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Tyrosyltyrosine

Alias: Tyrosyltyrosine Peptide tyrosine-tyrosineTyrosyl tyrosine Tyr-tyr
Cat No.:V8591 Purity: ≥98%
H-Tyr-Tyr-OH (L-Tyrosyl-L-tyrosine) is a blood pressure-lowering peptide.
Tyrosyltyrosine
Tyrosyltyrosine Chemical Structure CAS No.: 1050-28-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes
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Product Description
H-Tyr-Tyr-OH (L-Tyrosyl-L-tyrosine) is a blood pressure-lowering peptide. H-Tyr-Tyr-OH inhibits ACE (angiotensin-converting enzyme) with IC50 of 0.028 mg/mL. H-Tyr-Tyr-OH may be utilized in the research/study of hypertension.
Tyrosyltyrosine (CAS#: 1050-28-8) is a dipeptide composed of two tyrosine amino acids linked by a peptide bond. Its molecular formula is C18H20N2O5, and its molecular weight is 344.37. This compound is a naturally occurring substance found in various biological systems, including human plasma, urine, and cerebrospinal fluid. It is also known as L-tyrosyl-L-tyrosine, Tyr-Tyr, or YY. Tyrosyltyrosine is a metabolite of tyrosine and is of interest in nutritional and metabolic research. It is a substrate for various enzymes, including peptidases, and its presence in biological fluids is indicative of protein metabolism.
Biological Activity I Assay Protocols (From Reference)
Targets
Tyrosyltyrosine does not have a specific pharmacological target in the traditional sense. As a dipeptide, it is a natural substrate for peptidases and transporters. It may interact with the peptide transporter 1 (PEPT1) for absorption in the intestine. Once inside cells, it can be hydrolyzed by intracellular peptidases to release free tyrosine, which is then used for protein synthesis, neurotransmitter production (dopamine, norepinephrine, epinephrine), or melanin synthesis. Tyrosyltyrosine itself is not known to activate or inhibit specific receptors or signaling pathways directly. Its biological role is primarily as a nutrient and a metabolite, rather than as a signaling molecule.
ln Vitro
ACE is inhibited by H-Tyr-Tyr-OH, having an IC50 value of 0.028 mg/mL[2].
Tyrosyltyrosine does not exhibit specific pharmacological activity in cell-based assays in the same way that a drug would. However, it can be used as a substrate to study peptide transport and metabolism. In vitro, it can be added to cell culture media to provide a source of tyrosine to cells. It may also be used to study the activity of enzymes such as dipeptidyl peptidase IV (DPP-IV) or other peptidases that can cleave the dipeptide. Its effects are nutritional rather than pharmacological. There are no reported IC50 or EC50 values for tyrosyltyrosine against any biological target.
ln Vivo
In vivo systolic blood pressure is impacted by H-Tyr-Tyr-OH (12.5 mg/kg; once intraarterial injection) [1]. Blood pressure in spontaneously hypertensive rats is influenced by H-Tyr-Tyr-OH (0-100 mg/kg; once intraperitoneally injected) [1].
Tyrosyltyrosine is not a drug and is not administered for therapeutic purposes in vivo. However, it has been studied for its potential health benefits as a dietary supplement. For example, it may be used as a source of tyrosine to support cognitive function or stress response, as tyrosine is a precursor to catecholamines. When ingested, tyrosyltyrosine is likely absorbed as a dipeptide via the PEPT1 transporter or hydrolyzed in the intestine to free tyrosine before absorption. The free tyrosine then enters the bloodstream and is distributed to tissues. Its effects are mediated through the actions of tyrosine, not the dipeptide itself.
Enzyme Assay
Non-cellular in vitro assays for tyrosyltyrosine are primarily chemical or enzymatic. For example, its purity and identity can be determined using HPLC or mass spectrometry. It can also be used as a substrate in enzyme assays. A typical protocol for a peptidase assay involves incubating tyrosyltyrosine with a purified enzyme (e.g., DPP-IV) in a buffer at 37°C for a specified time. The reaction is stopped by the addition of acid, and the amount of tyrosine released is measured using a colorimetric or fluorometric assay. The enzyme activity is calculated based on the rate of substrate hydrolysis.
Cell Assay
Cellular assays for tyrosyltyrosine are not common, as it is not a bioactive compound. If studied, it would be to assess its effects on cell metabolism. For example, cells (e.g., Caco-2 intestinal cells) could be cultured in media containing tyrosyltyrosine. The uptake of the dipeptide via PEPT1 could be measured using radiolabeled compound. Alternatively, cells could be treated with tyrosyltyrosine to study its effect on tyrosine-related pathways, such as melanin synthesis in melanocytes. However, such studies are not standard and are typically focused on nutritional aspects.
Animal Protocol
Animal/Disease Models: Anesthetized male Sprague Dawley rats [1]
Doses: 12.5 mg/kg
Route of Administration: arterial injection; 12.5 mg/kg Primary
Experimental Results:Systolic blood pressure increased Dramatically, reaching a peak 5 minutes after administration.

Animal/Disease Models: Spontaneously hypertensive rats [1]
Doses: 0, 50, 100 mg/kg
Route of Administration: intraperitoneal (ip) injection;
Experimental Results: Even at a dose of 50 mg/kg, the blood pressure of spontaneously hypertensive rats was Dramatically diminished .
In vivo animal studies with tyrosyltyrosine are limited and typically focus on nutritional or metabolic effects. For example, rats could be orally administered tyrosyltyrosine, and blood samples could be collected at various time points to measure the levels of tyrosine and tyrosyltyrosine in plasma. This would help to assess the bioavailability of the dipeptide and its hydrolysis in the gastrointestinal tract. The compound is not used in disease models for therapeutic evaluation. Its primary value is in studying peptide absorption and metabolism.
ADME/Pharmacokinetics
Tyrosyltyrosine is a small dipeptide with a molecular weight of 344.37. When administered orally, it is absorbed via the PEPT1 transporter or hydrolyzed to free tyrosine before absorption. The absorbed tyrosine then enters the systemic circulation and is distributed to various tissues. Tyrosine is metabolized to catecholamines, melanin, and other compounds. The half-life of tyrosyltyrosine in the circulation is likely short due to rapid hydrolysis by peptidases. Specific pharmacokinetic parameters have not been extensively reported.
Toxicity/Toxicokinetics
Tyrosyltyrosine is a naturally occurring dipeptide and is generally considered safe. It is a normal constituent of human plasma, urine, and cerebrospinal fluid. As a dietary component, it is not associated with significant toxicity. High doses of tyrosine, which could be released from tyrosyltyrosine, may cause adverse effects such as gastrointestinal distress or headaches in sensitive individuals, but tyrosyltyrosine itself is not known to be toxic. It is not a regulated substance and is not classified as a drug.
References

[1]. Use of parenteral dipeptides to increase serum tyrosine levels and to enhance catecholamine-mediated neurotransmission. J Pharm Sci. 1990 Aug;79(8):685-7.

[2]. Purification and identification of angiotensin I-converting enzyme inhibitory peptides from Royal Jelly treated with protease. Nippon Shokuhin Kagaku Kogaku Kaishi. 2003.

Additional Infomation
Tyr-Tyr is tyrosine, in which each tyrosine residue has an L-configuration. It is a metabolite of Mycoplasma genitalium.
Tyrosyltyrosine is a dipeptide that is of interest in the fields of nutrition and metabolism. It is a component of protein metabolism and can be found in the diet as a result of protein digestion. It has been investigated for its potential as a nutritional supplement to provide a source of tyrosine in a form that may be more efficiently absorbed than free tyrosine. It is not a drug and has no clinical trials or regulatory approval for medical use. Its primary value is as a research tool and a nutritional compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H20N2O5
Molecular Weight
344.36
Exact Mass
344.137
CAS #
1050-28-8
PubChem CID
70590
Appearance
White to off-white solid powder
Vapour Pressure
9.55E-21mmHg at 25°C
LogP
1.87
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
7
Heavy Atom Count
25
Complexity
443
Defined Atom Stereocenter Count
2
SMILES
OC1=CC=C(CC(C(NC(CC2=CC=C(O)C=C2)C(=O)O)=O)N)C=C1
InChi Key
JAQGKXUEKGKTKX-HOTGVXAUSA-N
InChi Code
InChI=1S/C18H20N2O5/c19-15(9-11-1-5-13(21)6-2-11)17(23)20-16(18(24)25)10-12-3-7-14(22)8-4-12/h1-8,15-16,21-22H,9-10,19H2,(H,20,23)(H,24,25)/t15-,16-/m0/s1
Chemical Name
(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
Synonyms
Tyrosyltyrosine Peptide tyrosine-tyrosineTyrosyl tyrosine Tyr-tyr
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: (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)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~290.39 mM)
H2O : ~100 mg/mL (~290.39 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.26 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 (7.26 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 (7.26 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 2.9039 mL 14.5197 mL 29.0394 mL
5 mM 0.5808 mL 2.9039 mL 5.8079 mL
10 mM 0.2904 mL 1.4520 mL 2.9039 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00831818 COMPLETED Breastfeeding Medical University of Vienna 2008-07
NCT05953285 RECRUITING Other: Sleep restriction Obesity Northumbria University 2023-07-15 Not Applicable
NCT05654285 COMPLETED Other: Cola beverage with aspartame and acesulfame K
Other: Cola beverage with sucrose and stevia
Diabetes Mellitus, Type 2
Metabolic Syndrome
Obesity
Hospital Infantil de Mexico Federico Gomez 2016-02-08 Not Applicable
NCT02053025 COMPLETED Dietary Supplement: mycoprotein
Dietary Supplement: control protein
Appetite
Energy Intake
Imperial College London 2010-03 Not Applicable
NCT01456572 COMPLETED Dietary Supplement: ensure plus
Dietary Supplement: standardized test meal
Endocrine System Diseases University Hospital, Basel, Switzerland 2007-01 Phase 1
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