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Cucurbit[7]uril host-guest complexes of the histamine H2- receptor antagonist ranitidine
Wang R.; MacArtney D.H.
Source PublicationOrganic and Biomolecular Chemistry
AbstractThe macrocyclic host cucurbit[7]uril forms very stable complexes with the diprotonated (K = 1.8 × 10 dm mol), monoprotonated (K = 1.0 × 10 dm mol), and neutral (K = 1.2 × 10 dm mol) forms of the histamine H-receptor antagonist ranitidine in aqueous solution. The complexation behaviour was investigated using H NMR and UV-visible spectroscopy as a function of pH and the pK values of the guest were observed to increase (ΔpK = 1.5 and ΔpK = 1.6) upon host-guest complex formation. The energy-minimized structures of the host-guest complexes with the cationic guests were determined and provide agreement with the NMR results indicating the location of the CB[7] over the central portion of the guest. The inclusion of the monoprotonated form of ranitidine slows the normally rapid (E)-(Z) exchange process and generates a preference for the (Z) isomer. The formation of the CB[7] host-guest complex greatly increases the thermal stability of ranitidine in acidic aqueous solution at 50 °C, but has no effect on its photochemical reactivity. © The Royal Society of Chemistry.
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Cited Times [WOS]:72   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
AffiliationQueen's University, Kingston
Recommended Citation
GB/T 7714
Wang R.,MacArtney D.H.. Cucurbit[7]uril host-guest complexes of the histamine H2- receptor antagonist ranitidine[J]. Organic and Biomolecular Chemistry,2008,6(11):1955-1960.
APA Wang R.,&MacArtney D.H..(2008).Cucurbit[7]uril host-guest complexes of the histamine H2- receptor antagonist ranitidine.Organic and Biomolecular Chemistry,6(11),1955-1960.
MLA Wang R.,et al."Cucurbit[7]uril host-guest complexes of the histamine H2- receptor antagonist ranitidine".Organic and Biomolecular Chemistry 6.11(2008):1955-1960.
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