Tetrac

Modify Date: 2024-01-02 19:02:12

Tetrac Structure
Tetrac structure
 Common Name Tetrac
CAS Number 67-30-1 Molecular Weight 747.82900
Density 2.727g/cm3 Boiling Point 544.8ºC at 760 mmHg
Molecular Formula C14H8I4O4 Melting Point 230 °C
MSDS Chinese USA Flash Point 283.3ºC
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Tetrac


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].

 Names

Name 2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetic acid
Synonym More Synonyms

 Tetrac 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
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
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

3,5-Diiodothyroacetic Acid structure

3,5-Diiodothyro...

CAS#:1155-40-4

~90%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: Bridoux, Alexandre; Khan, Riaz A.; Chen, Celei; Cheve, Gwenael; Cui, Huadong; Dyskin, Evgeny; Yasri, Aziz; Mousa, Shaker A. Journal of Enzyme Inhibition and Medicinal Chemistry, 2011 , vol. 26, # 6 p. 871 - 882
(4-hydroxy-3,5-dinitro-phenyl)-acetic acid ethyl ester structure

(4-hydroxy-3,5-...

CAS#:83799-60-4

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: US2011/105482 A1, ;
[4-(4-methoxy-phenoxy)-3,5-dinitro-phenyl]-acetic acid ethyl ester structure

[4-(4-methoxy-p...

CAS#:861065-72-7

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: US2011/105482 A1, ;
Mequinol structure

Mequinol

CAS#:150-76-5

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: US2011/105482 A1, ;
ethyl 3,5-diiodo-4-(4-methoxyphenoxy)phenylacetate structure

ethyl 3,5-diiod...

CAS#:85828-82-6

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: Biochemical Journal, , vol. 63, p. 601,603
ethyl 2-(3,5-diamino-4-(4-methoxyphenoxy)phenyl)acetate structure

ethyl 2-(3,5-di...

CAS#:101588-11-8

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: US2011/105482 A1, ;
1-(4-chloromethyl-2,6-diiodo-phenoxy)-4-methoxy-benzene structure

1-(4-chlorometh...

CAS#:860687-73-6

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: Biochemical Journal, , vol. 50, p. 438
[3,5-diiodo-4-(4-methoxy-phenoxy)-phenyl]-acetonitrile structure

[3,5-diiodo-4-(...

CAS#:855937-68-7

~%

Tetrac Structure

Tetrac

CAS#:67-30-1

Literature: Biochemical Journal, , vol. 50, p. 438

 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%

 Articles28

More 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...

 Synonyms

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
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