Supramolecular Modulation of Antibacterial Activity of Ambroxol by Cucurbit[7]uril
Li,Shengke1; Kuok,Kit Ieng2; Ji,Xia3; Xu,Anni1; Yin,Hang2; Zheng,Jun3; Tan,Huaping1; Wang,Ruibing2
Source PublicationChemPlusChem

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. H 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 K of (6.69±0.11)×10 M 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 (MIC) against bacillary strains towards Pseudomonas aeruginosa and Escherichia coli strains was decreased from (5.11±0.31)×10 M and (2.63±0.34)×10 M 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].

KeywordAmbroxol Antibiotics Cucurbit[7]Uril Host–guest Systems Molecular Recognition
URLView the original
Indexed BySCIE
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000536499700011
Scopus ID2-s2.0-85083179180
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Cited Times [WOS]:1   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Corresponding AuthorLi,Shengke; Wang,Ruibing
Affiliation1.School of Materials Science and Engineering,Nanjing University of Science and Technology,Nanjing,210094,China
2.State Key Laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical Sciences,University of Macau,Taipa,Avenida da Universidade,999078,Macao
3.Faculty of Health Sciences,University of Macau,Taipa,Avenida da Universidade,999078,Macao
Corresponding Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Li,Shengke,Kuok,Kit Ieng,Ji,Xia,et al. Supramolecular Modulation of Antibacterial Activity of Ambroxol by Cucurbit[7]uril[J]. ChemPlusChem,2020,85(4):679-683.
APA Li,Shengke,Kuok,Kit Ieng,Ji,Xia,Xu,Anni,Yin,Hang,Zheng,Jun,Tan,Huaping,&Wang,Ruibing.(2020).Supramolecular Modulation of Antibacterial Activity of Ambroxol by Cucurbit[7]uril.ChemPlusChem,85(4),679-683.
MLA Li,Shengke,et al."Supramolecular Modulation of Antibacterial Activity of Ambroxol by Cucurbit[7]uril".ChemPlusChem 85.4(2020):679-683.
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