heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-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-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin
• 英文别名: per-6-cysteaminyl-β-cyclodextrin；per-6-cysteaminyl-β-CD；per-6-(2-aminoethylthio)per-6-deoxy-β-cyclodextrin；heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD；(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(2-aminoethylsulfanylmethyl)-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: C₅₆H₁₀₅N₇O₂₈S₇
• 分子量: 1548.94
• InChiKey: CMFSECFYQXHPCH-DXCNPSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.3
• 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：
  772
• 氢给体数：
  21
• 氢受体数：
  42

反应信息

• 作为反应物：
  描述：

  heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin 、 2-((4-(7-(diethylamino)-2-oxo-2H-chromene-3-carboxamido)butanoyl)thio)acetic acid 以0.0095 g的产率得到mono-[6-deoxy-6-(7-(diethylamino)-N-(4-((2-mercaptoethyl)amino)-4-oxobutyl))-2-oxo-2H-chromene-3-carboxamide]-hexakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin
  参考文献：
  名称：

  Mono-acylation of a polyamine-β-cyclodextrin based on guest mediated acyl migration

  摘要：

  测定了硫酯功能化香豆素在全-6-脱氧-6-(2-氨基乙硫基)-β-环糊精上的南-北酰化速率。获得了高产率的一酰化产物，这些产物形成了自包合物。功能化环糊精在结合生物大分子时表现出不同的荧光响应，表明这些构筑体具有作为探针的潜力。

  DOI：

  10.1039/c1cc12646f
• 作为产物：
  描述：

  per-6-(2-phthalimidoethylthio)per-6-deoxy-β-cyclodextrin 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以81%的产率得到heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin
  参考文献：
  名称：

  Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

  摘要：

  Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E-2) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E-2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E-2 conjugates, CD-E-2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.046
• 作为试剂：
  描述：

  对叔丁基苯甲醛 、 丙酮 在 heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin 作用下， 生成 4-(4-tert-Butyl-phenyl)-4-hydroxy-butan-2-one
  参考文献：
  名称：

  Cyclodextrin-based class I aldolase enzyme mimics to catalyze crossed aldol condensations

  摘要：

  A variety of mono- and unsymmetrical bifunctional P-cyclodextrins have been developed as efficient mimics of class I aldolases, some of which show a large rate acceleration and substrate selectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01717-1

文献信息

• Highly Functionalized β-Cyclodextrins by Solid-Supported Synthesis
  作者：Nesrin Vurgun、Mark Nitz

  DOI：10.1002/chem.201800028

  日期：2018.3.20

  immobilization of the mono‐thiol functionalized β‐CD on PEGA resin via a disulfide bond, enabling solid‐phase elaboration of the remaining six primary amines. To showcase the potential of this method, the amines were elaborated to tripeptides through standard Fmoc‐peptide chemistry. A small library of CD‐tripeptide conjugates was generated which, when reduced from the solid support, could be tagged at the

  使用共价捕获，可以实现具有5-巯基戊基官能团的庚基[6-脱氧-6-（2-氨基乙基硫烷基）]-β-CD的高产率选择性单官能化。在这里，我们证明了通过二硫键将单硫醇官能化的β-CD固定在PEGA树脂上，从而可以对其余6种伯胺进行固相精制。为了展示这种方法的潜力，通过标准的Fmoc-肽化学方法将胺精制为三肽。生成了一个CD-三肽偶联物的小文库，当从固相支持物中还原时，可以用对环境敏感的荧光团标记在释放的硫醇上。所得的传感器库显示出对各种胆汁盐进行差分感测的潜力。
• Access to Versatile β-Cyclodextrin Scaffolds through Guest-Mediated Monoacylation
  作者：Nesrin Vurgun、Rodolfo F. Gómez-Biagi、Mark Nitz

  DOI：10.1002/chem.201503131

  日期：2016.1.18

  mono‐derivatization of heptakis[6‐deoxy‐6‐(2‐aminoethylsulfanyl)]‐β‐CD (1) through a guest‐mediated covalent capture strategy. The use of guests functionalized with cleavable linkers enables the installation of an amine‐orthogonal thiol group on the primary rim of 1 as a handle for further transformations to the β‐CD scaffold. Applying this methodology, two novel monoderivatized β‐CDs were obtained

  在本文中，我们报告了通过客体介导的共价捕获策略对七[6-脱氧-6-（2-氨基乙基硫烷基）-β-CD（1）进行选择性单衍生化。通过使用可裂解的连接子进行功能化的客体的使用，可以在1的主要边缘上安装一个胺基-正交硫醇基团，作为进一步转化为β-CD支架的处理方法。应用这种方法，获得了两种新颖的单衍生β-CD，收率高，纯度高。这两种单酰化的CD都易于进行接头切割，并在所得的巯基上进一步修饰。该方法学可用于合成的杂功能化β-CD构建体，用于分析物感测，药物递送和其他应用。
• Improved Cyclodextrin-Based Receptors for Camptothecin by Inverse Virtual Screening
  作者：Andreas Steffen、Carolin Thiele、Simon Tietze、Christian Strassnig、Andreas Kämper、Thomas Lengauer、Gerhard Wenz、Joannis Apostolakis

  DOI：10.1002/chem.200700661

  日期：2007.8.17

  optimization of a synthetic receptor for a given guest molecule, based on inverse virtual screening of receptor libraries. As an example, a virtual set of beta-cyclodextrin (beta-CD) derivatives was generated as receptor candidates for the anticancer drug camptothecin. We applied the two docking tools AutoDock and GlamDock to generate camptothecin complexes of every candidate receptor. Scoring functions were

  我们报告了基于受体库的逆虚拟筛选的给定的来宾分子的计算机辅助的合成受体的优化。例如，生成了一组虚拟的β-环糊精（β-CD）衍生物作为抗癌药物喜树碱的候选受体。我们应用了两个对接工具AutoDock和GlamDock来生成每个候选受体的喜树碱复合物。评分功能用于对所有生成的复合物进行排名。从排名前10％的候选人中，选择了9人进行实验验证。它们是通过庚基-[6-脱氧-6-碘]-β-CD与硫醇化合物反应形成七取代的β-CD合成的。从九种CD衍生物中的五种CD的溶解度测量中获得的喜树碱复合物的稳定性显着高于文献中已知的任何其他CD衍生物。其余四种CD衍生物不溶于水。此外，合成了相应的单取代的CD衍生物，它们也显示出改善的结合常数。其中9-H-嘌呤衍生物是最好的，与研究的七取代的β-CD相当。由于测得的结合自由能与计算的分数令人满意地相关，因此所应用的评分功能似乎适合于选择有希望的受体合成候选物。合
• Recognition of Ionic Guests by Ionic β-Cyclodextrin Derivatives
  作者：Gerhard Wenz、Christian Strassnig、Carolin Thiele、Annegret Engelke、Bernd Morgenstern、Kaspar Hegetschweiler

  DOI：10.1002/chem.200800295

  日期：2008.8.18

  Inclusion compounds of cationic, anionic, and neutral p-substituted derivatives of tert-butylbenzene complexed in beta-cyclodextrin and its ionic 6-mono and 6-hepta derivatives were systematically investigated by isothermal titration calorimetry (ITC). All inclusion compounds showed 1:1 stoichiometry with binding constants ranging from 10 to 3 x 10(6) M(-1). The binding free energies could be subdivided

  通过等温滴定量热法（ITC）系统地研究了络合在β-环糊精中的叔丁基苯的阳离子，阴离子和中性对位取代衍生物的包合物。所有包含化合物均显示1：1的化学计量比，结合常数范围为10到3 x 10（6）M（-1）。结合自由能可细分为非极性和静电贡献。静电相互作用可以根据库仑定律通过考虑主体和客体的质子化程度，主体内客体的方向以及Debye-Huckel-Onsager理论描述的离子屏蔽来定量描述。客体在环糊精腔内的取向通过ROESY NMR光谱法确定。
• Comparative studies on lectin–carbohydrate interactions in low and high density homo- and heteroglycoclusters
  作者：Marta Gómez-García、Juan M. Benito、Ricardo Gutiérrez-Gallego、Alfredo Maestre、Carmen Ortiz Mellet、José M. García Fernández、José L. Jiménez Blanco

  DOI：10.1039/b920048g

  日期：——

  A versatile synthetic procedure to construct series of high- and low-density homo- and heteroglycoclusters is reported. The binding properties of these synthetic multivalent glycoconjugates to concanavalin A (Con A), a model lectin, have been assessed by using a range of competitive and non-competitive binding assays including enzyme-linked lectin assays (ELLA), isothermal titration microcalorimetry (ITC) and surface plasmon resonance (SPR). In all cases, highly dense glycoclusters showed a substantial amplification of the lectin-binding strength in comparison with low-density counterparts. Interestingly, highly-dense glycoligand presentations, regardless of their homo- or heteroglycoligand pattern, furnished similar Con A binding properties, supporting the existence of a synergic effect (heterocluster effect) due to secondary interactions of “non-active” structural motifs in the presence of a certain density of “active” glycoligands.

  报告采用了一种多功能合成程序来构建一系列高密度和低密度的同源和异源糖团。通过使用一系列竞争性和非竞争性结合测定法，包括酶联凝集素测定法（ELLA）、等温滴定微量热测定法（ITC）和表面等离子体共振（SPR），评估了这些合成多价糖簇与模型凝集素 concanavalin A（Con A）的结合特性。在所有情况下，与低密度糖团相比，高密度糖团的凝集素结合强度都有大幅提高。有趣的是，高密度的配糖体，不管是同源配糖体还是异源配糖体，都具有类似的Con A结合特性，这证明了在一定密度的 "活性 "配糖体存在的情况下，由于 "非活性 "结构基团的次级相互作用而产生的协同效应（异簇效应）的存在。