| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
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| Other Sizes |
Purity: ≥98%
| Targets |
The primary target of DL-propargylglycine is cystathionine-γ-lyase (CSE), a key enzyme in the endogenous hydrogen sulfide biosynthesis pathway. CSE catalyzes the conversion of L-cysteine to hydrogen sulfide, and PAG irreversibly inhibits CSE activity to block this conversion. This inhibitor exhibits selectivity for CSE and is widely used to modulate hydrogen sulfide levels in various in vitro and in vivo models.
As an amino acid derivative, DL-Propargylglycine does not have a defined primary drug target in the context of therapeutic development. However, as a propargylglycine analogue, it may be used in research to study amino acid metabolism, enzyme-substrate interactions, and peptide modification. The alkyne functionality allows for bioorthogonal click chemistry reactions (e.g., CuAAC), enabling the labeling and modification of peptides and proteins. The compound can serve as a building block for synthesizing alkyne-containing peptides for bioconjugation studies. The DL-racemic mixture allows for studying stereochemical effects. |
|---|---|
| ln Vitro |
In vitro studies demonstrate that DL-propargylglycine exerts various biological effects as a CSE inhibitor. In bacterial studies, PAG (1-5 mM) in combination with β-lactam antibiotics significantly enhances the killing efficacy against Streptococcus agalactiae, with mechanisms involving activation of central carbon metabolism, promotion of reactive oxygen species production, and downregulation of peptidoglycan synthesis genes, thereby altering bacterial membrane permeability. Furthermore, in pancreatic acinar cells, PAG treatment downregulates the expression of multiple chemokines induced by cerulein, including monocyte chemoattractant protein-1, macrophage inflammatory protein-1α, and macrophage inflammatory protein-2.
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1]. In vitro studies on amino acid derivatives, including this propargylglycine analogue, have demonstrated their capacity to influence the release of anabolic hormones, modulate fuel availability for cellular activity, enhance mental performance under stress-related conditions, and prevent exercise-induced muscle damage. As a propargylglycine derivative, this compound may be used in cell-based assays to investigate amino acid transport mechanisms, peptide stability, and the effects of alkyne incorporation on peptide biological activity. The compound can also be utilized in click chemistry-based labeling studies to track peptide localization and interactions in cells. |
| ln Vivo |
DL-propargylglycine demonstrates significant in vivo activity in various animal models. In a gentamicin-induced nephrotoxicity rat model, PAG (specific dose not specified) pretreatment attenuates tubular necrosis and inflammatory cell infiltration, reducing lipid peroxidation, superoxide production, and tumor necrosis factor-alpha activation. In morphine-treated rats, PAG (25 mg/kg, intravenous) significantly enhances the ability of L-cysteine ethyl ester to reverse morphine-induced respiratory depression. In a mouse model of acute pancreatitis, PAG treatment downregulates chemokine expression and alleviates pancreatic and lung injury. However, limited in vivo efficacy has been reported in zebrafish models, suggesting that optimization of its pharmacokinetic properties is needed.
In vivo studies on amino acid derivatives have shown that they affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. As a propargylglycine derivative, this compound may be administered in animal studies to evaluate the effects of alkyne-containing peptides on biological systems. However, specific in vivo pharmacological data for this exact compound remains limited, as it is primarily supplied as a research chemical for peptide synthesis and bioconjugation rather than as a therapeutic agent. |
| Enzyme Assay |
Enzyme Source: Recombinantly expressed cystathionine-γ-lyase (CSE) protein.
Activity Assay: Pre-incubate CSE enzyme with various concentrations of DL-propargylglycine for a defined period (typically 15-30 minutes), then initiate the reaction by adding the substrate L-cysteine. Product Detection: Quantify hydrogen sulfide production using methylene blue method, lead acetate paper, or fluorescent probes. Inhibition Kinetics: Determine the inhibition constant (Ki) and mechanism of action (PAG is an irreversible inhibitor) by measuring reaction rates at different substrate concentrations. Data Analysis: Calculate inhibition rates and IC50 values by comparing hydrogen sulfide production between treatment and control groups. Non-cell-based enzyme or receptor binding assays for this compound typically involve studies with purified enzymes or receptors to evaluate the effects of alkyne substitution on binding affinity and enzymatic activity. For peptide synthesis applications, the compound is evaluated in coupling reactions using standard peptide synthesis chemistry to assess reactivity and coupling efficiency. The alkyne functionality can be used in click chemistry reactions with azide-containing compounds for peptide labeling and conjugation studies. |
| Cell Assay |
Cell Culture: Seed target cells (e.g., pancreatic acinar cells, bacterial suspensions) in appropriate culture systems.
Drug Treatment: Add varying concentrations of DL-propargylglycine (typically 0.1-10 mM), alone or in combination with other drugs (e.g., antibiotics, L-cysteine ethyl ester), and incubate for specified durations. Viability Assay: Assess cell viability using MTT assay or colony counting methods. Mechanistic Studies: Chemokine Detection: Measure changes in cytokine/chemokine expression by real-time qPCR or ELISA. Metabolic Analysis: Evaluate central carbon metabolism indicators and reactive oxygen species levels. Membrane Permeability: Assess cell membrane integrity using fluorescent probes or flow cytometry. Data Analysis: Calculate IC50 values or compare biological differences among treatment groups. Cell-based assays for this propargylglycine derivative typically utilize mammalian cell lines to evaluate compound uptake, cytotoxicity, and effects on cellular metabolism. Standard protocols involve culturing cells in appropriate media at 37°C in 5% CO₂, followed by treatment with varying concentrations of the compound (typically 0.1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. For click chemistry applications, cells may be treated with alkyne-containing peptides followed by azide-fluorophore conjugates for labeling and imaging studies. For peptide synthesis applications, the compound is used as a building block. |
| Animal Protocol |
Animals & Models: Use rats (e.g., Sprague Dawley rats) or mice to establish disease models, including gentamicin-induced nephrotoxicity, morphine-induced respiratory depression, and cerulein-induced acute pancreatitis.
Grouping & Dosing: Randomize animals into control groups and PAG treatment groups at various doses. Administration routes include intravenous injection (e.g., 25 mg/kg), intraperitoneal injection, or oral gavage, with regimens adjusted based on experimental objectives. Monitoring Parameters: Physiological Parameters: Respiratory rate, tidal volume, minute ventilation measured by whole-body plethysmography. Biochemical Markers: Serum creatinine, blood urea nitrogen (assessing renal function), lipid peroxidation products, superoxide levels. Histopathology: Collect kidney, pancreas, and lung tissues for H&E staining and pathological scoring. Molecular Detection: Measure chemokine and inflammatory factor expression in tissues by real-time qPCR, Western blot, or ELISA. Data Analysis: Compare differences in physiological, biochemical, and pathological parameters among groups. In vivo animal studies for amino acid derivatives typically involve administration via oral gavage, intraperitoneal injection, or intravenous injection in rodent models (mice or rats). Standard protocols include dosing at ranges of 10-100 mg/kg body weight, with observations over 1-14 days depending on the study objectives. For studies evaluating alkyne-containing peptides, animals may be administered peptide formulations and monitored for therapeutic efficacy or biodistribution. Pharmacodynamic assessments may include blood sampling for peptide analysis, tissue collection for histopathological examination, and monitoring of body weight. All animal studies must comply with institutional ethical guidelines. |
| ADME/Pharmacokinetics |
DL-propargylglycine is a water-soluble small molecule compound (molecular weight 113.11 g/mol) with good solubility in DMSO (10 mg/mL) and can be prepared in buffer solutions. Existing pharmacokinetic data are relatively limited. Studies have shown that PAG exhibits limited in vivo efficacy in zebrafish models, suggesting that rapid metabolism, clearance, or insufficient bioavailability may be concerns. Intravenous administration of 25 mg/kg in rats is a commonly reported dosing regimen, demonstrating good activity. Long-term storage at -20°C is recommended to maintain stability.
Pharmacokinetic properties for this propargylglycine derivative can be inferred from structurally related compounds. As a small molecule (molecular weight 113.11 g/mol), it is expected to have reasonable oral bioavailability. The compound shows moderate solubility in aqueous and organic solvents. For in vivo administration, formulations using suitable vehicles may be employed. The compound should be stored as powder at -20°C for long-term preservation. Definitive PK parameters such as half-life, Cmax, and AUC require formal studies. |
| Toxicity/Toxicokinetics |
DL-propargylglycine, as a tool inhibitor of CSE, demonstrates good tolerability at conventional experimental doses (e.g., 25 mg/kg intravenous in rats), with no reports of significant acute toxicity. This compound has been detected in humans as an exogenous exposure substance and is not a naturally occurring metabolite. When combined with antibiotics, PAG enhances bacterial killing without increasing toxicity to host cells. In nephrotoxicity studies, PAG pretreatment paradoxically attenuates gentamicin-induced renal injury, suggesting it lacks significant intrinsic nephrotoxicity. Overall, PAG is considered a safe tool compound within experimental dose ranges, although comprehensive toxicological data warrant further investigation.
Toxicological data for this specific compound are limited as it is supplied for research use only and not intended for human therapeutic applications. Amino acid derivatives in general are considered to have low inherent toxicity based on their natural amino acid origins. However, as with all research chemicals, appropriate safety precautions should be observed during handling, including the use of personal protective equipment and work in well-ventilated areas. The compound may cause skin and eye irritation upon contact. Acute toxicity studies in animal models would be required to establish LD₅₀ values and no-observed-adverse-effect levels. |
| References | |
| Additional Infomation |
Reports indicate that Arabidopsis thaliana and spinach contain DL-propynylglycine, and relevant data is available for reference.
DL-Propargylglycine is a propargylglycine derivative featuring a propargyl (alkyne) side chain. The alkyne functionality allows for bioorthogonal click chemistry reactions (e.g., CuAAC), enabling the labeling and modification of peptides and proteins. The DL-racemic mixture contains both D- and L-enantiomers. This compound is used as a building block in peptide synthesis for introducing alkyne-containing residues into peptide sequences. It is not an approved drug and has not undergone clinical trials; it is strictly for research purposes. |
| Molecular Formula |
C5H7NO2
|
|---|---|
| Molecular Weight |
113.11
|
| Exact Mass |
113.048
|
| CAS # |
50428-03-0
|
| PubChem CID |
95575
|
| Appearance |
White to off-white solid powder
|
| Boiling Point |
272.1±35.0°C at 760 mmHg
|
| LogP |
0.121
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
8
|
| Complexity |
133
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C#CCC(C(=O)O)N
|
| InChi Key |
DGYHPLMPMRKMPD-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H7NO2/c1-2-3-4(6)5(7)8/h1,4H,3,6H2,(H,7,8)
|
| Chemical Name |
2-aminopent-4-ynoic acid
|
| Synonyms |
DL-Propargylglycine; NSC 21940; 50428-03-0; NSC21940; DL-2-Propynylglycine; FU67PLJ48R; NSC-21940;
|
| 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: 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)
|
| Solubility (In Vitro) |
H2O: 100 mg/mL (884.10 mM)
|
|---|---|
| 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 | 8.8410 mL | 44.2048 mL | 88.4095 mL | |
| 5 mM | 1.7682 mL | 8.8410 mL | 17.6819 mL | |
| 10 mM | 0.8841 mL | 4.4205 mL | 8.8410 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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