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Inclusion of paraoxon, parathion, and methyl parathion into α-cyclodextrin: a GFN2-xTB multi-equilibrium quantum study

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Abstract

A new theoretical approach was recently addressed to predict cyclodextrin host–guest binding constants with the GFN2-xTB semiempirical quantum method. Within such a strategy, a set of starting supramolecular arrangements is automatically obtained through the UD-APARM software, and many optimized host–guest systems are used to obtain each binding constant. In the present work, within the scope of the multi-equilibrium treatment, we carried out a theoretical study concerning the host–guest systems formed with paraoxon (PRX), methyl-parathion (MPTN), and parathion (PTN) into α-cyclodextrin (α-CD), for which experimental data were addressed. Those guests correspond to pesticides in use, and their inclusion plays a role in remediation technology. The procedure for estimating binding constants for the host–guest system is discussed in terms of the ranges for the supramolecular parameters employed in exploring the GFN2-xTB Potential Energy Surface (PES). As a result, by investigating an unprecedented number of starting systems (3,076), we identified that proper exploration of the GFN2-xTB PES gives a reliable prediction of the binding constant in solution. Furthermore, with the study of different starting associations, for PTN/α-CD, we found an excellent linear correlation (R2 = 0.987) between GFN2-xTB data and experimental information, which, as in our previous study, supports the discussed methodology for application in predicting binding constants for CD-based host–guest systems.

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Acknowledgements

The authors thank Professor Hélio Ferreira dos Santos for the access to the NEQC (Núcleo de Estudos em Química Computacional, UFJF, Brazil) computer facility and also thanks the Laboratório Central de Computação Científica (LCC) da UFLA for providing additional computing resources. Furthermore, professor Cleber Paulo Andrada Anconi also thanks the Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) for supporting the Laboratório de Química Fundamental (LQF), where the research was conducted.

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  1. Institute of Natural Sciences, Department of Chemistry, University of Lavras, Lavras-MG, Lavras, MG, 37200-900, Brazil

    Jonathan Campos Marcelino, Carolina Lúcia Cardoso Ribeiro, Gleicy Teixeira, Erick Ferreira Lacerda & Cleber Paulo Andrada Anconi

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Contributions

JCM made the first calculations and provided the critical analysis of the data and the expansion of the scan to explore the quantum Potential Energy Surface (PES). Furthermore, JCM wrote the first version of the results and discussion section of the manuscript. CLCR, GT, and EFL obtained outcomes from quantum calculations and, in conjunction with JCM, worked with the vast amount of data to estimate the binding constants in aqueous media through the use of in-house routines (python 3) written by Cleber Anconi. Finally, CPAA supervised the research and wrote the manuscript along with inputs from the authors that revised the results and the first versions of the contribution.

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Correspondence to Cleber Paulo Andrada Anconi.

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Marcelino, J.C., Ribeiro, C.L.C., Teixeira, G. et al. Inclusion of paraoxon, parathion, and methyl parathion into α-cyclodextrin: a GFN2-xTB multi-equilibrium quantum study. J Incl Phenom Macrocycl Chem 103, 263–276 (2023). https://doi.org/10.1007/s10847-023-01192-3

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