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| Targets |
L-Tyrosine (non-deuterated) targets and inhibits citrate synthase activity, an enzyme in the tricarboxylic acid (TCA) cycle, particularly in the posterior cortex. It is also a precursor for enzymes involved in catecholamine synthesis, including tyrosine hydroxylase (the rate-limiting enzyme for dopamine and norepinephrine synthesis), and enzymes in the melanogenesis pathway (tyrosinase). The ¹3C-labeled version (L-Tyrosine-4-13C) is used as a tracer to study these pathways and as an internal standard for quantification of L-tyrosine in biological samples.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
As a stable isotope tracer, L-Tyrosine-4-13C is not used to measure biological activity in the traditional sense. Instead, it is added to cell culture media to track the incorporation of the labeled amino acid into proteins and metabolites. The ¹3C label can be traced into downstream metabolites including dopamine, norepinephrine, melanin, and thyroid hormones. At 10-100 uM concentration, it is added to cultures of neuronal cells, melanoma cells, or hepatocytes, and the incorporation of ¹3C into metabolites is analyzed by LC-MS or NMR to quantify metabolic flux through catecholamine synthesis, melanogenesis, and protein synthesis pathways. L-Tyrosine (unlabeled) inhibits citrate synthase activity in vitro. |
| ln Vivo |
In vivo, L-Tyrosine-4-13C is administered to animals or humans to track tyrosine metabolism in real-time. It is used to assess the conversion of tyrosine to catecholamines, thyroid hormones, and melanin, as well as to study protein synthesis rates using stable isotope labeling with amino acids in cell culture (SILAC) or in vivo labeling techniques. The ¹3C-labeled tyrosine can be detected in blood, urine, and tissues after oral or intravenous administration, allowing for kinetic analysis of tyrosine metabolism and protein turnover. It is also used as a tracer in metabolic studies of phenylalanine/tyrosine metabolism in disorders such as phenylketonuria (PKU) and tyrosinemia.
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| Enzyme Assay |
For non-cellular assays (analytical quantification), L-Tyrosine-4-13C is prepared as a stock solution in 0.1 M HCl or water (1 mg/mL). For LC-MS/MS analysis, a calibration curve for L-tyrosine is prepared in human plasma or cell lysates (0.1-100 ug/mL) with a fixed concentration of L-Tyrosine-4-13C (e.g., 10 ug/mL). Sample preparation: 50 uL plasma + 10 uL internal standard + 150 uL acetonitrile for protein precipitation. After centrifugation, the supernatant is diluted with water (1:1) and injected onto a C18 column with a mobile phase of 0.1% formic acid in water and acetonitrile (gradient elution). MRM transitions: L-tyrosine 182→136, L-Tyrosine-4-13C 183→137. For enzyme activity assays, tyrosine hydroxylase activity is measured by incubating purified enzyme with L-Tyrosine-4-13C (10-100 uM) and quantifying L-DOPA-13C by LC-MS.
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| Cell Assay |
For cell-based assays, neuronal cells (e.g., PC12 cells, SH-SY5Y), melanoma cells (e.g., B16-F10), or hepatocytes (HepG2) are seeded in 6-well plates (1×10⁶ cells/well) in DMEM with 10% FBS. For metabolic labeling, cells are cultured in medium lacking unlabeled tyrosine and supplemented with L-Tyrosine-4-13C (10-100 uM) for 6-48 hours. Cell lysates are prepared in 80% methanol containing internal standards. Protein pellets are hydrolyzed with 6 M HCl at 110degC for 24 hours for amino acid analysis. ¹3C enrichment in tyrosine and its metabolites (e.g., dopamine, L-DOPA, tyramine) is analyzed by LC-MS/MS or GC-MS. For protein synthesis studies (SILAC), cells are cultured in media containing L-Tyrosine-4-13C for 5-7 population doublings, and proteins are analyzed by MS.
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| Animal Protocol |
For in vivo animal experiments, rats or mice are fasted overnight and then administered L-Tyrosine-4-13C orally (gavage) at a dose of 10-100 mg/kg or intravenously at 5-50 mg/kg. Blood samples are collected at multiple time points (0, 15, 30, 60, 90, 120 minutes) from the tail vein. Plasma is separated, and proteins are precipitated with methanol. At the end of the experiment, tissues (brain, liver, kidney, adrenal glands) are harvested and homogenized. L-Tyrosine-4-13C and its metabolites are analyzed by LC-MS/MS. For protein turnover studies, animals receive repeated doses of labeled tyrosine for 7-14 days, and tissue proteins are isolated, hydrolyzed, and analyzed by MS to determine the rate of protein synthesis.
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| ADME/Pharmacokinetics |
L-Tyrosine-4-13C has a molecular weight of 182.18, with the ¹3C label at the C4 position of the phenol ring (the carbon attached to the hydroxyl group). The compound is soluble in water, dilute acids, and bases. It should be stored as a powder at -20degC, protected from light, to prevent photodegradation. The ¹3C label is stable and non-radioactive. The compound is metabolically identical to unlabeled L-tyrosine, so its pharmacokinetics follow that of L-tyrosine: absorbed from the small intestine via amino acid transporters, distributed to all tissues, and either incorporated into proteins, converted to catecholamines, or catabolized via the tyrosine degradation pathway.
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| Toxicity/Toxicokinetics |
L-Tyrosine-4-13C is a stable isotope-labeled compound with the same low toxicity profile as natural L-tyrosine, an endogenous amino acid. At typical tracer doses (mg per sample or per kg body weight in animals), it poses no toxicity risk. L-Tyrosine is generally recognized as safe (GRAS) as a dietary supplement. High doses (≥10 g in humans) may cause gastrointestinal discomfort. The compound is non-radioactive and considered safe for research use with standard handling precautions for amino acids.
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| References |
[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.
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| Additional Infomation |
L-Tyrosine-4-13C is a research compound used as a stable isotope tracer, not an approved drug. It is not intended for therapeutic use and has not undergone clinical trials as a drug. Its primary applications are in metabolic research, including studying tyrosine and catecholamine metabolism, protein synthesis rates (SILAC), and as an internal standard for LC-MS analysis. The compound is used to investigate disorders of tyrosine metabolism including phenylketonuria (PKU), tyrosinemia, and alkaptonuria. It is also used in neurobiology research to study dopamine synthesis. L-Tyrosine-4-13C is available for research use only.
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| Molecular Formula |
C813CH11NO3
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|---|---|
| Molecular Weight |
182.18
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| Exact Mass |
182.077
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| CAS # |
81201-90-3
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| Related CAS # |
L-Tyrosine;60-18-4
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| PubChem CID |
12209719
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| Appearance |
White to off-white solid powder
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| LogP |
1.046
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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 |
13
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| Complexity |
176
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=C[13C](=CC=C1C[C@@H](C(=O)O)N)O
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| InChi Key |
OUYCCCASQSFEME-VGFAOSRESA-N
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| InChi Code |
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1/i7+1
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| Chemical Name |
(2S)-2-amino-3-(4-hydroxy(413C)cyclohexa-1,3,5-trien-1-yl)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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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: 10.87 mg/mL (59.67 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.4891 mL | 27.4454 mL | 54.8908 mL | |
| 5 mM | 1.0978 mL | 5.4891 mL | 10.9782 mL | |
| 10 mM | 0.5489 mL | 2.7445 mL | 5.4891 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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