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| 5mg |
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| 10mg |
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| 25mg |
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| Targets |
L-Cysteinesulfinic acid targets metabotropic glutamate receptors (mGluRs) including mGluR1, mGluR2, mGluR4, mGluR5, mGluR6, and mGluR8. It is a potent agonist at these receptors with pEC₅₀ values of 3.92±0.03 (mGluR1), 4.6±0.2 (mGluR5), 3.9±0.2 (mGluR2), 2.7±0.2 (mGluR4), 4.0±0.2 (mGluR6), and 3.94±0.08 (mGluR8). It is also an endogenous agonist of the PLD-coupled metabotropic excitatory amino acid receptor and shows activity at NMDA receptors.
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| ln Vitro |
The endogenous agonist of metabotropic receptors, L-cysteine sulfinic acid, increases the activity of phospholipase D (PLD). Endogenous agonist L-CSA binds to metabotropic excitatory amino acid (EAA) receptors that are connected to PLD. PLD-coupled receptors are preferentially activated by L-CSA. Hippocampal slices' PLD activity was significantly increased by 1 mM L-CSA, but L-glutamic acid, L-aspartic acid, and L-HCA had no effect at 1 mM. Rat hippocampal slices treated with L-CSA showed a dose-dependent increase in PLD activity with an EC50 of about 500 uM in the presence of iGluR antagonists. The PLD response elicited by 1 mM L-CSA did not significantly decrease in the presence of 1 uM tetrodotoxin, suggesting that the reaction was independent of the L-CSA-induced increase in cell firing [1].
In vitro, L-cysteinesulfinic acid is a potent agonist at several rat metabotropic glutamate receptors (mGluRs) with pEC₅₀ values of 3.92±0.03 (mGluR1), 4.6±0.2 (mGluR5), 3.9±0.2 (mGluR2), 2.7±0.2 (mGluR4), 4.0±0.2 (mGluR6), and 3.94±0.08 (mGluR8). It is an endogenous agonist of a metabotropic receptor coupled to stimulation of phospholipase D (PLD) activity. The compound also acts as an agonist at NMDA receptors and PLD-coupled mGlu receptors. Its activity has been characterized in various cell-based and receptor binding assays. |
| ln Vivo |
In vivo, L-cysteinesulfinic acid is an endogenous amino acid intermediate involved in taurine biosynthesis. It is formed by the enzymatic oxidation of L-cysteine and serves as the primary physiological precursor for hypotaurine and taurine. The compound plays important roles in sulfur amino acid metabolism and neurotransmitter signaling. Its presence in biological systems reflects its role in normal metabolic pathways and potential involvement in neurological functions.
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| Enzyme Assay |
For non-cell enzyme/receptor binding assays, L-cysteinesulfinic acid binding to mGluRs is assessed using membrane preparations from cells expressing the various receptor subtypes. Radioligand binding assays using [³H]labeled agonists or antagonists are employed. Membrane fractions are incubated with the labeled ligand and varying concentrations of unlabeled compound. Bound and free ligand are separated by filtration, and pEC₅₀ values are calculated from competition binding experiments. Receptor activation can also be assessed in cell-free signaling assays.
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| Cell Assay |
For in vitro cell-based assays, L-cysteinesulfinic acid activity is assessed in cell lines expressing mGluR subtypes. Cells are treated with the compound, and receptor activation is measured by intracellular Ca²⁺ mobilization, cAMP accumulation, or other signaling readouts depending on the receptor subtype. Phospholipase D activity can be measured in cells expressing PLD-coupled receptors. The compound's effects on neurotransmitter release and neuronal activity can be studied in neuronal cell cultures.
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| Animal Protocol |
For in vivo animal experiments, L-cysteinesulfinic acid can be administered to animals to study its effects on neurotransmitter systems and metabolism. The compound's role in taurine biosynthesis can be studied by measuring taurine and hypotaurine levels in tissues following administration. Its effects on glutamatergic signaling can be assessed in behavioral and electrophysiological studies. Metabolic studies track the conversion of L-cysteinesulfinic acid to taurine and other metabolites.
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| ADME/Pharmacokinetics |
L-Cysteinesulfinic acid has a molecular weight of 153.16 g/mol and molecular formula C₃H₇NO₄S. It is soluble in water at 15.31 mg/mL due to its polar nature. The compound exhibits a zwitterionic form at physiological pH. It should be stored as powder at -20°C for up to 3 years or at 4°C for up to 2 years. The compound is an endogenous metabolite and amino acid intermediate.
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| Toxicity/Toxicokinetics |
L-Cysteinesulfinic acid is an endogenous compound with low toxicity at physiological concentrations. It is a normal metabolite in sulfur amino acid pathways and is involved in taurine biosynthesis. No significant toxicity has been reported at physiological levels. The compound is for research use only and is not approved as a pharmaceutical drug. Standard safety precautions for handling amino acids and biochemicals should be followed.
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| References |
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| Additional Infomation |
3-Sylenyl-L-alanine is an organic sulfinic acid produced by the oxidation of the thiol group of L-cysteine. It is a metabolic glutamate receptor agonist and a metabolite in humans, E. coli, and mice. It is an organic sulfinic acid and an S-substituted L-cysteine. It is the conjugate acid of 3-sulfinyl-L-alanine (1-) and a tautomer of L-cysteine-S-dioxide. L-cysteine sulfinic acid has been reported in Homo sapiens, Euglena, and other organisms with relevant data. See also: 3-Sylenyl-L-alanine (note moved to).
L-Cysteinesulfinic acid is an endogenous sulfur-containing amino acid intermediate in the biosynthesis of taurine, formed by the enzymatic oxidation of L-cysteine. It is a potent agonist at metabotropic glutamate receptors and is involved in glutamatergic signaling. The compound is used in research on neurotransmitter systems, amino acid metabolism, and taurine biosynthesis. No clinical trials have been conducted for this compound as a therapeutic agent. It is available for research purposes only. |
| Molecular Formula |
C3H7NO4S
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| Molecular Weight |
153.15698
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| Exact Mass |
153.01
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| CAS # |
1115-65-7
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| Related CAS # |
L-Cysteinesulfinic acid monohydrate;207121-48-0
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| PubChem CID |
1549098
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| Appearance |
White to off-white solid powder
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| Density |
1.828g/cm3
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| Boiling Point |
492.8ºC at 760mmHg
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| Melting Point |
>130°C (dec.) (lit.)
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| Flash Point |
251.8ºC
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| Vapour Pressure |
4.68E-11mmHg at 25°C
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| Index of Refraction |
1.673
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| LogP |
0.186
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
9
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| Complexity |
136
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C([C@@H](C(=O)O)N)S(=O)O
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| InChi Key |
ADVPTQAUNPRNPO-REOHCLBHSA-N
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| InChi Code |
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
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| Chemical Name |
(2R)-2-amino-3-sulfinopropanoic acid
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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 (~816.14 mM)
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5291 mL | 32.6456 mL | 65.2912 mL | |
| 5 mM | 1.3058 mL | 6.5291 mL | 13.0582 mL | |
| 10 mM | 0.6529 mL | 3.2646 mL | 6.5291 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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