hydroxypropyl-β-cyclodextrin | 770728-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hydroxypropyl-β-cyclodextrin
• 英文别名: (2-hydroxypropyl)-β-cyclodextrin；HP-β-CD；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-37,39,41,43,45,47,49-heptakis(2-hydroxypropoxy)-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-36,38,40,42,44,46,48-heptol
• CAS: 770728-81-9
• 化学式: C₆₃H₁₁₂O₄₂
• 分子量: 1541.56
• InChiKey: NFUFCLOZQFLUAI-VCRDVHLZSA-N

物化性质

• 沸点：
  1536.6±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -13
• 重原子数：
  105
• 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：
  619
• 氢给体数：
  21
• 氢受体数：
  42

反应信息

• 作为反应物：
  描述：

  hydroxypropyl-β-cyclodextrin 、 花旗松素 以 乙醇 、 水 为溶剂， 反应 120.0h， 以91%的产率得到
  参考文献：
  名称：

  Host–guest system of taxifolin and native cyclodextrin or its derivative: Preparation, characterization, inclusion mode, and solubilization

  摘要：

  The inclusion complexation behavior, characterization and binding ability of taxifolin with native cyclodextrin (alpha-, beta-, or gamma-CD) and its derivative hydroxypropyl-beta-cyclodextrin (HP beta CD) were investigated in both solution and the solid state by means of XRD, DSC, SEM, H-1 and 2D NMR and UV-vis spectroscopy. The results showed that the water solubility and thermal stability of taxifolin were obviously increased in the inclusion complex with cyclodextrins. This satisfactory water solubility and high thermal stability of the taxifolin/CD complexes will be potentially useful for their application as herbal medicines or healthcare products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2011.03.029

文献信息

• Inclusion complex of magnolol with hydroxypropyl-β-cyclodextrin: characterization, solubility, stability and cell viability
  作者：Neng Qiu、Beilisha Shen、Xuebing Li、Xiaotong Zhang、Zitai Sang、Tao Yang、Lianying An、Junda Liu、Lijuan Chen、Lan Wang

  DOI：10.1007/s10847-016-0628-x

  日期：2016.8

  characterization information proved that MAG was able to form an inclusion complex with HP-β-CD (MAG-HP-β-CD). The inclusion complex had a stoichiometry of 1:1 and the stability constant (Kc) was calculated to be 2, 206 M−1. The aqueous solubility of MAG increased more than 500-fold and the stability of MAG was notably increased in the presence of HP-β-CD. Furthermore, preliminary in vitro cytotoxicity

  本研究的目的是研究羟丙基-β-环糊精 (HP-β-CD) 对厚朴酚 (MAG) 水溶性和稳定性的影响。通过共蒸发策略制备包合物，并使用粉末 X 射线衍射、紫外-可见光谱、1H 核磁共振光谱、2D NMR 光谱、分子建模、傅立叶变换研究 MAG 与 HP-β-CD 的相互作用-红外光谱、扫描电子显微镜和相溶解度研究。所有表征信息证明 MAG 能够与 HP-β-CD (MAG-HP-β-CD) 形成包合物。包合物的化学计量比为 1:1，计算出的稳定常数 (Kc) 为 2, 206 M-1。在 HP-β-CD 存在下，MAG 的水溶性增加了 500 倍以上，MAG 的稳定性显着增加。此外，初步的体外细胞毒性试验表明，与游离 MAG 相比，MAG-HP-β-CD 表现出增强的抗癌活性。MAG-HP-β-CD 包合物的这种令人满意的水溶性和稳定性将有可能用于其作为抗癌剂或保健产品的应用。
• 一种獐牙菜苦苷的配位包合物及其制备方法和应用
  申请人：云南民族大学

  公开号：CN109847068B

  公开（公告）日：2022-06-07

  本发明提供一种獐牙菜苦苷的配位包合物及其制备方法和应用，涉及獐牙菜苦苷衍生物技术领域，本发明提供的獐牙菜苦苷的配位包合物，所述配位包合物的主体分子为环糊精或环糊精衍生物，客体分子为獐牙菜苦苷，所述主体分子与客体分子的化学计量比为1:1。本发明采用1H NMR和2D NMR、XRD、FT‑IR等方法对所述配位包合物进行表征，结果显示，獐牙菜苦苷进入环糊精或环糊精衍生物的疏水空腔内并形成配位键，实现了分子结构的重排，进而獐牙菜苦苷的配位包合物相对于獐牙菜苦苷的水溶性、稳定性有显著提高，并减轻了獐牙菜苦苷的苦味。
• Physicochemical properties and fungicidal activity of inclusion complexes of fungicide chlorothalonil with β-cyclodextrin and hydroxypropyl-β-cyclodextrin
  作者：Shuang Gao、Yanyan Liu、Jingyu Jiang、Qiuyu Ji、Ying Fu、Lixia Zhao、Chunyan Li、Fei Ye

  DOI：10.1016/j.molliq.2019.111513

  日期：2019.11

  pollution due to the use of organic solvents. In our research, inclusion complexes of hydroxypropyl-β-cyclodextrin (HPβCD) and β-cyclodextrin (β-CD) with CHT were formed to investigate the effect of β-CD and HPβCD on the water solubility, antifungal activity and thermal stability of CHT. The structure and characteristics of the two inclusion complexes were systematically evaluated by nuclear magnetic resonance

  氯噻酮（CHT）的水溶性差，限制了CHT的应用，并可能由于使用有机溶剂而造成环境污染。在我们的研究中，形成了羟丙基-β-环糊精（HPβCD）和β-环糊精（β-CD）与CHT的包合物，以研究β-CD和HPβCD对CHT的水溶性，抗真菌活性和热稳定性的影响。 。通过核磁共振（1 H NMR），扫描电子显微镜（SEM），X射线衍射（XRD），傅里叶变换红外光谱（FT-IR）和热重分析系统地评估了两种包合物的结构和特性。（TGA）。结果11 H NMR，FT-IR，SEM和XRD表明CHT成功进入了β-CD和HPβCD的腔内。TGA结果证明，CHT的热稳定性得到了显着改善。分子建模表明环糊精可以有效地与CHT络合。此外，生物学活性测试表明，该复合物具有比原始CHT更好的抗真菌活性。我们的研究可以为更合理地使用CHT提供有用的信息，并且环糊精可以在农业中更多地用于改善农药的特性。
• Inclusion Complexes of Cyclodextrins with Galangin: a Thermodynamic and Reactivity Study
  作者：Carolina Jullian、Muriel Alfaro、Gerald Zapata-Torres、Claudio Olea-Azar

  DOI：10.1007/s10953-010-9574-1

  日期：2010.10

  The formation of the complexes of galangin (GAL) with native β-cyclodextrin (βCD), and with its substituted counterparts such as dimethyl-βCD (DMβCD) and hydroxypropyl-βCD (HPβCD), was studied by fluorescence spectra in aqueous medium. The binding association constants (K a) of the complexes were determined at different temperatures. The formation constants obtained have the following trend upon complex formation at the three temperatures studied: HPβCD > DMβCD > βCD. The thermodynamic data for the inclusion of GAL in DMβCD and HPβCD indicated that is mainly enthalpy driven whereas for βCD it is an entropy-driven process. The antioxidant ability studies of GAL and CD complexes showed practically no change in its activity when the β-cyclodextrin complex is formed. The decrease in the T eq observed for GAL-DMβCD and GAL-HPβCD in comparison with GAL-βCD could be due to effective protection of the phenol group in the cyclodextrin cavity, which is in agreement with molecular modeling studies.

  在水介质中，通过荧光光谱研究了高良姜素（GAL）与原生β-环糊精（βCD）及其替代品（如二甲基-βCD（DMβCD）和羟丙基-βCD（HPβCD））形成的复合物。在不同温度下测定了复合物的结合结合常数（K a）。在所研究的三个温度下，络合物形成时的形成常数有如下趋势：HPβCD > DMβCD > βCD。在 DMβCD 和 HPβCD 中加入 GAL 的热力学数据表明，这主要是一个焓驱动的过程，而在βCD 中则是一个熵驱动的过程。GAL 和 CD 复合物的抗氧化能力研究表明，当形成 β-环糊精复合物时，其活性几乎没有变化。与 GAL-βCD 相比，GAL-DMβCD 和 GAL-HPβCD 的 T eq 值有所降低，这可能是由于环糊精空腔中的苯酚基团得到了有效保护，这与分子模型研究结果一致。
• Enhanced Solubility and Anticancer Potential of Mansonone G By β-Cyclodextrin-Based Host-Guest Complexation: A Computational and Experimental Study
  作者：Mahalapbutr、Wonganan、Charoenwongpaiboon、Prousoontorn、Chavasiri、Rungrotmongkol

  DOI：10.3390/biom9100545

  日期：——

  molecular dynamics simulations and MM/GBSA-based binding free energy results suggested that DMβCD was the most preferential host molecule for MG inclusion complexation. The inclusion complex formation between MG and βCD(s) was confirmed by DSC and SEM techniques. Notably, the MG/βCDs inclusion complexes exerted significantly higher cytotoxic effect (2-7 fold) on A549 lung cancer cells than the uncomplexed MG

  Mansonone G（MG）是从Mansonia gagei心材中分离的植物来源化合物，对多种恶性肿瘤具有有效的抗肿瘤作用。然而，其差的溶解度限制了其在实际应用中的用途。β-环糊精（βCD）是一种由七个（1→4）连接的α-D-吡喃葡萄糖单元组成的环状寡糖，能够将多种难溶性化合物封装在其疏水内部。在这项工作中，我们旨在通过与βCD及其衍生物（2,6-二-O-甲基-βCD（DMβCD）和羟丙基-βCD）络合来增强MG的水溶性和抗癌活性。90 ns的分子动力学模拟和基于MM / GBSA的结合自由能结果表明DMβCD是MG包合物络合的最优先宿主分子。通过DSC和SEM技术证实了MG和βCD之间的包合物形成。值得注意的是，与未复合的MG相比，MG /βCDs包合物对A549肺癌细胞的细胞毒性作用明显更高（2-7倍）。