title: Deiodination of thyroid hormones by iodothyronine deiodinase mimics: does an increase in the reactivity alter the regioselectivity?
abstract: Organoselenium compounds as functional mimics of iodothyronine deiodinase are described. The naphthyl-based compounds having two selenol groups are remarkably efficient in the inner-ring deiodination of thyroxine. The introduction of a basic amino group in close proximity to one of the selenol moieties enhances the deiodination. This study suggests that an increase in the nucleophilic reactivity of the conserved Cys residue at the active site of deiodinases is very important for effective deiodination.
authors.affiliation: Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India.
authors.forename: Debasish
authors.initials: D
authors.lastname: Manna
authors.forename: Govindasamy
authors.initials: G
authors.lastname: Mugesh
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D054879:Halogenation; D007453:Iodide Peroxidase / Q000737:chemistry / Q000378:metabolism*; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013963:Thyroid Hormones / Q000737:chemistry* / Q000378:metabolism
chemical_list: D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; D013963:Thyroid Hormones; D007453:Iodide Peroxidase