Chiral recognition of Propranolol enantiomers by β-Cyclodextrin: Quantum chemical calculation and molecular dynamics simulation studies

Ghatee, Mohammad Hadi; Sedghamiz, Tahereh

doi:10.1016/j.chemphys.2014.10.008

Cited by 18 publications

(7 citation statements)

References 31 publications

(37 reference statements)

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“…Other references suggest that the complementarity of the cavity size is also an important factor for the complexation. Mechanism studies for CD complexes in the gas phase have been performed using a combination of the mass spectrometric methods, namely, gas chromatography–mass spectrometry (GC–MS), ion mobility mass spectrometry (IMS–MS), infrared multiphoton dissociation (IRMPD) spectroscopy, and theoretical calculations involving various combinations of molecular dynamics (MD), semi-empirical, and density functional theory (DFT) methods [ 2 , 26 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 ]. Recently, structural analysis was conducted using action–FRET (Fluorescence Resonance Energy Transfer), a gas phase version of FRET in which chromophore-tagged β-cyclodextrin and amyloid-β fragment peptides were utilized [ 61 ].…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations.

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Section: Introductionmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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“…There are many researchers using Arguslab program package to perform molecular docking simulation of inclusion complex between cyclodextrin and guest molecule [46][47][48][49][50][51][52][53]. In this molecular docking simulation, the guest molecule of enantiomer of carboxylic acid derivatives was treated as ligand and host molecule of DIMEB and TRIMEB was treated as binding site.…”

Section: Methodsmentioning

confidence: 99%

“…Molecular docking is one of methods using molecular mechanics principles. Some researchers have successfully modeled enantioseparation of guest molecule with host molecule, β-cyclodextrin derivatives, using molecular docking [31, [46][47][48][49][50][51][52][53].…”

mentioning

confidence: 99%

A Molecular docking study to predict enantioseparation of some chiral carboxylic acid derivatives by methyl-β-cyclodextrin

Nurhidayah

Ivansyah

Martoprawiro

et al. 2018

J. Phys.: Conf. Ser.

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Abstract. A molecular docking study, using molecular mechanics calculations with Arguslab, was used to help predict the enantioseparation of some guest molecules of chiral carboxylic acid derivatives by heptakis-2,6-di-O-methyl-β-cyclodextrin (DIMEB) and heptakis-2,3,6-tri-O-methyl-β-cyclodextrin (TRIMEB) as host molecules. The small differences in the binding free energy values (∆∆G) obtained from Arguslab did not indicate any significant enantioseparation. From the molecular docking simulation results, it is predicted that in the case of DIMEB as host molecule, R-enantiomer of Etodolac, Fenoprofen, Indoprofen, Ketorolac, and Naproxen will be eluted first than S-enantiomer; However, S-enantiomer of Carprofen, Flurbiprofen, Ketoprofen, Pirprofen, Proglumide, Sulindac, Surprofen, and Zaltoprofen will be eluted first than R-enantiomer by DIMEB as host molecule. When TRIMEB is used as a host molecule, R-enantiomer of Carprofen, Flurbiprofen, Indoprofen, Ketoprofen, Naproxen, Pirprofen, and Surprofen will be eluted first than S-enantiomer; However, S-enantiomer of Etodolac, Fenoprofen, Ketorolac, Proglumide, Sulindac and Zaltoprofen will be eluted first than R-enantiomer by TRIMEB as host molecule.

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“…Cyclodextrins (CDs) are prepared via enzymatic modification of starch to be composed of six, seven, or eight glucopyranoside units (α, β, and γ CD, respectively) chemically bonded together via an α-(1–4) ether linkages. , The arrangement of the glucopyranose moieties results in preparation of a cyclic oligosaccharide with a lipophilic central cavity. This characteristic structure promotes them to form a stable inclusion complex with a wide variety of guesting hydrophobic moieties . Therefore, PDs nucleated form CDs could be ascribed as excellent candidates for the preparation of selective and sensitive nano-objects for different targets since it could be concurrently exhibited with the molecular recognition properties of CDs and the optical activities of QDs .…”

Section: Introductionmentioning

confidence: 99%

Multifunctional Lipophobic Polymer Dots from Cyclodextrin: Antimicrobial/Anticancer Laborers and Silver Ions Chemo-Sensor

et al. 2023

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β-Cyclodextrin (CD) is currently exploited for the implantation of lipophobic polymer dots (PDs) for antimicrobial and anticancer laborers. Moreover, the PDs were investigated to act as a chemo-sensor for metal detection. The data revealed that under basic conditions, photoluminescent PDs (5.1 nm) were successively clustered with a controllable size at 190 °C, whereas under acidic conditions, smaller-sized non-photoluminescent carbon nanoparticles (2.9 nm) were obtained. The fluorescence intensity of synthesized PDs under basic conditions was affected by pH, and such an intensity was significantly higher compared to that prepared under acidic conditions. The PDs were exploited as florescent detectors in estimation of Ag + ions in aquatic streams. Treatment of Ag + ion colloids with PDs resulted in fluorescence quenching attributing to the production of AgNPs that approved by spectral studies. The cell viability percent was estimated for Escherichia coli, Staphylococcus aureus, and Candida albicans after incubation with PDs implanted under basic conditions for 24 h. The cell mortality percent was estimated for breast cancer (MCF-7) after incubation with different concentrations of PDs that were implanted under acidic versus basic conditions to show that treatment of the tested cells with 1000 μg/mL PDs prepared under basic (IC50 232.5 μg/ mL) and acidic (IC 50 88.6 μg/mL) conditions resulted in cell mortality percentages of 70 and 90%, respectively.

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Chiral recognition of Propranolol enantiomers by β-Cyclodextrin: Quantum chemical calculation and molecular dynamics simulation studies

Cited by 18 publications

References 31 publications

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

A Molecular docking study to predict enantioseparation of some chiral carboxylic acid derivatives by methyl-β-cyclodextrin

Multifunctional Lipophobic Polymer Dots from Cyclodextrin: Antimicrobial/Anticancer Laborers and Silver Ions Chemo-Sensor

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