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| Targets |
L-Tyrosine-13C9 is a stable isotope-labeled internal standard. Its unlabeled parent, L-tyrosine, is a naturally occurring non-essential amino acid that serves as a precursor for important neurotransmitters and hormones. L-tyrosine is synthesized from the essential amino acid phenylalanine by the enzyme phenylalanine hydroxylase. The primary targets of the tyrosine metabolic pathway include tyrosine hydroxylase (the rate-limiting enzyme in catecholamine synthesis), which converts L-tyrosine to L-DOPA; tyrosinase in melanocytes, which initiates melanin synthesis; and thyroid peroxidase in the thyroid gland, which incorporates tyrosine into thyroglobulin for thyroid hormone production. Additionally, L-tyrosine is incorporated into proteins as a building block. L-Tyrosine-13C9 is used as a tracer to study these pathways without altering the biological target.
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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].
The in vitro biological activity of L-Tyrosine-13C9 is not independently characterized, as it is an analytical internal standard. Its unlabeled parent, L-tyrosine, exhibits concentration-dependent effects in cell culture systems. In PC12 pheochromocytoma cells, L-tyrosine supplementation (25-200 uM) increases dopamine and norepinephrine synthesis by providing substrate for tyrosine hydroxylase, with maximal stimulation observed at 100 uM. In primary cultures of melanocytes, L-tyrosine (10-100 uM) is required for melanin production via tyrosinase activity. In hepatocyte cultures, L-tyrosine (50-500 uM) is incorporated into cellular proteins and can be metabolized to fumarate and acetoacetate. Excess L-tyrosine (>1 mM) can be cytotoxic, inducing oxidative stress and apoptosis in neuronal cells. The labeled L-Tyrosine-13C9 is used as an internal standard in LC-MS to accurately quantify tyrosine levels and its metabolic flux in these in vitro systems. |
| ln Vivo |
The in vivo activity of L-Tyrosine-13C9 is not directly evaluated, as it is an internal standard. L-tyrosine, its unlabeled parent, is an essential precursor in metabolic pathways. In humans, plasma tyrosine levels are maintained around 50-100 uM in healthy individuals. In animal models, acute tyrosine administration (100-300 mg/kg, i.p.) increases dopamine turnover in the prefrontal cortex and can reverse stress-induced cognitive deficits. Tyrosine is also a substrate for thyroid hormone synthesis; tyrosine deficiency or impaired tyrosine metabolism leads to hypothyroidism. In phenylketonuria (PKU) patients, tyrosine becomes an essential amino acid due to phenylalanine hydroxylase deficiency, and dietary tyrosine supplementation is required. L-Tyrosine-13C9 is used as a tracer to study tyrosine metabolism in these conditions, allowing precise quantification of the conversion of tyrosine to dopamine, thyroid hormones, and other metabolites by mass spectrometry.
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| Enzyme Assay |
A generic non-cell-based assay for L-Tyrosine-13C9 involves its use as an internal standard in an isotope dilution LC-MS/MS method for quantifying L-tyrosine in plasma. Prepare a standard stock solution of unlabeled L-tyrosine in 0.1 M HCl (1 mg/mL). Prepare a separate stock solution of the internal standard L-Tyrosine-13C9 at the same concentration. Prepare calibration standards by spiking the unlabeled analyte into a blank matrix (e.g., charcoal-stripped human plasma) to achieve concentrations ranging from 1 to 200 uM. Add a fixed concentration of the internal standard (e.g., 50 uM) to each calibration standard. Also prepare blank and double-blank samples. For sample preparation, add 100 uL of plasma to 300 uL of ice-cold acetonitrile containing 0.1% formic acid to precipitate proteins. Vortex, incubate at -20degC for 10 minutes, and centrifuge at 12,000g for 10 minutes at 4degC. Transfer the supernatant to an autosampler vial. Analyze by LC-MS/MS in positive ion mode. Monitor the mass transitions: m/z 182 → 136 for unlabeled L-tyrosine, and m/z 191 → 145 for L-Tyrosine-13C9 (representing +9 mass shift). Construct the calibration curve by plotting the peak area ratio (analyte/IS) vs. the nominal concentration.
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| Cell Assay |
A standard in vitro cell-based protocol for L-Tyrosine-13C9 involves a metabolic flux study in PC12 neuronal cells. Culture PC12 cells in RPMI 1640 medium supplemented with 10% horse serum, 5% FBS, and 1% penicillin/streptomycin at 37degC in a 5% CO2 incubator. Seed cells in 6-well plates at 1×10⁶ cells/well and allow to attach for 48 hours. Replace medium with tyrosine-free DMEM supplemented with varying concentrations of unlabeled L-tyrosine (0, 50, 100, 200, 500 uM) and a fixed concentration of L-Tyrosine-13C9 (e.g., 100 uM) as a metabolic tracer. Incubate for 0, 1, 3, 6, 12, and 24 hours. At each time point, harvest cells by scraping, wash twice with PBS, and lyse in 200 uL of 0.1 M HCl. Also collect culture media samples. For analysis of tyrosine metabolites, extract samples with ethyl acetate, evaporate to dryness, and derivatize with dansyl chloride. Analyze by LC-MS/MS to measure the conversion of ¹3C-labeled tyrosine to dopamine, L-DOPA, and other metabolites. Calculate the rate of metabolic conversion and the half-life of tyrosine in the cells.
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| Animal Protocol |
An in vivo protocol for L-Tyrosine-13C9 is used in a mouse model of phenylketonuria (PKU). Use 8-12 week old PKU mice (Pah(enu2) or similar strain, n = 5 per group) and wild-type controls. Fast mice overnight (12 hours) with free access to water. Administer unlabeled L-tyrosine (50 mg/kg) in saline via intraperitoneal injection, along with L-Tyrosine-13C9 as a tracer (5 mg/kg). Collect blood samples via tail vein at 0, 0.5, 1, 2, 4, 6, 8, 12, and 24 hours post-injection into heparinized tubes. At the end of the experiment, euthanize mice and collect liver, brain, and muscle tissues. For bioanalysis, spike plasma samples (50 uL) with additional internal standard if needed. Precipitate proteins with acetonitrile, centrifuge, and analyze supernatant by LC-MS/MS to quantify both unlabeled tyrosine and L-Tyrosine-13C9. Calculate pharmacokinetic parameters (Cmax, Tmax, AUC, t½) and metabolic conversion rates. This protocol is used to assess tyrosine hydroxylation efficiency and the impact of PKU mutations on tyrosine metabolism.
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| ADME/Pharmacokinetics |
L-Tyrosine-13C9 is an internal standard, so its PK is the same as its unlabeled parent. L-tyrosine is a naturally occurring amino acid with a well-characterized pharmacokinetic profile. Following oral administration, L-tyrosine is absorbed from the small intestine via active transport (system L amino acid transporter) with Tmax of approximately 1-2 hours in humans. Oral bioavailability is high (>70%). Tyrosine is distributed to all tissues, crossing the blood-brain barrier via the large neutral amino acid transporter (LAT1). Plasma half-life is approximately 2-4 hours. Tyrosine is metabolized via four major pathways: conversion to L-DOPA by tyrosine hydroxylase, transamination to 4-hydroxyphenylpyruvate (by tyrosine aminotransferase), decarboxylation to tyramine, and incorporation into proteins. The 4-hydroxyphenylpyruvate is further metabolized to homogentisic acid, then to fumarate and acetoacetate. Excretion occurs primarily in urine as unchanged tyrosine (<5%) and metabolites. L-Tyrosine-13C9 is used as a tracer to study these metabolic pathways.
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| Toxicity/Toxicokinetics |
L-Tyrosine-13C9 is a stable isotope-labeled research compound, not a drug. L-tyrosine, its unlabeled parent, is generally recognized as safe (GRAS) as a dietary supplement and is an endogenous amino acid. The oral LD₅0 of L-tyrosine in rats is >5,000 mg/kg, indicating very low acute toxicity. Long-term high-dose tyrosine administration (>100 mg/kg/day) has been associated with reversible elevations in liver enzymes in some animal studies. In humans, L-tyrosine is well-tolerated at doses up to 150 mg/kg/day. However, individuals with hereditary tyrosinemia (Type I, II, or III) cannot metabolize tyrosine properly, leading to accumulation and toxicity causing liver, kidney, and neurological damage. For laboratory personnel, standard safety precautions are sufficient. L-Tyrosine-13C9 should be stored as a powder at -20degC, protected from light and moisture, and solutions should be used within 24 hours to prevent degradation.
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| References | |
| Additional Infomation |
L-Tyrosine-13C9 is the stable isotope-labeled version of L-tyrosine, the fully ¹3C-labeled isotopologue with all nine carbon atoms replaced by carbon-13. It is intended for research use as an internal standard for the accurate quantification of L-tyrosine in biological samples by GC-MS or LC-MS. L-tyrosine is a non-essential, proteinogenic amino acid that serves as a precursor for the catecholamines dopamine, norepinephrine, and epinephrine; the melanin pigments; and the thyroid hormones thyroxine (T4) and triiodothyronine (T3). It is also a precursor for the alkaloid compounds in plants. L-tyrosine levels are clinically relevant: decreased plasma tyrosine is observed in chronic kidney disease, rheumatoid arthritis, and depression. This fully labeled compound is an essential tool for quantitative metabolomics, stable isotope tracing, and clinical chemistry research. For research use only, not for human consumption.
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| Molecular Formula |
13C9H11NO3
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| Molecular Weight |
190.12
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| Exact Mass |
181.073
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| CAS # |
55443-60-2
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| Related CAS # |
L-Tyrosine;60-18-4
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| PubChem CID |
16213583
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
385.2±32.0 °C at 760 mmHg
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| Melting Point |
>300ºC (dec.)(lit.)
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| Flash Point |
186.7±25.1 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.614
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| LogP |
0.38
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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 |
[13CH]1=[13CH][13C](=[13CH][13CH]=[13C]1[13CH2][13C@@H]([13C](=O)O)N)O
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| InChi Key |
OUYCCCASQSFEME-ZNZHEFIISA-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/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1
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| Chemical Name |
(2S)-2-amino-3-(4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl)(1,2,3-13C3)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) |
DMSO: 66.67 mg/mL (350.67 mM)
H2O: 4.85 mg/mL (25.51 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 | 5.2598 mL | 26.2992 mL | 52.5984 mL | |
| 5 mM | 1.0520 mL | 5.2598 mL | 10.5197 mL | |
| 10 mM | 0.5260 mL | 2.6299 mL | 5.2598 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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