Modified β-cyclodextrin/amlodipine inclusion complexes: Preparation and application in aqueous systems

Dalmolin, Mara C.; Silva, Cintia Enes da; Lunelli, Carlos Eduardo; Zaioncz, Soraia; Farago, Paulo Vítor; Zawadzki, Sônia Faria

doi:10.1016/j.molliq.2018.11.116

Cited by 15 publications

(6 citation statements)

References 30 publications

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“…As shown in Figure 3a, the characteristic peaks of 2-indanone, δ 7.29 and 7.24 (low-field field) and δ 3.53 (the high field), were not related with the peaks of β-CD, indicating that 2-indanone cannot enter the β-CD cavity. On the contrary, the amino characteristic peak of 2.2a at δ 4.35 and the amino characteristic peak of 2.2j at δ 4.94 showed a clear relation with the peak of β-CD (C 2 -OH and C 3 -OH) [28] (Figure 3b,c, the blue line). In addition, 2.2a and 2.2j were also related with β-CD near δ 3.30 (see the detailed information in Figures S53 and S54).…”

Section: Resultsmentioning

confidence: 90%

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

et al. 2022

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An efficient, mild, and green method was developed for the synthesis of indeno[1,2-b]quinoxaline derivatives via o-phenylenediamine (OPD) and 2-indanone derivatives utilizing β-cyclodextrin (β-CD) as the supramolecular catalyst. The reaction can be carried out in water and in a solid state at room temperature. β-CD can also catalyze the reaction of indan-1,2-dione with OPD with a high degree of efficiency. Compared to the reported methods, this procedure is milder, simpler, and less toxic, making it an eco-friendly alternative. In addition, the β-CD can be recovered and reused without the loss of activity.

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Section: Resultsmentioning

confidence: 90%

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

et al. 2022

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“…In order to determine the interaction between atomoxetine HCl and HP-β-CD, NMR analysis was conducted to supply more information on the inclusion complexes reported in the literature [40] , [41] , [42] . In order to clarify further the molecular mechanism of the inclusion complex, atomoxetine HCl/HP-β-CyD inclusion complexes with different molar ratios (3:7, 5:5, 7:3) were studied basing on the previous report [43] .…”

Section: Resultsmentioning

confidence: 99%

Quantitative prediction of the bitterness of atomoxetine hydrochloride and taste-masked using hydroxypropyl-β-cyclodextrin: A biosensor evaluation and interaction study

Zhang²,

Khan

et al. 2020

Asian Journal of Pharmaceutical Sciences

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The bitterness of a drug is a major challenge for patient acceptability and compliance, especially for children. Due to the toxicity of medication, a human taste panel test has certain limitations. Atomoxetine hydrochloride (HCl), which is used for the treatment of attention deficit/hyperactivity disorder (ADHD), has an extremely bitter taste. The aim of this work is to quantitatively predict the bitterness of atomoxetine HCl by a biosensor system. Based on the mechanism of detection of the electronic tongue (E-tongue), the bitterness of atomoxetine HCl was evaluated, and it was found that its bitterness was similar to that of quinine HCl. The bitterness threshold of atomoxetine HCl was 8.61 µg/ml based on the Change of membrane Potential caused by Adsorption (CPA) value of the BT0 sensor. In this study, the taste-masking efficiency of 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) was assessed by Euclidean distances on a principle component analysis (PCA) map with the SA402B Taste Sensing System, and the host–guest interactions were investigated by differential scanning calorimetry (DSC), powder X-ray diffraction (XRD), nuclear magnetic resonance (NMR) spectroscopy and scanning electron microscopy (SEM). Biosensor evaluation and characterization of the inclusion complex indicated that atomoxetine HCl could actively react with 2-hydroxypropyl-β-cyclodextrin.

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“…It is a useful technique for monitoring the process of inclusion of a drug into the CD cavity since it is possible to observe whether the dehydration stage of the CD or the volatilization of a volatile drug is modified, or if the thermal stability of both the CD and the drug is modified. Thus, Dalmolin et al [ 210 ] studied the thermal stability of β-CD and modified β-CD with hexanoic anhydride using this technique, finding that the latter increases its stability since the degradation temperature is shifted from 325 °C in β-CD to 354 °C in chemically modified β-CD. Moreover, in the case of the modified CD, dehydration is not observed, indicating that this CD presents higher hydrophobicity.…”

Section: Analytical Aspectsmentioning

confidence: 99%

Cyclodextrin Inclusion Complexes for Improved Drug Bioavailability and Activity: Synthetic and Analytical Aspects

Sarabia-Vallejo,

Caja,

Olives

et al. 2023

Pharmaceutics

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Many active pharmaceutical ingredients show low oral bioavailability due to factors such as poor solubility and physical and chemical instability. The formation of inclusion complexes with cyclodextrins, as well as cyclodextrin-based polymers, nanosponges, and nanofibers, is a valuable tool to improve the oral bioavailability of many drugs. The microencapsulation process modifies key properties of the included drugs including volatility, dissolution rate, bioavailability, and bioactivity. In this context, we present relevant examples of the stabilization of labile drugs through the encapsulation in cyclodextrins. The formation of inclusion complexes with drugs belonging to class IV in the biopharmaceutical classification system as an effective solution to increase their bioavailability is also discussed. The stabilization and improvement in nutraceuticals used as food supplements, which often have low intestinal absorption due to their poor solubility, is also considered. Cyclodextrin-based nanofibers, which are polymer-free and can be generated using environmentally friendly technologies, lead to dramatic bioavailability enhancements. The synthesis of chemically modified cyclodextrins, polymers, and nanosponges based on cyclodextrins is discussed. Analytical techniques that allow the characterization and verification of the formation of true inclusion complexes are also considered, taking into account the differences in the procedures for the formation of inclusion complexes in solution and in the solid state.

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Modified β-cyclodextrin/amlodipine inclusion complexes: Preparation and application in aqueous systems

Cited by 15 publications

References 30 publications

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

Quantitative prediction of the bitterness of atomoxetine hydrochloride and taste-masked using hydroxypropyl-β-cyclodextrin: A biosensor evaluation and interaction study

Cyclodextrin Inclusion Complexes for Improved Drug Bioavailability and Activity: Synthetic and Analytical Aspects

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