Thermal Analyses of Cyclodextrin Complexes

Hădărugă, Nicoleta G.; Bandur, Geza; Hădărugă, Daniel I.

doi:10.1007/978-3-319-76159-6_4

Cited by 10 publications

(13 citation statements)

References 173 publications

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“…This endothermal-exothermal effect that take place from 217.3 to 226.5°C (Figs 4–6) disappears in all β-CD/CBO complexes. This is a confirmation that the molecular inclusion process take place and the crystal structure of β-CD is broken after nanoencapsulation [34–36]. The endothermal effect of the dissociation of water molecules is much lower for complexes in comparison with that for β-CD hydrate (153.8–347.0 J/g and 479.9 J/g, respectively, Figs 4–6 and Table 2).…”

Section: Resultssupporting

confidence: 57%

Fatty acid profile of Romanian’s common bean (Phaseolus vulgaris L.) lipid fractions and their complexation ability by β-cyclodextrin

et al. 2019

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The goal of the present study was the evaluation of the fatty acid (FA) profile of lipid fraction from dry common beans (Phaseolus vulgaris L.) (CBO) harvested from North-East (NE) and South-West (SW) of Romania and to protect against thermal and oxidative degradation of the contained omega-3 and omega-6 polyunsaturated fatty acid (PUFA) glycerides by β-cyclodextrin (β-CD) nanoencapsulation, using kneading method. The most abundant FAs in the CBO samples were PUFAs, according to gas chromatography-mass spectrometry (GC-MS) analysis. Linoleic acid (methyl ester) was the main constituent, having relative concentrations of 43.4 (±1.95) % and 35.23 (±0.68) % for the lipid fractions separated from the common beans harvested from the NE and SW of Romania, respectively. Higher relative concentrations were obtained for the omega-3 α-linolenic acid methyl ester at values of 13.13 (±0.59) % and 15.72 (±0.30) % for NE and SW Romanian samples, respectively. The omega-3/omega-6 ratio consistently exceeds the lower limit value of 0.2, from where the PUFA glyceride mixture is valuable for the human health. This value was 0.32 (±0.02) for the NE samples and significantly higher for the CBO-SW samples, 0.51 (±0.01). These highly hydrophobic mixtures especially consisting of PUFA triglycerides provide β-CD complexes having higher thermal and oxidative stability. Kneading method allowed obtaining β-CD/CBO powder-like complexes with higher recovery yields of >70%. Thermal analyses of complexes revealed a lower content of hydration water (3.3–5.8% up to 110°C in thermogravimetry (TG) analysis and 154–347 J/g endothermal effect in differential scanning calorimetry (DSC) analysis) in comparison with the β-CD hydrate (12.1% and 479.5–480 J/g, respectively). These findings support the molecular inclusion process of FA moieties into the β-CD cavity. Attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR) analysis reveals the formation of the β-CD/CBO inclusion complexes by restricting the vibration and bending of some bonds from the host and guest molecules. Moreover, powder X-ray diffractometry (PXRD) analysis confirm the formation of the host-guest complexes by modifying the diffractograms for β-CD/CBO complexes in comparison with the β-CD and β-CD + CBO physical mixtures. A significant reduction of the level of crystallinity from 93.3 (±5.3) % for β-CD to 60–60.9% for the corresponding β-CD/CBO complexes have been determined. The encapsulation efficiency (EE), the profile of FAs, as well as the controlled release of the encapsulated oil have also been evaluated. The EE was >40% in all cases, the highest value being obtained for β-CD/CBO-SW complex. The SFA content increased, while the unsaturated FA glycerides had lower relative concentrations in the encapsulated CBO samples. It can be emphasized that the main omega-3 FA (namely α-linolenic acid glycerides) had close concentrations in the encapsulated and raw CBOs (13.13 (±0.59) % and 14.04 (±1.54) % for non-encapsulated and encapsulated CBO-NE samples, 15.72 (±0...

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Section: Resultssupporting

confidence: 57%

Fatty acid profile of Romanian’s common bean (Phaseolus vulgaris L.) lipid fractions and their complexation ability by β-cyclodextrin

et al. 2019

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“…Figure 8a shows the DSC thermograms of α-CD and TO/α-CD powder. According to Hădărugă et al [63] the large endothermic area displayed by α-CD up to around 160 • C corresponds to the loss of water. The different peaks observed in the thermogram (at around 80, 115, and 141 • C) are related to various physically bonded water molecules (i.e., "surface water" and "strongly-retained water").…”

Section: Dscmentioning

confidence: 98%

“…consistent to that reported in literature (i.e., 338 J/g). The smaller endothermic phenomena noticed at higher temperatures, with a peak at 224 °C, can be related to transitions of α-CD from a form to another, with possibly rearrangement of the crystal structure after the loss of water molecules Hădărugă et al [63]. The thermal decomposition of α-CD is reported to start at temperatures greater than 270-280 °C and it is completed around 400 °C [63].…”

Section: Dscmentioning

confidence: 98%

“…The smaller endothermic phenomena noticed at higher temperatures, with a peak at 224 °C, can be related to transitions of α-CD from a form to another, with possibly rearrangement of the crystal structure after the loss of water molecules Hădărugă et al [63]. The thermal decomposition of α-CD is reported to start at temperatures greater than 270-280 °C and it is completed around 400 °C [63]. The DSC thermogram of the crude TO (Figure 8) suggests that no thermal phenomena occur in the range of temperatures of interest, i.e., up to 250 °C.…”

Section: Dscmentioning

confidence: 99%

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Tomato Oil Encapsulation by α-, β-, and γ-Cyclodextrins: A Comparative Study on the Formation of Supramolecular Structures, Antioxidant Activity, and Carotenoid Stability

Durante

Milano

Caroli

et al. 2020

Foods

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Cyclodextrins (CDs) are oligosaccharides, comprising 6 (α), 7 (β), or 8 (γ) glucose residues, used to prepare oil-in-water emulsions and improve oil stability towards degradation. In this research, the aptitude of α-, β-, and γ-CDs to form complexes with a supercritical CO2 extracted lycopene-rich tomato oil (TO) was comparatively assessed. TO/CD emulsions and the resulting freeze-dried powders were characterized by microscopy, Fourier transform infrared-attenuated total reflection (FTIR-ATR), and differential scanning calorimetry (DSC), as well as for their antioxidant activity. Furthermore, carotenoid stability was monitored for 90 days at 25 and 4 °C. Confocal and SEM microscopy revealed morphological differences among samples. α- and β-CDs spontaneously associated into microcrystals assembling in thin spherical shells (cyclodextrinosomes, Ø ≈ 27 µm) at the oil/water interface. Much smaller (Ø ≈ 9 µm) aggregates were occasionally observed with γ-CDs, but most TO droplets appeared “naked”. FTIR and DSC spectra indicated that most CDs did not participate in TO complex formation, nevertheless structurally different interfacial complexes were formed. The trolox equivalent antioxidant capacity (TEAC) activity of emulsions and powders highlighted better performances of α- and β-CDs as hydrophobic antioxidants-dispersing agents across aqueous media. Regardless of CDs type, low temperature slowed down carotenoid degradation in all samples, except all-[E]-lycopene, which does not appear efficiently protected by any CD type in the long storage period.

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“…The isothermal titration calorimetry fulfills these requirements; the reactants are mixed in a single volume and the heat flow produced by the accompanying processes is measured. 32 , 33 The titration experiments were performed at two temperatures: 37 °C (normal physiological temperature) and 4 °C (intended temperature as induced locally by hyperthermia). Figure 2 shows examples of thermograms obtained at 37 °C from MPs formed from LAU and MYR/PAL.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of the In Vitro Stability of Stimuli-Sensitive Fatty Acid-Based Microparticles for the Treatment of Lung Cancer

Dałek

Borowik²,

Reczyńska

et al. 2020

Langmuir

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The fatty acid-based microparticles containing iron oxide nanoparticles and paclitaxel (PAX) are a viable proposition for the treatment of lung cancer. The microparticles inhaled as a dry powder can be guided to selected locations using an external magnetic field, and when accumulated there, the active compound release can be triggered by local hyperthermia. However, this general strategy requires that the active compound is released from microparticles and can reach the targeted cells before microparticles are removed. Isothermal titration calorimetry was used to demonstrate that the components of microparticles were released and transferred to albumins and lipid bilayers. The morphology of the measured particulates was studied with scanning electron microscopy and dynamic light scattering. To determine the cytotoxicity of microparticles, cell culture studies were done. It has been shown that the transfer efficiency depends predominantly on the fatty acid composition of microparticles, which, together with the active ingredient, accumulate predominantly in membrane structures after being released from microparticles and before entering the cytoplasm. The release process is sufficient; hence, paclitaxel-loaded microparticles effectively suppressed the proliferation of A549 human lung epithelial cells of malignant origin (IC 50 values for both lauric acid-based and myristic/palmitic-based microparticles containing paclitaxel were below 0.375 μg/mL), while reference microparticles were noncytotoxic.

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Thermal Analyses of Cyclodextrin Complexes

Cited by 10 publications

References 173 publications

Fatty acid profile of Romanian’s common bean (Phaseolus vulgaris L.) lipid fractions and their complexation ability by β-cyclodextrin

Fatty acid profile of Romanian’s common bean (Phaseolus vulgaris L.) lipid fractions and their complexation ability by β-cyclodextrin

Tomato Oil Encapsulation by α-, β-, and γ-Cyclodextrins: A Comparative Study on the Formation of Supramolecular Structures, Antioxidant Activity, and Carotenoid Stability

Evaluation of the In Vitro Stability of Stimuli-Sensitive Fatty Acid-Based Microparticles for the Treatment of Lung Cancer

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