Molecular encapsulation of histamine H2-Receptor antagonists by cucurbit[7]Uril: An experimental and computational study

Hang Yin; Runmiao Wang; Jianbo Wan; Ying Zheng; Defang Ouyang; Ruibing Wang

doi:10.3390/molecules21091178

Molecular encapsulation of histamine H₂-Receptor antagonists by cucurbit[7]Uril: An experimental and computational study

Hang Yin, Runmiao Wang, Jianbo Wan, Ying Zheng, Defang Ouyang, Ruibing Wang

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

6 Citations (Scopus)

Abstract

The histamine H₂ -receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 10³ M^-1 , 1.30 (±0.27) × 10⁴ M^-1 and 1.0⁵ (±0.33) × 105 M-1 , respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by ¹H-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 H₂ -receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes.

Original language	English
Article number	1178
Journal	Molecules
Volume	21
Issue number	9
DOIs	https://doi.org/10.3390/molecules21091178
Publication status	Published - Sept 2016
Externally published	Yes

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title = "Molecular encapsulation of histamine H2-Receptor antagonists by cucurbit[7]Uril: An experimental and computational study",

abstract = "The histamine H2 -receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 103 M-1 , 1.30 (±0.27) × 104 M-1 and 1.05 (±0.33) × 105 M-1 , respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by 1H-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 H2 -receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes.",

keywords = "Complexation, Cucurbit[7]uril, H -receptor antagonists, Host-guest interaction, Molecular modelling",

author = "Hang Yin and Runmiao Wang and Jianbo Wan and Ying Zheng and Defang Ouyang and Ruibing Wang",

note = "Publisher Copyright: {\textcopyright} 2016 by the authors; licensee MDPI, Basel, Switzerland.",

year = "2016",

month = sep,

doi = "10.3390/molecules21091178",

language = "English",

volume = "21",

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T1 - Molecular encapsulation of histamine H2-Receptor antagonists by cucurbit[7]Uril

T2 - An experimental and computational study

AU - Yin, Hang

AU - Wang, Runmiao

AU - Wan, Jianbo

AU - Zheng, Ying

AU - Ouyang, Defang

AU - Wang, Ruibing

PY - 2016/9

Y1 - 2016/9

N2 - The histamine H2 -receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 103 M-1 , 1.30 (±0.27) × 104 M-1 and 1.05 (±0.33) × 105 M-1 , respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by 1H-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 H2 -receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes.

AB - The histamine H2 -receptor antagonists cimetidine, famotidine and nizatidine are individually encapsulated by macrocyclic cucurbit[7]uril (CB[7]), with binding affinities of 6.57 (±0.19) × 103 M-1 , 1.30 (±0.27) × 104 M-1 and 1.05 (±0.33) × 105 M-1 , respectively. These 1:1 host-guest inclusion complexes have been experimentally examined by 1H-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 H2 -receptor antagonist drugs for potentially enhanced stability and controlled release based on different binding strengths of these host-guest complexes.

KW - Complexation

KW - Cucurbit[7]uril

KW - H -receptor antagonists

KW - Host-guest interaction

KW - Molecular modelling

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DO - 10.3390/molecules21091178

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C2 - 27608003

AN - SCOPUS:84987911935

SN - 1420-3049

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JO - Molecules

JF - Molecules

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M1 - 1178

ER -

Molecular encapsulation of histamine H₂-Receptor antagonists by cucurbit[7]Uril: An experimental and computational study

Abstract

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