Tuning protonation states of tripelennamine antihistamines by cucurbit[7]uril

Na'Il Saleh, Marieh B. Al-Handawi, Muna S. Bufaroosha, Khaleel I. Assaf, Werner M. Nau

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)


The formation of host-guest complexes of cucurbit[7]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.

Original languageEnglish
Pages (from-to)101-106
Number of pages6
JournalJournal of Physical Organic Chemistry
Issue number2
Publication statusPublished - Feb 1 2016


  • NMR
  • antihistamines
  • cucurbituril
  • host-guest chemistry
  • protonation states

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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