A Halogen Bonding Perspective on Iodothyronine Deiodinase Activity

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


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


Mar 1, 1979·Hormone and Metabolic Research = Hormon- Und Stoffwechselforschung = Hormones Et Métabolisme·K Sorimachi, H J Cahnmann
Dec 22, 1989·Science·M ParmentierG Vassart
Mar 1, 1994·Environmental Health Perspectives·J D McKinney, C L Waller
Jun 28, 2000·Toxicological Sciences : an Official Journal of the Society of Toxicology·I A MeertsA Brouwer
Sep 21, 2000·International Journal of Obesity and Related Metabolic Disorders : Journal of the International Association for the Study of Obesity·E RotiM Salvi
Jul 24, 2001·Chemistry : a European Journal·Pierangelo Metrangolo, Giuseppe Resnati
Apr 25, 2002·Journal of the American Chemical Society·Markéta L Munzarová, Roald Hoffmann
Nov 5, 2003·Environmental Health Perspectives·Arnold SchecterRobin Rosen
Apr 15, 2004·The Journal of Biological Chemistry·Therese EneqvistA Elisabeth Sauer-Eriksson
Jul 16, 2004·Toxicological Sciences : an Official Journal of the Society of Toxicology·Yoshihisa KatoMasakuni Degawa
May 18, 2005·Accounts of Chemical Research·Pierangelo MetrangoloGiuseppe Resnati
Jun 3, 2005·Clinical Medicine & Research·Muhammad Akmal SiddiqiKurt D Reed
Aug 30, 2006·Proceedings of the National Academy of Sciences of the United States of America·Aiwu ZhouRobin W Carrell
Oct 3, 2006·Journal of Molecular Modeling·Peter PolitzerJane S Murray
Oct 4, 2006·The Journal of Clinical Investigation·Antonio C Bianco, Brian W Kim
Dec 22, 2006·Environmental Science & Technology·Summer S StreetsDeborah L Swackhamer
Apr 12, 2007·Journal of Exposure Science & Environmental Epidemiology·Matthew Lorber
Jun 14, 2008·American Journal of Epidemiology·Jonathan ChevrierDana Boyd Barr
Mar 10, 2009·Environmental Health Perspectives·Heather M StapletonClaudia Gunsch
Nov 28, 2009·Best Practice & Research. Clinical Endocrinology & Metabolism·Elizabeth N Pearce, Lewis E Braverman
May 18, 2010·Mini Reviews in Medicinal Chemistry·P ZhouZ Shang
May 28, 2010·Inorganic Chemistry·Craig A Bayse, Erin R Rafferty
Jun 19, 2010·Environment International·Da Chen, Robert C Hale
Oct 14, 2010·Angewandte Chemie·Debasish Manna, Govindasamy Mugesh
Mar 3, 2011·Chemical Society Reviews·Emilio ParisiniGiancarlo Terraneo
May 7, 2011·Toxicological Sciences : an Official Journal of the Society of Toxicology·Pamela D NoyesHeather M Stapleton
May 14, 2011·Toxicological Sciences : an Official Journal of the Society of Toxicology·Craig M ButtHeather M Stapleton
May 21, 2011·Journal of Computational Chemistry·Mahmoud A A Ibrahim
Oct 4, 2011·Physical Chemistry Chemical Physics : PCCP·Stefano RendineMaurizio Sironi
Mar 22, 2012·Environmental Toxicology·C PellacaniL G Costa
Sep 5, 2012·The Journal of Clinical Investigation·Gregory A Brent
Nov 14, 2012·Journal of Medicinal Chemistry·Rainer WilckenFrank M Boeckler
Dec 12, 2012·Protein Science : a Publication of the Protein Society·Matthew R ScholfieldP Shing Ho
Dec 22, 2012·Chemical Communications : Chem Comm·Michal KolářAgnieszka K Bronowska
Jan 19, 2013·Journal of Chemical Theory and Computation·William L Jorgensen, Patric Schyman
Apr 12, 2013·Physical Chemistry Chemical Physics : PCCP·Sławomir J Grabowski
Sep 21, 2013·Environmental Science & Technology·Xiaoxiang WangHongxia Yu
Oct 5, 2013·Chemical Research in Toxicology·Craig M Butt, Heather M Stapleton
Oct 19, 2013·Journal of Chemical Information and Modeling·Suman SirimullaMahesh Narayan
Apr 1, 2012·ChemistryOpen·Lando P Wolters, F Matthias Bickelhaupt
Jul 9, 2014·Proceedings of the National Academy of Sciences of the United States of America·Ulrich SchweizerClemens Steegborn
Apr 9, 2015·Journal of Cancer Prevention·Oneyeol YangYoung Rok Seo
May 20, 2015·Environmental Science and Pollution Research International·Li JinhuiXiao Wenjing
May 26, 2015·Chemical Research in Toxicology·Simon C RobertsHeather M Stapleton
Sep 24, 2015·Journal of Molecular Endocrinology·Ulrich Schweizer, Clemens Steegborn
Nov 8, 2011·Journal of Chemical Theory and Computation·Samuel Genheden, Ulf Ryde
Jan 27, 2016·Chemical Reviews·Gabriella CavalloGiancarlo Terraneo
Feb 18, 2016·Chemical Reviews·Hui WangWei Jun Jin
May 20, 2016·Journal of Cheminformatics·Mathew R KoebelSuman Sirimulla
May 27, 2016·Angewandte Chemie·Santanu MondalGovindasamy Mugesh
Jun 30, 2016·Bioorganic & Medicinal Chemistry·Ignacio Soteras GutiérrezAlexander D MacKerell
Oct 7, 2016·The Science of the Total Environment·Shalini D SoechitramPieter J J Sauer
Jan 31, 2017·Molecular and Cellular Endocrinology·Ulrich SchweizerClemens Steegborn
Mar 3, 2017·Journal of Chemical Theory and Computation·Changwei WangYirong Mo
Mar 28, 2017·Biochemistry·Matthew R ScholfieldP Shing Ho
Aug 25, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lois MendezMahesh Narayan
Oct 4, 2017·Chemical Science·Craig C RobertsonLee Brammer
Nov 25, 2017·Critical Reviews in Toxicology·Peter MatthiessenLennart Weltje
Feb 10, 2018·Angewandte Chemie·Yuk-Cheung Chan, Ying-Yeung Yeung
Feb 13, 2018·Environmental Research·Anthony François, Jonathan Verreault
Feb 21, 2018·Environmental Health : a Global Access Science Source·Jan A MennigenAndrea C Gore
Mar 25, 2018·Endocrine Connections·Bilal B MughalBarbara A Demeneix
Jul 15, 2018·Journal of Molecular Endocrinology·Karen J OliveiraTania Maria Ortiga-Carvalho
Aug 4, 2018·International Journal of Environmental Research and Public Health·Elizabeth A GibsonPam Factor-Litvak
Oct 24, 2018·Journal of Toxicology and Environmental Health. Part B, Critical Reviews·David C DormanKatrina M Waters
Nov 30, 2018·Physical Chemistry Chemical Physics : PCCP·Timothy ClarkPeter Politzer
May 28, 2019·Expert Opinion on Drug Discovery·Paulo J CostaDiogo Vila-Viçosa
May 31, 2019·Environmental Science. Processes & Impacts·Wei-Ping QinJian-Qing Zhang
Jul 2, 2019·European Thyroid Journal·Josef Köhrle
Aug 25, 2019·Environmental Health : a Global Access Science Source·Sarah W CurtisMichele Marcus
Dec 19, 2019·Chemistry : a European Journal·Eric S Marsan, Craig A Bayse


Sep 23, 2020·Scientific Reports·Craig A BayseAlexis T Tran-Thompson
Oct 23, 2020·Journal of Labelled Compounds & Radiopharmaceuticals·Trevor FerrisEric O Aboagye

Methods Mentioned


Related Concepts

Immune complex
Endocrine System
Iodothyronine Deiodinase
Ocular Orbit
Polychlorinated Biphenyls
Thyroid Hormones

Trending Feeds


Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Alzheimer's Disease: MS4A

Variants within the membrane-spanning 4-domains subfamily A (MS4A) gene cluster have recently been implicated in Alzheimer's disease in genome-wide association studies. Here is the latest research on Alzheimer's disease and MS4A.

Pediculosis pubis

Pediculosis pubis is a disease caused by a parasitic insect known as Pthirus pubis, which infests human pubic hair, as well as other areas with hair including eye lashes. Here is the latest research.

Rh Isoimmunization

Rh isoimmunization is a potentially preventable condition that occasionally is associated with significant perinatal morbidity or mortality. Discover the latest research on Rh Isoimmunization here.

Genetic Screens in iPSC-derived Brain Cells

Genetic screening is a critical tool that can be employed to define and understand gene function and interaction. This feed focuses on genetic screens conducted using induced pluripotent stem cell (iPSC)-derived brain cells. It also follows CRISPR-Cas9 approaches to generating genetic mutants as a means of understanding the effect of genetics on phenotype.

Enzyme Evolution

This feed focuses on molecular models of enzyme evolution and new approaches (such as adaptive laboratory evolution) to metabolic engineering of microorganisms. Here is the latest research.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Pharmacology of Proteinopathies

This feed focuses on the pharmacology of proteinopathies - diseases in which proteins abnormally aggregate (i.e. Alzheimer’s, Parkinson’s, etc.). Discover the latest research in this field with this feed.

Alignment-free Sequence Analysis Tools

Alignment-free sequence analyses have been applied to problems ranging from whole-genome phylogeny to the classification of protein families, identification of horizontally transferred genes, and detection of recombined sequences. Here is the latest research.