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T3787

Sigma-Aldrich

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
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

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M E Everts et al.
Endocrinology, 136(10), 4454-4461 (1995-10-01)
We compared the uptake, metabolism, and biological effects of tetraiodothyroacetic acid (Tetrac) and rT3 in anterior pituitary cells with those of T4 and T3. Cells were isolated from adult male Wistar rats and cultured for 3 days in medium with
Mary K Luidens et al.
Vascular pharmacology, 52(3-4), 142-145 (2009-11-03)
In models of thyroid hormone-induced cardiac hypertrophy, there is appropriate, supportive angiogenesis. Twenty years ago in one such model, angiogenesis in response to the hormone was observed before hypertrophy developed and it is now understood that iodothyronines induce neovascularization in
Elevated serum tetrac in Graves disease: potential pathogenic role in thyroid-associated ophthalmopathy
Fernando R, et al.
The Journal of clinical endocrinology and metabolism, 102(3), 776-785 (2016)
Synthesis of new analogs of tetraiodothyroacetic acid (tetrac) as novel angiogenesis inhibitors for treatment of cancer
Rajabi M, et al.
Bioorganic & Medicinal Chemistry Letters, 28(7), 1223-1227 (2018)
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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