T3787
3,3′,5,5′-Tetraiodothyroacetic acid
≥98% (TLC), powder, thyrointegrin receptor antagonist
Synonym(s):
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetic acid, Tetrac
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About This Item
Linear Formula:
C14H8O4I4
CAS Number:
Molecular Weight:
747.83
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352106
EC Number:
200-649-1
MDL number:
Quality level:
Product Name
3,3′,5,5′-Tetraiodothyroacetic acid,
solubility
acetone: soluble 19.60-20.40 mg/mL, clear, colorless (or faintly yellow to yellow)
Quality Level
storage temp.
−20°C
SMILES string
OC(=O)Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1
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)
InChI key
PPJYSSNKSXAVDB-UHFFFAOYSA-N
Application
3,3′,5,5′-Tetraiodothyroacetic acid has been used:
- as a positive control to study the effects of ioxynil (IOX)
- diethylstilbestrol (DES) exposure on zebrafish embryos
- to study its effects on long-term potentiation (LTP) and long-term depression (LTD) in the dentate gyrus in urethane-anesthetized male rats
- to determine its influence on the actions of thyroid-stimulating hormone
- thyroid-stimulating immunoglobulins in orbital fibroblast
Biochem/physiol Actions
Studies in rats have reported that Tetrac may regulate TSH secretion under in vivo conditions1.
3,3′,5,5′-Tetraiodothyroacetic acid (Tetrac) is a deaminated analog of L-thyroxine (T4). It prevents the pro-angiogenesis actions of T4 and 3,5,3′-triiodo-L-thyronine. It is a thyrointegrin receptor antagonist. Tetrac prevents the binding of thyroid hormones.
Preparation Note
3,3′,5,5′-Tetraiodothyroacetic acid is soluble in acetone at 19.60 - 20.40 mg/ml and yields a clear, faint yellow to yellow solution.
Other Notes
Thyroid hormone analog
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 2 Oral
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Shaker A Mousa et al.
Angiogenesis, 11(2), 183-190 (2007-12-18)
Thyroid hormone has been recently shown to induce tumor growth and angiogenesis via a plasma-membrane hormone receptor on integrin alphaVbeta3. The receptor is at or near the Arg-Gly-Asp (RGD) recognition site on the integrin that is important to extracellular matrix
The Effects of Intra-hippocampal L-thyroxine Infusion on Long-term Potentiation and Long-term Depression: A Possible Role for the avb3 Integrin Receptor
Bitiktas S, et al.
Journal of Neuroscience Research (2016)
M Yalcin et al.
The Journal of clinical endocrinology and metabolism, 95(4), 1972-1980 (2010-02-06)
Tetraiodothyroacetic acid (tetrac) blocks angiogenic and tumor cell proliferation actions of thyroid hormone initiated at the cell surface hormone receptor on integrin alphavbeta3. Tetrac also inhibits angiogenesis initiated by vascular endothelial growth factor and basic fibroblast growth factor. We tested