A Halogen Bonding Perspective on Iodothyronine Deiodinase Activity

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Eric S Marsan, Craig A Bayse

Abstract

Iodothyronine deiodinases (Dios) are involved in the regioselective removal of iodine from thyroid hormones (THs). Deiodination is essential to maintain TH homeostasis, and disruption can have detrimental effects. Halogen bonding (XB) to the selenium of the selenocysteine (Sec) residue in the Dio active site has been proposed to contribute to the mechanism for iodine removal. Polybrominated diphenyl ethers (PBDEs) and polychlorinated biphenyls (PCBs) are known disruptors of various pathways of the endocrine system. Experimental evidence shows PBDEs and their hydroxylated metabolites (OH-BDEs) can inhibit Dio, while data regarding PCB inhibition are limited. These xenobiotics could inhibit Dio activity by competitively binding to the active site Sec through XB to prevent deiodination. XB interactions calculated using density functional theory (DFT) of THs, PBDEs, and PCBs to a methyl selenolate (MeSe-) arrange XB strengths in the order THs > PBDEs > PCBs in agreement with known XB trends. THs have the lowest energy C-X*-type unoccupied orbitals and overlap with the Se lp donor leads to high donor-acceptor energies and the greatest activation of the C-X bond. The higher energy C-Br* and C-Cl* orbitals similarly result in weaker d...Continue Reading

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Citations

Sep 23, 2020·Scientific Reports·Craig A BayseAlexis T Tran-Thompson
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Methods Mentioned

BETA
X-ray

Related Concepts

Immune complex
Bromine
Endocrine System
Iodine
Iodothyronine Deiodinase
Lipopolysaccharides
Ocular Orbit
Polychlorinated Biphenyls
Selenium
Thyroid Hormones

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