Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H8I4O4 |
| Molecular Weight | 747.8288 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1
InChI
InChIKey=PPJYSSNKSXAVDB-UHFFFAOYSA-N
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)
| Molecular Formula | C14H8I4O4 |
| Molecular Weight | 747.8288 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25628605 | https://www.ncbi.nlm.nih.gov/pubmed/19427201 | https://www.ncbi.nlm.nih.gov/pubmed/19381627 | https://www.drugbank.ca/drugs/DB01751
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25628605 | https://www.ncbi.nlm.nih.gov/pubmed/19427201 | https://www.ncbi.nlm.nih.gov/pubmed/19381627 | https://www.drugbank.ca/drugs/DB01751
3,3',5,5'-Tetraiodothyroacetic acid (Tetrac) is a deaminated analog of L-thyroxine (T4) that blocks the proangiogenesis actions of T4 and 3, 5, 3’-triiodo-L-thyronine as well as other growth factors at the cell surface receptor for thyroid hormone on integrin αvβ3. 3,3',5,5'-Tetraiodothyroacetic acid blocks the transcriptional activities directed by L-thyroxine (T4) and 3,5,3’-triiodo-L-thyronine (T3) at αvβ3, but, independently of T4 and T3, 3,3',5,5'-Tetraiodothyroacetic acid modulates transcription of cancer cell genes that are important to cell survival pathways, control of the cell cycle, angiogenesis (VEGFA, FGF), apoptosis, cell export of chemotherapeutic agents, and repair of double-strand DNA breaks. 3,3',5,5'-Tetraiodothyroacetic acid was found to perturb the angiogenesis process stimulated by VEGF (Vascular Endothelial Growth Factor) or FGF (Fibroblast Growth Factor) without influencing the preexisting blood vessels.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Low concentrations of bisphenol a suppress thyroid hormone receptor transcription through a nongenomic mechanism. | 2012-02-15 |
|
| Essential molecular determinants for thyroid hormone transport and first structural implications for monocarboxylate transporter 8. | 2010-09-03 |
|
| Active metabolism of thyroid hormone during metamorphosis of amphioxus. | 2010-07 |
|
| Human platelet aggregation and degranulation is induced in vitro by L-thyroxine, but not by 3,5,3'-triiodo-L-thyronine or diiodothyropropionic acid (DITPA). | 2010-06 |
|
| Thyroid hormones induce activation of rat hepatic stellate cells through increased expression of p75 neurotrophin receptor and direct activation of Rho. | 2010-05 |
|
| Tetraiodothyroacetic acid (tetrac) and nanoparticulate tetrac arrest growth of medullary carcinoma of the thyroid. | 2010-04 |
|
| Molecular aspects of thyroid hormone actions. | 2010-04 |
|
| Tetraiodothyroacetic acid and tetraiodothyroacetic acid nanoparticle effectively inhibit the growth of human follicular thyroid cell carcinoma. | 2010-03 |
|
| Mini-review: Cell surface receptor for thyroid hormone and nongenomic regulation of ion fluxes in excitable cells. | 2010-02-09 |
|
| Translational implications of nongenomic actions of thyroid hormone initiated at its integrin receptor. | 2009-12 |
|
| Modification of survival pathway gene expression in human breast cancer cells by tetraiodothyroacetic acid (tetrac). | 2009-11-01 |
|
| Thyroid hormone and angiogenesis. | 2009-10-08 |
|
| Tetraidothyroacetic acid (tetrac) and tetrac nanoparticles inhibit growth of human renal cell carcinoma xenografts. | 2009-10 |
|
| Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation. | 2009-09 |
|
| Radiosensitization of GL261 glioma cells by tetraiodothyroacetic acid (tetrac). | 2009-08-15 |
|
| Semisynthesis and pharmacological activities of Tetrac analogs: angiogenesis modulators. | 2009-06-15 |
|
| Molecular components underlying nongenomic thyroid hormone signaling in embryonic zebrafish neurons. | 2009-06-08 |
|
| L-Thyroxine vs. 3,5,3'-triiodo-L-thyronine and cell proliferation: activation of mitogen-activated protein kinase and phosphatidylinositol 3-kinase. | 2009-05 |
|
| Thyroid hormone-induced angiogenesis. | 2009-01 |
|
| Cytoplasm-to-nucleus shuttling of thyroid hormone receptor-beta1 (Trbeta1) is directed from a plasma membrane integrin receptor by thyroid hormone. | 2009 |
|
| Sensory neuron sodium current requires nongenomic actions of thyroid hormone during development. | 2008-11 |
|
| Stability indicating validated HPLC method for quantification of levothyroxine with eight degradation peaks in the presence of excipients. | 2008-08-06 |
|
| Metabolic effects of thyroid hormone derivatives. | 2008-02 |
|
| Resveratrol is pro-apoptotic and thyroid hormone is anti-apoptotic in glioma cells: both actions are integrin and ERK mediated. | 2008-01 |
|
| Novel function of the thyroid hormone analog tetraiodothyroacetic acid: a cancer chemosensitizing and anti-cancer agent. | 2008 |
|
| Tetraiodothyroacetic acid, a small molecule integrin ligand, blocks angiogenesis induced by vascular endothelial growth factor and basic fibroblast growth factor. | 2008 |
|
| Thyroid hormone is a MAPK-dependent growth factor for thyroid cancer cells and is anti-apoptotic. | 2007-02 |
|
| Molecular modeling of the thyroid hormone interactions with alpha v beta 3 integrin. | 2007-02 |
|
| Distribution patterns of small-molecule ligands in the protein universe and implications for origin of life and drug discovery. | 2007 |
|
| Pro-angiogenesis action of thyroid hormone and analogs in a three-dimensional in vitro microvascular endothelial sprouting model. | 2006-12 |
|
| Acting via a cell surface receptor, thyroid hormone is a growth factor for glioma cells. | 2006-07-15 |
|
| Proangiogenesis action of the thyroid hormone analog 3,5-diiodothyropropionic acid (DITPA) is initiated at the cell surface and is integrin mediated. | 2006-04 |
|
| Ligand binding at the transthyretin dimer-dimer interface: structure of the transthyretin-T4Ac complex at 2.2 Angstrom resolution. | 2005-10 |
|
| The proangiogenic action of thyroid hormone analogue GC-1 is initiated at an integrin. | 2005-09 |
|
| Integrin alphaVbeta3 contains a cell surface receptor site for thyroid hormone that is linked to activation of mitogen-activated protein kinase and induction of angiogenesis. | 2005-07 |
|
| Acetylation of nuclear hormone receptor superfamily members: thyroid hormone causes acetylation of its own receptor by a mitogen-activated protein kinase-dependent mechanism. | 2005-05-03 |
|
| T-Screen as a tool to identify thyroid hormone receptor active compounds. | 2005-02 |
|
| Thyroid hormone causes mitogen-activated protein kinase-dependent phosphorylation of the nuclear estrogen receptor. | 2004-07 |
|
| Proangiogenic action of thyroid hormone is fibroblast growth factor-dependent and is initiated at the cell surface. | 2004-06-11 |
|
| Disparate effects of thyroid hormone on actions of epidermal growth factor and transforming growth factor-alpha are mediated by 3',5'-cyclic adenosine 5'-monophosphate-dependent protein kinase II. | 2004-04 |
|
| Putative L-triiodothyronine receptors in the liver nuclei of mature tropical toad, Bufo melanostictus. | 2004-03-17 |
|
| Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs. | 2002-05 |
|
| In vitro free radical scavenging capacity of thyroid hormones and structural analogues. | 2001-07 |
|
| Thyroid hormone promotes serine phosphorylation of p53 by mitogen-activated protein kinase. | 2001-03-06 |
|
| Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy. | 2001-02 |
|
| Complex of rat transthyretin with tetraiodothyroacetic acid refined at 2.1 and 1.8 A resolution. | 2001 |
Patents
Sample Use Guides
Mice were treated with daily injection of tetrac (400 ng/g body weight) during the first postnatal week
Route of Administration:
Intravenous
RCC renal cell carcinoma (RCC) were grown in RPMI-1640 medium (Invitrogen, Grand Island, NY, USA) supplemented with 10% FCS (Atlanta Biologicals, Lawrenceville, GA, USA). Penicillin/streptomycin (1%) was present in both culture media. The cells were trypsinized, centrifuged, and the cell pellet was re-suspended in the corresponding media. Subsequently, 500 μl of the suspension (~50,000 cells) were transferred to each well of a 4-well glass slide, Chamber slide System (Nalge Nunc International, Naperville, IL, USA) and incubated for 24 h at 37˚C with 5% CO2 (Thermo Electron Corp., Forma Series II). The cells were treated with 20 μl of each free Tetrac tagged with Cy3 dye and PLGA-Tetrac tagged with Cy3 separately incubated (37˚C, 5% CO2) for around 2 h. After 2 h of incubation, the plates were taken out and washed several times with PBS and then fixed in 1% formaldehyde (Sigma), and mounted with the help of Vectashield (Vector Laboratories Inc, Burlingame, CA, USA.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:39:54 GMT 2025
by
admin
on
Mon Mar 31 19:39:54 GMT 2025
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| Record UNII |
PA7UX1FFYQ
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
485115
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FDA ORPHAN DRUG |
133100
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| Code System | Code | Type | Description | ||
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200-649-1
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C011126
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67-30-1
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PA7UX1FFYQ
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DTXSID5048186
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DB01751
Created by
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65552
Created by
admin on Mon Mar 31 19:39:54 GMT 2025 , Edited by admin on Mon Mar 31 19:39:54 GMT 2025
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