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

doi:10.1002/poc.3504

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

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 pK_a 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 language	English
Pages (from-to)	101-106
Number of pages	6
Journal	Journal of Physical Organic Chemistry
Volume	29
Issue number	2
DOIs	https://doi.org/10.1002/poc.3504
Publication status	Published - Feb 1 2016

Keywords

NMR
antihistamines
cucurbituril
host-guest chemistry
protonation states

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/poc.3504

Cite this

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title = "Tuning protonation states of tripelennamine antihistamines by cucurbit[7]uril",

abstract = "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.",

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AU - Saleh, Na'Il

AU - Al-Handawi, Marieh B.

AU - Bufaroosha, Muna S.

AU - Assaf, Khaleel I.

AU - Nau, Werner M.

PY - 2016/2/1

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N2 - 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.

AB - 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.

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KW - cucurbituril

KW - host-guest chemistry

KW - protonation states

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

Abstract

Keywords

ASJC Scopus subject areas

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