Enhancement of aqueous solubility of tricyclic acyclovir derivatives by their complexation with hydroxypropyl-β-cyclodextrin

Zielenkiewicz, W.; Koźbiał, Małgorzata; Golankiewicz, Bożenna; Poznański, Jarosław

doi:10.1007/s10973-010-0847-0

Cited by 19 publications

(5 citation statements)

References 19 publications

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“…Further, variation in the shape of H10 signal was also observed, which confirm the involvement of H10 in complex formation. These observations were in agreement with the earlier reports in the literature (Rossel et al, 2000;Ś wierzewski et al, 2002;Zielenkiewicz et al, 2010).…”

Section: Resultssupporting

confidence: 94%

“…Thus, disappearance of thermal features of drug ascertained the formation of true complex of drug-HP-b-cyclodextrin, wherein the drug molecules penetrated into the cyclodextrin cavity by replacing the water molecules. The possible mechanism of the complex formation between acyclovir and HP-b-cyclodextrin was reported in the literature (Świerzewski et al, 2002;Zielenkiewicz et al, 2010;Koźbiał & Gierycz, 2013). The authors suggest that the complexation of acyclovir by HP-b-cyclodextrin is likely due to the interaction/association between the hydroxyl ethoxy methyl group of acyclovir with the hydrophobic cavity of cyclodextrin.…”

Section: Resultsmentioning

confidence: 91%

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Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin

et al. 2013

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The therapeutic potential of acyclovir is limited by the low oral bioavailability owing to its limited aqueous solubility and low permeability. The present study was a systematic investigation on the development and evaluation of inclusion complex using hydroxypropyl-β-cyclodextrin for the enhancement of oral bioavailability of acyclovir. The inclusion complex of acyclovir was prepared by kneading method using drug: hydroxypropyl-β-cyclodextrin (1:1 mole). The prepared inclusion complex was characterized by Fourier transform infrared spectroscopy, differential scanning calorimetry, NMR spectroscopy and evaluated in vitro by dissolution studies. In vivo bioavailability of acyclovir was compared for inclusion complex and physical mixture in rat model. Phase solubility studies indicate the formation of acyclovir-hydroxypropyl-β-cyclodextrin complex with higher stability constant and linear enhancement in drug solubility with increase in hydroxypropyl-β-cyclodextrin concentration. Characterization of the prepared formulation confirms the formation of acyclovir-hydroxypropyl-β-cyclodextrin inclusion complex. Dissolution profile of inclusion complex demonstrated rapid and complete release of acyclovir in 30 min with greater dissolution efficiency (90.05 ± 2.94%). In vivo pharmacokinetic data signify increased rate and extent of acyclovir absorption (relative bioavailability ∼160%; p < 0.0001) from inclusion complex, compared to physical mixture. Given the promising results in the in vivo studies, it can be concluded that the inclusion complex of acyclovir could be an effective and promising approach for successful oral therapy of acyclovir in the treatment of herpes viruses.

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Section: Resultssupporting

confidence: 94%

Section: Resultsmentioning

confidence: 91%

Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin

et al. 2013

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“…Use of cyclodextrins, which can include aromatic groups into their cavity, may enhance the aqueous solubility of such compounds. For this purpose we used several cyclodextrins and hydroxypropyl-β-cyclodextrin was chosen as being more efficient for complexating the tricyclic acyclovir derivatives [20]. The investigations were performed, for chosen compounds, in various cyclodextrin HP-β-CD, buffered solutions (pH = 5.5 and 7.0) at 25 and 37 °C.…”

Section: Resultsmentioning

confidence: 99%

“…Our study on complexation of chosen tricyclic acyclovir derivatives in aqueous buffered solutions indicates significant enhancement of solubility of the studied compounds, especially these possessing aromatic substituents [20]. The increase of solubility is mainly caused by inclusion of hydrophobic groups inside the cyclodextrin cavity.…”

Section: Introductionmentioning

confidence: 99%

Comparison of Aqueous and 1-Octanol Solubility as well as Liquid–Liquid Distribution of Acyclovir Derivatives and Their Complexes with Hydroxypropyl-β-Cyclodextrin

Koźbiał

Gierycz

2013

J Solution Chem

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The aim of the presented work is the comparison of aqueous and 1-octanol solubilities of different acyclovir derivatives and their hydroxypropyl-β-cyclodextrin inclusion complexes. The solubility measurements were carried out at different temperatures over the range 25–45 °C using water, 1-octanol, water saturated with 1-octanol, 1-octanol saturated with water, buffered aqueous solutions (pH = 5.5 and 7.0) and buffered aqueous solutions containing cyclodextrin as solvents. The aqueous solubilities of the compounds are very low but may be enhanced by complexation with hydroxypropyl-β-cyclodextrin, especially if the acyclovir derivatives have aromatic groups which may be included in the cyclodextrin cavity. The values of 1-octanol–water partition coefficients of acyclovir derivatives, obtained using extraction experiments, showed a similar sequence as the solubility results in 1-octanol. Additionally, some molecular mechanics and molecular dynamic calculations were performed to determine optimized structures of acyclovir derivative complexes with β-cyclodextrin treated as a model.

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“…The complexation of tricyclic ACV derivatives in buffered aqueous solutions of hydroxypropyl-β-cyclodextrin at pH 5.5 or 7.0 has led to a noticeable increase in their solubility at 25 °C and 37 °C. The formation and presence of this inclusion complex were proven by 1H-NMR and differential scanning calorimetry analysis [ 91 ]. The complexing capacity of β-cyclodextrin/poly (amidoamine) copolymer with ACV was determined and the antiviral activity of complexed ACV was evaluated against virus cell cultures of HSV type I, for which the complex was found to elicit greater antiviral activity than the pure drug [ 92 ].…”

Section: Dosage Forms and Drug Delivery Systems For Antiviralsmentioning

confidence: 99%

Advances in Antiviral Delivery Systems and Chitosan-Based Polymeric and Nanoparticulate Antivirals and Antiviral Carriers

Dominika

Mikušová

Mikuš

2023

Viruses

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Current antiviral therapy research is focused on developing dosage forms that enable highly effective drug delivery, providing a selective effect in the organism, lower risk of adverse effects, a lower dose of active pharmaceutical ingredients, and minimal toxicity. In this article, antiviral drugs and the mechanisms of their action are summarized at the beginning as a prerequisite background to develop relevant drug delivery/carrier systems for them, classified and briefly discussed subsequently. Many of the recent studies aim at different types of synthetic, semisynthetic, and natural polymers serving as a favorable matrix for the antiviral drug carrier. Besides a wider view of different antiviral delivery systems, this review focuses on advances in antiviral drug delivery systems based on chitosan (CS) and derivatized CS carriers. CS and its derivatives are evaluated concerning methods of their preparation, their basic characteristics and properties, approaches to the incorporation of an antiviral drug in the CS polymer as well as CS nanoparticulate systems, and their recent biomedical applications in the context of actual antiviral therapy. The degree of development (i.e., research study, in vitro/ex vivo/in vivo preclinical testing), as well as benefits and limitations of CS polymer and CS nanoparticulate drug delivery systems, are reported for particular viral diseases and corresponding antivirotics.

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Enhancement of aqueous solubility of tricyclic acyclovir derivatives by their complexation with hydroxypropyl-β-cyclodextrin

Cited by 19 publications

References 19 publications

Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin

Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin

Comparison of Aqueous and 1-Octanol Solubility as well as Liquid–Liquid Distribution of Acyclovir Derivatives and Their Complexes with Hydroxypropyl-β-Cyclodextrin

Advances in Antiviral Delivery Systems and Chitosan-Based Polymeric and Nanoparticulate Antivirals and Antiviral Carriers

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