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T3787

Sigma-Aldrich

3,3′,5,5′-Tetraiodothyroacetic acid

≥98% (TLC), powder, thyrointegrin receptor antagonist

Sinónimos:

4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetic acid, Tetrac

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About This Item

Fórmula lineal:
C14H8O4I4
Número de CAS:
67-30-1
Peso molecular:
747.83
EC Number:
200-649-1
MDL number:
MFCD00055932
UNSPSC Code:
12352106
PubChem Substance ID:
24900169
NACRES:
NA.77

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

200

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

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.
Studies in rats have reported that Tetrac may regulate TSH secretion under in vivo conditions1.

Linkage

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
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
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
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)
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