| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Targets |
The Cysteine thiol probe targets free thiol groups in cysteine residues of proteins and peptides. By targeting the reactive sulfhydryl (-SH) group, this probe enables sensitive monitoring of redox states, post-translational modifications, and protein folding dynamics. The probe is designed to label electrophilic metabolites, enabling the detection and identification of reactive natural products. It does not have a classical pharmacological target but serves as a chemical biology tool.
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| ln Vitro |
When it comes to β-lactam and β-lactone-based electrophilic natural products, the cysteine thiol probe (probe 1) responds more easily, whereas it reacts less quickly with epoxide-based electrophilic natural products. Probe 2 reacts with natural compounds containing epoxides substantially more quickly. Their simultaneous usage in extracts is made possible by their orthogonal reactivity. The isotopic pattern of the tagged natural product indicates the structural origin of the product because probe 2 is chlorinated and the cysteine thiol probe is brominated. Competition studies with the cysteine thiol probe and 2 revealed that the chlorinated probe 2 reacts alone with the epoxide in salt amide A, while the brominated cysteine thiol probe only reacts with the β-lactam in penicillin G and the β-lactone in salinosporamide A [1].
In vitro, the Cysteine thiol probe functions as a chemoselective tool for detecting and labeling electrophilic metabolites. It reacts much more readily with β-lactam- and β-lactone-based electrophilic natural products, while its reactivity with epoxide-based electrophilic natural products is poor. The probe possesses a chromophore, enabling detection by spectroscopic methods. Its activity is typically evaluated by monitoring the formation of labeled products using HPLC, LC-MS, or spectrophotometric methods. |
| ln Vivo |
In vivo, the Cysteine thiol probe is used as a chemical biology tool to study the reactivity of electrophilic metabolites in biological systems. It can be used to label and track electrophilic natural products in complex biological matrices. However, specific in vivo applications and efficacy data are not extensively detailed in the available literature, as the compound is primarily used as a research probe in biochemical and analytical applications. Further studies are needed to fully characterize its in vivo utility.
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| Enzyme Assay |
Cell-free assays for the Cysteine thiol probe involve evaluating its reactivity with various electrophilic metabolites. The probe is incubated with model electrophilic compounds (β-lactams, β-lactones, enones, ketenes, epoxides) in buffered solutions. The formation of labeled products is monitored by HPLC, LC-MS, or spectrophotometric methods. Reaction kinetics and selectivity are assessed by comparing the reactivity of the probe with different classes of electrophilic compounds. The probe's chromophore enables detection by UV-visible spectroscopy.
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| Cell Assay |
In vitro cellular assays for the Cysteine thiol probe typically involve treating cells or cell lysates with the probe to label electrophilic metabolites. Cells are incubated with the probe for defined periods. Labeled metabolites are extracted and analyzed by HPLC or LC-MS. The probe's ability to detect and identify electrophilic natural products in complex biological samples is assessed. Cellular uptake and labeling efficiency are evaluated. Cytotoxicity is assessed to ensure that the probe is well-tolerated at effective concentrations.
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| Animal Protocol |
In vivo animal studies for the Cysteine thiol probe are limited, as the compound is primarily used as a research probe in biochemical and analytical applications. The probe may be administered to animals to study the reactivity of electrophilic metabolites in vivo. Tissue samples are collected and analyzed for labeled metabolites. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. The probe is intended for research use only.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of the Cysteine thiol probe include a molecular weight of 318.17 g/mol (approximate) and molecular formula C11H12BrNO3S (approximate). The compound has a purity of ≥95%. As a chemical probe, its pharmacokinetic properties are not the primary focus of study. The compound is typically stored at appropriate conditions as a research reagent. Detailed ADME parameters are not extensively reported in the available literature.
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| Toxicity/Toxicokinetics |
The toxicity profile of the Cysteine thiol probe has not been extensively characterized in published literature. As a chemical probe, it is intended for research use at carefully controlled concentrations. Standard safety precautions should be followed when handling this compound, including the use of personal protective equipment. The compound is intended for research use only and not for therapeutic applications in humans.
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| References | |
| Additional Infomation |
The Cysteine thiol probe is a chemoselective thiol-based probe designed to label electrophilic natural products. It reacts with β-lactam-, β-lactone-, enone-, and ketene-based electrophilic metabolites and possesses a chromophore for detection. The probe is used to detect and identify reactive electrophilic metabolites in complex biological samples. It is a research tool for chemical biology and metabolomics studies.
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| Molecular Formula |
C11H12BRNO3S
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|---|---|
| Molecular Weight |
318.186881065369
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| Exact Mass |
316.972
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| CAS # |
1947408-74-3
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| PubChem CID |
145925689
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| Appearance |
White to off-white solid powder
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| LogP |
2.1
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
17
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| Complexity |
280
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC(=O)[C@H](CS)NC(=O)C1=CC=C(C=C1)Br
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| InChi Key |
QLAHQHTYCQKQLI-VIFPVBQESA-N
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| InChi Code |
InChI=1S/C11H12BrNO3S/c1-16-11(15)9(6-17)13-10(14)7-2-4-8(12)5-3-7/h2-5,9,17H,6H2,1H3,(H,13,14)/t9-/m0/s1
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| Chemical Name |
methyl (2R)-2-[(4-bromobenzoyl)amino]-3-sulfanylpropanoate
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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) |
DMSO : ~250 mg/mL (~785.69 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.54 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 (6.54 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 | 3.1428 mL | 15.7139 mL | 31.4278 mL | |
| 5 mM | 0.6286 mL | 3.1428 mL | 6.2856 mL | |
| 10 mM | 0.3143 mL | 1.5714 mL | 3.1428 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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