mono-6'-deoxy-6'-amidosuccinyl-β-cyclomaltoheptaose | 136790-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-6'-deoxy-6'-amidosuccinyl-β-cyclomaltoheptaose
• 英文别名: N-succinyl-mono(6-amino-6-deoxy)-β-cyclodextrin；6-monodeoxy-6-amidosuccinyl-β-cyclodextrin；6I-amidosuccinyl-6I-deoxycyclomaltoheptaose；mono-(6-deoxy-6-succinylamino)-β-cyclodextrin
• CAS: 136790-52-8
• 化学式: C₄₆H₇₅NO₃₇
• 分子量: 1234.09
• InChiKey: YKASWWMZIVMTPB-MZIFCKCGSA-N

物化性质

• 熔点：
  155-159 °C
• 沸点：
  1643.7±65.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -15.24
• 重原子数：
  84.0
• 可旋转键数：
  11.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  600.22
• 氢给体数：
  22.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  单-6-O-氨基-Β-环糊精 、 mono-6'-deoxy-6'-amidosuccinyl-β-cyclomaltoheptaose 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以36%的产率得到66βCD2suc
  参考文献：
  名称：

  鬼臼毒素与β-环糊精衍生物的主客体包合系统具有低细胞毒性

  摘要：

  靶向或响应系统是用于下一代精密药物开发的有吸引力的治疗平台。本文首次对鬼臼毒素（POD）与三种β-环糊精（β-CD）衍生物（NH 2 -β-CD，SA-β-CD和桥连β-CD）的络合进行了实验和理论研究。包合物的特征为1H和2D核磁共振（NMR），热重分析（TGA）和X射线粉末衍射（XRD）。细胞毒性试验通过MTT测定法提供。结果表明，POD包裹在β-CD衍生物的空腔中，形成具有不同稳定性常数（Ks）的包合物。这些包合物对正常人肾细胞293 T的细胞毒性显着降低，而SA-β-CD/ POD和Bridged-β-CD/ POD的包合物对癌细胞HCT116，HepG2和HCT116具有相同的细胞毒性。与本地POD相比，SY5Y。此外，包合物的稳定性常数会影响其细胞毒性，这为POD的低细胞毒性系统提供了一种策略，可用于临床。

  DOI：

  10.1016/j.jddst.2019.101280
• 作为产物：
  描述：

  丁二酸酐 、 单-6-O-氨基-Β-环糊精 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以90%的产率得到mono-6'-deoxy-6'-amidosuccinyl-β-cyclomaltoheptaose
  参考文献：
  名称：

  On the synthesis of new amphiphilic entities by the succinic coupling of β-cyclodextrins to calixarenes

  摘要：

  新颖的分子，由β-环糊精通过琥珀二酰二胺连接剂偶联到二-正辛基-杯[4]芳烃单冠-6或双冠-6-杯[4]芳烃中，通过两种独立途径合成：从单-6'-去氧-6'-氨基-β-环糊精，以及从四氨基杯[4]芳烃衍生物。关键词：β-环糊精-杯[4]芳烃偶联，氨基琥珀酸酯-β-CD，氨基琥珀酸酯-杯[4]芳烃，辛氧基-杯[4]芳烃-单冠-6，杯[4]芳烃-双冠-6。

  DOI：

  10.1139/v05-070

文献信息

• Media-dependent morphology of supramolecular aggregates of β-cyclodextrin-grafted chitosan and insulin through multivalent interactions
  作者：Yuki Daimon、Hironori Izawa、Kohsaku Kawakami、Paweł Żywicki、Hideki Sakai、Masahiko Abe、Jonathan P. Hill、Katsuhiko Ariga

  DOI：10.1039/c3tb21528h

  日期：——

  A supramolecular protein-binding system based on multivalent interactions was investigated using β-cyclodextrin-grafted chitosan (BCC) and insulin. 1H NMR and fluorescence analyses revealed that BCC binds to insulin through electrostatic and host–guest interactions. The binding constant KBCC for the host–guest interaction between cyclodextrin (CyD) residues in BCC and Tyr and Phe residues in insulin was 478.7 M−1 in acetate buffer at pH 3.6, which was ca. 3-fold greater than the Kchi attributed to electrostatic interactions between chitosan and the Tyr residues of insulin. Furthermore, KBCC was ∼10 times greater than that of β-CyD (KCyD), suggesting that multivalent interactions composed of electrostatic and host–guest interactions strongly enhance the host–guest interaction, similar to enzymes and antibodies in living systems. Enhanced host–guest interactions resulted in effective insulin binding over a wide pH range (3.6–7.4) as well as stabilization against digestive enzymes. BCC and insulin formed supramolecular aggregates with significantly different morphologies depending on the buffer species used: a network structure in acetate buffer, nanoparticles in citrate buffer, and large aggregates in phosphate buffer. The network structure formed in acetate buffer was maintained even after dilution with phosphate buffer, a situation that mimics the environment after oral administration. In addition, the structure was fragmented easily after application of a mild force, which could be an important property for achieving absorption of protein–peptide drugs from the gastrointestinal tract. This study provides new insights for the development of CyD-based nanoarchitectures suitable for application as protein–peptide carriers for oral drug delivery.

  基于多价相互作用的超分子蛋白质结合系统已通过β-环糊精接枝壳聚糖（BCC）和胰岛素进行了研究。1H NMR和荧光分析表明，BCC通过静电和主客体相互作用与胰岛素结合。在pH 3.6的醋酸盐缓冲液中，BCC中的环糊精（CyD）残基与胰岛素中的酪氨酸和苯丙氨酸残基之间主客体相互作用的结合常数KBCC为478.7 M⁻¹，大约是巯基之间静电相互作用结合常数Kchi的3倍。此外，KBCC大约是β-CyD（KCyD）的10倍，这表明静电和主客体相互作用组成的多价相互作用强烈增强了主客体相互作用，类似于生命系统中的酶和抗体。增强的主客体相互作用导致胰岛素在广泛的pH范围（3.6-7.4）内有效结合以及抵抗消化酶的稳定性。BCC和胰岛素根据使用的缓冲液种类不同，形成了具有显著不同形态的超分子聚集体：醋酸盐缓冲液中的网络结构，柠檬酸盐缓冲液中的纳米颗粒，以及磷酸盐缓冲液中的大聚集体。在醋酸盐缓冲液中形成的网络结构甚至在用磷酸盐缓冲液稀释后仍保持不变，这种情况模拟了口服给药后的环境。此外，该结构在施加轻微力后易于破碎，这可能是蛋白质-肽药物从胃肠道吸收的重要特性。这项研究为开发适用于口服药物递送的蛋白质-肽载体提供了新的纳米建筑设计思路。
• Amphiphilic cyclodextrin derivatives, method for preparation thereof and uses thereof
  申请人：Perly Bruno

  公开号：US20070142324A1

  公开（公告）日：2007-06-21

  The invention relates to cyclodextrin derivatives of formula (I): in which: R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q where E=a linear or branched Cl-Cl 5 hydrocarbon-based group with, optionally, one or more hetero atoms; AA=the residue of an amino acid; L 1 and L 2 =a C 6 -C 24 hydrocarbon-based group with, optionally, one or more hetero atoms; p and q=0 or 1, at least one being ≠0; R 2 ═H, —CH 3 , isopropyl, hydroxypropyl, sulphobutyl ether; R 3 ═H or R 2 , except when R 2 =hydroxypropyl; all the R 4 ═—OH or R 2 , except when R 2 =hydroxypropyl, or at least one of the R 4 ═R 1 ; n=5, 6 or 7. The invention also relates to a process for preparing them, and to inclusion complexes and organized surfactant systems comprising them.

  该发明涉及以下式（I）的环糊精衍生物： 其中： R 1 ═—NH-E-AA-(L 1 ) p (L 2 ) q 其中E=线性或支链的Cl-Cl 5 碳氢基团，可选地，含有一个或多个杂原子；AA=氨基酸的残基；L 1 和L 2 =含有一个或多个杂原子的C 6 -C 24 碳氢基团；p和q=0或1，至少一个不等于0； R 2 ═H，—CH 3 ，异丙基，羟丙基，磺丁基醚； R 3 ═H或R 2 ，除非R 2 =羟丙基； 所有的R 4 ═—OH或R 2 ，除非R 2 =羟丙基，或者至少一个R 4 ═R 1 ；n=5、6或7。该发明还涉及一种制备它们的方法，以及包含它们的包合物和有序表面活性剂系统。
• Synthesis and characterization of mannosyl mimetic derivatives based on a β-cyclodextrin core
  作者：Duplex Yockot、Vincent Moreau、Gilles Demailly、Florence Djedaïni-Pilard

  DOI：10.1039/b301670f

  日期：——

  The synthesis of branched β-cyclodextrins substituted with mannosyl mimetic derivatives at one primary hydroxy group is described. It was shown that the self-inclusion phenomenon observed for the target compounds in water did not preclude the inclusion properties of the cyclodextrin moiety.

  本研究介绍了在一个伯羟基上被甘露糖基拟态衍生物取代的支链δ-环糊精的合成。研究表明，目标化合物在水中的自包容现象并不排除环糊精分子的包容特性。
• Functionalization using biocompatible carboxylated cyclodextrins of iron-based nanoMIL-100
  作者：Thais Carmona、José F. Marco、Mónica Giménez-Marqués、Walter Cañón-Mancisidor、Marlen Gutiérrez-Cutiño、Patricio Hermosilla-Ibáñez、Edwin G. Pérez、Guillermo Mínguez Espallargas、Diego Venegas-Yazigi

  DOI：10.1016/j.poly.2021.115509

  日期：2021.12
• Proline–cyclodextrin conjugates: synthesis and evaluation as catalysts for aldol reaction in water
  作者：Elisa G. Doyagüez、Alfonso Fernández-Mayoralas

  DOI：10.1016/j.tet.2012.06.089

  日期：2012.9

  The synthesis of six conjugates of L-proline and beta-cyclodextrin and their evaluation as catalysts of aldol reaction in water are described. The results indicated that the nature of the linker between proline and beta-cyclodextrin is important for catalytic activity: the one with the most flexible linker gave the best results. Inhibition experiments showed that the cavity of beta-cyclodextrin plays a role in the catalysis. Permethylation of the cyclodextrin hydroxyl groups led to higher conversion rates. (C) 2012 Elsevier Ltd. All rights reserved.