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Regioselective Deiodination of Iodothyronamines, Endogenous Thyroid Hormone Derivatives, by Deiodinase Mimics

Mondal, Santanu and Mugesh, Govindasamy (2014) Regioselective Deiodination of Iodothyronamines, Endogenous Thyroid Hormone Derivatives, by Deiodinase Mimics. In: CHEMISTRY-A EUROPEAN JOURNAL, 20 (35, SI). pp. 11120-11128.

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Official URL: http://dx.doi.org/ 10.1002/chem.201403248


Iodothyronine deiodinases (IDs) are mammalian selenoenzymes that play an important role in the activation and inactivation pound of thyroid hormones. It is known that iodothyronamines (TnAMs), produced by the decarboxylation of thyroid hormones, act as substrates for deiodinases. To understand whether decarboxylation alters the rate and/or regioselectivity of deiodination by using synthetic deiodinase mimics, we studied the deiodination of different iodothyronamines. The triiodo derivative 3,3',5-triiodothyronamine (T3AM) is deiodinated at the inner ring by naphthyl-based deiodinase mimics, which is similar to the deiodination of 3,3',5-triiodothyronine (T3). However, T3AM under-goes much slower deiodination than T3. Detailed experimental and theoretical investigations suggest that T3AM forms a weaker halogen bond with selenium donors than T3. Kinetic studies and single-crystal X-ray structures of T3 and T3AM reveal that intermolecular I center dot center dot center dot I interactions may play an important role in deiodination. The formation of hydrogen- and halogen-bonding assemblies, which leads to the formation of a dimeric species of T3 in solution, facilitates the interactions between the selenium and iodine atoms. In contrast, T3AM, which does not have I center dot center dot I interactions, undergoes much slower deiodination.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 10 Oct 2014 09:12
Last Modified: 10 Oct 2014 09:12
URI: http://eprints.iisc.ac.in/id/eprint/49975

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