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| Targets |
The primary target of N-Acetyl lysyltyrosylcysteine amide is myeloperoxidase (MPO), a heme-containing enzyme that produces toxic oxidants, such as hypochlorous acid (HOCl), from hydrogen peroxide and chloride. The compound inhibits MPO-dependent HOCl generation, protein nitration, and LDL oxidation. It inhibits MPO-mediated HOCl formation with an IC50 of 7 µM. By inhibiting MPO, the compound reduces oxidative stress and inflammation.
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| ln Vitro |
In vitro, N-Acetyl lysyltyrosylcysteine amide inhibits MPO-dependent HOCl generation with an IC50 of 7 µM. It also inhibits protein nitration and LDL oxidation. The compound acts as a potent antioxidant and free radical scavenger. These in vitro data demonstrate the compound's efficacy in reducing MPO-mediated oxidative damage.
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| ln Vivo |
In the brains of middle cerebral artery occlusion (MCAO) mice, N-acetyl lysyltyrosylcysteine amide (KYC) dramatically reduces infarct size, blood-brain barrier leakage, myeloid cell infiltration, neuronal loss, and apoptosis[1]. In MCAO mice, N-acetyl lysyltyrosylcysteine amide (10 mg/kg; ip; daily for 3–7 days) dramatically lowers infarct size and neurological severity scores[1]. N-Acetyl lysyltyrosylcysteine amide (10 mg/kg; intraperitoneally; daily for 7 days) dramatically reduces neutrophil infiltration and preserves BBB function. In MCAO mice, N-acetyl lysyltyrosylcysteine amide (10 mg/kg; ip; daily 7 days) dramatically decreases neuron loss and microglia/macrophage activation. In the brains of MCAO mice, N-acetyl lysyltyrosylcysteine amide (10 mg/kg; ip; daily for 3–7 days) reduces cell damage and apoptosis. In MCAO mice's brains, N-acetyl lysyltyrosylcysteine amide decreased MPO.
In vivo, N-Acetyl lysyltyrosylcysteine amide (KYC) has been shown to effectively inhibit MPO production of toxic oxidants. In a study, the compound was administered to C57BL/6 mice at a dose of 10 mg/kg via intraperitoneal injection daily for 3-7 days. It has potential applications in neuroprotection, cardiovascular health, and inflammatory disease models. |
| Enzyme Assay |
The in vitro enzyme assay for N-Acetyl lysyltyrosylcysteine amide involves measuring the inhibition of MPO activity. MPO is incubated with hydrogen peroxide and a chromogenic or fluorogenic substrate, such as Amplex Red or taurine, in the presence of the compound. The production of the oxidized product is measured spectrophotometrically or fluorometrically. The IC50 value is calculated by fitting dose-response curves to the inhibition data.
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| Cell Assay |
Cellular assays for N-Acetyl lysyltyrosylcysteine amide typically involve the use of immune cells, such as neutrophils or macrophages, that express MPO. Cells are stimulated to produce reactive oxygen species, and the compound's ability to inhibit MPO activity and reduce oxidative stress is assessed. The compound's effects on cell viability, inflammatory cytokine production, and signaling pathways may also be evaluated.
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| Animal Protocol |
Animal/Disease Models: 8-10 weeks old C57BL/6J mice (middle cerebral artery occlusion (MCAO) mode)[1]
Doses: 10 mg/kg Route of Administration: Ip; daily for 3-7 days Experimental Results: Dramatically decreased neurological deficit and brain infarct size in mice subjected to MCAO. In vivo animal studies for N-Acetyl lysyltyrosylcysteine amide typically involve the administration of the compound to rodent models of inflammation, cardiovascular disease, or neurological disorders. In one study, the compound was administered to C57BL/6 mice at a dose of 10 mg/kg via intraperitoneal injection daily for 3-7 days. Following treatment, markers of oxidative stress, inflammation, and tissue damage are assessed. The compound's effects on neurological function in the stroked brain have also been studied. |
| ADME/Pharmacokinetics |
As a tripeptide, the pharmacokinetic properties of N-Acetyl lysyltyrosylcysteine amide would depend on its absorption, distribution, metabolism, and excretion characteristics. The compound has a molecular weight of 453.56 g/mol. It is likely to be rapidly cleared from circulation and may be subject to proteolytic degradation. Detailed ADME parameters such as half-life, bioavailability, and tissue distribution are not available in the public domain.
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| Toxicity/Toxicokinetics |
There is no specific toxicity data reported for N-Acetyl lysyltyrosylcysteine amide in the available literature. The compound is described as non-toxic. As a research chemical, it is intended for laboratory use only and should be handled with standard safety precautions. Toxicity studies would be required if the compound were to be developed further for therapeutic applications.
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| References |
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| Additional Infomation |
N-Acetyl lysyltyrosylcysteine amide (CAS#: 1287585-40-3) is a synthetic tripeptide derivative designed as a potent antioxidant and free radical scavenger. It is composed of N-acetylated lysine, tyrosine, and cysteine residues, terminated with an amide group. The compound has a molecular formula of C20H31N5O5S and a molecular weight of 453.56. It is a potent, reversible, specific, and non-toxic tripeptide inhibitor of myeloperoxidase (MPO). It has potential applications in neuroprotection, cardiovascular health, and inflammatory disease models.
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| Molecular Formula |
C20H31N5O5S
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| Molecular Weight |
453.555643320084
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| Exact Mass |
453.204
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| CAS # |
1287585-40-3
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| PubChem CID |
51352312
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| Appearance |
White to off-white solid powder
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| LogP |
-0.9
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
31
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| Complexity |
613
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| Defined Atom Stereocenter Count |
3
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| SMILES |
SCC(C(N)=O)NC(C(CC1C=CC(=CC=1)O)NC(C(CCCCN)NC(C)=O)=O)=O
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| InChi Key |
JTHKLTJLEVKKFW-ULQDDVLXSA-N
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| InChi Code |
InChI=1S/C20H31N5O5S/c1-12(26)23-15(4-2-3-9-21)19(29)24-16(10-13-5-7-14(27)8-6-13)20(30)25-17(11-31)18(22)28/h5-8,15-17,27,31H,2-4,9-11,21H2,1H3,(H2,22,28)(H,23,26)(H,24,29)(H,25,30)/t15-,16-,17-/m0/s1
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| Chemical Name |
(2S)-2-acetamido-6-amino-N-[(2S)-1-[[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]hexanamide
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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: 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)
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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.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2048 mL | 11.0239 mL | 22.0478 mL | |
| 5 mM | 0.4410 mL | 2.2048 mL | 4.4096 mL | |
| 10 mM | 0.2205 mL | 1.1024 mL | 2.2048 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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