Complex of Rutin with β-Cyclodextrin as Potential Delivery System

Paczkowska, Magdalena; Mizera, Mikołaj; Piotrowska, H.; Szymanowska, Daria; Lewandowska, Kornelia; Gościańska, Joanna; Pietrzak, Robert; Bednarski, Waldemar; Majka, Z.; Cielecka‐Piontek, Judyta

doi:10.1371/journal.pone.0120858

Cited by 52 publications

(34 citation statements)

References 18 publications

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“…According to the XRPD pattern of the system, the peaks from the CA crystalline fraction completely disappeared, which can be attributed to the interaction between CA and HPβCD in the co-precipitation process, leading to the formation of an amorphous system. A decrease in the peak on the DSC thermogram of the CA-HPβCD system by~7 • C compared to those reported for CA and HPβCD was also observed for other systems prepared by the co-precipitation method [14]. It may be suggested that the preparation of the CA-HPβCD system using co-precipitation promotes dehydrogenation of cyclodextrin during the preparation of systems (changes at~90 • C).…”

Section: Discussionsupporting

confidence: 51%

“…The eligibility of certain kinds of cyclodextrin to achieve the desired stability of the system in solution is determined by the structure of CD and guest API [13]. The thermodynamic effect described by Gibbs free energy of complex formation, as well as by entailed stability constant Ks, can be estimated by structure-based modeling with in silico methods [11,12,[14][15][16][17][18]. Application of theoretical approaches, considering a vast number of testable cyclodextrin derivatives, is an essential tool for streamlining experimental investigation.…”

Section: Introductionmentioning

confidence: 99%

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Computer-Aided Design of Cefuroxime Axetil/Cyclodextrin System with Enhanced Solubility and Antimicrobial Activity

et al. 2019

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This study aimed to investigate changes in the solubility and antimicrobial efficacy of cefuroxime axetil (CA) when incorporated into cyclodextrin (CD). While choosing the CD, the validated in silico model was used. A theoretical model based on docking and molecular mechanics/generalized born surface area was validated using a curated dataset of API (active pharmaceutical ingredient)–CD stability constants. The library of commonly used cyclodextrins was virtually screened, indicating CA –hydroxypropyl-βCD (HPβCD) as the most thermodynamically favored system. Solid-state CA–HPβCD system was prepared and characterized by differential scanning calorimetry (DSC), Fourier-transform infrared (FT-IR), and X-ray diffraction (XRPD) methods. The dissolution profiles of the CA and its cyclodextrin system were evaluated. Microbiological activity of the CA–HPβCD inclusion system was studied based on changes in minimal inhibitory concentration (MIC) values and related to ones of the pure CA. The theoretical model was successfully validated, obtaining an average correlation with experimental data R = 0.7. The dissolution study showed significantly improved dissolution profiles of CA–HPβCD compared to CA. HPβCD increases the antimicrobial efficacy of CA up to 4-fold compared to pure CA.

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Section: Discussionsupporting

confidence: 51%

Section: Introductionmentioning

confidence: 99%

Computer-Aided Design of Cefuroxime Axetil/Cyclodextrin System with Enhanced Solubility and Antimicrobial Activity

et al. 2019

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“…Equally importantly, such a process is easily scalable. A similar phenomenon of spontaneous and permanent inclusion has been observed for other active pharmaceutical substances 32 , 33 . Spectroscopic (FT-IR, NMR) and thermal (DSC) methods were used to confirm the identity of the complexes.…”

Section: Discussionsupporting

confidence: 80%

Enhanced pharmacological efficacy of sumatriptan due to modification of its physicochemical properties by inclusion in selected cyclodextrins

Paczkowska

Mizera

Sałat

et al. 2018

Sci Rep

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The study focused on the pharmacological action of sumatriptan, in particular its antiallodynic and antihyperalgesic properties, as an effect of cyclodextrinic inclusion of sumatriptan, resulting in changes of its physicochemical qualities such as dissolution and permeability through artificial biological membranes, which had previously been examined in vitro in a gastro-intestinal model. The inclusion of sumatriptan into β-cyclodextrin and 2-hydroxylpropylo-β-cyclodextrin by kneading was confirmed with the use of spectral (fourier-transform infrared spectroscopy (FT-IR); solid state nuclear magnetic resonance spectroscopy with magic angle spinning condition, 1H and 13C MAS NMR) and thermal (differential scanning calorimetry (DSC)) methods. A precise indication of the domains of sumatriptan responsible for its interaction with cyclodextrin cavities was possible due to a theoretical approach to the analysis of experimental spectra. A high-performance liquid chromatography with a diode-array detector method (HPLC-DAD) was employed to determine changes in the concentration of sumatriptan during dissolution and permeability experiments. The inclusion of sumatriptan in complex with cyclodextrins was found to significantly modify its dissolution profiles by increasing the concentration of sumatriptan in complexed form in an acceptor solution compared to in its free form. Following complexation, sumatriptan manifested an enhanced ability to permeate through artificial biological membranes in a gastro-intestinal model for both cyclodextrins at all pH values. As a consequence of the greater permeability of sumatriptan and its increased dissolution from the complexes, an improved pharmacological response was observed when cyclodextrin complexes were applied.

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“…Due to its useful properties, the Dietary Supplement Label Database lists over 1100 currently marketed products that contain rutin [8]. However, both its low solubility in aqueous and non-toxic organic solvents, which imply scarce bioavailability, and poor thermal stability [9][10][11], restrict its application. Enzymatic polymerization of polyphenolic monomers has been shown to produce higher molecular weight polyphenols with improved solubility, thermostability, and superior antioxidant properties [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Laccase Activity as an Essential Factor in the Oligomerization of Rutin

et al. 2018

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The enzyme-mediated polymerization of bioactive phenolic compounds, such as the flavonoid rutin, has gained interest due to the enhanced physico-chemical and biological properties of the products, which increases their potential application as a nutraceutical. In this work, the influence of enzyme activity on rutin oligomerization was evaluated in reactions with low (1000 U/L) and high (10,000 U/L) initial laccase activities. For both reactions, high molecular weight oligomer fractions showed better properties compared to lower weight oligomers. Products of the reaction with low laccase activity exhibited thermal stability and antioxidant potential similar to control reaction, but led to higher inhibitory activity of xanthine oxidase and apparent aqueous solubility. Oligomers obtained in the reaction with high laccase activity showed better apparent aqueous solubility but decreased biological activities and stability. Their low antioxidant activity was correlated with a decreased phenolic content, which could be attributed to the formation of several bonds between rutin molecules.

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Complex of Rutin with β-Cyclodextrin as Potential Delivery System

Cited by 52 publications

References 18 publications

Computer-Aided Design of Cefuroxime Axetil/Cyclodextrin System with Enhanced Solubility and Antimicrobial Activity

Computer-Aided Design of Cefuroxime Axetil/Cyclodextrin System with Enhanced Solubility and Antimicrobial Activity

Enhanced pharmacological efficacy of sumatriptan due to modification of its physicochemical properties by inclusion in selected cyclodextrins

Laccase Activity as an Essential Factor in the Oligomerization of Rutin

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