Analysis of computational models of β-cyclodextrin complexes: structural studies of morniflumate hydrochloride and β-cyclodextrin complex in aqueous solution by quantitative ROESY analysis

Ali, Sk Ajim; Shamim, Shazia

doi:10.1007/s10847-015-0534-7

Cited by 10 publications

(4 citation statements)

References 24 publications

(23 reference statements)

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“…To unambiguously confirm the encapsulation, ROESY is the preferred NMR tool. ROESY studies have been extensively used to get information on inclusion complexes with βCD through analysis of intermolecular peaks between cavity protons and a part of the guest involved in complexation. ,,− ,, Figure shows representative ROESY spectra obtained for the sample ChU/βCD/H 2 O/AN and ChU/βCD/H 2 O/Tol. The host–guest interactions are displayed as intermolecular correlation peaks between aromatic protons of AN and Tol and protons H 3′ and H 5′ of βCD.…”

Section: Resultsmentioning

confidence: 99%

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Pietro

Dugoni

Ferro

et al. 2019

ACS Sustainable Chem. Eng.

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Efficient renewable and non-toxic absorbents can now be designed to eliminate air pollutants such as volatile organic compounds (VOCs) from confined atmospheres. New hybrid materials result from the combination of Deep Eutectic Systems (DES) with well-known VOCs capture agents like β-cyclodextrin (βCD). Yet, a question arises: does βCD retain its encapsulation ability in DES? Multiple NMR techniques are used here to demonstrate the formation of inclusion complexes of βCD with two VOCs, aniline and toluene, in the pure DES reline and in reline/water mixtures. Complexation-induced chemical shift changes and intermolecular hostguest NOEs in the rotating frame give evidence of a genuine encapsulation in the βCD cavity, and complementary information on the dynamics of the VOC is gathered via relaxation and diffusion experiments. This work shows how different NMR techniques can contribute to the design of task-specific sustainable materials for absorption/extraction processes.

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Section: Resultsmentioning

confidence: 99%

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Pietro

Dugoni

Ferro

et al. 2019

ACS Sustainable Chem. Eng.

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“…Also, the intermolecular proton distances obtained from quantum chemical calculations are shown in Table . A major point to be noted here is that in the case of supramolecular complexes, the internuclear distance between the host and guest is measured mostly by employing NOE-based experiments, viz., ROESY , for intermediate-sized molecules. In the present study, we have demonstrated that by selecting a pair of nuclei, one hailing from the host molecule and one from the guest molecule, and measuring the bi-selective relaxation rates, one can evaluate the internuclear distance using prior knowledge of the molecular rotational correlation time of the encapsulated species.…”

Section: Resultsmentioning

confidence: 99%

Analysis of Molecular Interaction of Drugs within β-Cyclodextrin Cavity by Solution-State NMR Relaxation

et al. 2017

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The prime focus of the present study is to employ NMR relaxation measurement to address the intermolecular interactions, as well as motional dynamics, of drugs, viz., paracetamol and aspirin, encapsulated within the β-cyclodextrin (β-CD) cavity. In this report, we have attempted to demonstrate the applicability of nonselective (R), selective (R), and bi-selective (R) spin-lattice relaxation rates to infer dynamical parameters, for example, the molecular rotational correlation times (τ) and cross-relaxation rates (σ) of the encapsulated drugs. Molecular rotational correlation times of the free drugs were calculated using the selective relaxation rate in the fast molecular motion time regime (ωτ ≪ 1 and R/R ≈ 1.500), whereas that of the 1:1 complexed drugs were found from the ratio of R/R in the intermediate motion time regime (ωτ ∼ 1 and R/R ≈ 1.054), and these values were compared with each other to confirm the formation of inclusion complexes. Furthermore, the cross-relaxation rates were used to evaluate the intermolecular proton distances. Also, density functional theory calculations were performed to determine the minimum energy geometry of the inclusion complexes and the results compared with those from experiments. The report, thus, presents the possibility of utilizing NMR relaxation data, a more cost-effective experiment, to calculate internuclear distances in the case of drug-supramolecule complexes that are generally obtained by extremely time consuming two-dimensional nuclear Overhauser enhancement-based methods. A plausible mode of insertion of the drug molecules into the β-CD cavity has also been described based on experimental NMR relaxation data analysis.

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“…The chemical formulas for quercetin (QUR) (PubChem ID: 5280343), linalool (LIN) (PubChem ID: 6549), and the standard drug diazepam (DZP) (PubChem ID: 3016) ( Figure 1 ) were taken from the PubChem chemical database in the ‘sdf’ file format. The Allinger’s force field (MM2) method was used for energy minimization of the ligands by Chem3D Pro21.0 software [ 108 ].…”

Section: Methodsmentioning

confidence: 99%

Quercetin Antagonizes the Sedative Effects of Linalool, Possibly through the GABAergic Interaction Pathway

Bappi,

Prottay,

Kamli

et al. 2023

Molecules

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Sedatives promote calmness or sleepiness during surgery or severely stressful events. In addition, depression is a mental health issue that negatively affects emotional well-being. A group of drugs called anti-depressants is used to treat major depressive illnesses. The aim of the present work was to evaluate the effects of quercetin (QUR) and linalool (LIN) on thiopental sodium (TS)-induced sleeping mice and to investigate the combined effects of these compounds using a conventional co-treatment strategy and in silico studies. For this, the TS-induced sleeping mice were monitored to compare the occurrence, latency, and duration of the sleep-in response to QUR (10, 25, 50 mg/kg), LIN (10, 25, 50 mg/kg), and diazepam (DZP, 3 mg/kg, i.p.). Moreover, an in silico investigation was undertaken to assess this study’s putative modulatory sedation mechanism. For this, we observed the ability of test and standard medications to interact with various gamma-aminobutyric acid A receptor (GABAA) subunits. Results revealed that QUR and LIN cause dose-dependent antidepressant-like and sedative-like effects in animals, respectively. In addition, QUR-50 mg/kg and LIN-50 mg/kg and/or DZP-3 mg/kg combined were associated with an increased latency period and reduced sleeping times in animals. Results of the in silico studies demonstrated that QUR has better binding interaction with GABAA α3, β1, and γ2 subunits when compared with DZP, whereas LIN showed moderate affinity with the GABAA receptor. Taken together, the sleep duration of LIN and DZP is opposed by QUR in TS-induced sleeping mice, suggesting that QUR may be responsible for providing sedation-antagonizing effects through the GABAergic interaction pathway.

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Analysis of computational models of β-cyclodextrin complexes: structural studies of morniflumate hydrochloride and β-cyclodextrin complex in aqueous solution by quantitative ROESY analysis

Cited by 10 publications

References 24 publications

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems?

Analysis of Molecular Interaction of Drugs within β-Cyclodextrin Cavity by Solution-State NMR Relaxation

Quercetin Antagonizes the Sedative Effects of Linalool, Possibly through the GABAergic Interaction Pathway

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