3,3’,5’-Triiodo-L-thyronine

• CAT Number: I012041
• CAS Number: 5817-39-0
• Molecular Formula: C15H12I3NO4
• Molecular Weight: 650.977
• Purity: ≥95%
• Synonyms: Reverse T3
• Target: Thyroid Hormone Receptor
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid
• InChI: InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1
• InChIKey: HZCBWYNLGPIQRK-LBPRGKRZSA-N
• SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I

3,3′,5′-Triiodo-L-thyronine(CAT: I012041), also known as reverse triiodothyronine (rT3), is a naturally occurring thyroid hormone derivative. It is derived from the conversion of thyroxine (T4) and is considered an inactive form of thyroid hormone. Unlike the biologically active form of thyroid hormone, triiodothyronine (T3), rT3 has a lower affinity for thyroid hormone receptors and does not exert the same physiological effects. rT3 is mainly produced in response to stress or during certain medical conditions, and its levels can serve as an indicator of altered thyroid function.

Reference

1. Steroids. 2009 Feb;74(2):270-6. doi: 10.1016/j.steroids.2008.11.014. Epub 2008
Nov 27.

Characterization of ligands for thyroid receptor subtypes and their interactions
with co-regulators.

Koury EJ(1), Pawlyk AC, Berrodin TJ, Smolenski CL, Nagpal S, Deecher DC.

Author information:
(1)Women/’s Health and Musculoskeletal Biology, Wyeth Research, RN3164, 500 Arcola
Road, Collegeville, PA 19426, United States.

Thyroid hormone receptors (TRs) are nuclear receptors that are activated by
thyroid hormone ligands and co-regulator proteins. Two receptor subtypes, TRalpha
and TRbeta, have been suggested to play a role in numerous physiological
functions. However, specificity of receptor subtype function and co-regulator
interaction is unclear due to the lack of TR subtype-specific ligands. Five TR
ligands were evaluated for their selectivity and interaction with the TR
subtypes. A multiplex assay was used to identify co-regulator peptide
interaction, and biochemical assays were used to characterize ligand-receptor
specificity. In the biochemical assay, rank order ligand potencies were similar
in the presence of co-activator peptides, SRC1-2 and SRC3-2, and the co-repressor
peptide, NCoR1-2, with T3 and Triac potencies greater in the presence of the
co-repressor. The potency of Tetrac was similar regardless of the co-regulator
used while T4 and rT3 demonstrated selectivity for TRalpha subtype. The rank
order among TR ligands at either receptor subtype in the biochemical assay
correlated with the multiplex assay. These assays can be used to identify new
ligands that can provide further insight into TR biology.