Tetrac

Names

[ CAS No. ]:
67-30-1

[ Name ]:
Tetrac

[Synonym ]:
5-diiodophenoxy)-3
Thyroacetic acid,3,3',5,5'-tetraiodo
3,5-Diiodo-4-(4-hydroxy-3,5-diiodophenoxy)benzeneacetic acid
Tetrac
MFCD00055932
[4-(4-hydroxy-3
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenylacetic acid
Benzeneacetic acid,3,5-diiodo-4-(4-hydroxy-3,5-diiodophenoxy)
3,3',5,5'-TETRAIODOTHYROACETIC ACID
Tetraiodothyroacetic acid
Acide 3,5,3',5'-tetraiodothyroacetique [French]
5-diiodophenyl] acetic acid
EINECS 200-649-1

Biological Activity

[Description]:

Tetrac (Tetraiodothyroacetic acid), a deaminated analogue of L-thyroxine (T4), and is a thyrointegrin receptor antagonist. Tetrac blocks the actions of T3 and T4 as well as different growth factors-mediated angiogenesis. Tetra also has anticancer activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

[In Vitro]

Tetrac (0.01-1 μM; 2-6 d) induces anti-proliferation in HT-29 and HCT116 cells with different K-RAS status[3]. Tetrac (0.1 μM; 30 min) inhibits activation of ERK1/2 in HT-29 and HCT116 cells[3]. Tetrac (0.1 μM; 24 h) inhibits expression of CCND1 and c-Myc, but promotes expression of CASP2 and THBS1[3]. Cell Proliferation Assay[3] Cell Line: HT-29 and HCT116 cells Concentration: 0.01, 0.1, 1 μM Incubation Time: 0, 2, 4, 6 days Result: Induced anti-proliferation of K-RAS wild-type colorectal cancer cells. Western Blot Analysis[3] Cell Line: HT-29 and HCT116 cells Concentration: 0.1 μM Incubation Time: 30 min Result: Inhibited constitutively activated ERK1/2, and this inhibition can remove by anti-integrin αvβ3 antibody pretreatment.

[In Vivo]

Tetrac (35 μg; p.o. for 40 days) inhibits tumor inoculation, growth and integrin expression in mice[4]. Animal Model: Wild-type male Balb/C mice aged 8 weeks are inoculated with 102B16F10 or B16LS9 cells[4] Dosage: 35 μg per day Administration: P.o. (added to the drinking water) daily for 40 days Result: Delayed the onset of ocular melanoma. Reduced the S-100 and integrin staining level in the B16F10 mice model.

[References]

[1]. Schmohl KA, et, al. Tetrac as an anti-angiogenic agent in cancer. Endocr Relat Cancer. 2019 Jun 1; 26(6):R287-R304.

[2]. Davis PJ, et, al. Nongenomic Actions of Thyroid Hormone: the Integrin Component. Physiol Rev. 2020 Jun 25.

[3]. Chin YT, et, al. Tetrac and NDAT Induce Anti-proliferation via Integrin αvβ3 in Colorectal Cancers With Different K-RAS Status. Front Endocrinol (Lausanne). 2019 Mar 12; 10:130.

[4]. Ashur-Fabian O, et, al. Tetrac Delayed the Onset of Ocular Melanoma in an Orthotopic Mouse Model. Front Endocrinol (Lausanne). 2019 Jan 8; 9:775.

[5]. Rajabi M, et, al. Synthesis of new analogs of tetraiodothyroacetic acid (tetrac) as novel angiogenesis inhibitors for treatment of cancer. Bioorg Med Chem Lett. 2018 Apr 15;28(7):1223-1227.

Chemical & Physical Properties

[ Density]:
2.727g/cm3

[ Boiling Point ]:
544.8ºC at 760 mmHg

[ Melting Point ]:
230 °C

[ Molecular Formula ]:
C₁₄H₈I₄O₄

[ Molecular Weight ]:
747.82900

[ Flash Point ]:
283.3ºC

[ Exact Mass ]:
747.66000

[ PSA ]:
66.76000

[ LogP ]:
5.23000

[ Index of Refraction ]:
1.801

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
28

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1/PG 1

[ RTECS ]:
CY1585800

[ Hazard Class ]:
6.1

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Tetraiodothyroacetic acid-tagged liposomes for enhanced delivery of anticancer drug to tumor tissue via integrin receptor

J. Control. Release 164(2) , 213-20, (2012)

Nanoparticles have demonstrated potential for promoting drug delivery to tumor sites and enhancing uptake. Here, we report tetraiodothyroacetic acid (tetrac) as a promising new targeting moiety for de...

Tetraiodothyroacetic acid and tetraiodothyroacetic acid nanoparticle effectively inhibit the growth of human follicular thyroid cell carcinoma.

Thyroid 20(3) , 281-6, (2010)

Tetraiodothyroacetic acid (tetrac) is a deaminated analogue of L-thyroxine that blocks the actions of L-thyroxine and 3,5,3'-triiodo-L-thyronine at the cell surface receptor for thyroid hormone on int...

Tetraiodothyroacetic acid and its nanoformulation inhibit thyroid hormone stimulation of non-small cell lung cancer cells in vitro and its growth in xenografts.

Lung Cancer 76(1) , 39-45, (2012)

Thyroid hormone stimulates cell proliferation of several types of cancers and stimulates cancer-relevant angiogenesis. In the present study, we investigated the proliferative effect of thyroid hormone...

Related Compounds

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