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Supramolecular encapsulation of benzocaine and its metabolite para-aminobenzoic acid by cucurbit[7]uril
Li S.3; Yin H.3; Martinz G.3; Wyman I.W.2; Bardelang D.1; Macartney D.H.2; Wang R.3
2016-04-01
Source PublicationNew Journal of Chemistry
ISSN13699261 11440546
Volume40Issue:4Pages:3484-3490
Abstract

An ester-type local anesthetic agent, benzocaine (BZC), and its metabolite, para-aminobenzoic acid (PABA), both form 1 : 1 host-guest complexes with cucurbit[7]uril (CB[7]) in aqueous solution and has been observed by H NMR, UV-visible spectroscopic titrations (including Job's plot), electrospray ionization (ESI) mass spectrometry, and density functional theory (DFT) molecular modeling. The host-guest binding affinities are (2.2 ± 0.2) × 10 M and (1.5 ± 0.2) × 10 M for the protonated BZC and PABA, respectively, in acidic solutions. The binding constants decrease by ∼100-fold to approximately 300 and 200 M for BZC and PABA, respectively, upon deprotonation of these guest molecules in PBS buffered solution (pH = 7.4). However, the encapsulation of these guest molecules by CB[7] only resulted in very moderate pK shifts. This supramolecular encapsulation of BZC and PABA could potentially find applications in drug formulation for the purpose of enhancing bio-absorption as well as reducing methemoglobinemia and allergic reactions caused by the derivation of PABA during the metabolism of BZC.

DOI10.1039/c5nj03259h
URLView the original
Indexed BySCI
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000373993600063
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被引频次[WOS]:14   [WOS记录]     [WOS相关记录]
Document TypeJournal article
专题Institute of Chinese Medical Sciences
Affiliation1.Institut de Chimie Radicalaire
2.Queen's University, Kingston
3.University of Macau
First Author AffilicationUniversity of Macau
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Li S.,Yin H.,Martinz G.,et al. Supramolecular encapsulation of benzocaine and its metabolite para-aminobenzoic acid by cucurbit[7]uril[J]. New Journal of Chemistry,2016,40(4):3484-3490.
APA Li S..,Yin H..,Martinz G..,Wyman I.W..,Bardelang D..,...&Wang R..(2016).Supramolecular encapsulation of benzocaine and its metabolite para-aminobenzoic acid by cucurbit[7]uril.New Journal of Chemistry,40(4),3484-3490.
MLA Li S.,et al."Supramolecular encapsulation of benzocaine and its metabolite para-aminobenzoic acid by cucurbit[7]uril".New Journal of Chemistry 40.4(2016):3484-3490.
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