Tuning protonation states of tripelennamine antihistamines by cucurbit[7]uril |
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| Authors: | Na'il Saleh Marieh B Al‐Handawi Muna S Bufaroosha Khaleel I Assaf Werner M Nau |
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| Institution: | 1. Chemistry Department, College of Science, United Arab Emirates University, Al‐Ain, United Arab Emirates;2. Department of Life Sciences and Chemistry, Jacobs University Bremen, Bremen, Germany |
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| Abstract: | The formation of host–guest complexes of cucurbit7]uril (CB7) with the antihistamine drug tripelennamine (TRP) was studied by optical and NMR spectroscopy. The experimental and computational results are consistent with inclusion of a single TRP molecule in CB7. Addition of CB7 has tuned drug protonation states associated with (de)protonation of the ethyldimethylammonium and exocyclic nitrogens with an increase in the associated pKa values by 1.5 and 2.5 units, respectively. The incorporation of antihistamines drugs such as TRP in cucurbiturils could be utilized for switching their capability for selective binding to histamine H1‐receptors, in the future. Copyright © 2015 John Wiley & Sons, Ltd. |
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| Keywords: | antihistamines cucurbituril host– guest chemistry NMR protonation states |
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