Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC

Cabral-Marques, Helena; Hadgraft, Jonathan; Kellaway, I.W.

doi:10.1016/0378-5173(90)90132-n

Cited by 174 publications

(57 citation statements)

References 22 publications

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“…When guest molecules are embedded in CD cavities, their melting, boiling or degradation points generally shift to a different temperature or disappear. 6,24,25 Analyzing the 6CN10 and physical mixture, DTA curves with a peak at 186 ºC can be observed with an onset temperature (T ONSET ) 183 ºC, corresponding to the melting point of the drug. However, in the complex this T ONSET changes to 181 ºC.…”

Section: Thermogravimetric Analysismentioning

confidence: 99%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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This study aimed to prepare a complex of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and 6CN10, a poorly water soluble 2-aminothiophene derivative with antifungal properties, by freeze-drying technique. The complex was characterized by thermal analysis, infrared/Raman spectroscopy, X-ray diffraction and scanning electron microscopy. In addition, we used the data of the phase solubility study, 1 H, and 2D NMR spectroscopy and molecular modeling in order to investigate the interactions between 6CN10 and HP-β-CD. The apparent solubility of 6CN10 with HP-β-CD increased more than 29 fold. The phase solubility assay in water at 25 ºC showed an A P -type curve, with an apparent stability constant K 1:1 and K 1:2 of 96 and 0.1989 M -1 , respectively. The results of IR, NMR and docking indicate that 6CN10 is able to form complexes with HP-β-CD (1:1 and 1:2 stoichiometric ratios), generating the formation of inclusion and preferably, non-inclusion complexes. The antifungal activity against Cryptococcus neoformans demonstrated the superior performance of the complex (46.66 μg mL -1 ) when compared with the free drug (166.66-333.33 μg mL -1 ). The present study provides useful information for the potential application of complexation with low soluble compounds and about the type of complex formation between 6CN10 and HP-β-CD.

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Section: Thermogravimetric Analysismentioning

confidence: 99%

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Eleamen¹,

Costa²,

Lima-Neto³

et al. 2016

Journal of the Brazilian Chemical Society

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“…[34][35][36] The absence or the presence of the melting point of organic compounds in their free or complex form could be used to confirm the formation of the inclusion complex within fiber mats. 33 Figure 2 shows that pure AC powder exhibited a broad endothermic peak over a temperature range of 40 to 160 o C, associating with the loss of moisture during the heating process, and a melting peak at about 248 o C, corresponding to the melting point of pure AC.…”

Section: Resultsmentioning

confidence: 99%

Electrospinning of Asiaticoside/2-Hydroxypropyl-β-cyclodextrin Inclusion Complex-loaded Cellulose Acetate Fiber Mats: Release Characteristics and Potential for Use as Wound Dressing

Panichpakdee¹,

Pavasant²,

Supaphol³

2014

Polymer Korea

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Cellulose acetate (CA) fiber mats containing inclusion complexes of asiaticoside (AC) in 2-hydroxypropyl-β-cyclodextrin (HPβCD) for potential usage as wound dressings were developed. The AC/HPβCD complex-loaded CA fibers at various HPβCD to AC molar ratios of 0.5, 1, and 2 were prepared in 90:10 v/v mixture of 80% (v/v) acetic acid and N,N-dimethylacetamide (DMAc) via electrospinning. The maximum released amounts of AC depended on the HPβCD content and were much greater than those released from the AC-loaded CA fiber mat. In the in vitro study, indirect cytotoxic evaluation with human dermal fibroblasts (HDFa) showed that these materials released no substances in the levels that were harmful to the cells and the cells appeared to attach and proliferate well on these substrates. However, only the CA fiber mats containing AC/HPβCD complexes at the HPβCD to AC molar ratio of 0.5 was effective in upregulating the production of collagen of the cultured cells.

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“…In addition, the characteristic endothermic effect of b-CD was slightly shifted to higher temperature, indicating that FD had complexed with b-CD. In fact, even though not unambiguously attributable to inclusion complexation, this phenomenon is indicative of a stronger interaction between the drug and b-CD in the solid state (20,21). (Table II), suggesting a strong interaction between the drug and b-cyclodextrin.…”

Section: Effect Of Formulation Variablesmentioning

confidence: 99%

Felodipine β-cyclodextrin complex as an active core for time delayed chronotherapeutic treatment of hypertension

Pagar

Vavia²

2012

Acta Pharmaceutica

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The key to the success of any drug delivery system depends upon the development of formulations that accomplish the therapeutic needs associated with a particular pathological condition or disease state (1). Many physiological body functions (e.g., blood The present research work deals with the development of a time delayed chronotherapeutic formulation of felodipine (FD) aimed at rapid drug release after a desired lag time in the management of hypertension. The developed system comprises a drug core embedded within a swellable layer and coated with an insoluble, water permeable polymeric system. FD cyclodextrin complex was used as an active core while ethyl cellulose was used as an effective coating layer. Dissolution studies of the complex revealed that there was a 3-fold increase in dissolution of the complex compared to plain FD. This dissolution enhancement and rapid drug release resulted from FD amorphisation, as confirmed by XRD, DSC and SEM studies. FTIR and 1 H NMR studies confirmed the complex formation between FD and cyclodextrin based on the observed hydrogen bond interactions. FD release was adequately adjusted by using a pH independent polymer, i.e., ethyl cellulose, along with dibutyl phthalate as plasticizer. Influence of formulation variables like polymer viscosity, plasticizer concentration, super disintegrant concentration in the swellable layer and percent coating weight gain was investigated to characterize the lag time. Upon permeation of water, the core tablet swelled, resulting in the rupture of the coating layer, followed by rapid drug release. The developed formulation of FD showed a lag time of 5-7 h, which is desirable for chronotherapeutic application.

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Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC

Cited by 174 publications

References 22 publications

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Improvement of Solubility and Antifungal Activity of a New Aminothiophene Derivative by Complexation with 2-Hydroxypropyl-β-cyclodextrin

Electrospinning of Asiaticoside/2-Hydroxypropyl-β-cyclodextrin Inclusion Complex-loaded Cellulose Acetate Fiber Mats: Release Characteristics and Potential for Use as Wound Dressing

Felodipine β-cyclodextrin complex as an active core for time delayed chronotherapeutic treatment of hypertension

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