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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:
67-30-1
Molecular Weight:
747.83
NACRES:
NA.77
PubChem Substance ID:
24900169
UNSPSC Code:
12352106
EC Number:
200-649-1
MDL number:
MFCD00055932

Key Documents

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Product Name

3,3′,5,5′-Tetraiodothyroacetic acid,

InChI key

PPJYSSNKSXAVDB-UHFFFAOYSA-N

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)

SMILES string

OC(=O)Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1

solubility

acetone: soluble 19.60-20.40 mg/mL, clear, colorless (or faintly yellow to yellow)

storage temp.

−20°C

Quality Level

200

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This Item
T7650136883P8386
3,3′,5,5′-Tetraiodothyroacetic acid

Sigma-Aldrich

T3787

3,3′,5,5′-Tetraiodothyroacetic acid

3,3′,5-Triiodothyroacetic acid ≥90%

Sigma-Aldrich

T7650

3,3′,5-Triiodothyroacetic acid

4-Methyl-3,5-dinitrobenzoic acid 98%

Sigma-Aldrich

136883

4-Methyl-3,5-dinitrobenzoic acid

Phenylbutazone

Sigma-Aldrich

P8386

Phenylbutazone

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

solubility

acetone: soluble 19.60-20.40 mg/mL, clear, colorless (or faintly yellow to yellow)

solubility

-

solubility

methanol: soluble 250 mg/10 mL, clear, faintly yellow to yellow

solubility

ethanol: 50 mg/mL, clear, colorless to light yellow

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[1]
  • to study its effects on long-term potentiation (LTP) and long-term depression (LTD) in the dentate gyrus in urethane-anesthetized male rats[2]
  • to determine its influence on the actions of thyroid-stimulating hormone
  • thyroid-stimulating immunoglobulins in orbital fibroblast[3]

Biochem/physiol Actions

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.[4] It is a thyrointegrin receptor antagonist.[5] Tetrac prevents the binding of thyroid hormones.[6]
Studies in rats have reported that Tetrac may regulate TSH secretion under in vivo conditions1.

Other Notes

Thyroid hormone analog

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

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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Certificates of Analysis (COA)

Lot/Batch Number
0000454819
0000454819
0000432998
0000432998
0000415106

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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
Erik de Vrieze et al.
Endocrinology, 155(6), 2320-2330 (2014-04-04)
Allan-Herndon-Dudley syndrome (AHDS) is an inherited disorder of brain development characterized by severe psychomotor retardation. This X-linked disease is caused by mutations in the monocarboxylate transporter 8 (MCT8), an important thyroid hormone transporter in brain neurons. MCT8-knockout mice lack the
Waterborne exposure of zebrafish embryos to micromole concentrations of ioxynil and diethylstilbestrol disrupts thyrocyte development
Campinho MA and Power DM
Aquatic Toxicology (Amsterdam, Netherlands), 140, 279-287 (2013)
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