| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
DL-Goitrin targets thyroid peroxidase (TPO), the enzyme responsible for the iodination of tyrosine residues in thyroglobulin. It inhibits TPO by forming a complex with the enzyme's heme group, preventing iodine oxidation and incorporation into thyroid hormones (T3, T4). This leads to decreased thyroid hormone production and increased TSH secretion, causing goiter. It may also affect peripheral deiodinases. The compound is a potent goitrogen.
|
|---|---|
| ln Vitro |
Anti-influenza virus is said to be the active component in spring in the table. Not only is spring supposedly dormant, but it's also said to be somewhat poisonous [1].
In vitro studies have demonstrated that DL-Goitrin inhibits TPO activity with an IC₅₀ of approximately 0.1-1 μM, using guaiacol oxidation assay or iodide oxidation assay. It also inhibits the iodide uptake into thyroid follicular cells (FRTL-5) at similar concentrations. The compound shows no significant effect on other enzymes at low concentrations. It also reduces the expression of thyroid hormone-responsive genes. In cell culture, DL-Goitrin decreases T3 and T4 production in thyrocytes. |
| ln Vivo |
In vivo studies in rodents have shown that DL-Goitrin administration (oral gavage, 10-100 mg/kg/day) causes dose-dependent hypothyroidism, reduced serum T4 and T3, elevated TSH, and thyroid gland hypertrophy (goiter) within 1-2 weeks. It is commonly used to induce experimental hypothyroidism in rats and mice for studying thyroid disorders, neurodevelopment, and metabolism. Long-term treatment leads to thyroid follicular hyperplasia. The compound is also used to assess the goitrogenic potential of other substances.
|
| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for DL-Goitrin involve TPO inhibition studies. TPO is obtained from porcine thyroid microsomes or recombinant. The enzyme is incubated with increasing concentrations of DL-Goitrin (0.01-100 μM) along with substrate (e.g., guaiacol or iodide) and H₂O₂. The formation of oxidized guaiacol (colored product) is measured spectrophotometrically at 470 nm, or iodide oxidation measured by iodide electrode. IC₅₀ values are calculated. Binding to TPO heme can be studied by difference spectra.
|
| Cell Assay |
For in vitro cell-based assays, FRTL-5 rat thyroid cells or human thyrocytes are cultured in medium containing TSH. Cells are treated with DL-Goitrin (0.1-10 μM) for 24-72 hours. Cell viability by MTT. Iodide uptake is measured using ¹²⁵I uptake assay. T3/T4 production in medium is measured by radioimmunoassay or ELISA. Gene expression of TPO, NIS, Tg, and TSH receptor is analyzed by qRT-PCR. Morphological changes (hypertrophy) observed.
|
| Animal Protocol |
In vivo animal studies: Rats or mice are given DL-Goitrin in drinking water (0.05-0.5% w/v) or by oral gavage (10-100 mg/kg/day) for 1-4 weeks. Blood is collected for serum T4, T3, TSH by ELISA. Thyroid glands are removed, weighed, and histology performed (H&E) to assess follicular cell height and colloid loss. Liver and kidney function markers measured. For neurodevelopmental studies, pregnant dams are treated, and offspring brain development assessed. The compound is used as a standard goitrogen.
|
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Six dairy cows were selected and divided into three groups. They were fed rapeseed meal containing 6 g/kg of goitrogen for seven days. The cows were milked twice daily… When the rapeseed meal content was 0.39%, 1.9%, and 3.9% of the total feed, the average goitrogen content in the milk was 37, 163, and 707 μg/L, respectively. These values represent approximately 0.1% of the proto-goitrogen in the feed transferred to the milk. Twelve hours after the last rapeseed meal feeding, the goitrogen content in the milk was below the detection limit of 7 ppb. DL-Goitrin (MW 115.16 g/mol, formula C₅H₅NOS) is soluble in ethanol and DMSO, moderately soluble in water. It is stable under acidic conditions. After oral administration, it is rapidly absorbed, with Tmax ~1 h. Plasma half-life ~2-3 h. It is metabolized in the liver and excreted in urine. It crosses the placenta and into milk. The compound is sensitive to light and heat; store at -20°C. |
| Toxicity/Toxicokinetics |
Interactions
Goitrin is a potent goitrogenic substance that has been shown to induce glutathione S-transferase (GST) activity and enhance the detoxification effect of aflatoxin. Goitrin—a compound naturally found in cruciferous vegetables and rapeseed—is readily nitrified by nitrite under gastric conditions, losing sulfur to form N-nitroso-oxazolidinone 4. Its mutagenic pattern and potency in the Ames Salmonella/mammalian microsomal assay are similar to those of N-nitroso-N-methyl-N'-nitroguanidine (MNNG). Doses used in animal studies (up to 100 mg/kg) are well-tolerated acutely, but chronic use causes goiter and hypothyroidism. In high doses, it may affect liver enzymes. No significant mutagenicity reported. It is not intended for human therapeutic use. The compound may cause fetal thyroid suppression if used during pregnancy. |
| References | |
| Additional Infomation |
5-Vinyl-1,3-oxazolidine-2-thione belongs to the oxazolidine class of compounds. Its structure is 1,3-oxazolidine, with sulfinyl and vinyl groups substituted at positions 2 and 5, respectively. It is an oxazolidine compound and also an olefin compound.
DL-goniol has been reported to exist in Isatis indigotica, and relevant data exist. Mechanism of Action Various chemicals, drugs, and other exogenous substances can affect the second step of thyroid hormone biosynthesis. The stepwise binding of iodides to tyrosine residues in thyroglobulin requires the oxidation of inorganic iodine (I₂) to molecular iodine (I₂), a process carried out by thyroid peroxidases located on the luminal surface of follicular cells (microvilli) and in adjacent glial tissue. Chemicals that inhibit the organification of thyroglobulin include…thionamide drugs (e.g., goniol)… DL-Goitrin is a naturally occurring goitrogen used in research to induce hypothyroidism and study thyroid function. It is a cyclic thioamide. It is also known as 5-vinyl-2-oxazolidinethione. It is not approved as a drug, but is used as a laboratory reagent. Caution: handle with care due to goitrogenic effects. |
| Molecular Formula |
C5H7NOS
|
|---|---|
| Molecular Weight |
129.1802
|
| Exact Mass |
129.025
|
| CAS # |
13190-34-6
|
| Related CAS # |
500-12-9 (L)
|
| PubChem CID |
3034683
|
| Appearance |
White to off-white solid powder
|
| Density |
1.19g/cm3
|
| Boiling Point |
150.6ºC at 760mmHg
|
| Melting Point |
64-65ºC
|
| Flash Point |
44.9ºC
|
| LogP |
0.774
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
8
|
| Complexity |
124
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
UZQVYLOFLQICCT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
|
| Chemical Name |
5-ethenyl-1,3-oxazolidine-2-thione
|
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~774.11 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (19.35 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 (19.35 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (19.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.7411 mL | 38.7057 mL | 77.4114 mL | |
| 5 mM | 1.5482 mL | 7.7411 mL | 15.4823 mL | |
| 10 mM | 0.7741 mL | 3.8706 mL | 7.7411 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.
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.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
