Document Type

Article

Publication Date

2023

DOI

10.1002/slct.202300781

Publication Title

ChemistrySelect

Volume

8

Issue

24

Pages

e202300781 (1-8)

Abstract

Halogen bonding (XB) is a potential mechanism for the inhibition of the thyroid-activating/deactivating iodothyronine deiodinase family of selenoproteins through interactions with halogenated endocrine disrupting compounds (EDCs). Trends in XB interactions were examined using density functional theory for a series of polyhalogenated dibenzo-1,4-dioxins, biphenyls, and other EDCs with methylselenolate, a simple model of the Dio active site selenocysteine. The strengths of the interactions depend upon the halogen (Br>Cl), the degree of substitution, and the position of the acceptor. In terms of donor-acceptor energies, interactions at the meta position are often the strongest, suggesting a link to the topology of THs, especially for outer-ring deiodination of thyroxine, which occurs at a meta iodine, and produces the active TH. However, relationships between XB interaction strengths and potential for Dio inhibition should be made in the context of the binding to the active sites, the topology of which are not fully characterized.

Rights

© 2023 The Author.

This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Data Availability

Article states: The data that support the findings of this study are available from the corresponding author upon reasonable request.

Original Publication Citation

Bayse, C. A. (2023). Halogen bonding interactions of haloaromatic endocrine disruptors and the potential for inhibition of iodothyronine deiodinases. ChemistrySelect 8(24), 1-8, Article e202300781. https://doi.org/10.1002/slct.202300781

ORCID

0000-0002-3490-576X (Bayse)

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