective chiral selector. Factors influencing enantioseparation were systematically optimized, using an orthogonal experimental design. Optimal parameters (background electrolyte [BGE]: 50 mM Tris‐acetate buffer, pH 6.5, containing 15 mM CM‐β‐CD; capillary temperature: 20°C; voltage applied +15 kV) allowed baseline separation of POM enantiomers with a resolution as high as 4.87. The developed method was

  pomalidomide（POM）的外消旋混合物是第二代免疫调节性不带电药物，首次通过毛细管区带电泳分离为对映体。筛选了7种不同的带电环糊精（CD）衍生物作为络合剂和手性选择剂，研究了POM-CD包合物的稳定性及其对映体的能力。根据初步实验，发现羧甲基-β-CD（CM-β-CD）是最有效的手性选择剂。使用正交实验设计，系统地优化了影响对映体分离的因素。最佳参数（背景电解质[BGE]：50 mM Tris-乙酸盐缓冲液，pH 6.5，含15 mMCM-β-CD；毛细管温度：20°C；施加的电压（+15 kV）可实现POM对映体的基线分离，分离度高达4.87。在灵敏度（检测限和定量限），线性，准确性，可重复性和中间精度方面验证了所开发方法的有效性。手性28：199–203，2016。©2015 Wiley Periodicals，Inc.
• MRI probes based on C6-peracetate β-cyclodextrins: Synthesis, gadolinium complexation and in vivo relaxivity studies
  作者：Anais Biscotti、Cécile Barbot、Lionel Nicol、Paul Mulder、Célia Sappei、Marie-Hubert Roux、Isabelle Déchamps-Olivier、François Estour、Géraldine Gouhier

  DOI：10.1016/j.poly.2018.03.013

  日期：2018.7

  The initial synthesis of two p-cyclodextrin derivatives bearing seven carboxylate ligands was optimized in order to improve the production of contrast agents. A speciation study using potentiometric analysis was performed on a gadolinium(III) complex. The in vivo myocardic activity was evaluated on mice. This study highlights the best efficiency for the cyclodextrin derivative having free hydroxyl groups and validated the biomedical potential of the flexible cyclodextrin scaffold as a cardiac MRI probe. (C) 2018 Elsevier Ltd. All rights reserved.