β-cyclodextrin 2-(4-isobutylphenyl)propanoic acid complex 1:1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cyclodextrin 2-(4-isobutylphenyl)propanoic acid complex 1:1
• 英文别名: β-cyclodextrin*1-(4-isobutylphenyl)propionic acid；ibuprofen-β-cyclodextrin inclusion complex；β-cyclodextrin ibuprofen complex (1:1)；β-CD*BF；Ibuprofen beta-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(hydroxymethyl)-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;2-[4-(2-methylpropyl)phenyl]propanoic acid
• 化学式: C₁₃H₁₈O₂*C₄₂H₇₀O₃₅
• 分子量: 1341.28
• InChiKey: AYTBBNADZMSWNR-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.16
• 重原子数：
  92
• 可旋转键数：
  11
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  591
• 氢给体数：
  22
• 氢受体数：
  37

反应信息

• 作为产物：
  描述：

  布洛芬 、 β-环糊精 以 aq. phosphate buffer 为溶剂， 生成 β-cyclodextrin 2-(4-isobutylphenyl)propanoic acid complex 1:1
  参考文献：
  名称：

  天然和改性环糊精与乙酰水杨酸和布洛芬的包合物在 298K 水溶液中的热力学

  摘要：

  摘要 天然和取代的 α-、β- 和 γ-环糊精与乙酰水杨酸、水杨酸和布洛芬结合的热力学参数已通过等温滴定量热法测定。数据分析表明复合物的形成，全部具有 1:1 的化学计量比。主体和客体之间的形状匹配是决定热力学量值的因素。在最小的环糊精与乙酰水杨酸和水杨酸相互作用的情况下，参数表明疏水相互作用起主要作用。缔合是通过将苯环浅包含在空腔中而发生的。在取代β-环糊精的情况下，相反，苯环的包含更深，客体分子与空腔的紧密配合使得焓和熵都为负。布洛芬通过其异丁基相互作用：β-环糊精的缔合常数值非常高，这是由大的正熵决定的，这是由于水分子从腔和相互作用物质的水合球体中松弛而产生的。对于所有系统，都存在补偿性焓-熵关系，除非涉及 β-环糊精和布洛芬。β-环糊精的缔合常数值非常高，这是由空腔中的水分子和相互作用物质的水合球体中的水分子弛豫而产生的大和正熵所决定的。对于所有系统，都存在补偿性焓-熵关系，除非涉及

  DOI：

  10.1016/j.tca.2013.01.037

文献信息

• Special Features of Formation of Inclusion Complexes of Mono-Substituted β-Cyclodextrin Derivatives
  作者：N. V. Kutyasheva、G. I. Kurochkina、V. V. Glushko、M. K. Grachev

  DOI：10.1134/s107036322106013x

  日期：2021.6

  attempt to obtain inclusion compounds of a series of mono derivatives of β-cyclodextrin containing ester and ether bonds with certain aromatic and aliphatic carboxylic acids, unexpected guest-host inclusion compounds have been obtained, presumably due to the preliminary inclusion of the guest into the of β-cyclodextrin cavity. Structure and composition of the inclusion complexes have been confirmed

  摘要 在尝试获得包含酯和醚键的 β-环糊精的一系列单衍生物与某些芳香族和脂肪族羧酸的包合物时，已经获得了意想不到的客体包合物，推测是由于客体被预先包合到β-环糊精腔。包合物的结构和组成已通过1 H 和13 C NMR 光谱证实。
• Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability
  作者：Kata Tuza、László Jicsinszky、Tamás Sohajda、István Puskás、Éva Fenyvesi

  DOI：10.3762/bjoc.10.301

  日期：——

  We compared the complex forming ability of α-, β- and γ-cyclodextrins (α-CD, β-CD and γ-CD) with their open ring analogs. In addition to the native cyclodextrins also modified cyclodextrins and the corresponding maltooligomers, functionalized with neutral 2-hydroxypropyl moieties, were synthesized. A new synthetic route was worked out via bromination, benzylation, deacetylation and debenzylation to obtain the 2-hydroxypropyl maltooligomer counterparts. The complexation properties of non-modified and modified cyclic and acyclic dextrins were studied and compared by photon correlation spectroscopy (PCS) and capillary electrophoresis (CE) using model guest compounds. In some cases cyclodextrins and their open-ring analogs (acyclodextrins) show similar complexation abilities, while with other guests considerably different behavior was observed depending on the molecular dimensions and chemical characteristics of the guests. This was explained by the enhanced flexibility of the non-closed rings. Even the signs of enantiorecognition were observed for the chloropheniramine/hydroxypropyl maltohexaose system. Further studies are planned to help the deeper understanding of the interactions.

  我们比较了α-、β-和γ-环糊精（α-CD、β-CD和γ-CD）及其开环类似物的复合物形成能力。除了天然环糊精外，还合成了修饰环糊精和相应的中性2-羟基丙基基团的马尔托寡糖。通过溴化、苄基化、脱乙酰和脱苄基等步骤，制备了2-羟基丙基马尔托寡糖。采用光子相关光谱（PCS）和毛细管电泳（CE）研究了非修饰和修饰的环状和非环状葡萄糖聚合物的复合物性质，并使用模型客体化合物进行比较。在某些情况下，环糊精及其开环类似物（非环状葡萄糖聚合物）表现出相似的复合能力，而对于其他客体，观察到了明显不同的行为，这取决于客体的分子尺寸和化学特性。这可以通过非闭合环的增强柔性来解释。甚至在氯苯那敏/羟丙基马尔托六糖系统中观察到了对映体识别的迹象。进一步的研究计划有助于更深入地理解相互作用。
• Competitive phosphorylation of some β-cyclodextrin-based inclusion compounds with phosphorous diamidoester
  作者：I. A. Senyushkina、G. I. Kurochkina、M. K. Grachev、N. M. Pugashova、E. E. Nifant’ev

  DOI：10.1134/s1070363208010106

  日期：2008.1

  Inclusion compounds of β-cyclodextrin with hexane-1-ol and 1-(4-isobutylphenyl)propanoic acid were subjected to competitive phosphorylation with phosphorous diamidoester derived from 1,2-O-isopropylideneglycerol to show that the reactions occur under mild conditions but with different efficiencies depending on the nature of the “guest.”

  将β-环糊精与1-己醇和1-(4-异丁基苯基)丙酸的包合物与1,2-O-异丙叉甘油衍生的亚磷二酰胺酯进行竞争性磷酸化，结果表明该反应在温和的条件下发生，但根据“客人”的性质，效率会有所不同。
• Inclusion complexes of ibuprofen and β-cyclodextrin: Supramolecular structure and stability
  作者：Stiliyana Pereva、Valya Nikolova、Tsveta Sarafska、Silvia Angelova、Tony Spassov、Todor Dudev

  DOI：10.1016/j.molstruc.2019.127575

  日期：2020.4

  Abstract The 1:1 β-CD/ibuprofen complex formation was studied by means of theoretical (DFT calculations) and experimental (NMR) methods. The results show that both enantiomeric forms of ibuprofen can freely enter and leave the host cavity. According to the DFT computations, the binding mode I (less polar part of the ibuprofen molecule inserted into the host cavity) appears to be the preferable mode

  摘要 通过理论（DFT 计算）和实验（NMR）方法研究了 1:1 β-CD/布洛芬复合物的形成。结果表明，布洛芬的两种对映体形式都可以自由进出宿主腔。根据 DFT 计算，结合模式 I（布洛芬分子的极性较小部分插入宿主腔）似乎是 β-CD 宿主腔内客体布洛芬分子的优选结合模式。这种类型的结合对应于实验观察：布洛芬与 β-CD 的 2D-ROESY 光谱仅显示针对结合模式 I 讨论的那些交叉峰。
• Isothermal Titration Calorimetry and Theoretical Studies on Host-guest Interaction of Ibuprofen with α-, β- and γ-Cyclodextrin
  作者：Shengkai Xing、Qian Zhang、Chong Zhang、Qiang Zhao、Hongqi Ai、Dezhi Sun

  DOI：10.1007/s10953-009-9394-3

  日期：2009.5

  Thermodynamic parameters for formation of the inclusion complexes of α-, β- and γ-cyclodextrin (α-, β- and γ-CD) with ibuprofen (BF) in Tris-HCl buffer solutions (pH=7.0) have been determined by isothermal titration calorimetry (ITC) with nanowatt sensitivity, and the inclusion structures have been investigated by using 1H-NMR spectra at 298.15 K. A theoretical study on the inclusion processes between BF and CDs has been performed with the B3LYP/6-31G*//PM3 method in order to investigate the formation mechanism of the inclusion complexes. An analysis of the thermodynamic data indicates that the stoichiometries of α-, β- and γ-CD with BF are all 1:1 and formation of the inclusion complexes α-CD⋅BF and β-CD⋅BF are driven by enthalpy and entropy, whereas formation of γ-CD⋅BF is an entropy driven process. The 1H-NMR spectra provide clear evidence for the inclusion phenomenon, and show that the isobutyl group and aromatic ring of the guest molecule are trapped inside the cavity of the CDs. Theoretical calculations suggest that the complex formed by the BF molecule entering into the cavity of the CD molecule from the wide side is more stable than that from the narrow side.

  通过纳瓦灵敏度的等温滴定量热法（ITC）测定了α-、β-和γ-环糊精（α-、β-和γ-CD）与布洛芬（BF）在 Tris-HCl 缓冲溶液（pH=7.0）中形成包合物的热力学参数，并利用 298.15 K 下的 1H-NMR 光谱研究了包合物的结构。为了研究包合物的形成机理，我们采用 B3LYP/6-31G*//PM3 方法对 BF 和 CD 之间的包合过程进行了理论研究。对热力学数据的分析表明，α-、β- 和 γ-CD 与 BF 的化学计量比均为 1:1，α-CD⋅BF 和 β-CD⋅BF 的形成受焓和熵的驱动，而 γ-CD⋅BF 的形成是一个熵驱动过程。1H-NMR 光谱为包合现象提供了明确的证据，并表明客体分子的异丁基和芳香环被困在 CD 的空腔内。理论计算表明，BF 分子从宽侧进入 CD 分子空腔所形成的复合物比从窄侧进入的复合物更稳定。