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3,3'-Diiodo-L-thyronine

Cat No.:V38001 Purity: ≥98%
3,3'-Diiodo-L-thyronine (3,3'-T2) is an endogenously produced metabolite of thyroid hormone.
3,3'-Diiodo-L-thyronine
3,3'-Diiodo-L-thyronine Chemical Structure CAS No.: 4604-41-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of 3,3'-Diiodo-L-thyronine:

  • 3,3'-Diiodo-L-thyronine-13C6 (3,3'-T2-13C6)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
3,3'-Diiodo-L-thyronine (3,3'-T2) is an endogenously produced metabolite of thyroid hormone. 3,3'-Diiodo-L-thyronine significantly enhances COX activity.
3,3'-Diiodo-L-thyronine (CAS 4604-41-5), also known as 3,3'-T2 or T2, is a naturally occurring iodinated derivative of the thyroid hormone family and a metabolite of thyroid hormone. With the molecular formula C₁₅H₁₃I₂NO₄ and a molecular weight of 525.08 g/mol, this compound is structurally related to triiodothyronine (T3) and thyroxine (T4), containing two iodine atoms on the inner rings of the thyronine backbone. T2 is derived enzymatically from triiodothyronine isoforms T3 and reverse T3. It is studied for its rapid metabolic effects and potential therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
3,3'-Diiodo-L-thyronine targets various cellular processes involved in metabolism, including mitochondrial function and energy expenditure. It has been shown to significantly enhance cytochrome c oxidase (COX) activity, which is a key enzyme in the mitochondrial electron transport chain. By enhancing COX activity, T2 can increase mitochondrial respiration and ATP production. The compound also affects lipid metabolism, promoting fatty acid oxidation and reducing lipid accumulation. These effects are mediated through both genomic and non-genomic mechanisms.
ln Vitro
3,3'-Diiodo-L-thyronine (3,3'-T2; 1 μM; 30 minutes) increases COX activity considerably [2]. The maximum effect is achieved at 1 μM of 3,3'-diiodo-L-thyronine [2]. T3 and rT3 are further broken down to create 3,3'-Diiodo-L-thyronine [3].
In vitro, 3,3'-Diiodo-L-thyronine has been shown to significantly enhance COX activity in various cell types. It also stimulates mitochondrial respiration and increases the expression of genes involved in lipid metabolism. The compound has been reported to have anti-obesity effects by promoting fatty acid oxidation and reducing lipid accumulation. In addition, T2 has been shown to have antioxidant properties, protecting cells from oxidative stress.
ln Vivo
In vivo, 3,3'-Diiodo-L-thyronine has been studied for its metabolic effects in animal models. Administration of T2 has been shown to reduce body weight and fat mass in obese animals. It also improves lipid profiles and reduces hepatic steatosis. The compound's effects on metabolism are rapid and occur at doses that do not cause the typical thyrotoxic side effects associated with T3 and T4. These findings suggest that T2 may have therapeutic potential for the treatment of obesity and metabolic disorders.
Enzyme Assay
In vitro enzyme assays for 3,3'-Diiodo-L-thyronine involve measuring its effect on COX activity. The assay is performed using mitochondrial preparations or purified COX enzyme. The enzyme is incubated with the substrate cytochrome c and varying concentrations of T2. The oxidation of cytochrome c is measured spectrophotometrically, and the effect of T2 on the reaction rate is determined. The compound's effect on other mitochondrial enzymes can also be assessed.
Cell Assay
In vitro cellular experiments for 3,3'-Diiodo-L-thyronine are performed using various cell lines, including hepatocytes and adipocytes. Cells are treated with varying concentrations of T2, and the effects on mitochondrial respiration, lipid metabolism, and gene expression are assessed. Mitochondrial respiration is measured using a Seahorse analyzer. Lipid accumulation is assessed by Oil Red O staining. Gene expression is measured by qPCR.
Animal Protocol
In vivo animal studies for 3,3'-Diiodo-L-thyronine are conducted using mouse or rat models of obesity and metabolic syndrome. The compound is administered via oral gavage or intraperitoneal injection. Body weight, food intake, and metabolic parameters such as glucose, insulin, and lipid levels are measured. The effects on liver and adipose tissue are assessed by histology and gene expression analysis. The compound's safety and tolerability are also assessed.
ADME/Pharmacokinetics
The pharmacokinetic properties of 3,3'-Diiodo-L-thyronine are characterized by its rapid absorption and distribution. The compound has a short half-life in circulation, as it is rapidly metabolized and cleared. It is primarily metabolized in the liver and excreted via the biliary and renal routes. The compound's pharmacokinetic profile supports its use in acute in vivo studies.
Toxicity/Toxicokinetics
The toxicity profile of 3,3'-Diiodo-L-thyronine is considered to be favorable compared to T3 and T4. At therapeutic doses, T2 does not cause the typical thyrotoxic side effects associated with T3 and T4, such as tachycardia and increased metabolic rate. However, high doses may lead to thyroid hormone-like effects. Standard toxicology studies would be required to fully characterize its safety profile.
References

[1]. Assay of Endogenous 3,5-diiodo-L-thyronine (3,5-T2) and 3,3'-diiodo-L-thyronine (3,3'-T2) in Human Serum: A Feasibility Study. Front Endocrinol (Lausanne). 2019 Feb 19;10:88.

[2]. Rapid stimulation in vitro of rat liver cytochrome oxidase activity by 3,5-diiodo-L-thyronine and by 3,3'-diiodo-L-thyronine. Mol Cell Endocrinol. 1994 Feb;99(1):89-94.

[3]. Simultaneous quantification of T4, T3, rT3, 3,5-T2 and 3,3'-T2 in larval zebrafish (Danio rerio) as a model to study exposure to polychlorinated biphenyls. Biomed Chromatogr. 2018 Jun;32(6):e4185.

Additional Infomation
3,3'-Diiodo-L-thyroxine is a derivative of 3,3'-diiodothyroxine. It is a human metabolite. Reports have indicated the presence of 3,3'-diiodo-L-thyroxine in humans, and relevant data are available for reference.
3,3'-Diiodo-L-thyronine is a naturally occurring metabolite of thyroid hormone that has been shown to have significant metabolic effects, including enhanced mitochondrial respiration and fatty acid oxidation. It has been studied for its potential therapeutic applications in the treatment of obesity and metabolic disorders. Unlike T3 and T4, T2 does not cause typical thyrotoxic side effects at therapeutic doses, making it an attractive candidate for further development. The compound is also a valuable tool for studying the non-genomic effects of thyroid hormones.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H13NO4I2
Molecular Weight
525.07602
Exact Mass
524.893
CAS #
4604-41-5
Related CAS #
3,3'-Diiodo-L-thyronine-13C6;1217459-13-6
PubChem CID
107564
Appearance
White to off-white solid powder
Density
2.1±0.1 g/cm3
Boiling Point
520.7±50.0 °C at 760 mmHg
Melting Point
178-180ºC
Flash Point
268.7±30.1 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.726
LogP
4.55
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
22
Complexity
385
Defined Atom Stereocenter Count
1
SMILES
C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C=C2)O)I
InChi Key
CPCJBZABTUOGNM-LBPRGKRZSA-N
InChi Code
InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m0/s1
Chemical Name
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~190.45 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.76 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (4.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9045 mL 9.5224 mL 19.0447 mL
5 mM 0.3809 mL 1.9045 mL 3.8089 mL
10 mM 0.1904 mL 0.9522 mL 1.9045 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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