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Supramolecular Modulation of Antibacterial Activity of Ambroxol by Cucurbit[7]uril.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-04-06 , DOI: 10.1002/cplu.202000119 Shengke Li 1 , Kit Ieng Kuok 2 , Xia Ji 3 , Anni Xu 1 , Hang Yin 2 , Jun Zheng 3 , Huaping Tan 1 , Ruibing Wang 2
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-04-06 , DOI: 10.1002/cplu.202000119 Shengke Li 1 , Kit Ieng Kuok 2 , Xia Ji 3 , Anni Xu 1 , Hang Yin 2 , Jun Zheng 3 , Huaping Tan 1 , Ruibing Wang 2
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Supramolecular encapsulation by cucurbit[7]uril (CB[7]) was recently demonstrated to provide a simple and efficient method for antibacterial activity regulation of antibiotics. In this work, CB[7] was shown to form binary host‐guest complex with ambroxol hydrochloride (ABX), a clinical mucokinetic and expectorant drug, which was reported to exhibit certain antibacterial activity. 1H NMR titration and isothermal titration calorimetry experiment results suggested that the 4‐hydroxyl cyclohexylamine group of ABX was included inside the CB[7] cavity, with a binding constant Ka of (6.69±0.11)×105 M−1 in phosphate buffered saline (PBS) solution, thermodynamically driven by both enthalpy change (ΔH=−12.2 kJ/mol) and entropy change (TΔS=21.1 kJ/mol). More importantly, ABX's inhibitory activity (MIC50) against bacillary strains towards Pseudomonas aeruginosa and Escherichia coli strains was decreased from (5.11±0.31)×10−6 M−1 and (2.63±0.34)×10−5 M−1 to zero upon encapsulation by CB[7], and was subsequently recovered to almost its original activity when a competitive guest, amantadine hydrochloride, for disassembling CB[7]‐ABX complex, was added, suggesting that the antibacterial activity of ABX could be readily “turned off/on” upon its complexation and decomplexation with CB[7].
中文翻译：
葫芦[7] uril的超分子调节氨溴索的抗菌活性。
最近证明了葫芦[7]尿嘧啶（CB [7]）的超分子包封提供了一种简单有效的方法来调节抗生素的抗菌活性。在这项工作中，CB [7]已显示与盐酸氨溴索（ABX）形成二元主客体复合物，后者是一种临床的粘液动力学和祛痰药，据报道具有一定的抗菌活性。1 H NMR滴定和等温滴定量热实验结果表明，ABX的4-羟基环己胺基团包含在CB [7]腔内，结合常数K a为（6.69±0.11）×10 5 M -1在磷酸盐缓冲盐水（PBS）溶液中，热力学由焓变（ΔH= -12.2 kJ / mol）和熵变（TΔS= 21.1 kJ / mol）驱动。更重要的是，ABX对细菌菌株对铜绿假单胞菌和大肠杆菌的抑制活性（MIC 50）从（5.11±0.31）×10 -6 M -1和（2.63±0.34）×10 -5 M -1降低 被CB [7]包封后降至零，随后加入竞争性客体金刚烷胺盐酸盐以分解CB [7] -ABX复合物，随后恢复到几乎原始活性，这表明ABX的抗菌活性很容易与CB的复合和解复合“关闭/打开” [7]。
更新日期：2020-04-22
中文翻译：
葫芦[7] uril的超分子调节氨溴索的抗菌活性。
最近证明了葫芦[7]尿嘧啶（CB [7]）的超分子包封提供了一种简单有效的方法来调节抗生素的抗菌活性。在这项工作中，CB [7]已显示与盐酸氨溴索（ABX）形成二元主客体复合物，后者是一种临床的粘液动力学和祛痰药，据报道具有一定的抗菌活性。1 H NMR滴定和等温滴定量热实验结果表明，ABX的4-羟基环己胺基团包含在CB [7]腔内，结合常数K a为（6.69±0.11）×10 5 M -1在磷酸盐缓冲盐水（PBS）溶液中，热力学由焓变（ΔH= -12.2 kJ / mol）和熵变（TΔS= 21.1 kJ / mol）驱动。更重要的是，ABX对细菌菌株对铜绿假单胞菌和大肠杆菌的抑制活性（MIC 50）从（5.11±0.31）×10 -6 M -1和（2.63±0.34）×10 -5 M -1降低 被CB [7]包封后降至零，随后加入竞争性客体金刚烷胺盐酸盐以分解CB [7] -ABX复合物，随后恢复到几乎原始活性，这表明ABX的抗菌活性很容易与CB的复合和解复合“关闭/打开” [7]。
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