3,5,3’,5’-Tetraiodo Thyroacetic Acid

• CAT Number: R049770
• CAS Number: 67-30-1
• Molecular Formula: C14H8I4O4
• Molecular Weight: 747.832
• Purity: ≥95%
• Synonyms: 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetic Acid; [4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic Acid; 3,3’,5,5’-Tetraiodothyroacetic Acid; 3,5,3’,5’-Tetraiodothyroacetic Acid; Tetrac
• Target: Metabolic Enzyme/Protease
• Storage: Store at RT
• IUPAC Name: 2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid
• InChI: InChI=1S/C14H8I4O4/c15-8-4-7(5-9(16)13(8)21)22-14-10(17)1-6(2-11(14)18)3-12(19)20/h1-2,4-5,21H,3H2,(H,19,20)
• InChIKey: PPJYSSNKSXAVDB-UHFFFAOYSA-N
• SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(=O)O

3,5,3’,5’-Tetraiodo Thyroacetic Acid (CAS 67-30-1; Tetrac)  is a deaminated analog of L-thyroxine (T4). It prevents the pro-angiogenesis actions of T4 and 3,5,3′-triiodo-<sc style="color: rgb(102, 94, 88); font-family: Arial, Helvetica, sans-serif; orphans: 2; widows: 2;">L</sc>-thyronine. It is a thyrointegrin receptor antagonist. Tetrac prevents the binding of thyroid hormones.Studies in rats have reported that Tetrac may regulate TSH secretion under  in vivo conditions.

Reference

1. Bioorg Med Chem Lett. 2018 Apr 15;28(7):1223-1227. doi: 10.1016/j.bmcl.2018.02.045. Epub 2018 Feb 26.Synthesis of new analogs of tetraiodothyroacetic acid (tetrac) as novel angiogenesis inhibitors for treatment of cancer.Rajabi M(1), Yalcin M(2), Mousa SA(3).

 

In the angiogenesis process, integrins, which are members of a family of cell surface transmembrane receptors, play a critical role particularly in blood vessel formation and the local release of vascular growth factors. Thyroid hormones such as l-thyroxine (T4) and 3,5,3'-triiodo-l-thyronine (T3) promote angiogenesis and tumor cell proliferation via integrin αvβ3 receptor. At or near an arginine-glycine-aspartate (RGD) recognition site on the binding pocket of integrin αvβ3, tetraiodothyroacetic acid (tetrac, a deaminated derivative of T4) is a thyrointegrin receptor antagonist and blocks the actions of T3 and T4 as well as different growth factors-mediated angiogenesis. In this study, we synthesized novel tetrac analogs by modifying the phenolic moiety of tetrac and tested them for their anti-angiogenesis activity using a Matrigel plug model for angiogenesis in mice. Pharmacological activity results showed that tetrac can accommodate numerous modifications and maintain its anti-angiogenesis activity.


2.Chin, Yu-Tang, et al. "Tetrac and NDAT induce anti-proliferation via integrin αvβ3 in colorectal cancers with different k-RAS status." Frontiers in endocrinology 10 (2019): 130.