DFT investigation of host–guest interactions between α-Terpineol and β-cyclodextrin

Bouchemela, Houria; Fatiha, Madi; Leila, Nouar

doi:10.1007/s10847-019-00940-8

Cited by 18 publications

(6 citation statements)

References 29 publications

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“…More recently, DFT methods have become the method of choice in computational chemistry because, at a reasonable computational cost, they are able to provide accurate geometrical parameters, properties, such as IR spectra, and complexation energies for a wide variety of systems, including organic systems. Therefore, they were used extensively to study these host–guest partners [ 20 , 22 , 38 , 39 , 40 ], often accompanied by experimental techniques, showing a good agreement, in particular between experimental and calculated IR spectra [ 21 , 24 , 41 ]. In recent years, to increase the complexity and realism of the studied systems, DFT methods have been often replaced by cheaper semi-empirical and force-field-based methods.…”

Section: Introductionmentioning

confidence: 99%

On the Interactions of Melatonin/β-Cyclodextrin Inclusion Complex: A Novel Approach Combining Efficient Semiempirical Extended Tight-Binding (xTB) Results with Ab Initio Methods

et al. 2021

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Melatonin (MT) is a molecule of paramount importance in all living organisms, due to its presence in many biological activities, such as circadian (sleep–wake cycle) and seasonal rhythms (reproduction, fattening, molting, etc.). Unfortunately, it suffers from poor solubility and, to be used as a drug, an appropriate transport vehicle has to be developed, in order to optimize its release in the human tissues. As a possible drug-delivery system, β-cyclodextrin (βCD) represents a promising scaffold which can encapsulate the melatonin, releasing when needed. In this work, we present a computational study supported by experimental IR spectra on inclusion MT/βCD complexes. The aim is to provide a robust, accurate and, at the same time, low-cost methodology to investigate these inclusion complexes both with static and dynamic simulations, in order to study the main actors that drive the interactions of melatonin with β-cyclodextrin and, therefore, to understand its release mechanism.

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Section: Introductionmentioning

confidence: 99%

On the Interactions of Melatonin/β-Cyclodextrin Inclusion Complex: A Novel Approach Combining Efficient Semiempirical Extended Tight-Binding (xTB) Results with Ab Initio Methods

et al. 2021

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“…The modified co-precipitation method used in our study was found to be effective for the formation of ICs of β-CD with FEO and BEO, and included the use of ethanol as a co-solvent for both EOs and β-CD. The greater proportion of water (75%) compared to ethanol (25%) affects the flexibility of the β-CD molecule and simplifies the formation of ICs and volatile nesting, while the addition of ethanol to water may improve the solubility of β-CD [ 62 ]. The co-precipitation technique was used for the successful IC formation of β-CD with linalool [ 58 ] and trans-anethole [ 63 ].…”

Section: Discussionmentioning

confidence: 99%

Encapsulation of Fennel and Basil Essential Oils in β-Cyclodextrin for Novel Biopesticide Formulation

Devrnja,

Anđelković,

Ljujić

et al. 2024

Biomolecules

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β-cyclodextrin (β-CD) is a good host for the encapsulation of fennel and basil essential oils (FEO and BEO, respectively) and the formation of inclusion complexes (ICs) using the co-precipitation method. According to the results of the GC/MS analysis conducted in this study, monoterpenes and monoterpenoids were the dominant chemical groups in total FEO, while in BEO, these two groups occurred along with sesquiterpenes and sesquiterpenoids. The presence of dominant compounds from both EOs was validated using the FT-IR spectra of ICs, which indicated successful complexation. Analyses conducted using SPME/GC-MS showed the continuous emission of volatiles over 24 h from both ICs. Under SEM, particles of both ICs appeared to have a rectangular or rhomboid morphology and few aggregates. The insecticidal properties of EOs and ICs with β-CD were tested on the Colorado potato beetle (CPB) as a model pest. The inclusion complex of β-CD with FEO altered the developmental dynamic and body mass of the CPB. The initial increase in the proteolytic activity of CPB larvae fed with potato plants sprayed with ICs was not maintained for long, and the proteolytic efficacy of treated larvae remained in line with that of the control larvae. Future investigations will focus on manipulating the volume of EOs used and the treatment duration for optimal efficacy and potential application.

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“…The energy gap (EHOMO-ELUMO) is an important stability scale with large energy gap values, indicating higher stability [15]. As shown in Table 3, the HOMO-LUMO energy gap in the water solvent is the most stable and less reactive conformation with a value of about 9.4775 eV for the PM3 method and 5.0262 eV for the B3LYP method.…”

Section: Homo-lumo Parametersmentioning

confidence: 99%

Theoretical Study of Complex Aspirin and Hydroxypropyl-β-cyclodextrin in Solvent Phase

Jayyinunnisya

Solihat

Sugimori

et al. 2022

J. Phys.: Conf. Ser.

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We estimate the configuration of complex ASA/HPCD in the gas phase by using PM3 and B3LYP methods. Some physical properties in the gas phase, such as complexation energy, deformation energy, dipole moment, etc., are calculated by using PM3 and B3LYP methods. We investigate the dependence of physical properties such as complexation energy, etc., on solvation by using PM3 and B3LYP methods with the PCM method. Complex ASA/HPCD becomes more stable than the dissociation state. The present results suggest that the effect of solvent can be increasing the energy complexation, LUMO energy, HOMO energy, HOMO-LUMO gap energy, electronic potential, and chemical hardness, whereas the electrophilicity decrease.

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DFT investigation of host–guest interactions between α-Terpineol and β-cyclodextrin

Cited by 18 publications

References 29 publications

On the Interactions of Melatonin/β-Cyclodextrin Inclusion Complex: A Novel Approach Combining Efficient Semiempirical Extended Tight-Binding (xTB) Results with Ab Initio Methods

On the Interactions of Melatonin/β-Cyclodextrin Inclusion Complex: A Novel Approach Combining Efficient Semiempirical Extended Tight-Binding (xTB) Results with Ab Initio Methods

Encapsulation of Fennel and Basil Essential Oils in β-Cyclodextrin for Novel Biopesticide Formulation

Theoretical Study of Complex Aspirin and Hydroxypropyl-β-cyclodextrin in Solvent Phase

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