Temperature-Dependent Dynamical Evolution in Coum/SBE-β-CD Inclusion Complexes Revealed by Two-Dimensional FTIR Correlation Spectroscopy (2D-COS)

Paladini, Giuseppe; Caridi, F.; Crupi, V.; Gaetano, Federica De; Majolino, D.; Tommasini, S.; Ventura, Cinzia Anna; Venuti, Valentina; Stancanelli, Rosanna

doi:10.3390/molecules26123749

Cited by 13 publications

(3 citation statements)

References 60 publications

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“…This shift may be due to the formation of a-β-CD by hydrogen bonding between AEO and β-CD and the change in electron cloud density, resulting in the shift in the characteristic absorption peak frequency of the groups in a-β-CD; alternatively, it may be that the included guest is wrapped within the hydrophobic cavity of β-CD, and the original characteristic peak is covered by the characteristic peak of β-CD. The infrared absorption of a-β-CD is different from that of the physical mixture mainly at 1650 cm −1 and 1350 cm −1 , indicating the formation of a-β-CD [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

The Effect of Chinese Agarwood Essential Oil with Cyclodextrin Inclusion against PCPA-Induced Insomnia Rats

et al. 2023

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Objective: To study the extraction process of agarwood active ingredients (AA) and investigate the safety and effectiveness of AA in the treatment of insomnia rats by nasal administration. Method: A β-cyclodextrin (β-CD) inclusion compound (a-β-CD) was prepared from agarwood essential oil (AEO), and the preparation process was optimized and characterized. The safety of AA in nasal mucosa was evaluated through Bufo gargarizans maxillary mucosa and rat nasal mucosa models. Insomnia animal models were replicated by injecting p-chlorophenylalanine (PCPA), conducting behavioral tests, and detecting the expression levels of monoamine neurotransmitters (NE and 5-HT) and amino acids (GABA/Glu) in the rat hypothalamus. Results: The optimum inclusion process conditions of β-CD were as follows: the feeding ratio was 0.35:1.40 (g:g), the inclusion temperature was 45 °C, the inclusion time was 2 h, and the ICY% and IEO% were 53.78 ± 2.33% and 62.51 ± 3.21%, respectively. The inclusion ratio, temperature, and time are the three factors that have significant effects on the ICY% and IEO% of a-β-CD. AA presented little damage to the nasal mucosa. AA increased the sleep rate, shortened the sleep latency, and prolonged the sleep time of the rats. The behavioral test results showed that AA could ameliorate depression in insomnia rats to a certain extent. The effect on the expression of monoamine neurotransmitters and amino acids in the hypothalamus of rats showed that AA could significantly reduce NE levels and increase the 5-HT level and GABA/Glu ratio in the hypothalamus of insomnia rats. Conclusion: The preparation of a-β-CD from AEO can reduce its irritation, improve its stability, increase its curative effect, and facilitate its storage and transport. AA have certain therapeutic effects on insomnia. The mechanism of their effect on rat sleep may involve regulating the expression levels of monoamine neurotransmitters and amino acids in the hypothalamus.

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Section: Resultsmentioning

confidence: 99%

The Effect of Chinese Agarwood Essential Oil with Cyclodextrin Inclusion against PCPA-Induced Insomnia Rats

et al. 2023

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“…Cyclodextrins (CDs) could be used to overcome this drawback. They are cyclic oligosaccharides that are able to complex apolar drugs and effectively improve their physicochemical properties, including water solubility [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ] and biological effects [ 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Rutin/Sulfobutylether-β-Cyclodextrin as a Promising Therapeutic Formulation for Ocular Infection

De Gaetano,

Pastorello,

Pistarà

et al. 2024

Pharmaceutics

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Ocular pathologies present significant challenges to achieving effective therapeutic results due to various anatomical and physiological barriers. Natural products such as flavonoids, alone or in association with allopathic drugs, present many therapeutic actions including anticancer, anti-inflammatory, and antibacterial action. However, their clinical employment is challenging for scientists due to their low water solubility. In this study, we designed a liquid formulation based on rutin/sulfobutylether-β-cyclodextrin (RTN/SBE-β-CD) inclusion complex for treating ocular infections. The correct stoichiometry and the accurate binding constant were determined by employing SupraFit software (2.5.120) in the UV-vis titration experiment. A deep physical–chemical characterization of the RTN/SBE-β-CD inclusion complex was also performed; it confirmed the predominant formation of a stable complex (Kc, 9660 M−1) in a 1:1 molar ratio, with high water solubility that was 20 times (2.5 mg/mL) higher than the free molecule (0.125 mg/mL), permitting the dissolution of the solid complex within 30 min. NMR studies revealed the involvement of the bicyclic flavonoid moiety in the complexation, which was also confirmed by molecular modeling studies. In vitro, the antibacterial and antibiofilm activity of the formulation was assayed against Staphylococcus aureus and Pseudomonas aeruginosa strains. The results demonstrated a significant activity of the formulation than that of the free molecules.

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“…Recently, authors demonstrated that anionic cyclodextrins (CDs), such as carboxymethyl-β-CD (CM-β-CD) and sulfobutylether-β-CD (SBE-β-CD), can electrostatically interact with CS to develop NPs for drug delivery [ 43 , 44 , 45 , 46 ]. Moreover, due to their hosting capacities, these CDs can include hydrophobic drugs [ 47 , 48 , 49 , 50 ], improving their physical–chemical properties (first of all, aqueous solubility). In this way, anionic CDs can act as gelling agents for CS, to prepare NPs, and in the meantime, they increase water solubility of lipophilic drugs, by complexation, permitting their encapsulation within CS NPs prepared in aqueous medium.…”

Section: Introductionmentioning

confidence: 99%

Chitosan/Cyclodextrin Nanospheres for Potential Nose-to-Brain Targeting of Idebenone

et al. 2022

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Idebenone (IDE) is a powerful antioxidant that is potentially active towards cerebral diseases, but its low water solubility and fast first pass metabolism reduce its accumulation in the brain, making it ineffective. In this work, we developed cyclodextrin-based chitosan nanospheres (CS NPs) as potential carriers for nose-to-brain targeting of IDE. Sulfobutylether-β-cyclodextrin (SBE-β-CD) was used as a polyanion for chitosan (CS) and as a complexing agent for IDE, permitting its encapsulation into nanospheres (NPs) produced in an aqueous solution. Overloading NPs were obtained by adding the soluble IDE/hydroxypropyl-β-CD (IDE/HP-β-CD) inclusion complex into the CS or SBE-β-CD solutions. We obtained homogeneous CS NPs with a hydrodynamic radius of about 140 nm, positive zeta potential (about +28 mV), and good encapsulation efficiency and drug loading, particularly for overloaded NPs. A biphasic release of IDE, finished within 48 h, was observed from overloaded NPs, whilst non-overloaded CS NPs produced a prolonged release, without a burst effect. In vitro biological studies showed the ability of CS NPs to preserve the antioxidant activity of IDE on U373 culture cells. Furthermore, Fourier transform infrared spectroscopy (FT-IR) demonstrated the ability of CS NPs to interact with the excised bovine nasal mucosa, improving the permeation of the drug and potentially favoring its accumulation in the brain.

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Temperature-Dependent Dynamical Evolution in Coum/SBE-β-CD Inclusion Complexes Revealed by Two-Dimensional FTIR Correlation Spectroscopy (2D-COS)

Cited by 13 publications

References 60 publications

The Effect of Chinese Agarwood Essential Oil with Cyclodextrin Inclusion against PCPA-Induced Insomnia Rats

The Effect of Chinese Agarwood Essential Oil with Cyclodextrin Inclusion against PCPA-Induced Insomnia Rats

Rutin/Sulfobutylether-β-Cyclodextrin as a Promising Therapeutic Formulation for Ocular Infection

Chitosan/Cyclodextrin Nanospheres for Potential Nose-to-Brain Targeting of Idebenone

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