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| Targets |
H-Tyr(3-I)-OH targets tyrosine hydroxylase (TH), the enzyme that catalyzes the conversion of L-tyrosine to L-DOPA, the rate-limiting step in catecholamine biosynthesis. It acts as a potent inhibitor of this enzyme, with a reported Ki of 0.39 M. By inhibiting TH, the compound reduces the production of dopamine, norepinephrine, and epinephrine, which are critical neurotransmitters and hormones. At a concentration of 10 μM, it inhibits tyrosine hydroxylase activity by 60-70%. This mechanism makes it a valuable tool for studying the role of catecholamines in various physiological and pathological processes, including neurotransmission, stress response, and cardiovascular function.
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| ln Vitro |
The efficient tyrosine hydroxylase inhibitor is H-Tyr(3-I)-OH (3-iodo-L-tyrosine). The enzyme activity is 100% inhibited by 3-iodo-L-tyrosine at a concentration of 100μM and 60–70% inhibited at a concentration of 10μM[1].
In vitro, H-Tyr(3-I)-OH is an effective inhibitor of tyrosine hydroxylase (TH), with a Ki of 0.39 M. At 10 μM, it inhibits TH activity by 60-70%. Its activity is typically assessed in enzyme assays using purified TH or tissue homogenates, where the conversion of tyrosine to DOPA is measured. The compound is also used as a reference standard in analytical chemistry to study iodinated amino acids and thyroid hormone metabolism. Its role as an intermediate in thyroid hormone synthesis makes it a subject of interest in endocrinology research. |
| ln Vivo |
In vivo, H-Tyr(3-I)-OH is an intermediate in the biosynthesis of thyroid hormones, playing a critical role in the production of T3 and T4. It is formed by the iodination of tyrosine in the thyroid gland and is subsequently coupled to form the active hormones. Its levels are regulated by thyroid-stimulating hormone (TSH) and reflect the activity of the thyroid gland. As an inhibitor of tyrosine hydroxylase, it also has the potential to modulate catecholamine synthesis in vivo, although this is not its primary physiological role. It is not used as a therapeutic agent but is studied in the context of thyroid disorders and catecholamine-related diseases.
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| Enzyme Assay |
In vitro non-cell enzyme assays for H-Tyr(3-I)-OH typically involve measuring its inhibition of tyrosine hydroxylase (TH) activity. The enzyme is incubated with the compound, its substrate L-tyrosine, and the cofactor tetrahydrobiopterin (BH4). The production of L-DOPA is measured using HPLC with electrochemical detection or by a coupled enzyme assay. The Ki value of 0.39 M is determined from steady-state kinetic analysis. The compound's ability to inhibit TH is compared to other known inhibitors, such as alpha-methyl-tyrosine. These assays are fundamental for studying the regulation of catecholamine synthesis.
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| Cell Assay |
In vitro cell-based assays for H-Tyr(3-I)-OH use neuronal cell lines, such as PC12 cells or primary neurons, to study its effects on catecholamine synthesis. Cells are treated with the compound, and the levels of dopamine, norepinephrine, and their metabolites are measured by HPLC. The compound's effects on cell viability and differentiation can also be assessed. These studies help to elucidate the role of tyrosine hydroxylase in neuronal function and the potential consequences of its inhibition. The compound's effects on thyroid hormone synthesis can be studied in thyroid cell lines.
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| Animal Protocol |
In vivo animal studies for H-Tyr(3-I)-OH are typically conducted to study thyroid hormone metabolism or catecholamine regulation. Animals may be treated with the compound to assess its effects on thyroid hormone levels or to model conditions of altered catecholamine synthesis. For example, inhibition of tyrosine hydroxylase can lead to decreased blood pressure and heart rate. These studies are important for understanding the physiological roles of the enzymes that H-Tyr(3-I)-OH targets. However, comprehensive in vivo data for this specific compound are limited.
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| ADME/Pharmacokinetics |
H-Tyr(3-I)-OH has a molecular weight of 307.09 g/mol and a molecular formula of C₉H₁₀INO₃. It is a white to off-white powder. The compound is soluble in water at 6.25 mg/mL (20.35 mM) with ultrasonic assistance, but is practically insoluble in DMSO. It should be stored at -20°C, protected from light, to maintain its stability. As a small, polar amino acid derivative, it is expected to be absorbed and distributed to tissues, but its pharmacokinetic properties are not well characterized.
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| Toxicity/Toxicokinetics |
H-Tyr(3-I)-OH is considered to have moderate toxicity, as it is a halogenated amino acid. It should be handled with appropriate safety precautions, including the use of personal protective equipment. The compound is not intended for human therapeutic use and is classified as a research reagent. Its safety profile has not been extensively studied in humans.
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| References | |
| Additional Infomation |
3-Iodotyrosine is a monoiodotyrosine, specifically an L-tyrosine with an iodine substituent at the C-3 position of its benzyl group. It is a human metabolite, an inhibitor of EC 1.14.16.2 (tyrosine 3-monooxygenase), and a murine metabolite. It is an L-tyrosine derivative, a non-protein L-α-amino acid, and also a monoiodotyrosine. It is a zwitterion tautomer of 3-iodotyrosine. Iodotyrosine is present in or produced by Escherichia coli (K12 strain, MG1655 strain). Monoiodotyrosine has been reported to exist in humans, and relevant data are available. 3-Iodotyrosine is an intermediate in the synthesis of thyroid hormones and is a derivative of tyrosine, with its benzyl group at the C-3 position iodinated by thyroid peroxidase. 3-Iodotyrosine (monoiodotyrosine) can be further iodinated by thyroid peroxidase to form diiodo and triiodoform forms. Monoiodotyrosine can combine with diiodotyrosine to form triiodothyronine (T3), and two diiodotyrosines can combine to form thyroxine (T4).
H-Tyr(3-I)-OH (3-Iodo-L-tyrosine, Monoiodotyrosine) is an iodinated amino acid and a potent inhibitor of tyrosine hydroxylase (Ki = 0.39 M). It is an intermediate in thyroid hormone synthesis. The compound is used in biochemical research to study catecholamine biosynthesis and thyroid hormone metabolism. It is not approved for clinical use and is intended for research purposes only. |
| Molecular Formula |
C9H10INO3
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|---|---|
| Molecular Weight |
307.0851
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| Exact Mass |
306.97
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| CAS # |
70-78-0
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| PubChem CID |
439744
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| Appearance |
White to off-white solid powder
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| Density |
1.9±0.1 g/cm3
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| Boiling Point |
391.0±42.0 °C at 760 mmHg
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| Melting Point |
210 °C (dec.)(lit.)
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| Flash Point |
190.3±27.9 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.689
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| LogP |
1.54
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
212
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)O
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| InChi Key |
UQTZMGFTRHFAAM-ZETCQYMHSA-N
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| InChi Code |
InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
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| Chemical Name |
(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O : ~5 mg/mL (~16.28 mM)
DMSO : ~1 mg/mL (~3.26 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 3.33 mg/mL (10.84 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2564 mL | 16.2819 mL | 32.5637 mL | |
| 5 mM | 0.6513 mL | 3.2564 mL | 6.5127 mL | |
| 10 mM | 0.3256 mL | 1.6282 mL | 3.2564 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.
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