☆ 4.6 Article

Host-guest complexations of local anaesthetics by cucurbit[7]uril in aqueous solution

ORGANIC & BIOMOLECULAR CHEMISTRY (2010)

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY

卷 8, 期 1, 页码 247-252

出版社

ROYAL SOC CHEMISTRY

DOI: 10.1039/b915694a

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Chemistry, Organic

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Natural Sciences and Engineering Research Council of Canada (NSERC)
The Government of Ontario, Ministry of Training and Universities
Walter C Sumner Foundation

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摘要

The cucurbit[7]uril (CB[7]) host molecule forms very stable host-guest complexes with the local anaesthetics procaine (K-CB[7] = (3.5 +/- 0.7) 10(4) dm(3) mol(-1)), tetracaine (K-CB[7] = (1.5 +/- 0.4) x 10(4) dm(3) mol(-1)), procainamide (K-CB[7] = (7.8 +/- 1.6) 10(4) dm(3) mol(-1)), dibucaine (K-CB[7] = (1.8 +/- 0.4) x 10(5) dm(3) mol(-1)) and prilocaine (K-CB[7] = (2.6 +/- 0.6) 10(4) dm(3) mol(-1)) in aqueous solution (pD = 4.75). The stability constants are 2-3 orders of magnitude greater than the values reported for binding by the comparably sized beta-cyclodextrin host molecule. The inclusion by CB[7] raises the first pK(a) values of the anaesthetics by 0.5-1.9 pK units, as the protonated forms are bound more strongly in acidic solution. The complexation-induced chemical shift changes in the guest proton resonances provide an indication of the site(s) of binding and the effects of protonation on the location of the binding sites.

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