Study of Flavonoid/Hydroxypropyl-β-Cyclodextrin Inclusion Complexes by UV-Vis, FT-IR, DSC, and X-Ray Diffraction Analysis

Kim, Ji-Sang

doi:10.3746/pnf.2020.25.4.449

Cited by 37 publications

(25 citation statements)

References 26 publications

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“…Figure 8A shows that HP-β-CD has no absorption peak within the recorded spectrum as it does not have any double bond (π-electrons) to absorb UV energy, as previously reported [49]. As depicted in Figure 8A, the UV-Vis absorption spectra of free and complexed PTN have two characteristic absorption peaks at λmax = 290 nm and 434 nm, respectively, similar to those reported before [17].…”

Section: Uv/vis Absorption Spectroscopysupporting

confidence: 81%

Parietin Cyclodextrin-Inclusion Complex as an Effective Formulation for Bacterial Photoinactivation

et al. 2022

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Multidrug resistance in pathogenic bacteria has become a significant public health concern. As an alternative therapeutic option, antimicrobial photodynamic therapy (aPDT) can successfully eradicate antibiotic-resistant bacteria with a lower probability of developing resistance or systemic toxicity commonly associated with the standard antibiotic treatment. Parietin (PTN), also termed physcion, a natural anthraquinone, is a promising photosensitizer somewhat underrepresented in aPDT because of its poor water solubility and potential to aggregate in the biological environment. This study investigated whether the complexation of PTN with (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) could increase its solubility, enhance its photophysical properties, and improve its phototoxicity against bacteria. At first, the solubilization behavior and complexation constant of the PTN/HP-β-CD inclusion complexes were evaluated by the phase solubility method. Then, the formation and physicochemical properties of PTN/HP-β-CD complexes were analyzed and confirmed in various ways. At the same time, the photodynamic activity was assessed by the uric acid method. The blue light-mediated photodegradation of PTN in its free and complexed forms were compared. Complexation of PTN increased the aqueous solubility 28-fold and the photostability compared to free PTN. PTN/HP-β-CD complexes reduce the bacterial viability of Staphylococcus saprophyticus and Escherichia coli by > 4.8 log and > 1.0 log after irradiation, respectively. Overall, the low solubility, aggregation potential, and photoinstability of PTN were overcome by its complexation in HP-β-CD, potentially opening up new opportunities for treating infections caused by multidrug-resistant bacteria.

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Section: Uv/vis Absorption Spectroscopysupporting

confidence: 81%

Parietin Cyclodextrin-Inclusion Complex as an Effective Formulation for Bacterial Photoinactivation

et al. 2022

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“…Ji-Sang Kim [ 37 ] indicated that the fundamental changes that appear in the FT-IR spectra of inclusion complexes of flavonoid with HP-β-CD are reflected mainly in the C=O stretching spectral region. These observations indicate the presence of a similar complexing mechanism for the guest molecule (flavonoid) in the host cavity (cyclodextrin molecule), which is reflected in our results.…”

Section: Resultsmentioning

confidence: 99%

“…The melting endotherm disappeared in scans of 1:1 and 1:2 flavonoid–cyclodextrin binary formulations, which indicated loss of crystallinity Hed and Het, as well as formation intermolecular interactions between the system’s two components. According to the literature [ 37 , 44 , 45 ], when the guest molecule is embedded in the cyclodextrin cavity to form an amorphous inclusion complex, its melting point is either shifted to a different temperature or disappears. Therefore, the obtained results supplement FT-IR analysis.…”

Section: Resultsmentioning

confidence: 99%

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Wdowiak

Rosiak

Tykarska

et al. 2022

IJMS

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This study aimed at obtaining hesperidin (Hed) and hesperetin (Het) systems with HP-β-CD by means of the solvent evaporation method. The produced systems were identified using infrared spectroscopy (FT-IR), X-ray powder diffraction (XRPD), and differential scanning calorimetry (DSC). Moreover, in silico docking and molecular dynamics studies were performed to assess the most preferable site of interactions between tested compounds and HP-β-CD. The changes of physicochemical properties (solubility, dissolution rate, and permeability) were determined chromatographically. The impact of modification on biological activity was tested in an antioxidant study as well as with regards to inhibition of enzymes important in pathogenesis of neurodegenerative diseases. The results indicated improvement in solubility over 1000 and 2000 times for Hed and Het, respectively. Permeability studies revealed that Hed has difficulties in crossing biological membranes, in contrast with Het, which can be considered to be well absorbed. The improved physicochemical properties influenced the biological activity in a positive manner by the increase in inhibitory activity on the DPPH radical and cholinoesterases. To conclude the use of HP-β-CD as a carrier in the formation of an amorphous inclusion complex seems to be a promising approach to improve the biological activity and bioavailability of Hed and Het.

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“…The DSC curves of the physical mixture and inclusion complexes obtained using the kneading and coprecipitation methods showed the presence of the melting peak of AML with lower intensities and shifted at lower temperatures. In the case of the lyophilization method, the melting peak of ALM disappeared, providing evidence of the complexation of the drug into the HP-β-CD cavity [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

Design and Evaluation of Orally Dispersible Tablets Containing Amlodipine Inclusion Complexes in Hydroxypropyl-β-cyclodextrin and Methyl-β-cyclodextrin

et al. 2022

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The development of new orally dispersible tablets containing amlodipine (AML) inclusion complexes in hydroxypropyl-β-cyclodextrin (HP-β-CD) and in methyl-β-cyclodextrin (Me-β-CD) was studied. The methods of obtaining amlodipine and the physical and chemical properties of the inclusion complexes using the two cyclodextrins was investigated separately. Solid inclusion complexes were obtained by three methods: kneading, coprecipitation, and lyophilization, at a molar ratio of 1:1. For comparison, a physical mixture in the same molar ratio was prepared. The aim of the complexation process was to improve the drug solubility. As the lyophilization method leads to a complete inclusion of the drug in the guest molecule cavity, for both used cyclodextrins, these types of compounds were selected as active ingredients for the design of orally dispersible tablets. Subsequently, the formulation of the orodispersible tablets containing AML-HP-β-CD and AML-Me-β-CD inclusion complexes and quality parameters of the final formulation were evaluated. The results prove that F1 and F4 formulations, based on silicified microcrystalline cellulose, which contains insignificant proportions of very small or very large particles, had the lowest moisture degree (3.52% for F1 and 4.03% for F4). All of these demonstrate their porous structure, which led to good flowability and compressibility performances. F1 and F4 formulations were found to be better to manufacture orally dispersible tablets.

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Study of Flavonoid/Hydroxypropyl-β-Cyclodextrin Inclusion Complexes by UV-Vis, FT-IR, DSC, and X-Ray Diffraction Analysis

Cited by 37 publications

References 26 publications

Parietin Cyclodextrin-Inclusion Complex as an Effective Formulation for Bacterial Photoinactivation

Parietin Cyclodextrin-Inclusion Complex as an Effective Formulation for Bacterial Photoinactivation

Amorphous Inclusion Complexes: Molecular Interactions of Hesperidin and Hesperetin with HP-Β-CD and Their Biological Effects

Design and Evaluation of Orally Dispersible Tablets Containing Amlodipine Inclusion Complexes in Hydroxypropyl-β-cyclodextrin and Methyl-β-cyclodextrin

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