Betulin/2-hydroxypropyl-β-cyclodextrin inclusion complex: Physicochemical characterization and hepatoprotective activity

Buko, Vyacheslav; Заводник, И. Б.; Pałecz, Bartłomiej; Stępniak, Artur; Kirko, Siarhei; Shlyahtun, A. G.; Misiuk, Wieslawa; Belonovskaya, Elena; Lukivskaya, O.; Naruta, Elena; Kuzmitskaya, Irina; Ilyich, T. V.; Erdenebayar, Bayarmaa; Rakhmadieva, S. B.

doi:10.1016/j.molliq.2020.113118

Cited by 18 publications

(9 citation statements)

References 21 publications

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“…HP-β-CD/betulin complex was studied by calorimetry (DSC and ITC), IR spectroscopy and phase solubility. The hepatoprotective and anti-inflammatory activities have been also checked [30]. The complex formation, in line with many other HP-β-CD/guest systems, is both enthalpically and entropically favoured and the binding constant is 1330 M −1 .…”

Section: Hp-β-cd Interaction With Nutraceuticals/natural Productsmentioning

confidence: 86%

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

D’Aria

Pagano

Giancola

2021

J Therm Anal Calorim

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For many years, cyclodextrins (CDs) have been the object of attention for their capability of improving the stability, solubility and bioavailability of numerous molecules of interest, including drugs and nutraceuticals. They have low toxicity and for this reason have been employed for different routes of administration, including oral, ocular, nasal and parenteral. Among them, the hydroxypropyl-β-cyclodextrin (HP-β-CD) is the least toxic. Several physicochemical methodologies have been employed for studying cyclodextrin/guest interaction, but isothermal titration calorimetry (ITC) is the only one capable of simultaneously providing the binding constant, ΔH°, ΔS°, ΔG° and the binding stoichiometry. Here, we present the state of the art of ITC studies applied to HP-β-CD/guest complexes, discussing selected publications of the last five years, highlighting the thermodynamic factors that are decisive for optimal encapsulation.

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Section: Hp-β-cd Interaction With Nutraceuticals/natural Productsmentioning

confidence: 86%

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

D’Aria

Pagano

Giancola

2021

J Therm Anal Calorim

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“…This gives CDs the unique ability to trap hydrophobic molecules. 16 Therefore, the solubility in water and chemical stability of naturally occurring active ingredients are always improved by CDs, for example, d -limonene and d -limonene, 17 liquiritin, 18 betulin, 19 ursolic acid, 15 etc. β-cyclodextrin (β-CD) is one of the most widely used CDs due to the fact that its cavity size is most suitable for inclusion of 200–800 g moL −1 of natural active substance, 20 and there is no accumulation effect and non-toxicity.…”

Section: Introductionmentioning

confidence: 99%

Preparation of phillyrin/cyclodextrin inclusion complexes and study of their physical properties, solubility enhancement, molecular docking and antioxidant activity

Qin,

Zhao,

et al. 2023

New J. Chem.

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“…Betulin is widely distributed in nature, its content in birch bark, which is a waste of wood and activated charcoal production, reaches 30% [1]. It has been shown that betulin and its derivatives are characterized by anticancer, antiviral, anti‐inflammatory, hepatoprotective, antimicrobial, and others effects [2, 3]. Most of these compounds are practically insoluble in water, which limits their bioavailability.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the effect of background electrolyte composition and independence of parameters in determining binding constants of betulin derivatives to β‐ and dimethyl‐β‐cyclodextrins by affinity capillary electrophoresis

Sursyakova

Levdansky

Rubaylo

2022

J of Separation Science

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The values of the apparent binding constants for β-cyclodextrin complexes of betulin derivatives determined by mobility shift affinity capillary electrophoresis were found to be independent of the composition of the two background electrolytes used (tetraborate buffer, pH 9.18, and phosphate buffer, pH 8.00, both of them with 20 mM ionic strength). It has been found that if there is not a constant plateau on the binding curve then four independent parameters can be determined: binding constants (also referred to as stability, association, or formation constants) and ionic mobilities of 1:1 and 1:2 complexes. However, at least 10-12 data points in the binding curve should be used to reliably estimate the parameters. For the first time, the apparent binding constants for complexes of ester betulin derivatives with dimethyl-β-cyclodextrin have been determined by mobility shift affinity capillary electrophoresis. The logarithms of the constants for 1:1 and 1:2 complexes at 25 • C for betulin 3,28-diphthalate with a 95% confidence interval are 4. 98 (4.95-5.01) and 7.52 (7.26-7.68); for betulin 3,28-disulfate, the values are 4.97 (4.89-5.03) and 8.24 (6.82-8.52). It has been found that betulin 3,28-disuccinate forms only a 1:1 complex and the binding constant logarithm is 5.25 ± 0.02.

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Betulin/2-hydroxypropyl-β-cyclodextrin inclusion complex: Physicochemical characterization and hepatoprotective activity

Cited by 18 publications

References 21 publications

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

Preparation of phillyrin/cyclodextrin inclusion complexes and study of their physical properties, solubility enhancement, molecular docking and antioxidant activity

Evaluation of the effect of background electrolyte composition and independence of parameters in determining binding constants of betulin derivatives to β‐ and dimethyl‐β‐cyclodextrins by affinity capillary electrophoresis

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