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T3787

Sigma-Aldrich

3,3′,5,5′-Tetraiodothyroacetic acid

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

Synonyme(s) :

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

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About This Item

Formule linéaire :
C14H8O4I4
Numéro CAS:
67-30-1
Poids moléculaire :
747.83
Numéro CE :
200-649-1
Numéro MDL:
MFCD00055932
Code UNSPSC :
12352106
ID de substance PubChem :
24900169
Nomenclature NACRES :
NA.77

product name

3,3′,5,5′-Tetraiodothyroacetic acid,

Solubilité

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

Niveau de qualité

200

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

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

Actions biochimiques/physiologiques

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.

Liaison

Thyroid hormone analog

Notes préparatoires

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300

Conseils de prudence

P264 - P301 + P310

Classification des risques

Acute Tox. 2 Oral

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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L-Thyroxine ≥98% (HPLC)

Sigma-Aldrich

T2376

L-Thyroxine

3,3′,5′-Triiodo-L-thyronine (Reverse T3) solution 100 μg/mL in methanol with 0.1N NH3, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

T-075

3,3′,5′-Triiodo-L-thyronine (Reverse T3) solution

Liothyronine United States Pharmacopeia (USP) Reference Standard

USP

1368008

Liothyronine

Liothyronine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1504

Liothyronine

L-Thyroxine (T4) solution 100 μg/mL in methanol with 0.1N NH3, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

T-073

L-Thyroxine (T4) solution

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)
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
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