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D-Cysteine

Alias: DCysteine; D Cysteine
Cat No.:V38868 Purity: ≥98%
D-Cysteine is the D-isomer of cysteine and a potent inhibitor of E. coli growth.
D-Cysteine
D-Cysteine Chemical Structure CAS No.: 921-01-7
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
D-Cysteine is the D-isomer of cysteine and a potent inhibitor of E. coli growth. D-Cysteine produces H2S mediated by D-amino acid (AA) oxidase and is a neuro-protective (neuro-protection) agent against cerebellar ataxia. D-Cysteine suppresses the growth and cariogenicity of dual-species biofilms formed by Streptococcus mutans and Streptococcus sanguineus.
D-Cysteine is the D-isomer of the amino acid cysteine, a non-proteinogenic amino acid. It has the molecular formula C3H7NO2S and a molecular weight of 121.16. D-Cysteine is a strong inhibitor of Escherichia coli growth. It also functions to provide inorganic sulfates for the sulfation of xenobiotics. The compound has various biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects. D-Cysteine is a crucial building block in the biosynthesis of various biologically active molecules.
Biological Activity I Assay Protocols (From Reference)
Targets
The targets of D-Cysteine are not as well-defined as those of its L-enantiomer. As a non-physiological isomer, D-Cysteine is not involved in protein or glutathione synthesis. However, it has been found to have various biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects. D-Cysteine is a strong inhibitor of Escherichia coli growth. Its mechanism of antibacterial activity may involve interference with bacterial cell wall synthesis or metabolism. It also provides inorganic sulfates for the sulfation of xenobiotics.
ln Vitro
D-Cysteine exhibits potent in vitro activity as an inhibitor of Escherichia coli growth. Its antibacterial activity is assessed using standard broth microdilution or agar diffusion methods to determine the minimum inhibitory concentration (MIC). The compound also exhibits antioxidant activity, which can be measured using DPPH, ABTS, or other radical scavenging assays. Anti-inflammatory activity can be assessed by measuring cytokine production in immune cells. Neuroprotective effects can be studied in neuronal cell cultures.
ln Vivo
D-Cysteine has been studied in vivo for its various biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects. Its antibacterial activity against E. coli has also been evaluated in animal models of infection. The compound's ability to provide inorganic sulfates for sulfation reactions may also have physiological relevance. Further studies are needed to fully characterize its therapeutic potential.
Enzyme Assay
In vitro antibacterial assays for D-Cysteine involve measuring its activity against Escherichia coli and other bacterial strains. Standard broth microdilution or agar diffusion methods are employed to determine the minimum inhibitory concentration (MIC). Bacterial cultures are grown in appropriate media, and serial dilutions of D-Cysteine are added. After incubation, the MIC is determined. Antioxidant activity is measured using DPPH or ABTS assays. These assays confirm the compound's biological activities.
Cell Assay
In vitro cellular assays for D-Cysteine are conducted in bacterial cultures for antibacterial studies. For antioxidant and anti-inflammatory studies, immune cells or neuronal cells are used. Cells are treated with the compound at various concentrations, and cytokine production, cell viability, and oxidative stress markers are measured. These assays characterize the compound's cellular effects.
Animal Protocol
In vivo animal experiments with D-Cysteine are conducted in mouse models of bacterial infection, inflammation, or neurological disorders. The compound is administered orally or by injection at varying doses. Bacterial load is measured in infection models. Inflammatory markers and oxidative stress are assessed in inflammation models. Behavioral and biochemical assays are performed in neurological models. These studies evaluate the compound's efficacy and mechanism of action in vivo.
ADME/Pharmacokinetics
D-Cysteine is a small, polar molecule with a molecular weight of 121.16. It is soluble in water and is absorbed after oral administration. Its pharmacokinetic properties are similar to those of other amino acids. The compound is metabolized and excreted in urine. Its half-life is relatively short.
Toxicity/Toxicokinetics
D-Cysteine is considered to have low toxicity based on its use as a research compound. However, comprehensive toxicological evaluations have not been extensively published. The compound is intended for research use only and is not approved for human therapeutic use. Standard laboratory safety precautions should be followed when handling this compound.
References

[1]. Seki T. Availability of D-cysteine as a protectant for cerebellar neurons. Nihon Yakurigaku Zasshi. 2019;154(3):133-137.

[2]. Role of D-cysteine desulfhydrase in the adaptation of Escherichia coli to D-cysteine. J Biol Chem. 2001 Nov 2;276(44):40864-72.

[3]. Effect of D-cysteine on dual-species biofilms of Streptococcus mutans and Streptococcus sanguinis. Sci Rep. 2019 Apr 30;9(1):6689.

Additional Infomation
D-cysteine is an optically active cysteine with the D-configuration. It is a cysteine and also a D-α-amino acid. It is the conjugate base of D-cysteine salt. It is the conjugate acid of D-cysteine (1-). It is the enantiomer of L-cysteine. It is the zwitterion tautomer of D-cysteine. It is a thiol-containing non-essential amino acid that oxidizes to cysteine. D-cysteine is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). D-cysteine has also been reported in Indigofera tinctoria, Upland cotton, and other organisms with relevant data. See also: Cysteine (note moved to).
D-Cysteine is the D-isomer of the amino acid cysteine, a non-proteinogenic amino acid. It is a strong inhibitor of Escherichia coli growth. The compound has various biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects. D-Cysteine is a crucial building block in the biosynthesis of various biologically active molecules. It is available in high purity (≥99%) for research applications. Its unique biological activities make it a valuable tool for biochemical and pharmaceutical research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₃H₇NO₂S
Molecular Weight
121.16
Exact Mass
121.019
CAS #
921-01-7
PubChem CID
92851
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
293.9±35.0 °C at 760 mmHg
Melting Point
230ºC
Flash Point
131.5±25.9 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.550
LogP
0.23
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
7
Complexity
75.3
Defined Atom Stereocenter Count
1
SMILES
C([C@H](C(=O)O)N)S
InChi Key
XUJNEKJLAYXESH-UWTATZPHSA-N
InChi Code
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1
Chemical Name
(2S)-2-amino-3-sulfanylpropanoic acid
Synonyms
DCysteine; D Cysteine
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 : ~1 mg/mL (~8.25 mM)
H2O : ~1 mg/mL (~8.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 7.69 mg/mL (63.47 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.2535 mL 41.2677 mL 82.5355 mL
5 mM 1.6507 mL 8.2535 mL 16.5071 mL
10 mM 0.8254 mL 4.1268 mL 8.2535 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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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)
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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.

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