Theoretical and Molecular Docking Study of Ketoconazole on Heptakis(2,3,6‐tri‐<i>O</i>‐methyl)‐β‐cyclodextrin as Chiral Selector

Arsad, Siti Rosilah; Maarof, Hasmerya; Ibrahim, Wan Aini Wan; Aboul‐Enein, Hassan Y.

doi:10.1002/chir.22554

Cited by 24 publications

(11 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Negative formation energy shows a thermodynamically favored complex; the most stable conformation is indicated by the higher formation energy [32,33].…”

Section: Molecular Modeling Studiesmentioning

confidence: 99%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

The aim of this study is to confirm the formation of inclusion complexes between bifonazole (BFZ) and different cyclodextrin (CD) derivatives. BFZ, an imidazole antifungal derivative, is a very hydrophobic compound, which is a major drawback in obtaining topical pharmaceutical formulations with optimal bioavailability. CDs may increase local drug delivery by enhancing the drug release and/or permeation. Several native and derivatized CD derivatives were tested in the experiments. The binary systems between BFZ and CDs were prepared in two molar ratios by physical mixing methods. The physicochemical properties of these complexes were studied by differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy methods. The results showed favorable molecular interaction between the components in solid state and in solution. 1 H NMR-CD titrations and molecular modeling study showed that the most stable complex was obtained when using γ-CD. The Job's method and 2D NMR spectroscopy support the 2 : 1 stoichiometry of the BFZ : γ-CD complex.Keywords: bifonazole; cyclodextrins; differential scanning calorimetry; Fourier transform infrared spectroscopy; H NMR-CD titrations КАРАКТЕРИЗАЦИЈА НА ИНКЛУЗИОНИ КОМПЛЕКСИ МЕЃУ БИФОНАЗОЛ И РАЗЛИЧНИ ЦИКЛОДЕКСТРИНИ ВО ЦВРСТА СОСТОЈБА И ВО РАСТВОРЦелта на ова истражување е да се потврди образувањето на инклузиони комплекси меѓу бифоназол (BFZ) и различни циклодекстрински (CD) деривати. BFZ, кој претставува имидазолски фунгициден дериват, е силно хидрофобно соединение, што претставува голем недостаток при добивање топични фармацевтски препарати со оптимална биорасположливост. CD може да ја зголеми локалната испорака на лекот со подобрување на ослободувањето и/или пропустливоста на лекот. Експериментално беа тестирани неколку нативни и дериватизирани CD. Бинарните системи меѓу BFZ и CD беа подготвени во два моларни односа со методи на физичко мешање. Физичкохемиските својства на овие комплекси беа испитувани со диференцијална скенирачка калориметрија (DSC), Фуриеова трансформна инфрацрвена (FTIR) спектроскопија и со нуклеарно-магнетни резонантни спектроскопски методи. Резултатите покажуваат позитивна молекулска интеракција меѓу компонентите во цврста фаза и во раствор. Титрациите на 1 H NMR-CD и испитувањето со молекулско моделирање покажуваат дека најстабилен комплекс се добива со

show abstract

“…Negative formation energy shows a thermodynamically favored complex; the most stable conformation is indicated by the higher formation energy [32,33].…”

Section: Molecular Modeling Studiesmentioning

confidence: 99%

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Kelemen

Csillag

Hancu

et al. 2017

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…Another question concerns the choice to have built TM-β-CD starting from the coordinates of β-CD crystal structure, while several TM-β-CD crystal structures are available in the Cambridge Crystallographic Data Center [114,115,183]. Otherwise, later Ibrahim and co-authors modeled TM-β-CD starting from the crystal structure of the CD as released from the CCDC (entry XAQ JII) [183,184]. The authors performed a molecular docking study using MM calculations and semiempirical PM3 calculations to explore at microscopic level the enantiodiscrimination of TM-β-CD toward ketoconazole.…”

Section: Methylated β-Cyclodextrinsmentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

View full text Add to dashboard Cite

CDs are cyclic oligosaccharides consisting of α‐d‐glucopyranosyl units linked through 1,4‐linkages, which are obtained from enzymatic degradation of starch. The coexistence of hydrophilic and hydrophobic regions in the same structure makes these macrocycles extremely versatile as complexing host with application in food, cosmetics, environmental, agriculture, textile, pharmaceutical, and chemical industries. Due to their inherent chirality, CDs have been also successfully used as chiral selectors in enantioseparation science, in particular, for CE enantioseparations. In the last decades, multidisciplinary approaches based on CE, NMR spectroscopy, X‐ray crystallography, microcalorimetry, and molecular modeling have shed light on some aspects of recognition mechanisms underlying enantiodiscrimination. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a useful tool to model at molecular level the dynamics of diastereomeric associate formation to sample low‐energy conformations, the binding energies between the enantiomer and the CD, and to profile noncovalent interactions contributing to the stability of CD/enantiomer association. On this basis, the aim of this review is to provide the reader with a critical overview on the applications of CDs in CE. In particular, the contemporary theory of the electrophoretic technique and the main structural features of CDs are described, with a specific focus on techniques, methods, and approaches to model CE enantioseparations promoted by native and substituted CDs. A systematic compilation of all published literature has not been attempted.

show abstract

“…Studies related to chiral recognition mechanisms of this type of CSPs using diverse methodologies, such as nuclear magnetic resonance, docking, or molecular modeling, were also addressed to understand the molecular interactions as well as the effect of some chromatographic conditions, such as pH, temperature, or organic modifier, in the enantioseparation [146,147].…”

Section: Chiral Stationary Phases: Recent Developmentsmentioning

confidence: 99%

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

et al. 2019

View full text Add to dashboard Cite

The planning and development of new chiral stationary phases (CSPs) for liquid chromatography (LC) are considered as continuous and evolutionary issues since the introduction of the first CSP in 1938. The main objectives of the development strategies were to attempt the improvement of the chromatographic enantioresolution performance of the CSPs as well as enlarge their versatility and range of applications. Additionally, the transition to ultra-high-performance LC were underscored. The most recent strategies have comprised the introduction of new chiral selectors, the use of new materials as chromatographic supports or the reduction of its particle size, and the application of different synthetic approaches for preparation of CSPs. This review gathered the most recent developments associated to the different types of CSPs providing an overview of the relevant advances that are arising on LC.

show abstract

Theoretical and Molecular Docking Study of Ketoconazole on Heptakis(2,3,6‐tri‐O‐methyl)‐β‐cyclodextrin as Chiral Selector

Cited by 24 publications

References 25 publications

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Characterisation of Inclusion Complexes Between Bifonazole and Different Cyclodextrins in Solid and Solution State

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

Contact Info

Product

Resources

About