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Stability constants of Cu(II)-piroxicam complexes in solution: a DFT study

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Abstract

Knowledge of coordination modes of metal and pharmaceuticals are crucial for gaining understanding of the chemical mechanisms underlying their biological activity, in particular for systems where there is a synergism based on the fact that complexes can provide enhanced activity of the drug with fewer side effects. Quantum chemistry calculations represent a unique and complementary approach to experimental methods to understand the thermodynamics of reactions in terms of structural details of the participating species. Here, the coordination modes between Cu(II) and piroxicam and their stability constants were studied, by means of DFT molecular modeling, in gas phase and in solution (water and ethanol) at the RevTPSS/def-SVP and (SMD- and CPCM-RevTPSS)/def-SVP levels of theory, respectively. Octahedral bidentate geometries are found to be the more stable, likely due to the chelate effect. Thermodynamic results on the stability of the formed complexes revealed that complexation is favored in ethanol. The calculated logK s with the (SMD-RevTPSS)/def-SVP level of theory are in better agreement to the experimental values than (CPCM-RevTPSS)/def-SVP results.

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Acknowledgments

L. G. L. -O acknowledges Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México, for the scholarship to pursue her major in Chemistry. This research was conducted under grants PAPIIT Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México IN222914 and PIAPI Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México C23. Authors acknowledge Red Mexicana de Fisicoquímica Teórica (CONACyT) under grants 253498 and 271361, for supporting this investigation. We gratefully acknowledge the generous computing time provided by Dirección General de Cómputo y de Tecnologías de Información y Comunicación, Universidad Nacional Autónoma de México through the grants SC16-1-IR-100 and SC16-1-IR-112.

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  1. Centro de Investigaciones Teóricas, Facultad de Estudios Superiores Cuautitlan, Universidad Nacional Autónoma de México, Ave 1º de Mayo s/n, 54740, Cuautitlan Izcalli, Estado de México, México

    Lydia G. Ledesma-Olvera & Esther Agacino-Valdés

  2. Laboratorio de Fisicoquímica Analítica, Unidad de Investigación Multidisciplinaria, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Carretera Cuautitlán-Teoloyucan Km. 2.5, 54714, Cuautitlan Izcalli, Estado de México, México

    Rodolfo Gómez-Balderas

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  1. Lydia G. Ledesma-Olvera
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  2. Esther Agacino-Valdés
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Correspondence to Esther Agacino-Valdés.

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Published as part of the special collection of articles “Festschrift in honour of A. Vela.”

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Ledesma-Olvera, L.G., Agacino-Valdés, E. & Gómez-Balderas, R. Stability constants of Cu(II)-piroxicam complexes in solution: a DFT study. Theor Chem Acc 135, 241 (2016). https://doi.org/10.1007/s00214-016-1996-4

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