Non-covalent interactions between sertraline stereoisomers and 2-hydroxypropyl-β-cyclodextrin: a quantum chemistry analysis

Bautista-Renedo, Joanatan-Michael; Cuevas-Yáñez, Erick; Reyes-Pérez, Horacio; Vargas, Rubicelia; Garza, Jorge; González‐Rivas, Nelly

doi:10.1039/c9ra10218c

Cited by 8 publications

(15 citation statements)

References 39 publications

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“…Later, in 2010, it was compared with Glycam06 FF and defined as far less accurate [44]; the newest computational approaches and the increasing computational power shed new light on this abandoned carbohydrate FF. In 2020, an article applying the MM3 FF for the MD simulation of CD and sertraline was published [45]. According to our best knowledge, it is the only example of MM3 application in the CD MD simulations.…”

Section: Force Fields Dedicated To Cyclodextrinsmentioning

confidence: 99%

“…As a result, the application of such FFs is much more computationally expensive. As stated above, among all gathered from the articles in this literature review, there is only one in which MM3 FF is used [45]. These calculations are run with the Tinker code [47].…”

Section: Force Fields Dedicated To Cyclodextrinsmentioning

confidence: 99%

“…Implicit solvent models were developed for the QM calculations, which could have prevented their application to MD simulations. One interesting approach was represented in an article about the CD-sertraline complex [45], where, first, the MD output was optimized with the QM method DFT/PBE0/6-31G(d,p)., and, second, binding energies were calculated by performing single-point calculations with the COSMO model. A similar case was reported for the complex of CD with ginsenosides [58].…”

Section: Simulations Of CD Complexes In Water Environmentmentioning

confidence: 99%

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Application of Molecular Dynamics Simulations in the Analysis of Cyclodextrin Complexes

Mazurek

Szeleszczuk

Gubica

2021

IJMS

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Cyclodextrins (CDs) are highly respected for their ability to form inclusion complexes via host–guest noncovalent interactions and, thus, ensofance other molecular properties. Various molecular modeling methods have found their applications in the analysis of those complexes. However, as showed in this review, molecular dynamics (MD) simulations could provide the information unobtainable by any other means. It is therefore not surprising that published works on MD simulations used in this field have rapidly increased since the early 2010s. This review provides an overview of the successful applications of MD simulations in the studies on CD complexes. Information that is crucial for MD simulations, such as application of force fields, the length of the simulation, or solvent treatment method, are thoroughly discussed. Therefore, this work can serve as a guide to properly set up such calculations and analyze their results.

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Section: Force Fields Dedicated To Cyclodextrinsmentioning

confidence: 99%

Section: Force Fields Dedicated To Cyclodextrinsmentioning

confidence: 99%

Section: Simulations Of CD Complexes In Water Environmentmentioning

confidence: 99%

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Application of Molecular Dynamics Simulations in the Analysis of Cyclodextrin Complexes

Mazurek

Szeleszczuk

Gubica

2021

IJMS

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“…Lately, the interactions between antidepressant drugs and cyclodextrins were examined [22][23][24][25][26], mostly in order to gain the better water solubility of the drug [27][28][29], or to decrease its toxicity [30,31] or even for taste-masking [32]. One of the antidepressants, sertraline hydrochloride, belonging to the class of selective serotonin reuptake inhibitors (SSRIs) [33,34] and also tested as potential anti-Helicobacter pylori compound [35] has already been tested in the presence of β-cyclodextrin and the derivatives [36][37][38][39][40] inter alia in our laboratory [31,41,42].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results

Belica-Pacha

Daśko

Buko

et al. 2021

IJMS

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The interaction between sertraline hydrochloride (SRT) and randomly methylated β-cyclodextrin (RMβCD) molecules have been investigated at 298.15 K under atmospheric pressure. The method used—Isothermal Titration Calorimetry (ITC) enabled to determine values of the thermodynamic functions like the enthalpy (ΔH), the entropy (ΔS) and the Gibbs free energy (ΔG) of binding for the examined system. Moreover, the stoichiometry coefficient of binding (n) and binding/association constant (K) value have been calculated from the experimental results. The obtained outcome was compared with the data from the literature for other non-ionic βCD derivatives interacting with SRT and the enthalpy-entropy compensation were observed and interpreted. Furthermore, the connection of RMβCD with SRT was characterized by circular dichroism spectroscopy (CD) and complexes of βCD derivatives with SRT were characterized through the computational studies with the use of molecular docking (MD).

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“…Quite recently Bautista‐Renedo et al reported a detailed study about the interactions observed between β CD, and 2‐hydroxypropyl‐ β CD (HP‐ β CD), with sertraline (SRT) [23], which is an inhibitor of serotonin to relieve some depressant symptoms [24–27]. In this study, the CMD was coupled with some quantum chemistry methods to reveal the interactions that command on some host‐guest adducts.…”

Section: Introductionmentioning

confidence: 99%

Deformations of cyclodextrins and their influence to form inclusion compounds

Bautista-Renedo

Hernández‐Esparza

Cuevas-Yáñez

et al. 2021

Int J of Quantum Chemistry

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Deformations of the three most common cyclodextrins (α, β, and γ) were induced to form inclusion compounds with sertraline and abacavir. The deformations were obtained from classical molecular dynamics (CMD) using as starting point X‐ray structures. The molecular dynamics were performed in two ways, over the cyclodextrins with and without the presence of a guest. Two characteristic rings within these cyclodextrins were used to measure the distortions observed along with the molecular dynamics. A docking approach was used to build inclusion compounds over the structures obtained from CMD without the presence of sertraline or abacavir. Thus, we compared structures of inclusion compounds obtained from deformations induced by the presence of a guest or with intrinsic deformations exhibited by each cyclodextrin. After this step, each structure was optimized by the PBE0‐D3/6‐31G(d,p) method, and the electron density delivered by this method was used to perform the quantum theory of atoms in molecules approach to analyze intermolecular contacts between sertraline, or abacavir, and three cyclodextrins. From this procedure, we found that inclusion compounds obtained from X‐ray structures present the highest energies over the potential energy surface. Thus, for getting low‐lying energy structures of inclusion compounds, deformations on cyclodextrins are necessary.

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Non-covalent interactions between sertraline stereoisomers and 2-hydroxypropyl-β-cyclodextrin: a quantum chemistry analysis

Abstract: Inclusion compounds formed between sertraline stereoisomers and β-cyclodextrin, and 2-hydroxypropyl-β-cyclodextrin, were analyzed by using quantum chemistry methods.

Cited by 8 publications

References 39 publications

Application of Molecular Dynamics Simulations in the Analysis of Cyclodextrin Complexes

Application of Molecular Dynamics Simulations in the Analysis of Cyclodextrin Complexes

Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results

Deformations of cyclodextrins and their influence to form inclusion compounds

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