Kinetic and physical-chemical study of the inclusion complex of β-cyclodextrin containing carvacrol

Menezes, Paula dos Passos; Serafini, Mairim Russo; Carvalho, Yasmim Maria Barbosa Gomes de; Santana, Dayanne Valéria Soares; Lima, Bruno S.; Marreto, Ricardo Neves; Aquino, Thiago Mendonça de; Sabino, Adilson Rodrigues; Scotti, Luciana; Grangeiro-Júnior, Severino; Araújo, Adriano Antunes de Souza

doi:10.1016/j.molstruc.2016.06.062

Cited by 34 publications

(17 citation statements)

References 35 publications

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“…The inclusion complex has one signal at ca. 285-295 • C; therefore, the β-CD enhances the thermal stability of the essential oils and the active compounds as described by Wang et al [46] and Menezes et al [47]. The TGA results confirm the inclusion of active agents in β-CD.…”

Section: Samplesupporting

confidence: 75%

Fungicides Films of Low-Density Polyethylene (LDPE)/Inclusion Complexes (Carvacrol and Cinnamaldehyde) Against Botrytis Cinerea

et al. 2019

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Low density polyethylene (LDPE) films were prepared with the incorporation of natural agents (carvacrol and trans-cinnamaldehyde) by the melting process. The co-precipitation method was used successfully to complex the carvacrol or trans-cinnamaldehyde with β-cyclodextrin (β-CD). The active compounds encapsulated in β-CD achieved ca. 90% encapsulation efficiency (E.E.). The inclusion complex studied by scanning electron microscopy (SEM) found particles of different sizes, ca. 4 μm. The active compounds were added directly (1 and 5 wt %) into the polymer matrix, yielding LDPE + carvacrol and LDPE + cinnamaldehyde films. The active compounds encapsulated in β-cyclodextrin (β-CD) were added to LDPE, yielding LDPE + β-CD-carvacrol and LDPE + β-CD-cinnamaldehyde films. The incorporation of carvacrol and trans-cinnamaldehyde, and their corresponding inclusion complexes with β-cyclodextrin, did not affect the thermal properties of LDPE. The microcapsules distributed in all polymer matrices had sizes of 5–20 μm as shown by scanning electron microscopy (SEM). In terms of mechanical properties, the polymers showed a slight decrease of Young’s modulus (12%) and yield stress compared (14%) to neat LDPE. This could be due to the essential oil acting as a plasticizer in the polymer matrix. The LDPE + carvacrol and LDPE + cinnamaldehyde films had the capacity to inhibit fungi by 99% compared to neat LDPE. The effectiveness against fungi of LDPE+β-CD + active agent was slower than by the direct incorporation of the essential oil in the LDPE in the same amount of active agent. The biocidal properties were related to the gradual release of active compound from the polymer. The results confirm the applicability of carvacrol, trans-cinnamaldehyde, and their corresponding inclusion complexes in active packaging, as well as their use in the food delivery industry.

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Section: Samplesupporting

confidence: 75%

Fungicides Films of Low-Density Polyethylene (LDPE)/Inclusion Complexes (Carvacrol and Cinnamaldehyde) Against Botrytis Cinerea

et al. 2019

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“…CMO presents a mass loss of 74.9% within the temperature range of 25–200 °C ( Figure 6 A,B) due to its volatilization and another mass loss of 23.2% in the 200–600 °C range. β-CD ( Figure 6 A) presents two events of mass loss: the first one of 13.6% within the temperature range of 25–200 °C, which is associated with the release of water molecules from its surface [ 38 ]; and a second event of 79.4% of mass loss within the temperature range of 200–400 °C, followed by degradation. The curves also showed that the method of complexation influenced on the TG/DTG results, as a mass loss of 18.1% was observed between 25 and 200 °C in the sample obtained by PM, whereas a mass loss of only 4.06% and 6.34% were achieved in the samples obtained by KND and SL, respectively ( Figure 6 A).…”

Section: Resultsmentioning

confidence: 99%

Inclusion Complexes of Copaiba (Copaifera multijuga Hayne) Oleoresin and Cyclodextrins: Physicochemical Characterization and Anti-Inflammatory Activity

Pinheiro

Tavares

Silva

et al. 2017

IJMS

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Complexation with cyclodextrins (CDs) is a technique that has been extensively used to increase the aqueous solubility of oils and improve their stability. In addition, this technique has been used to convert oils into solid materials. This work aims to develop inclusion complexes of Copaifera multijuga oleoresin (CMO), which presents anti-inflammatory activity, with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) by kneading (KND) and slurry (SL) methods. Physicochemical characterization was performed to verify the occurrence of interactions between CMO and the cyclodextrins. Carrageenan-induced hind paw edema in mice was carried out to evaluate the anti-inflammatory activity of CMO alone as well as complexed with CDs. Physicochemical characterization confirmed the formation of inclusion complex of CMO with both β-CD and HP-β-CD by KND and SL methods. Carrageenan-induced paw edema test showed that the anti-inflammatory activity of CMO was maintained after complexation with β-CD and HP-β-CD, where they were able to decrease the levels of nitrite and myeloperoxidase. In conclusion, this study showed that it is possible to produce inclusion complexes of CMO with CDs by KND and SL methods without any change in CMO’s anti-inflammatory activity.

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“…The event related to mass loss occurred in the range of 200-400 °C with 95.01 % mass loss ( Figure 5A,B). β-CD ( Figure 5A) exhibited mass losses of 13.60 and 69.18 % in the ranges of 40-200 and 200-400 °C, respectively, which were likely associated with the release of surface water molecules followed by degradation [39]. Curves of EOO-β-CD complexes prepared by KND and SL showed at 40-200 °C mass losses of 7.19 and 7.39% ( Figure 5A), respectively, suggesting water loss from cyclodextrin since EOO did not lose A comparison of the diffractogram of EOO-β-CD complex prepared by kneading ( Figure 4B) with that of β-CD ( Figure 4A) points out the appearance of a peak at 6.67 • , the disappearance of β-CD peaks at 8.98 and 10.60 • , a shift of the peak at 12.44 to 12.88 • , and a decrease in its intensity.…”

Section: Thermogravimetry Analysis (Tg/dtg)mentioning

confidence: 99%

“…The event related to mass loss occurred in the range of 200-400 • C with 95.01 % mass loss ( Figure 5A,B). β-CD ( Figure 5A) exhibited mass losses of 13.60 and 69.18 % in the ranges of 40-200 and 200-400 • C, respectively, which were likely associated with the release of surface water molecules followed by degradation [39]. Curves of EOO-β-CD complexes prepared by KND and SL showed at 40-200 • C mass losses of 7.19 and 7.39% ( Figure 5A), respectively, suggesting water loss from cyclodextrin since EOO did not lose mass in that range.…”

Section: Thermogravimetry Analysis (Tg/dtg)mentioning

confidence: 99%

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

Magalhães

Macedo

Pacheco

et al. 2020

IJMS

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The development of inclusion complexes is used to encapsulate nonpolar compounds and improve their physicochemical characteristics. This study aims to develop complexes made up of Euterpe oleracea Mart oil (EOO) and β-cyclodextrin (β-CD) or hydroxypropyl-β-cyclodextrin (HP-β-CD) by either kneading (KND) or slurry (SL). Complexes were analyzed by molecular modeling, Fourier-transform infrared spectroscopy, scanning electron microscopy, powder X-ray diffraction, thermogravimetry analysis and differential scanning calorimetry. The antibacterial activity was expressed as Minimum Inhibitory Concentration (MIC), and the antibiotic resistance modulatory activity as subinhibitory concentration (MIC/8) against Escherichia coli, Streptomyces aureus, Pseudomonas aeruginosa and Enterococcus faecalis. Inclusion complexes with β-CD and HP-β-CD were confirmed, and efficiency was proven by an interaction energy between oleic acid and β-CD of −41.28 ± 0.57 kJ/mol. MIC values revealed higher antibacterial activity of complexes compared to the isolated oil. The modulatory response of EOO and EOO-β-CD prepared by KND as well as of EOO-β-CD and EOO-HP-β-CD prepared by SL showed a synergistic effect with ampicillin against E. coli, whereas it was not significant with the other drugs tested, maintaining the biological response of antibiotics. The antimicrobial response exhibited by the complexes is of great significance because it subsidizes studies for the development of new pharmaceutical forms.

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Kinetic and physical-chemical study of the inclusion complex of β-cyclodextrin containing carvacrol

Cited by 34 publications

References 35 publications

Fungicides Films of Low-Density Polyethylene (LDPE)/Inclusion Complexes (Carvacrol and Cinnamaldehyde) Against Botrytis Cinerea

Fungicides Films of Low-Density Polyethylene (LDPE)/Inclusion Complexes (Carvacrol and Cinnamaldehyde) Against Botrytis Cinerea

Inclusion Complexes of Copaiba (Copaifera multijuga Hayne) Oleoresin and Cyclodextrins: Physicochemical Characterization and Anti-Inflammatory Activity

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

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