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| Targets |
L-Cysteic acid monohydrate serves as a competitive inhibitor of the bacterial aspartate:alanine antiporter (AspT), which exchanges aspartate and alanine across bacterial membranes. As a sulfur-containing aspartate analogue, it targets the substrate binding site of the AspT transporter. The compound also functions as a substrate for glutamate decarboxylase (GADCase), with a Km intermediate between L-glutamate and cysteine sulfinic acid. In addition to its role as a competitive inhibitor, L-cysteic acid is involved in various metabolic processes and has been studied for its potential neuroprotective and antioxidant properties. As an aspartate mimic, it may interact with glutamate receptors and transporters in the central nervous system, although its primary research applications are in bacterial systems and amino acid metabolism studies. The compound's sulfonic acid group, which replaces the thiol group of cysteine, makes it a stable oxidized form that cannot participate in redox reactions, distinguishing it from cysteine and other sulfur-containing amino acids. This stability makes L-cysteic acid a useful tool for studying the role of sulfur oxidation states in biological systems.
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| ln Vitro |
In vitro, L-Cysteic acid monohydrate is used as a substrate for glutamate decarboxylase (GADCase), with a Km intermediate between L-glutamate and cysteine sulfinic acid. It is also used as a competitive inhibitor of the bacterial aspartate:alanine antiporter (AspT). In studies of antifolate analogues, L-cysteic acid has been incorporated into compounds tested in L1210 cells, with ID₅₀ values ranging from 0.03-0.05 μM for AMT analogues and 0.1-0.4 μM for MTX analogues. As a zwitterionic compound, it exhibits excellent water solubility, making it ideal for biochemical assays and solution-based applications. The compound is often utilized as a substrate in studies of amino acid metabolism and sulfur pathway elucidation, enabling exploration of oxidative mechanisms and enzyme specificity. Its potential neuroprotective and antioxidant properties have also been studied in vitro. The compound's stability as a sulfonic acid derivative makes it useful for studying the effects of oxidation on amino acid function and metabolism. In enzyme kinetics studies, L-cysteic acid is used to characterize the substrate specificity and catalytic mechanism of enzymes that act on sulfur-containing amino acids.
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| ln Vivo |
In vivo, L-Cysteic acid monohydrate is studied for its potential neuroprotective and antioxidant properties. As an oxidized form of cysteine, it represents an endpoint of cysteine oxidation and is involved in sulfur amino acid metabolism. The compound is an endogenous metabolite that can be found in biological systems as a result of cysteine oxidation. Studies have investigated its potential role in protecting cells from oxidative stress, although detailed in vivo efficacy data are limited. The compound's zwitterionic nature and high water solubility suggest that it would be rapidly cleared by the kidneys. In animal models, L-cysteic acid has been studied for its effects on amino acid metabolism and neurotransmitter systems. However, comprehensive in vivo pharmacokinetic and toxicology studies have not been extensively reported. The compound is primarily used as a research tool for studying amino acid metabolism, enzyme specificity, and oxidative mechanisms. Its role as a stable analog of oxidized cysteine makes it useful for studying the biological consequences of cysteine oxidation and the role of sulfur amino acids in health and disease.
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| Enzyme Assay |
In vitro enzyme assays for L-Cysteic acid monohydrate typically involve incubating the compound with enzymes such as glutamate decarboxylase (GADCase) or aspartate:alanine antiporter (AspT). For GADCase assays, the enzyme is incubated with L-cysteic acid and appropriate cofactors (e.g., pyridoxal phosphate) in a buffered solution at physiological pH and temperature. The reaction products are analyzed by HPLC, mass spectrometry, or enzymatic coupled assays to measure the production of CO₂ or the corresponding amine. Kinetic parameters such as Km and Vmax are determined by measuring reaction rates at various substrate concentrations. For AspT inhibition assays, membrane vesicles or proteoliposomes containing the transporter are incubated with radiolabeled or fluorescently labeled aspartate in the presence of varying concentrations of L-cysteic acid. The inhibition constant (Ki) is determined from competitive binding curves. The compound's excellent water solubility facilitates its use in these biochemical assays. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems (pH 7.4), with reaction products measured by spectrophotometry, fluorometry, or radiometric detection. The compound's stability as a sulfonic acid derivative ensures reproducible results in enzyme kinetics studies.
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| Cell Assay |
In vitro cell-based assays for L-Cysteic acid monohydrate are performed using various cell lines to study its effects on cell function and metabolism. For example, L1210 cells have been used to test antifolate analogues containing L-cysteic acid, with ID₅₀ values of 0.03-0.05 μM for AMT analogues and 0.1-0.4 μM for MTX analogues. In studies of amino acid metabolism, cells are cultured in appropriate medium and treated with L-cysteic acid at various concentrations (typically 0.1-10 mM) for 24-72 hours. Following treatment, cells are harvested, and markers of oxidative stress, amino acid metabolism, and cell viability are measured. The compound's potential neuroprotective and antioxidant properties are assessed by measuring reactive oxygen species (ROS) levels, glutathione levels, and markers of oxidative damage. Cell viability is routinely monitored using MTT or LDH assays to ensure that observed effects are not due to cytotoxicity. Each experiment includes appropriate controls (untreated cells, vehicle controls, and positive controls such as cysteine or glutamate) and is performed in triplicate to ensure statistical reliability. The compound is typically dissolved in water or culture medium due to its excellent water solubility.
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| Animal Protocol |
In vivo animal experiments with L-Cysteic acid monohydrate are limited, as the compound is primarily used as a research tool for in vitro studies. However, studies have been conducted to investigate its effects on amino acid metabolism and oxidative stress in animal models. Typically, rodents are administered L-cysteic acid via intraperitoneal injection or oral gavage at doses ranging from 10-100 mg/kg. Following administration, blood and tissue samples are collected at various time points to measure the compound's concentration and its effects on metabolic parameters. Markers of oxidative stress, amino acid levels, and enzyme activities are measured in plasma and tissues. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=6-10 per group) to ensure statistical power. The compound is formulated for administration using appropriate vehicles such as saline or water, in which it is readily soluble due to its zwitterionic nature. Endpoints include biochemical markers, histopathological examination, and behavioral assessments if applicable. Further in vivo studies are needed to fully characterize the compound's pharmacokinetic and pharmacodynamic properties.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of L-Cysteic acid monohydrate are characteristic of a small, highly polar zwitterionic molecule. With excellent water solubility and a molecular weight of approximately 201 g/mol, the compound is expected to be rapidly absorbed following oral administration. However, its high polarity and zwitterionic nature may limit its ability to cross biological membranes, potentially resulting in low oral bioavailability. Following absorption, the compound is distributed primarily in the extracellular space due to its limited membrane permeability. The compound is expected to be rapidly cleared by the kidneys through glomerular filtration, with minimal metabolism. The elimination half-life is likely to be short (hours) due to rapid renal clearance. The compound's pharmacokinetic profile makes it suitable for studying amino acid transport and metabolism in the kidney and other organs. As with all research chemicals, appropriate pharmacokinetic studies should be conducted to fully characterize the compound's absorption, distribution, metabolism, and excretion. The compound's excellent water solubility facilitates its formulation for administration in various experimental settings.
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| Toxicity/Toxicokinetics |
The toxicological profile of L-Cysteic acid monohydrate has not been extensively characterized in formal toxicology studies. As an endogenous metabolite and a naturally occurring amino acid derivative, it is expected to be relatively non-toxic at physiological concentrations. The compound is a zwitterionic compound with excellent water solubility. In cell-based assays, the compound has been shown to have potential neuroprotective and antioxidant properties, suggesting that it may be beneficial rather than toxic at certain concentrations. However, comprehensive toxicology studies including acute, subchronic, and chronic toxicity assessments, as well as genotoxicity and reproductive toxicity evaluations, have not been reported. The compound is classified as a research chemical and is not approved for human use. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment. As with all chemicals, ingestion, inhalation, and skin contact should be avoided. The compound should be stored in a cool, dry place, away from light and moisture. The absence of reported severe adverse effects in published studies suggests a favorable safety profile, but formal toxicological characterization would be required for clinical development.
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| Additional Infomation |
L-Cysteic acid monohydrate is a valuable research tool for studying amino acid metabolism, sulfur pathway elucidation, and enzyme specificity. It is often utilized as a substrate in studies of amino acid metabolism and sulfur pathway elucidation, enabling exploration of oxidative mechanisms and enzyme specificity. As a sulfur-containing aspartate analogue, it may be used as a competitive inhibitor of the bacterial aspartate:alanine antiporter (AspT). The compound has been studied for its potential neuroprotective and antioxidant properties. As a zwitterionic compound, it exhibits excellent water solubility, making it ideal for biochemical assays and solution-based applications. L-Cysteic acid is the fully oxidized sulfonate form of L-cysteine, functioning as a non-reducible, stable aspartate mimic. It appears as an off-white to light yellow solid powder. The compound is not approved for any clinical indication and is strictly for research use only. Its stability as a sulfonic acid derivative makes it useful for studying the effects of oxidation on amino acid function and metabolism, and for characterizing the substrate specificity and catalytic mechanism of enzymes that act on sulfur-containing amino acids.
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| Molecular Formula |
C3H9NO6S
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| Molecular Weight |
187.17
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| Exact Mass |
187.015
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| CAS # |
23537-25-9
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| PubChem CID |
12308854
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.775g/cm3
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| Melting Point |
267ºC (dec.)(lit.)
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| LogP |
0.002
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
11
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| Complexity |
214
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C([C@@H](C(=O)O)N)S(=O)(=O)O.O
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| InChi Key |
PCPIXZZGBZWHJO-DKWTVANSSA-N
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| InChi Code |
InChI=1S/C3H7NO5S.H2O/c4-2(3(5)6)1-10(7,8)9;/h2H,1,4H2,(H,5,6)(H,7,8,9);1H2/t2-;/m0./s1
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| Chemical Name |
(2R)-2-amino-3-sulfopropanoic acid;hydrate
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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) |
H2O: 125 mg/mL (667.84 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (534.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3427 mL | 26.7137 mL | 53.4274 mL | |
| 5 mM | 1.0685 mL | 5.3427 mL | 10.6855 mL | |
| 10 mM | 0.5343 mL | 2.6714 mL | 5.3427 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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