Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole

Alamdarnejad, Ghazaleh; Sharif, Alireza; Taranejoo, Shahrouz; Kalaee, Mohammadreza; Dadgar, Mohsen; Khakpour, Mazyar

doi:10.1007/s10856-013-4947-9

Cited by 34 publications

(19 citation statements)

References 38 publications

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“…Cyclodextrins (CDs) are cup-shaped molecules with hydrophobic cavities and hydrophilic exteriors that can interact with various hydrophobic guest molecules to form supramolecular inclusion complexes [6,7]. CDs have been exploited to enhance the bioavailability of insoluble drugs by increasing drug solubility and permeability.…”

Section: Introductionmentioning

confidence: 99%

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Exploring the Preparation of Albendazole-Loaded Chitosan-Tripolyphosphate Nanoparticles

Kang

Lee

et al. 2015

Materials

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Abstract:The objective of this study was to improve the solubility of albendazole and optimize the preparation of an oral nanoparticle formulation, using β-cyclodextrin (βCD) and chitosan-tripolyphosphate (TPP) nanoparticles. The solubility of albendazole in buffers, surfactants, and various concentrations of acetic acid solution was investigated. To determine drug loading, the cytotoxic effects of the albendazole concentration in human hepatocellular carcinoma cells (HepG2) were investigated. The formulations were prepared by mixing the drug solution in Tween 20 with the chitosan solution. TPP solution was added dropwise with sonication to produce a nanoparticle through ionic crosslinking. Then the particle size, polydispersity index, and zeta potential of the nanoparticles were investigated to obtain an optimal composition. The solubility of albendazole was greater in pH 2 buffer, Tween 20, and βCD depending on the concentration of acetic acid. Drug loading was determined as 100 µg/mL based on the results of cell viability. The optimized ratio of Tween 20, chitosan/hydroxypropyl βCD, and TPP was 2:5:1, which resulted in smaller particle size and proper zeta positive values of the zeta potential. The chitosan-TPP nanoparticles increased the drug solubility and had a small particle size with homogeneity in formulating albendazole as a potential anticancer agent.

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Section: Introductionmentioning

confidence: 99%

“…CDs have been exploited to enhance the bioavailability of insoluble drugs by increasing drug solubility and permeability. Moreover, the safety of CDs in humans has been well established [6,8]. …”

Section: Introductionmentioning

confidence: 99%

Exploring the Preparation of Albendazole-Loaded Chitosan-Tripolyphosphate Nanoparticles

Kang

Lee

et al. 2015

Materials

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“…Different strategies have been investigated to solve the limited aqueous solubility of benzimidazoles, including the use of surfactants, such as polysorbates and bile salts, or co-solvents (Daniel-Mwambete et al, 2004;Miranda et al, 2011;Pradines et al, 2014). There is evidence that complexation with cyclodextrins (CDs) can increase the oral bioavailability of benzimidazoles (Evrard et al, 2002;Moriwaki et al, 2008;Pourgholami, Wangoo, Morris, 2008;Palomares-Alonso et al, 2010;Kumar et al, 2011a;Kumar et al, 2011b;Alamdarnejad et al, 2013;De Jaeghere et al, 2013;Pradines et al, 2014;Ferreira et al, 2015). CDs are known for increasing the solubility, dissolution efficiency, and bioavailability of different drugs through the formation of inclusion complexes.…”

Section: Introductionmentioning

confidence: 99%

Inclusion complexes and self-assembled cyclodextrin aggregates for increasing the solubility of benzimidazoles

Rodrigues

Tavares

Ferreira

et al. 2019

Braz. J. Pharm. Sci.

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Albendazole and fenbendazole are imidazole derivatives that exhibit broad spectrum activity against parasites, but the low solubility of these drugs considerably reduces their effectiveness. Complexation of albendazole and fenbendazole with cyclodextrins (β-cyclodextrin and hydroxypropyl-β-cyclodextrin) in both water and an aqueous solution of polyvinylpyrrolidone (PVP-k30) was studied to determine if it could increase the solubility and dissolution rate of the drugs. In an aqueous solution, β-cyclodextrin increased the solubility of albendazole from 0.4188 to ∼93.47 µg mL-1 (223×), and of fenbendazole from 0.1054 to 45.56 µg mL-1 (432×); hydroxypropyl-β-cyclodextrin, on the other hand, increased solubility to ∼443.06 µg mL-1 (1058×) for albendazole and ∼159.36 μg mL-1 (1512×) for fenbendazole. The combination of hydroxypropyl-β-cyclodextrin and polyvinylpyrrolidone enabled a solubility increase of 1412× (∼591.22 µg mL-1) for albendazole and 1373× (∼144.66 µg mL-1) for fenbendazole. The dissolution rate of the drugs was significantly increased in binary and ternary systems, with hydroxypropyl-β-cyclodextrin proving to be more effective. The presence of the water-soluble PVP-k30 increased the dissolution rate and amorphization of the complexes. Analysis of the changes in displacement and the profile of the cyclodextrin bands in the 1 H NMR spectra revealed a molecular interaction and pointed to an effective complexation in the drug/cyclodextrin systems. Monomeric forms and nanoclusters of cyclodextrins were observed in the drug/cyclodextrin systems, suggesting that the increase in solubility of the drugs in the presence of cyclodextrins should not be attributed only to the formation of inclusion complexes, but also to the formation of cyclodextrin aggregates.

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“…Polymeric carriers are one of the most commonly used approaches (Alamdarnejad et al, 2013;Taranejoo et al 2014). Soluble polymeric drug carriers can improve drug pharmacokinetics and reduce systemic toxicity by delivering the drug to the tumor tissue, thanks to the higher permeability of tumor vasculature, known as the enhanced permeability and retention (EPR) effect (Matsumura & Maeda, 1986).…”

Section: Introductionmentioning

confidence: 99%

Classification of stimuli–responsive polymers as anticancer drug delivery systems

et al. 2014

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Although several anticancer drugs have been introduced as chemotherapeutic agents, the effective treatment of cancer remains a challenge. Major limitations in the application of anticancer drugs include their nonspecificity, wide biodistribution, short half-life, low concentration in tumor tissue and systemic toxicity. Drug delivery to the tumor site has become feasible in recent years, and recent advances in the development of new drug delivery systems for controlled drug release in tumor tissues with reduced side effects show great promise. In this field, the use of biodegradable polymers as drug carriers has attracted the most attention. However, drug release is still difficult to control even when a polymeric drug carrier is used. The design of pharmaceutical polymers that respond to external stimuli (known as stimuli-responsive polymers) such as temperature, pH, electric or magnetic field, enzymes, ultrasound waves, etc. appears to be a successful approach. In these systems, drug release is triggered by different stimuli. The purpose of this review is to summarize different types of polymeric drug carriers and stimuli, in addition to the combination use of stimuli in order to achieve a better controlled drug release, and it discusses their potential strengths and applications. A survey of the recent literature on various stimuli-responsive drug delivery systems is also provided and perspectives on possible future developments in controlled drug release at tumor site have been discussed.

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Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole

Cited by 34 publications

References 38 publications

Exploring the Preparation of Albendazole-Loaded Chitosan-Tripolyphosphate Nanoparticles

Exploring the Preparation of Albendazole-Loaded Chitosan-Tripolyphosphate Nanoparticles

Inclusion complexes and self-assembled cyclodextrin aggregates for increasing the solubility of benzimidazoles

Classification of stimuli–responsive polymers as anticancer drug delivery systems

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