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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Paul J Davis et al.
Annual review of pharmacology and toxicology, 51, 99-115 (2010-09-28)
Plasma membrane integrin αvβ3 is a cell surface receptor for thyroid hormone at which nongenomic actions are initiated. L-thyroxine (T₄) and 3,3',5-triiodo-L-thyronine (T₃) promote angiogenesis and tumor cell proliferation via the receptor. Tetraiodothyroacetic acid (tetrac), a deaminated T₄ derivative, blocks
Tetrac and NDAT induce Anti-proliferation via Integrin alphavbeta3 in Colorectal Cancers with Different K-RAS Status
Chin YT, et al.
Frontiers in Endocrinology, 10, 130-130 (2019)
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)