A computational study of the inclusion of β-cyclodextrin and nicotinic acid: DFT, DFT-D, NPA, NBO, QTAIM, and NCI-RDG studies

Abstract

HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

Role of Noncovalent Interactions in N,P-Functionalized Luminescent Carbon Dots for Ultrasensitive Detection of Moisture in D2O: Boosting Visible-NIR Light Sensitivity

“…A comparison of the donor-acceptor interaction of N,P-CDs in water and acetone can be better visualized from the color-coded map of the donor-acceptor mapping (Figure S13). Finally, in contrast to the acetone medium (Figure S14), the much intense spikes (region corresponding to sign (λ2) ρ range of −0.035 to −0.015) are shown in RDG scatter plot in aqueous medium (Figure f) suggest that a strong H-bonding interaction is operative in between the model N,P-CDs and the water molecules. , …”

“…Finally, in contrast to the acetone medium (Figure S14), the much intense spikes (region corresponding to sign (λ2) ρ range of −0.035 to −0.015) are shown in RDG scatter plot in aqueous medium (Figure 3f) suggest that a strong H-bonding interaction is operative in between the model N,P-CDs and the water molecules. 58,59 Therefore, the above combined experimental and computational studies suggest that N,P-CDs can form a strong intermolecular hydrogen bonding with a polar protic solvent in two different ways, i.e., through the interactions of both protons and free oxygen coming from the surface functional groups (preferably surface state-II) of the N,P-CDs with the surrounding solvent medium. 60 Considering this exceptional noncovalent interaction of N,P-CDs with the surrounding medium, we can probe N,P-CDs as an optical sensor for moisture detection in useful costly solvents/media.…”

Three-in-one: exploration of co-encapsulation of cabazitaxel, bicalutamide and chlorin e6 in new mixed cyclodextrin-crosslinked polymers

“…Being the polymer a large molecule the computational DFT study has been conducted on a model consisting of the drug encapsulated by either 1 or 2bCyD units chosen as the pbCyD seems the most promising for the drug delivery purpose. In previous works, DFT methods have been extensively used to study the inclusion process of drugs in bCyD, [52][53][54][55][56] with the inclusion of the dispersion correction method. 57 In these works, calculations of the interaction energy (IE), binding free energy, natural bond orbital (NBO) and natural population analysis (NPA) were used to investigate the inclusion process, while the non-covalent interaction method (NCI) 58 or independent gradient model (IGM) analysis 49 were employed to study indepth the non-covalent interaction in the host guest complex.…”

Exploration of the Conformational Scenario for α-, β-, and γ-Cyclodextrins in Dry and Wet Conditions, from Monomers to Crystal Structures: A Quantum-Mechanical Study

“…In recent years, CDs have received much attention from the scientific community in a wider variety of applicative fields: in cosmetics [9][10][11] and in the food industry for odor and taste control [12][13][14][15][16]; in the environmental sector for heavy metal and pollutant removal [17][18][19][20][21][22]; and in the chemical/pharmaceutical sector as Drug Delivery Systems (DDS), i.e., high-performance carrier materials to deliver an established amount of drug to the targeted site within a specific period of time [6,[23][24][25][26][27][28]. In the last decade, many computational works have been conducted aiming at an atomistic interpretation of the inclusion and release processes for several different guest molecules [29][30][31][32][33][34][35][36], such as amino acids [37][38][39], vitamins [40], unsaturated acids [41], and antioxidants molecules [42]. The broad applicability of the CD molecule is due to its very versatile properties: it can form 1:1, 2:1, and 2:2 type complexes (even if other ratios are also possible [43]), adapting itself to the size and properties of the guest molecule, by either complexing the guest dimers of small molecules or forming host dimers with large guest molecules [44].…”

“…At present, systematic works exploring the potential energy surface of the cyclodextrin bare system, its dimerization reaction, and its interaction with a solvent have been mostly carried out at a molecular mechanic level by means of large molecular dynamics simulations, therefore exploring all the possible conformations of such flexible systems, without, however, reaching the accuracy of quantum mechanically based methods [39,48,[50][51][52]. On the other side, Density Functional Theory (DFT) studies are limited to arbitrarily selected conformations, in many cases neglecting the solvent, or at best using implicit (i.e., structureless) models [37,38,[40][41][42]49,[53][54][55][56][57][58]. However, a workflow combining these two techniques is still missing in the literature.…”