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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H9I2NO3
Molecular Weight 432.9816
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIIODOTYROSINE

SMILES

N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(O)=O

InChI

InChIKey=NYPYHUZRZVSYKL-ZETCQYMHSA-N
InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1

HIDE SMILES / InChI

Description

Diiodotyrosine (DIT) is a regulatory ligand for thyroid peroxidase, enzyme, which is involved in the production of thyroxine (T4) and triiodothyronine (T3), the thyroid hormones. Diiodotyrosine was proposed to be a new marker of leukocyte phagocytic activity in sepsis and severe infections.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Inhibition of thyroglobulin iodination catalyzed by thyroid peroxidase was observed when free diiodotyrosine concentration was higher than 5 muM. This inhibition was competitive, suggesting that free diiodotyrosine interacts with the substrate site(s) of thyroid peroxidase. Free diiodotyrosine also competively inhibited iodide peroxidation to I2. 2. Free diiodotyrosine, when incubated with thyroid peroxidase in the absence of iodide was recovered unmodified; in the presence of iodide an exchange reaction was observed between the iodine atoms present in the diiodotyrosine molecule and iodide present in the medium. Using 14C-labelled diiodotyrosine, 14C-labelled non-iodinated products were also observed, showing that deiodination occurred as a minor degradation pathway.