Multimodal molecular encapsulation of nicardipine hydrochloride by β-cyclodextrin, hydroxypropyl-β-cyclodextrin and triacetyl-β-cyclodextrin in solution. Structural studies by 1H NMR and ROESY experiments

Fernandes, Catarina Marques; Carvalho, Rui A.; Costa, Saul C.; Veiga, Francisco

doi:10.1016/s0928-0987(03)00025-3

Cited by 112 publications

(43 citation statements)

References 22 publications

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“…In fact, it is known that the inclusion of a guest molecule in a CD ring shifts the 1 H NMR signals of the included guest downfield and those of affected CD protons upfield, 21 as a consequence of hydrophobic interaction between host and guest molecules. 22 The fact that all aromatic protons of DCF are shifted suggests that both aromatic rings (Figure 1) may be involved in the complex formation, as already reported by different authors. 17,23 However, it must be pointed out that other investigators found different chemical shift behavior, which led them to suggest that only the aromatic ring holding the …”

supporting

confidence: 69%

Diclofenac-β-cyclodextrin binary systems: Physicochemical characterization and in vitro dissolution and diffusion studies

et al. 2005

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The aim of this work was to study the influence of β-cyclodextrin (β-CD) on the biopharmaceutic properties of diclofenac (DCF). To this purpose the physicochemical characterization of diclofenac-β-cyclodextrin binary systems was performed both in solution and solid state. Solid phase characterization was performed using differential scanning calorimetry (DSC), powder x-ray diffractometry (XRD), and Fourier transform infrared spectroscopy (FTIR). Phase solubility analyses, and in vitro permeation experiments through a synthetic membrane were performed in solution. Moreover, DCF/β-CD interactions were studied in DMSO by 1 H nuclear magnetic resonance (NMR) spectroscopy. The effects of different preparation methods and drug-to-β-CD molar ratios were also evaluated. Phase solubility studies revealed 1:1 M complexation of DCF when the freeze-drying method was used for the preparation of the binary system. The true inclusion for the freeze-dried binary system was confirmed by 1 H NMR spectroscopy, DSC, powder XRD, and IR studies. The dissolution study revealed that the drug dissolution rate was improved by the presence of CDs and the highest and promptest release was obtained with the freeze-dried binary system. Diffusion experiments through a silicone membrane showed that DCF diffusion was higher from the saturated drug solution (control) than the freeze-dried inclusion complexes, prepared using different DCF-β-CD molar ratios. However, the presence of the inclusion complex was able to stabilize the system giving rise to a more regular diffusion profile.

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supporting

confidence: 69%

Diclofenac-β-cyclodextrin binary systems: Physicochemical characterization and in vitro dissolution and diffusion studies

et al. 2005

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“…Chemical shift changes were determined to some extent for all CTZ protons, and the highest change was observed at the phenyl and chlorophenyl ring protons. Therefore, this shift provided the indication for the formation of the inclusion complex between β-CD and CTZ [30][31][32][33][34] .…”

Section: Dmentioning

confidence: 96%

Cetirizine Dihydrochloride, beta-Cyclodextrin Inclusion Complex by Ethanol Kneading for Taste Masking

Katewongsa¹,

Lertsuphotvanit²,

Phaechamud³

2017

pharmaceutical-sciences

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Katewongsa, et al.: Cetirizine Dihydrochloride and β-Cyclodextrin Complex by Ethanol KneadingCetirizine dihydrochloride has a very unpleasant bitter taste. To mask the bitter taste, complexation with β-cyclodextrin using ethanol as a kneading solvent was investigated and evaluated by Fourier transform infrared spectroscopy, differential scanning calorimetry, powder X-ray diffractometry, thermogravimetric analysis, simultaneous X-ray diffractometry-differential scanning calorimetry measurement and 1 H-nuclear magnetic resonance spectroscopy. Taste was evaluated by human volunteers using an unstructured line scale. The basic characterization of the prepared tablets including in vivo disintegration time and drug dissolution was studied. Fourier transform infrared spectroscopy, differential scanning calorimetry and powder X-ray diffractometry data confirmed the inclusion complex formation. Thermogravimetric analysis, simultaneous X-ray diffractometry-differential scanning calorimetry measurements revealed the reduction of crystalline β-cyclodextrin due to the displacement of water molecules from complex formation. Proton nuclear magnetic resonance spectroscopy indicated an intermolecular interaction between protons of cetirizine dihydrochloride with the cavity of β-cyclodextrin. The prepared complex showed an unstructured line scale with apparent low average rating of 1.70. The inclusion complex-loaded fast disintegrating tablet prepared with direct compression had short disintegration time and good taste with an unstructured line scale with average rating of 0.28. Cetirizine dihydrochloride, β-cyclodextrin inclusion complex was successfully prepared by kneading method using ethanol as solvent. The inclusion complex-loaded fast disintegrating tablet had good taste and good perception in the mouth.

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“…The first report on stability constants for G:CD formation was due to Sun et al [287] They studied the complexation between α-CD and bis(alkyl dimethylammonium)-2- 14,16 [289,290]. A structural analysis of the complex has been done by rotating frame nuclear…”

Section: CDmentioning

confidence: 99%

The formation of host–guest complexes between surfactants and cyclodextrins

Valente

Söderman

2014

Advances in Colloid and Interface Science

183

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Cyclodextrins are able to act as host molecules in supramolecular chemistry with applications ranging from pharmaceutics to detergency. Among guest molecules surfactants play an important role with both fundamental and practical applications. The formation of cyclodextrin/surfactant host-guest compounds leads to an increase in the critical micelle concentration and in the solubility of surfactants. The possibility of changing the balance between several intermolecular forces, and thus allowing the study of, e.g., dehydration and steric hindrance effects upon association, makes surfactants ideal guest molecules for fundamental studies. Therefore, these systems allow for obtaining a deep insight into the host-guest association mechanism. In this paper, we review the influence on the thermodynamic properties of CD-surfactant association by highlighting the effect of different surfactant architectures (single tail, double-tailed, gemini and bolaform), with special emphasis on cationic surfactants. This is complemented with an assessment of the most common analytical techniques used to follow the association process. The applied methods for computation of the association stoichiometry and stability constants are also reviewed and discussed; this is an important point since there are significant discrepancies and scattered data for similar systems in the literature.In general, the surfactant-cyclodextrin association is treated without reference to the kinetics of the process. However, there are several examples where the kinetics of the process can be investigated, in particular those where volumes of the CD cavity and surfactant (either the tail or in special cases the head group) are similar in magnitude.This will also be critically reviewed.

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Multimodal molecular encapsulation of nicardipine hydrochloride by β-cyclodextrin, hydroxypropyl-β-cyclodextrin and triacetyl-β-cyclodextrin in solution. Structural studies by 1H NMR and ROESY experiments

Cited by 112 publications

References 22 publications

Diclofenac-β-cyclodextrin binary systems: Physicochemical characterization and in vitro dissolution and diffusion studies

Diclofenac-β-cyclodextrin binary systems: Physicochemical characterization and in vitro dissolution and diffusion studies

Cetirizine Dihydrochloride, beta-Cyclodextrin Inclusion Complex by Ethanol Kneading for Taste Masking

The formation of host–guest complexes between surfactants and cyclodextrins

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