heptakis-6-(2-hydroxyethylamino)-6-deoxy-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis-6-(2-hydroxyethylamino)-6-deoxy-β-cyclodextrin
• 英文别名: hepta-6-(2'-hydroxyethyl)amino-β-CD；per-6-[(2-hydroxyethyl)amino]-6-deoxy-β-cyclodextrin；(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)-5,10,15,20,25,30,35-heptakis[(2-hydroxyethylamino)methyl]-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]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₅₆H₁₀₅N₇O₃₅
• 分子量: 1436.48
• InChiKey: QXTMOAYONGDUNS-DXCNPSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -18
• 重原子数：
  98
• 可旋转键数：
  28
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  638
• 氢给体数：
  28
• 氢受体数：
  42

反应信息

• 作为产物：
  描述：

  C.I.酸性橙108 以70%的产率得到heptakis-6-(2-hydroxyethylamino)-6-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Nucleic acid complexes

  摘要：

  这项发明涉及核酸复合物、其制备方法以及将其用于将核酸输送到细胞中的用途。

  公开号：

  US08916697B2
• 作为试剂：
  描述：

  4-硝基苯基戊酸酯 在 heptakis-6-(2-hydroxyethylamino)-6-deoxy-β-cyclodextrin 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  新型环糊精二聚体在对硝基苯基链烷酸酯水解裂解中的催化性能

  摘要：

  新颖的环糊精（CD）二聚体（3A-C通过齿配体连接）由6-脱氧-6-（羟基乙基氨基）反应，制备-β-CD（2）与p -和米双（溴甲基）苯和2,6- -双（溴甲基）吡啶。的催化性质2，图3b和图3c中的水解裂解p硝基苯基链烷酸酯，即乙酸酯（PNPA），丁酸乙酯（PNPB），己酸盐（PNPH）和辛酸（PNPO），进行了研究。CD二聚体3b和3c在中性附近显示出适度的速率增强。尽管在3b存在下催化速率常数（k c）或3c随酯链长度的变化不显着，“长链”酯（PNPH和PNPO）的米氏常数K M远小于“短链”酯（PHPA和PNPB）的米氏常数，因此，“长链”酯的选择性因子（k c / K M）比“短链”酯的选择性因子大得多，这表明CD二聚体在水解过程中具有良好的尺寸识别能力和底物选择性。对硝基苯基链烷酸酯。向反应介质中添加Cu 2+对K M的影响不大，但导致K M的显着增加。ķ Ç在，因此增加ķ Ç

  DOI：

  10.1002/poc.379

文献信息

• Development of a Low Toxicity, Effective pDNA Vector Based on Noncovalent Assembly of Bioresponsive Amino-β-cyclodextrin:Adamantane–Poly(vinyl alcohol)–Poly(ethylene glycol) Transfection Complexes
  作者：Aditya Kulkarni、Wei Deng、Seok-hee Hyun、David H. Thompson

  DOI：10.1021/bc2005158

  日期：2012.5.16

  main chain polymer bearing poly(ethylene glycol) (MW 750) (PEG) or MW 2000 PEG and acid-labile adamantane-modified (Ad) grafts through an acid-sensitive benzylidene acetal linkage. These components were investigated for their ability to promote supramolecular complex formation with pDNA using two different assembly schemes, involving either precomplexation of the pendent Ad-PVA-PEG polymer with the cationic

  基于阳离子β-CD衍生物与带有聚（乙二醇）的聚（乙烯醇）（MW 27 kDa）（PVA）主链聚合物的自组装，已经开发了一种宿主：客源基因递送载体（ MW 750) (PEG) 或 MW 2000 PEG 和酸不稳定金刚烷改性 (Ad) 通过酸敏感亚苄基缩醛键接枝。使用两种不同的组装方案研究了这些组分促进与 pDNA 形成超分子复合物的能力，包括在 pDNA 缩合之前将悬垂的 Ad-PVA-PEG 聚合物与阳离子 β-CD 衍生物进行预络合（方法 A）或 pDNA 与在添加 Ad-PVA-PEG 以参与宿主：客体复合之前的阳离子 β-CD 衍生物（方法 B）。当采用方法 A 组装方案时，细胞毒性比 25 kDa bPEI 低3倍，同时保持优于针对该基准阳离子聚合物转染试剂观察到的转染效率。这些发现表明，采用多价宿主：客体相互作用的可降解阳离子聚合物构建体可能是一种有效且低毒的载体，用于将核酸货物递送至靶细胞。
• A Persubstituted Cationic β-Cyclodextrin for Chiral Separations
  作者：Frank O'Keeffe、Shahab A. Shamsi、Raphael Darcy、P. Schwinté、Isiah M. Warner

  DOI：10.1021/ac970370e

  日期：1997.12.1

  The applications of a novel polycationic derivative of β-cyclodextrin (β-CD), heptakis(6-hydroxyethylamino-6-deoxy-β-cyclodextrin) (β-CD-EA), as a chiral host−guest additive for the enantioseparation of various classes of chiral anionic analytes are presented. The cationic β-CD described in this paper is persubstituted with seven ethanolamine side arms at the primary rim of each cyclodextrin (CD) molecule. It is found that the electrophoretic mobility of β-CD-EA can be adjusted to influence the chiral selectivity by changing the pH of the background electrolyte. Most of the observed CD capillary zone electrophoresis (CZE) separations of anionic drugs and herbicides were accomplished in the pH range of 4.0−7.0 with a reverse polarity configuration. At pH 5.0, enantioseparation of a mixture of three structurally related antiinflammatory agents (fenoprofen, flurbiprofen, and ibuprofen) was possible in about 30 min. However, other chiral acids, such as a series of phenoxypropionic acid herbicides and dansylated amino acids (glutamic acid and aspartic acids), were best separated at pH 6.0 or 7.0. An impressive separation of a mixture of six structurally related anionic herbicides [(±)-2-phenoxypropionic acid, (±)-2-(2-chlorophenoxy)propionic acid, (±)-2-(3-chlorophenoxy)propionic acid, (±)-2-(4-chlorophenoxy)propionic acid, (±)-2-(2,4-dichlorophenoxy)propionic acid, and (±)-2-(2,4,5-trichlorophenoxy)propionic acid] was achieved for the first time in about 15 min during a single run with 20 mM β-CD-EA. The analytical applicability of this cationic CD molecule for chiral separations is discussed in detail.

  本文介绍了β-环糊精（β-CD）的一种新型多阳离子衍生物--七（6-羟乙氨基-6-脱氧-β-环糊精）（β-CD-EA）作为手性主-客添加剂在手性阴离子分析物对映体分离中的应用。本文中描述的阳离子 β-CD 在每个环糊精（CD）分子的主边缘处有七个乙醇胺侧臂。研究发现，可以通过改变背景电解质的 pH 值来调节 β-CD-EA 的电泳迁移率，从而影响手性选择性。大多数阴离子药物和除草剂的毛细管区带电泳（CZE）分离实验都是在 pH 值为 4.0-7.0 的反极性配置条件下完成的。在 pH 值为 5.0 时，三种结构相关的消炎药（非诺洛芬、氟比洛芬和布洛芬）的混合物可在约 30 分钟内完成对映体分离。然而，其他手性酸，如一系列苯氧基丙酸除草剂和丹酰化氨基酸（谷氨酸和天冬氨酸），在 pH 值为 6.0 或 7.0 时分离效果最佳。(±)-2-(4-氯苯氧基)丙酸、(±)-2-(2,4-二氯苯氧基)丙酸和(±)-2-(2,4,5-三氯苯氧基)丙酸]首次在 20 mM β-CD-EA 下单次运行约 15 分钟内实现。详细讨论了这种阳离子 CD 分子在手性分离方面的分析应用。
• Synthesis of Monofacially Functionalized Cyclodextrins Bearing Amino Pendent Groups
  作者：Dragos Vizitiu、Caroline S. Walkinshaw、Borio I. Gorin、Gregory R. J. Thatcher

  DOI：10.1021/jo9711549

  日期：1997.12.1

  Derivatives of the cyclodextrins, alpha CD, beta CD, and gamma CD, in which all primary hydroxyls are substituted by amine pendant groups, may be synthesized efficiently from the per-6-bromo-6-deoxy-CD derivatives by direct reaction with amines. These ACD derivatives, which bear six, seven! or eight amine pendent groups, represent interesting biomimetic receptors and catalysts. The synthetic strategy relies on quantitative transformation and efficient purification as is demonstrated by preparation of 11 homogeneous ACD derivatives. The limitations of the synthesis and potential adaptations are illustrated by the synthesis of several more ACD derivatives to >95% purity. A synthetic route to a CD persubstituted with primary amine functionalities at the primary face, per-6-(aminomethyl)-6-deoxy-CD, yields an alternative reagent to the simple per-6-amino-6-deoxy-CD, which is more suitable for further synthetic transformations. The synthetic strategy is further adapted to preparation of a prototypical (6 + 1)-ACD derivative in which one primary position is substituted with a sulfide group and the remaining six primary face positions are substituted with amine pendent groups.
• Binding of Phosphates to Aminocyclodextrin Biomimetics
  作者：Dragos Vizitiu、Gregory R. J. Thatcher

  DOI：10.1021/jo9902392

  日期：1999.8.1

  Aminocyclodextrins (ACDs) in which the primary face is perfacially substituted with amino pendant groups provide three potential biomimetic binding domains: the hydrophobic cavity, the cationic annulus, and the corona formed by the pendant tendrils. Binding of phosphate monoester dianions and diester monoanions by ACDs and native CDs is compared to that of neutral guest molecules. Binding to ACDs can be understood in terms of cooperativity between binding domains in which electrostatic and hydrophobic forces may be additive or compromised. Unexpectedly, slow chemical exchange is observed, in particular for dianionic aryl ester guest molecules. The substantial kinetic barriers for dissociation of these pseudorotaxane complexes are explained by the unfavorable passage of the anionic phosphate headgroup through the relatively hydrophobic ACD cavity.