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Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study

The histamine H(2)-receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 10(3) M(−1), 1.30 (±0.27) × 10(4) M(−1) and 1.05 (±0.33) × 10(5) M(−1), respectively. These 1:1 host-guest inc...

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Autores principales: Yin, Hang, Wang, Runmiao, Wan, Jianbo, Zheng, Ying, Ouyang, Defang, Wang, Ruibing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274153/
https://www.ncbi.nlm.nih.gov/pubmed/27608003
http://dx.doi.org/10.3390/molecules21091178
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author Yin, Hang
Wang, Runmiao
Wan, Jianbo
Zheng, Ying
Ouyang, Defang
Wang, Ruibing
author_facet Yin, Hang
Wang, Runmiao
Wan, Jianbo
Zheng, Ying
Ouyang, Defang
Wang, Ruibing
author_sort Yin, Hang
collection PubMed
description The histamine H(2)-receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 10(3) M(−1), 1.30 (±0.27) × 10(4) M(−1) and 1.05 (±0.33) × 10(5) M(−1), respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by (1)H-NMR, UV-visible spectroscopic titrations (including Job plots), electrospray ionization mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC), as well as theoretically by molecular dynamics (MD) computation. This study may provide important insights on the supramolecular formulation of H(2)-receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes.
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spelling pubmed-62741532018-12-28 Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study Yin, Hang Wang, Runmiao Wan, Jianbo Zheng, Ying Ouyang, Defang Wang, Ruibing Molecules Article The histamine H(2)-receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 10(3) M(−1), 1.30 (±0.27) × 10(4) M(−1) and 1.05 (±0.33) × 10(5) M(−1), respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by (1)H-NMR, UV-visible spectroscopic titrations (including Job plots), electrospray ionization mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC), as well as theoretically by molecular dynamics (MD) computation. This study may provide important insights on the supramolecular formulation of H(2)-receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes. MDPI 2016-09-06 /pmc/articles/PMC6274153/ /pubmed/27608003 http://dx.doi.org/10.3390/molecules21091178 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yin, Hang
Wang, Runmiao
Wan, Jianbo
Zheng, Ying
Ouyang, Defang
Wang, Ruibing
Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title_full Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title_fullStr Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title_full_unstemmed Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title_short Molecular Encapsulation of Histamine H(2)-Receptor Antagonists by Cucurbit[7]Uril: An Experimental and Computational Study
title_sort molecular encapsulation of histamine h(2)-receptor antagonists by cucurbit[7]uril: an experimental and computational study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274153/
https://www.ncbi.nlm.nih.gov/pubmed/27608003
http://dx.doi.org/10.3390/molecules21091178
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