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Supramolecular self-assemblies of inverted cucurbit[7]uril with biogenic amines

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Abstract

The interactions between inverted cucurbit[7]uril (iQ[7]) and six biogenic amines, namely tyramine (TA), 2-phenylethylamine (PEA), histamine (HI), tryptamine (TR), spermine (SPM), and spermidine (SPD), were studied through 1H nuclear magnetic resonance (NMR) spectroscopy, UV/vis absorption spectroscopy, fluorescence spectroscopy, isothermal titration calorimetry (ITC), and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS). The results showed that iQ[7] exhibits binding affinity towards five of these biogenic amines, with the exception of HI, and that the host–guest binding sites differ depending on the structure of the biogenic amine. For the aromatic amines (TA and PEA), the phenyl groups are completely encapsulated within iQ[7]; for the heterocyclic aromatic amine TR, there is deep inclusion of its indole group in the cavity of iQ[7]; for the fatty amines (SPM and SPD), the central alkyl chain is bound within the central cavity of iQ[7].

Graphical abstract: Supramolecular self-assemblies of inverted cucurbit[7]uril with biogenic amines

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Publication details

The article was received on 14 Sep 2018, accepted on 14 Nov 2018 and first published on 16 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ04697B
Citation: New J. Chem., 2019, Advance Article
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    Supramolecular self-assemblies of inverted cucurbit[7]uril with biogenic amines

    P. Shan, Z. Zhang, D. Bai, B. Bian, Z. Tao and X. Xiao, New J. Chem., 2019, Advance Article , DOI: 10.1039/C8NJ04697B

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