mono<6-(p-tolylsulfonyl)-6-deoxy>-β-cyclodextrin | 139143-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono<6-(p-tolylsulfonyl)-6-deoxy>-β-cyclodextrin
• 英文别名: mono-6-(p-toluenesulfonyl)-6-deoxy-β-cyclodextrin；6-O-p-toluenesulfonyl-β-cyclodextrin；mono-6-deoxy-6-tosyl-β-cyclodextrin；6‐mono‐O‐tosyl‐β‐CD；mono-6-deoxy-6-(p-toluenesulfonyl)-β-CD；6-monotosylated β-cyclodextrin；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23S,25S,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-[(4-methylphenyl)sulfonylmethyl]-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
• CAS: 139143-55-8
• 化学式: C₄₉H₇₆O₃₆S
• 分子量: 1273.19
• InChiKey: MORPSENQQNJTHQ-XISQNVKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13
• 重原子数：
  86
• 可旋转键数：
  9
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  576
• 氢给体数：
  20
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  乙二醇双(3-胺丙基)醚 、 mono<6-(p-tolylsulfonyl)-6-deoxy>-β-cyclodextrin 生成 2,2'-(ethylenedioxy)bis(propylamine)-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and different molecular recognition of two dye-modified cyclodextrins with spacer of different length

  摘要：

  Two beta-cyclodextrin derivatives (1 and 2) bearing a hydroxyazobenzene unit, each having a butylene or a 4,7-dioxadecylene spacer between the cyclodextrin and the dye, were prepared. which showed guest-induced color changes with a marked difference in molecular recognition behavior in aqueous solution. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.056
• 作为产物：
  描述：

  1-对甲基苯磺酰咪唑 、 β-环糊精 以 水 为溶剂， 反应 4.0h， 以18%的产率得到mono<6-(p-tolylsulfonyl)-6-deoxy>-β-cyclodextrin
  参考文献：
  名称：

  A biodegradable adamantane polymer with ketal linkages in its backbone for gene therapy

  摘要：

  我们提出了一种聚酮醚，称为pADK，它可以将PEI1800-环糊精共轭物的基因转染效率提高60倍，并降解为无毒、中性和可排泄的化合物。

  DOI：

  10.1039/c5cc05242d

文献信息

• Supramolecular nanoparticle carriers self-assembled from cyclodextrin- and adamantane-functionalized polyacrylates for tumor-targeted drug delivery
  作者：Chung Yen Ang、Si Yu Tan、Xiaoling Wang、Quan Zhang、Majad Khan、Linyi Bai、Subramanian Tamil Selvan、Xing Ma、Liangliang Zhu、Kim Truc Nguyen、Nguan Soon Tan、Yanli Zhao

  DOI：10.1039/c3tb21325k

  日期：——

  The advancement of nanobiotechnology has led to the development of various techniques for addressing target-specific drug delivery issues. In this article, we successfully developed a supramolecular self-assembly approach for the fabrication of polyacrylate-based nanoparticles with simultaneous loading of the anticancer drug doxorubicin (DOX) for targeted delivery towards cancer treatment in vitro and in vivo. Two types of polyacrylates functionalized with adamantane and β-cyclodextrin respectively could self-assemble to form supramolecular nanoparticles through strong host–guest complexation between adamantane and β-cyclodextrin. Folic acid was incorporated within the supramolecular nanoparticles in order to impart the targeting specificity towards selected cancerous cell lines, namely MDA-MB231 and B16-F10. The as-synthesized supramolecular nanoparticles were fully characterized by several techniques, revealing an average nanoparticle size of 35 nm in diameter, which is small enough for excellent blood circulation. The cytotoxicity studies indicate that the supramolecular nanoparticles without drug loading were non-cytotoxic under the concentrations measured, while DOX-loaded supramolecular nanoparticles showed significant cytotoxicity. In order to investigate the targeting specificity of DOX-loaded supramolecular nanoparticles towards the cancerous cells, a healthy cell line model HEK293 was employed for carrying out the comparison studies. Due to the presence of the targeting ligand, experimental results demonstrate that the supramolecular nanoparticles were highly specific for targeting the cancerous cells, but not for HEK293 cells. After the in vitro investigations, the in vivo drug delivery study using DOX-loaded supramolecular nanoparticles was performed. Tumor-bearing nude mice were treated with DOX-loaded supramolecular nanoparticles, and the analysis results indicate that DOX-loaded supramolecular nanoparticles have the capability to enhance the therapeutic effects of DOX for effectively inhibiting the tumor growth. Thus, the self-assembled polymeric nanoparticles exhibit a highly promising potential to serve as drug carriers for targeted drug delivery towards improved cancer treatment.

  纳米生物技术的进步导致了解决特定目标药物输送问题的各种技术的发展。在本文中，我们成功开发了一种超分子自组装方法，用于制造基于聚丙烯酸酯的纳米颗粒，同时负载抗癌药物阿霉素（DOX），用于体外和体内癌症治疗的靶向递送。两种分别用金刚烷和β-环糊精功能化的聚丙烯酸酯可以通过金刚烷和β-环糊精之间的强主客体络合自组装形成超分子纳米粒子。将叶酸掺入超分子纳米颗粒中，以赋予针对选定癌细胞系（即 MDA-MB231 和 B16-F10）的靶向特异性。通过多种技术对合成的超分子纳米颗粒进行了全面表征，显示平均纳米颗粒尺寸为直径 35 nm，足够小，可以实现良好的血液循环。细胞毒性研究表明，未负载药物的超分子纳米颗粒在测量浓度下无细胞毒性，而负载DOX的超分子纳米颗粒则表现出显着的细胞毒性。为了研究负载DOX的超分子纳米粒子对癌细胞的靶向特异性，采用健康细胞系模型HEK293进行比较研究。由于靶向配体的存在，实验结果表明超分子纳米颗粒对于靶向癌细胞具有高度特异性，但对于 HEK293 细胞则不然。在体外研究之后，进行了使用负载DOX的超分子纳米颗粒的体内药物递送研究。用负载DOX的超分子纳米颗粒治疗荷瘤裸鼠，分析结果表明负载DOX的超分子纳米颗粒能够增强DOX的治疗效果，有效抑制肿瘤生长。因此，自组装聚合物纳米颗粒表现出作为药物载体用于靶向药物递送以改善癌症治疗的非常有前途的潜力。
• Single Isomer N-Heterocyclic Cyclodextrin Derivatives as Chiral Selectors in Capillary Electrophoresis
  作者：Ida Fejős、Eszter Kalydi、Edit Luca Kukk、Mimimorena Seggio、Milo Malanga、Szabolcs Béni

  DOI：10.3390/molecules26175271

  日期：——

  recognition mechanisms of positively charged cyclodextrin (CD) derivatives, the synthesis, the pKa determination by 1H nuclear magnetic resonance (NMR)-pH titration and a comparative chiral capillary electrophoretic (CE) study were performed with two series of mono-substituted cationic single isomer CDs. The first series of selectors were mono-(6-N-pyrrolidine-6-deoxy)-β-CD (PYR-β-CD), mono-(6-N-p

  为了更好地了解带正电荷的环糊精（CD）衍生物的手性识别机制，进行了合成、 1 H核磁共振（NMR）-pH滴定测定p K a和比较手性毛细管电泳（CE）研究具有两个系列的单取代阳离子单一异构体CD。第一个系列的选择器是单-(6- N-吡咯烷-6-脱氧)-β-CD (PYR-β-CD)、单-(6- N-哌啶-6-脱氧)-β-CD (PIP -β-CD)、单-(6- N-吗啉-6-脱氧)-β-CD (MO-β-CD) 和单-(6- N-哌嗪-6-脱氧)-β-CD (PIPA) -β-CD)，在空腔较窄的边缘携带 pH 值可调的部分，而第二组由其季铵化、永久阳离子对应物代表：单-(6- N- ( N-甲基-吡咯烷)-6-脱氧）-β-CD（MePYR-β-CD），单-（6- N- （ N-甲基哌啶）-6-脱氧）-β-CD（MePIP-β-CD），单-（6- N -( N-甲基吗啉)-6-脱氧)-β-CD
• Spin-labelled cyclodextrins as hosts for large supramolecular assemblies
  作者：Gabriela Ionita、Victor Chechik

  DOI：10.1039/b508256k

  日期：——

  EPR spectroscopy was used to study formation of inclusion complexes of monofunctionalised spin-labelled β-cyclodextrins; this method is very sensitive to the interactions of cyclodextrins with large guest molecules.

  利用 EPR 光谱研究了单官能团自旋标记的 β-环糊精包合物的形成；这种方法对环糊精与大客体分子的相互作用非常敏感。
• Enantioselective sorption of some chiral carboxylic acids by various cyclodextrin-grafted iron oxide magnetic nanoparticles
  作者：Mustafa Arslan、Serkan Sayin、Mustafa Yilmaz

  DOI：10.1016/j.tetasy.2013.07.015

  日期：2013.9

  A new enantioselective sorption approach to chiral carboxylic acid molecules such as (R)-(-)-N-(3,5-dinitrobenzoyl)phenylglycine (R)-(-)DNBPG, (S)-(+)-N-(3,5-dinitrobenzoyl)phenylglycine (S)-(+)DNBPG, (R)-(+)-N-(1-phenylethyl)phthalamic acid (R)-(+)PEPA and (S)-()-N-(1-phenylethyl)phthalamic acid (S)-(-)PEP A regarding their complexation with three diversely functionalized beta-cyclodextrin grafted iron oxide nanoparticles in the aqueous phase, was developed. The sorption efficiencies of these carboxylic acids were carried out by high-performance liquid chromatography (HPLC) with an Ace 5 C18 column. The effects of temperatures on the sorption were also investigated. The results showed that the ether functionalized derivative of beta-cyclodextrin Al-CD-MNPs has a specific affinity for (R)-(-)DNBPG at 30 degrees C and pH 7.0. The amine functionalized derivative of beta-cyclodextrin Am-CD-MNPs has a greater affinity towards not only (S)-()DNBPG, but also (R)-(+)PEPA compared with their other isomers, which are the (R)-isomer of DNBPG and the (S)-isomer of PEPA at 30 degrees C and pH 7.0. In addition, although amide functionalized derivatives of beta-cyclodextrin (Amd-CD-MNPs) have an affinity towards both isomers of some chiral carboxylic acids; no selective affinity was observed at 30 degrees C and pH 7.0. (C) 2013 Elsevier Ltd. All rights reserved.
• A biodegradable adamantane polymer with ketal linkages in its backbone for gene therapy
  作者：Santanu Maity、Priya Choudhary、Manu Manjunath、Aditya Kulkarni、Niren Murthy

  DOI：10.1039/c5cc05242d

  日期：——

  We present a polyketal, termed pADK, which can increase the gene transfection efficiency of PEI1800–cyclodextran conjugates 60 fold and degrade into nontoxic, neutral and excretable compounds.

  我们提出了一种聚酮醚，称为pADK，它可以将PEI1800-环糊精共轭物的基因转染效率提高60倍，并降解为无毒、中性和可排泄的化合物。