Dataset Information

Inclusion of the Phytoalexin trans-Resveratrol in Native Cyclodextrins: A Thermal, Spectroscopic, and X-Ray Structural Study.

ABSTRACT: The aim of the study was to determine the feasibility of complexation between the antioxidant trans-resveratrol (RSV) and underivatized cyclodextrins (CDs) using a variety of preparative methods, including physical mixing, kneading, microwave irradiation, co-evaporation, and co-precipitation techniques. Products were characterized using differential scanning calorimetry (DSC), simultaneous thermogravimetric/DSC analysis (TGA/DSC), Fourier transform infrared (FT-IR) spectroscopy, and powder X-ray diffraction (PXRD). With ?-CD and RSV, sample amorphization was revealed by PXRD and FT-IR, but no definitive inclusion complexation was evident. Similar results were obtained in attempts to complex RSV with ?-CD. However, complex formation between ?-CD and RSV was evident from observation of an endo-/exothermic effect appearing in the DSC trace of the product from kneading and was further corroborated by FT-IR and PXRD methods. The latter technique indicated complexation unequivocally as the diffraction peak profile for the product matched that for known isostructural ?-CD complexes. Single crystal X-ray analysis followed, confirming the predicted complex between ?-CD and RSV. A combination of 1H NMR and TGA data yielded the complex formula (?-CD)3·(RSV)4·(H2O)62. However, severe disorder of the RSV molecules prevented their modeling. In contrast, our previous studies of the inclusion of RSV in methylated CDs yielded crystals with only minor guest disorder.

SUBMITTER: Catenacci L

PROVIDER: S-EPMC7070755 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Publications

Inclusion of the Phytoalexin <i>trans</i>-Resveratrol in Native Cyclodextrins: A Thermal, Spectroscopic, and X-Ray Structural Study.

Catenacci Laura L Sorrenti Milena M Bonferoni Maria Cristina MC Hunt Lee L Caira Mino R MR

Molecules (Basel, Switzerland) 20200224 4

The aim of the study was to determine the feasibility of complexation between the antioxidant <i>trans</i>-resveratrol (RSV) and underivatized cyclodextrins (CDs) using a variety of preparative methods, including physical mixing, kneading, microwave irradiation, co-evaporation, and co-precipitation techniques. Products were characterized using differential scanning calorimetry (DSC), simultaneous thermogravimetric/DSC analysis (TGA/DSC), Fourier transform infrared (FT-IR) spectroscopy, and powde ...[more]

PMID: 32102298

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Project description:A detailed comprehensive study on how the formation of soluble and insoluble carbamazepine/cyclodextrins (CBZ/CD) complexes (with consequent changes in the solid-phase composition) depends on the CD structure is not yet available. Moreover, the study of possible influence of this drug on the tendency of CDs and their complexes to self-aggregate is still lacking. Phase-solubility studies demonstrated that CDs and CBZ form a range of soluble (AL-type: αCD, βCD, and hydroxypropylated CDs) and insoluble (BS-type: γCD) complexes depending on CD used. HPβCD proved to be the best CD solubilizer for CBZ forming the most stable complex with highest apparent solubility, whereas γCD was shown to be the best native CD. For the native CDs, CBZ solubilization increases with increasing CD cavity diameter (αCD ≪ βCD < γCD). Solid phases collected from phase-solubility studies were characterized by Fourier-transformed infrared spectroscopy, differential scanning calorimetry, and X-ray powder diffraction to elucidate their composition and crystalline structure. They provided similar conclusions being overall supportive of phase-solubility, osmolality, and permeation studies results. Solid CBZ was the only detected component for AL-type profiles over the CD concentration range studied, whereas precipitation of poorly soluble CBZ/γCD complexes (BS-type) was observed (i.e., at and beyond plateau region). Osmometry and permeation studies were applied to evaluate the effect of CBZ on the aggregate formation and also to elucidate their influence on CD complex solubility and permeation profile. Permeation method was shown to be the most effective method to detect and evaluate aggregate formation in aqueous γCD and HPβCD solutions containing CBZ. CBZ did not affect the HPβCD tendency to self-aggregate but CBZ did modify the aggregation behavior of γCD decreasing the apparent critical aggregation concentration value from 4.2% (w/v) (in pure aqueous γCD solution) to 2.5% (w/v) (when CBZ was present).

Dataset Information

Inclusion of the Phytoalexin trans-Resveratrol in Native Cyclodextrins: A Thermal, Spectroscopic, and X-Ray Structural Study.

Publications

Inclusion of the Phytoalexin <i>trans</i>-Resveratrol in Native Cyclodextrins: A Thermal, Spectroscopic, and X-Ray Structural Study.

Similar Datasets

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