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Procysteine (propylene cysteine; Oxothiazolidinecarboxylic acid)

Cat No.:V61902 Purity: ≥98%
Procysteine is an antioxidant and a precursor to cysteine, which is inert and metabolized intracellularly to cysteine, thereby stimulating glutathione synthesis.
Procysteine (propylene cysteine; Oxothiazolidinecarboxylic acid)
Procysteine (propylene cysteine; Oxothiazolidinecarboxylic acid) Chemical Structure CAS No.: 19771-63-2
Product category: Others 12
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
Procysteine is an antioxidant and a precursor to cysteine, which is inert and metabolized intracellularly to cysteine, thereby stimulating glutathione synthesis.
Procysteine (L-2-Oxothiazolidine-4-carboxylic acid, OTC) (CAS 19771-63-2) is a synthetic cysteine prodrug with the molecular formula C₄H₅NO₃S and a molecular weight of 147.15 g/mol. It is an inert compound that is metabolized intracellularly to cysteine, which then stimulates the synthesis of glutathione (GSH), the body's primary antioxidant. Its ability to replenish intracellular cysteine, the rate-limiting amino acid for glutathione synthesis, underpins its primary antioxidant function. It has garnered significant attention for its therapeutic potential in conditions involving oxidative stress and inflammation.
Biological Activity I Assay Protocols (From Reference)
Targets
Glutathione synthesis pathway; cysteine uptake. Procysteine is a cysteine prodrug that is metabolized intracellularly to cysteine. Cysteine is the rate-limiting amino acid for glutathione (GSH) synthesis. By replenishing intracellular cysteine, procysteine stimulates glutathione synthesis and enhances cellular antioxidant capacity.
ln Vitro
Procysteine is an inert compound that is metabolized intracellularly to cysteine, which then stimulates the synthesis of glutathione (GSH). Its ability to replenish intracellular cysteine, the rate-limiting amino acid for glutathione synthesis, underpins its primary antioxidant function. In vitro studies have demonstrated its capacity to increase intracellular glutathione levels in various cell types.
ln Vivo
Treatment with oxothiazolidinecarboxylic acid reduced plantaris atrophy, raised glutathione levels, and increased the expression of the catalase, Cu/Zn-SOD1, and Mn-SOD2 mRNAs, but it did not lower the levels of these catabolic factors or other oxidant stress markers[1].
In vivo, procysteine is metabolized to cysteine, which stimulates glutathione synthesis. It has been studied for its therapeutic potential in conditions involving oxidative stress and inflammation. By increasing glutathione levels, it may protect cells and tissues from oxidative damage. Further in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic properties, as well as its efficacy and safety profile.
Enzyme Assay
Non-cell-based assays for procysteine include measurement of its conversion to cysteine in vitro using enzymatic or chemical methods. Glutathione levels can be measured using colorimetric or fluorometric assays in cell lysates or tissue homogenates. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment.
Cell Assay
Cell-based assays for procysteine use various cell lines to assess its effects on intracellular glutathione levels. Cells are treated with the compound at various concentrations, and glutathione levels are measured using colorimetric, fluorometric, or HPLC-based assays. Cytotoxicity is assessed using standard cell viability assays. The compound's protective effects against oxidative stress can be assessed by exposing cells to oxidative stress inducers.
Animal Protocol
Animal/Disease Models: Male SD (Sprague-Dawley) rats (200-250 g, n= 6-7 rats/group)[1].
Doses: 0.35% (w/v).
Route of Administration: Added to their diets at a concentration of 0.35% (w/v) ) for the final 12 wk.
Experimental Results: Increased fiber CSAs compared to the non-supplemented, alcohol-fed group.
In vivo studies of procysteine are conducted in animal models of oxidative stress and inflammation. The compound is administered via oral or intraperitoneal injection. Tissue glutathione levels, oxidative stress markers, and inflammatory markers are assessed. The compound's therapeutic potential is evaluated in models of conditions such as ischemia-reperfusion injury, neurodegenerative diseases, and inflammatory disorders.
ADME/Pharmacokinetics
Procysteine has a molecular formula of C₄H₅NO₃S and a molecular weight of 147.15 g/mol. The IUPAC name is (4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid. Purity is ≥98%. It appears as a solid at room temperature. It is a synthetic cysteine prodrug that is metabolized intracellularly to cysteine. It should be stored under recommended conditions.
Toxicity/Toxicokinetics
Procysteine is a cysteine prodrug that is metabolized intracellularly to cysteine, which stimulates glutathione synthesis. It has garnered significant attention for its therapeutic potential in conditions involving oxidative stress and inflammation. It is not intended for human therapeutic use without further validation. Standard laboratory safety practices should be followed when handling this compound.
References
[1]. Jeffrey S Otis, et al. Procysteine Stimulates Expression of Key Anabolic Factors and Reduces Plantaris Atrophy in Alcohol-Fed Rats. Alcohol Clin Exp Res. 2009 Aug;33(8):1450-9.
[2]. Saito K, Kimura S, Saga T, et al. Protective effect of procysteine on Acinetobacter pneumonia in hyperoxic conditions. J Antimicrob Chemother. 2013;68(10):2305-2310.
Additional Infomation
(4R)-2-oxo-4-thiazolidinic acid is an organic nitrogen and organic oxygen compound whose function is related to α-amino acids. Cysteine has been used in clinical trials investigating the treatment of HIV infection.
Procysteine (L-2-Oxothiazolidine-4-carboxylic acid, OTC) is a synthetic cysteine prodrug. It is an inert compound that is metabolized intracellularly to cysteine, which then stimulates the synthesis of glutathione (GSH), the body's primary antioxidant. Its ability to replenish intracellular cysteine, the rate-limiting amino acid for glutathione synthesis, underpins its primary antioxidant function. It has been studied for its therapeutic potential in conditions involving oxidative stress and inflammation. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H5NO3S
Molecular Weight
147.15
Exact Mass
146.999
CAS #
19771-63-2
PubChem CID
72390
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Melting Point
174 °C (dec.)(lit.)
Index of Refraction
1.595
LogP
-1.11
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
9
Complexity
158
Defined Atom Stereocenter Count
1
SMILES
S1C(N([H])[C@]([H])(C(=O)O[H])C1([H])[H])=O
InChi Key
BMLMGCPTLHPWPY-REOHCLBHSA-N
InChi Code
InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1
Chemical Name
(4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid
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

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: 250 mg/mL (1698.95 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (14.14 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 20.8 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: ≥ 2.08 mg/mL (14.14 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 20.8 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: ≥ 2.08 mg/mL (14.14 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 20.8 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 6.7958 mL 33.9789 mL 67.9579 mL
5 mM 1.3592 mL 6.7958 mL 13.5916 mL
10 mM 0.6796 mL 3.3979 mL 6.7958 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.

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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
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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
Title:A Double-Blind, Randomized Parallel Group Study Comparing Procysteine to Placebo in HIV-Infected Patients Who Are Taking Antiretroviral Nucleosides
Status:Completed
updateDate:2005-06-24
Ctid:NCT00002114

Link: https://clinicaltrials.gov/ct2/show/NCT00002114

Conditions:HIV Infections
Interventions:Procysteine
Phase:Phase 2
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