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S-1-Propenyl-L-cysteine

Cat No.:V30294 Purity: ≥98%
S-1-Propenyl-L-cysteine is the stereoisomer of S-allyl-l-cysteine, which is found in garlic and has Immune-modulatory effects; it can lower blood pressure in animal models of hypertension.
S-1-Propenyl-L-cysteine
S-1-Propenyl-L-cysteine Chemical Structure CAS No.: 52438-09-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
S-1-Propenyl-L-cysteine is the stereoisomer of S-allyl-l-cysteine, which is found in garlic and has Immune-modulatory effects; it can lower blood pressure in animal models of hypertension.
S-1-Propenyl-L-cysteine (CAS#: 52438-09-2) is a stereoisomer of S-allyl-L-cysteine, a sulfur-containing amino acid derivative found in garlic. The compound has the molecular formula C6H11NO2S and a molecular weight of 161.22. It exhibits immunomodulatory effects and has been shown to decrease blood pressure in hypertensive animal models. The compound suppresses LPS-induced TLR4 signaling by promoting denaturation and autophagy-dependent degradation of MyD88, thereby attenuating pro-inflammatory responses.
Biological Activity I Assay Protocols (From Reference)
Targets
S-1-Propenyl-L-cysteine targets the TLR4 signaling pathway. It suppresses LPS-induced TLR4 signaling by promoting denaturation and autophagy-dependent degradation of MyD88, a key adaptor protein in the TLR4 signaling cascade. By promoting MyD88 degradation, the compound attenuates pro-inflammatory responses downstream of TLR4 activation. The compound's immunomodulatory effects are mediated through this mechanism, leading to reduced production of pro-inflammatory cytokines. The compound also exhibits antihypertensive properties, likely through its effects on vascular function and inflammation.
ln Vitro
In vitro studies have demonstrated that S-1-Propenyl-L-cysteine suppresses LPS-induced TLR4 signaling. The compound promotes denaturation and autophagy-dependent degradation of MyD88, a key adaptor protein in the TLR4 signaling pathway, thereby attenuating pro-inflammatory responses. This results in reduced production of pro-inflammatory cytokines such as TNF-alpha, IL-6, and IL-1beta in response to LPS stimulation. The compound's immunomodulatory effects are consistent with those of other garlic-derived sulfur compounds. The in vitro activity has been characterized in cell-based assays using macrophages or other immune cells stimulated with LPS.
ln Vivo
In vivo studies have shown that S-1-Propenyl-L-cysteine reduces blood pressure in hypertensive animal models. The compound exhibits immunomodulatory effects in vivo, consistent with its mechanism of action involving TLR4 signaling suppression and MyD88 degradation. The compound is orally active and has been shown to be effective in animal models of hypertension. Its antihypertensive and immunomodulatory properties make it a compound of interest for studying the cardiovascular and immune effects of garlic-derived sulfur compounds.
Enzyme Assay
The in vitro enzyme/receptor binding assay for S-1-Propenyl-L-cysteine typically involves studying its effects on TLR4 signaling pathway components. Immune cells such as macrophages (e.g., RAW 264.7 cells) are treated with S-1-Propenyl-L-cysteine (typically 1-100 uM) for 1-4 hours prior to stimulation with LPS (typically 0.1-1 ug/mL). After stimulation, cells are lysed and MyD88 protein levels are measured by Western blotting to assess MyD88 degradation. TLR4 signaling activation is assessed by measuring phosphorylation of downstream signaling molecules such as IRAK1, TRAF6, and IKKalpha/beta by Western blotting. Cytokine production (TNF-alpha, IL-6, IL-1beta) is measured by ELISA in cell culture supernatants. NF-kappaB activation is assessed by measuring NF-kappaB p65 nuclear translocation by immunofluorescence or by reporter gene assays.
Cell Assay
In vitro cellular assays for S-1-Propenyl-L-cysteine are conducted using immune cell lines such as macrophages (RAW 264.7), dendritic cells, or primary macrophages. Cells are seeded in 96-well or 24-well plates and treated with varying concentrations of S-1-Propenyl-L-cysteine (typically 1-100 uM) for 1-24 hours, with or without LPS stimulation. Cell viability is monitored using MTT or similar assays to ensure that observed effects are not due to cytotoxicity. Pro-inflammatory cytokine production is measured by ELISA or multiplex cytokine assays. MyD88 protein levels are assessed by Western blotting or immunofluorescence. Autophagy induction is assessed by measuring LC3-II levels and p62 degradation by Western blotting. TLR4 surface expression is measured by flow cytometry.
Animal Protocol
In vivo animal studies for S-1-Propenyl-L-cysteine typically involve oral administration to hypertensive rodent models (e.g., spontaneously hypertensive rats or angiotensin II-infused mice). The compound is administered by oral gavage at doses ranging from 1-50 mg/kg/day for 2-8 weeks. Blood pressure is measured by tail-cuff plethysmography or radiotelemetry at regular intervals. Inflammatory markers are measured in plasma by ELISA. At study termination, tissues are harvested for histological examination, gene expression analysis, and measurement of MyD88 protein levels by Western blotting. The compound's effects on vascular function may also be assessed by measuring vascular reactivity in isolated aortic rings.
ADME/Pharmacokinetics
Pharmacokinetic properties of S-1-Propenyl-L-cysteine have been partially characterized. The compound has a molecular weight of 161.22 and a molecular formula of C6H11NO2S. It is orally active and appears as a solid. The compound should be stored at 4degC. As a small amino acid derivative, it is expected to have good oral absorption and distribution. The compound is a stereoisomer of S-allyl-L-cysteine, which is known to be enriched in garlic preparations and has documented oral bioavailability. Detailed ADME parameters such as half-life, Cmax, and bioavailability are not extensively documented in the available literature.
Toxicity/Toxicokinetics
S-1-Propenyl-L-cysteine is a naturally occurring compound found in garlic. As a sulfur-containing amino acid derivative, it is generally considered to have low toxicity, consistent with its presence in dietary garlic. The compound has immunomodulatory effects and has been shown to reduce blood pressure in hypertensive animal models. No significant toxicity has been reported at the doses used in research studies. The compound is for research use only and is not intended for human therapeutic use. Standard safety precautions should be followed when handling the compound in a laboratory setting.
References

[1]. Chemical and Biological Properties of S-1-Propenyl-l-Cysteine in Aged Garlic Extract. Molecules. 2017 Mar 31;22(4).

[2]. S-1-Propenylcysteine augments BACH1 degradation and heme oxygenase 1 expression in a nitric oxide-dependent manner in endothelial cells. Nitric Oxide. 2019 Mar 1;84:22-29.

[3]. Metabolomic study reveals the acute hypotensive effect of S-1-propenylcysteine accompanied by alteration of the plasma histidine level in spontaneously hypertensive rats. J Pharm Biomed Anal. 2019 May 10;168:148-154.

[4]. Anti-inflammatory action of cysteine derivative S-1-propenylcysteine by inducing MyD88 degradation. Sci Rep. 2018 Sep 20;8(1):14148.

Additional Infomation
S-1-Propenyl-L-cysteine (CAS 52438-09-2) is a stereoisomer of S-allyl-L-cysteine, a sulfur-containing amino acid found in garlic. The compound's chemical name is 2-amino-3-(prop-1-en-1-ylsulfanyl)propanoic acid. It exhibits immunomodulatory effects by suppressing LPS-induced TLR4 signaling through promotion of denaturation and autophagy-dependent degradation of MyD88, thereby attenuating pro-inflammatory responses. The compound also reduces blood pressure in hypertensive animal models. It is a research compound with potential applications in studying the immunomodulatory and cardiovascular effects of garlic-derived compounds. The compound is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H11NO2S
Molecular Weight
161.222
Exact Mass
161.051
CAS #
52438-09-2
PubChem CID
11989381
Appearance
White to off-white solid powder
LogP
-2
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
10
Complexity
136
Defined Atom Stereocenter Count
1
SMILES
C(/SCC(C(O)=O)N)=C\C
InChi Key
HYGGRRPFVXHQQW-HRJJCQLASA-N
InChi Code
InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2+/t5-/m0/s1
Chemical Name
(2R)-2-amino-3-[(E)-prop-1-enyl]sulfanylpropanoic 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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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)
H2O : ~2.6 mg/mL (~16.13 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 5 mg/mL (31.01 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 6.2027 mL 31.0135 mL 62.0270 mL
5 mM 1.2405 mL 6.2027 mL 12.4054 mL
10 mM 0.6203 mL 3.1014 mL 6.2027 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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