The role of the halogen bond in iodothyronine deiodinase: Dependence on chalcogen substitution in naphthyl‐based mimetics

Diego Cesario; Mariagrazia Fortino; Tiziana Marino; Francesca Nunzi; Nino Russo; Emilia Sicilia

doi:10.1002/jcc.25775

journal article Jan 25, 2019

The role of the halogen bond in iodothyronine deiodinase: Dependence on chalcogen substitution in naphthyl‐based mimetics

Diego Cesario Mariagrazia Fortino Tiziana Marino

Francesca Nunzi Nino Russo

Emilia Sicilia

Journal of Computational Chemistry Vol. 40 No. 8 pp. 944-951 · Wiley

View at Publisher Save 10.1002/jcc.25775

Abstract

The effects on the activity of thyroxine (T4) due to the chalcogen replacement in a series of peri‐substituted naphthalenes mimicking the catalytic function of deiodinase enzymes are computationally examined using density functional theory. In particular, T4 inner‐ring deiodination pathways assisted by naphthyl‐based models bearing two tellurols and a tellurol‐thiol pair in peri‐position are explored and compared with the analogous energy profiles for the naphthalene mimic having two selenols. The presence of a halogen bond (XB) in the intermediate formed in the first step and involved in the rate‐determining step of the reaction is assumed to facilitate the process increasing the rate of the reaction. The rate‐determining step calculated energy barrier heights allow rationalizing the experimentally observed superior catalytic activity of tellurium containing mimics. Charge displacement analysis is used to ascertain the presence and the role of the electron density charge transfer occurring in the rate‐determining step of the reaction, suggesting the incipient formation or presence of a XB interaction. © 2019 Wiley Periodicals, Inc.

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Details

Published: Jan 25, 2019
Vol/Issue: 40(8)
Pages: 944-951
License: View

Authors

D

Diego Cesario

Department of Chemistry and Pharmaceutical Sciences, Amsterdam Center for Multiscale Modeling Vrije Universiteit Amsterdam 1081 HV, Amsterdam The Netherlands; Department of Chemistry, Biology and Biotechnology University of Perugia I‐06123, Perugia Italy

M

Mariagrazia Fortino

Dipartimento di Chimica e Tecnologie Chimiche Università della Calabria I‐87030, Arcavacata di Rende Italy

T

Tiziana Marino

Dipartimento di Chimica e Tecnologie Chimiche Università della Calabria I‐87030, Arcavacata di Rende Italy

F

Francesca Nunzi

Department of Chemistry, Biology and Biotechnology University of Perugia I‐06123, Perugia Italy; Istituto di Scienze e Tecnologie Molecolari del CNR (ISTM‐CNR) I‐06123, Perugia Italy; Consortium for Computational Molecular and Materials Sciences (CMS)<sup>2</sup> I‐06123, Perugia Italy

N

Nino Russo

Dipartimento di Chimica e Tecnologie Chimiche Università della Calabria I‐87030, Arcavacata di Rende Italy

E

Emilia Sicilia

Dipartimento di Chimica e Tecnologie Chimiche Università della Calabria I‐87030, Arcavacata di Rende Italy

Funding

MIUR

Università della Calabria

Cite This Article

Diego Cesario, Mariagrazia Fortino, Tiziana Marino, et al. (2019). The role of the halogen bond in iodothyronine deiodinase: Dependence on chalcogen substitution in naphthyl‐based mimetics. Journal of Computational Chemistry, 40(8), 944-951. https://doi.org/10.1002/jcc.25775

The role of the halogen bond in iodothyronine deiodinase: Dependence on chalcogen substitution in naphthyl‐based mimetics

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