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T3787

Sigma-Aldrich

3,3′,5,5′-Tetraiodothyroacetic acid

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

Sinônimo(s):

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

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About This Item

Fórmula linear:
C14H8O4I4
Número CAS:
67-30-1
Peso molecular:
747.83
Número CE:
200-649-1
Número MDL:
MFCD00055932
Código UNSPSC:
12352106
ID de substância PubChem:
24900169
NACRES:
NA.77

product name

3,3′,5,5′-Tetraiodothyroacetic acid,

solubilidade

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

Nível de qualidade

200

temperatura de armazenamento

−20°C

cadeia de caracteres 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)

chave InChI

PPJYSSNKSXAVDB-UHFFFAOYSA-N

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Ligação

Thyroid hormone analog

Nota de preparo

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.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H300

Declarações de precaução

P264 - P301 + P310

Classificações de perigo

Acute Tox. 2 Oral

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “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 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

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)
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
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)
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