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Quality Control of [ 52-90-4 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Citations Show More

Rebamipide and Derivatives are Potent, Selective Inhibitors of Histidine Phosphatase Activity of the Suppressor of T Cell Receptor Signaling Proteins

Faisal Aziz ; Kanamata Reddy ; Virneliz Fernandez Vega , et al. JMC,2024,67(3):1949-1960.

DOI: 10.1021/acs.jmedchem.3c01763

Abstract: The suppressor of T cell receptor signaling (Sts) proteins are negative regulators of immune signaling. Genetic inactivation of these proteins leads to significant resistance to infection. From a 590,000 compound high-throughput screen, we identified the 2-(1H)-quinolinone derivative, rebamipide, as a putative inhibitor of Sts phosphatase activity. Rebamipide, and a small library of derivatives, are competitive, selective inhibitors of Sts-1 with IC50 values from low to submicromolar. SAR analysis indicates that the quinolinone, the acid, and the amide moieties are all essential for activity. A crystal structure confirmed the SAR and reveals key interactions between this class of compound and the protein. Although rebamipide has poor cell permeability, we demonstrated that a liposomal preparation can inactivate the phosphatase activity of Sts-1 in cells. These studies demonstrate that Sts-1 enzyme activity can be pharmacologically inactivated and provide foundational tools and insights for the development of immune-enhancing therapies that target the Sts proteins.

Purchased from AmBeed: 2251-65-2 ; 90098-04-7 ; 4876-14-6 ; 90098-08-1 ; 874-60-2 ; 4876-10-2 ; 7158-32-9 ; 5271-67-0 ; 118-45-6 ; 73-22-3 ; 56-41-7 ; 34893-92-0 ; 403-43-0 ; 58757-38-3 ; 76903-88-3 ; 52-90-4 ; 6068-72-0 ; 2243-83-6 ; 38818-50-7 ; 16331-45-6 ; 36823-88-8 ; 90098-06-9 ; 90098-05-8 ; 3024-72-4 ; 618-46-2 ; 63024-43-1 ; 4122-68-3 ; 22980-09-2 ; 681806-75-7 ; 39544-74-6

Extensive Thiol Profiling for Assessment of Intracellular Redox Status in Cultured Cells by HPLC-MS/MS

Wu, Jiandong ; Chernatynskaya, Anna ; Pfaff, Annalise , et al. Antioxidants,2022,11(1):24.

DOI: 10.3390/antiox11010024 PubMed ID: 35052528

Abstract: Oxidative stress may contribute to the pathol. of many diseases, and endogenous thiols, especially glutathione (GSH) and its metabolites, play essential roles in the maintenance of normal redox status. Understanding how these metabolites change in response to oxidative insult can provide key insights into potential methods of prevention and treatment. Most existing methodologies focus only on the GSH/GSH disulfide (GSSG) redox couple, but GSH regulation is highly complex and depends on several pathways with multiple redox-active sulfur-containing species. In order to more fully characterize thiol redox status in response to oxidative insult, a high-performance liquid chromatog. with tandem mass spectrometry (HPLC-MS/MS) method was developed to simultaneously determine seven sulfur-containing metabolites, generating a panel that systematically examines several pathways involved in thiol metabolism and oxidative stress responses. The sensitivity (LOQ as low as 0.01 ng/mL), accuracy (88-126% spike recovery), and precision (=12% RSD) were comparable or superior to those of existing methods. Addnl., the method was used to compare the baseline thiol profiles and oxidative stress responses of cell lines derived from different tissues. The results revealed a previously unreported response to oxidative stress in lens epithelial (B3) cells, which may be exploited as a new therapeutic target for oxidative-stress-related ocular diseases. Further application of this method may uncover new pathways involved in oxidative-stress-related diseases and endogenous defense mechanisms.

Keywords: HPLC-MS/MS ; biomarker ; cancer cells ; glutathione ; lens epithelial cells ; thiol

Purchased from AmBeed: 52-90-4

Development of a HPLC-MS/MS method for assessment of thiol redox status in human tear fluids

Wu, Jiandong ; Sigler, Austin ; Pfaff, Annalise , et al. Anal. Biochem.,2021,629,114295.

DOI: 10.1016/j.ab.2021.114295 PubMed ID: 34186074

Abstract: Oxidative stress is reported to be part of the pathol. of many ocular diseases. For the diagnosis of ocular diseases, tear fluid has unique advantages. Although numerous anal. methods exist for the measurement of different types of biomols. in tear fluid, few have been reported for comprehensive understanding of oxidative stress-related thiol redox signaling. In this study, a high-performance liquid chromatog.-tandem mass spectrometry (HPLC-MS/MS) method was developed to determine a panel of twelve metabolites that systematically covered several thiol metabolic pathways. With optimization of MS/MS parameters and HPLC mobile phases, this method was sensitive (LOQ as low as 0.01 ng/mL), accurate (80-125% spike recovery) and precise (<10% RSD). This LC-MS/MS method combined with a simple tear fluid collection with Schirmer test strip followed by ultrafiltration allowed the high-throughput anal. for efficient determination of metabolites associated with thiol redox signaling in human tear fluids. The method was then applied to a small cohort of tear fluids obtained from healthy individuals. The method presented here provides a new technique to facilitate future work aiming to determine the complex thiol redox signaling in tear fluids for accurate assessment and diagnosis of ocular diseases.

Keywords: Biomarker ; Glutathione ; HPLC-MS/MS ; Ocular disease ; Tear fluid ; Thiol

Purchased from AmBeed: 52-90-4 ; 923-32-0

Product Details of [ 52-90-4 ]

CAS No. :	52-90-4
Formula :	C₃H₇NO₂S
M.W :	121.16
SMILES Code :	N[C@@H](CS)C(O)=O
Synonyms :	Cysteine; L-Cys; Cysteinum
MDL No. :	MFCD00064306
InChI Key :	XUJNEKJLAYXESH-REOHCLBHSA-N
Pubchem ID :	5862

Safety of [ 52-90-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P501-P270-P264-P301+P312+P330

Application In Synthesis [ 52-90-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 52-90-4 ]
Downstream synthetic route of [ 52-90-4 ]

[ 52-90-4 ] Synthesis Path-Upstream 1~7

1
[ 52-90-4 ]
[ 1483-72-3 ]
[ 34317-61-8 ]

References: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 1550.

2
[ 52-90-4 ]
[ 34317-61-8 ]

References: [1] Biochemical Journal, 1951, vol. 48, p. 624,625.

3
[ 2684-02-8 ]
[ 52-90-4 ]
[ 34317-61-8 ]

References: [1] Journal of Biological Chemistry, 1943, vol. 151, p. 211,212.
[2] Journal of Biological Chemistry, 1931, vol. 94, p. 541,544.
[3] Journal of Biological Chemistry, 1931, vol. 94, p. 541,544.

4
[ 52-90-4 ]
[ 1483-72-3 ]
[ 7732-18-5 ]
[ 34317-61-8 ]

References: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 1550.

5
[ 52-90-4 ]
[ 32315-10-9 ]
[ 19771-63-2 ]

References: [1] Synthetic Communications, 1993, vol. 23, # 20, p. 2839 - 2844.
[2] Patent: US10239847, 2019, B1, . Location in patent: Page/Page column 9; 10.

6
[ 75-44-5 ]
[ 52-90-4 ]
[ 19771-63-2 ]

References: [1] Bulletin of the Chemical Society of Japan, 1964, vol. 37, # 2, p. 242 - 244.

7
[ 52-90-4 ]
[ 19771-63-2 ]

References: [1] Patent: EP1462444, 2004, A1, . Location in patent: Page 12.

[ 52-90-4 ] Synthesis Path-Downstream 1~26

1
[ 52-90-4 ]
[ 939-69-5 ]
[ 34500-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 20℃; for 3h;	General procedure: The hydroxy- or methoxycarbonitrile derivative (1 eq) was added to the cysteine derivative (1.05 eq) and sodium carbonate (3 eq) in 5 ml water. The mixture was stirred at room temperature for three hours before addition of dilute HCl (1 M) to pH ? 3.5 ? 4.0. The product was isolated by extraction with diethyl ether, washed by water, followed by evaporation

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.
[2]Chemical Communications,2015,vol. 51,p. 5425 - 5428.
[3]European Journal of Medicinal Chemistry,2015,vol. 94,p. 140 - 148.

2
[ 52-90-4 ]
[ 142-47-2 ]
[ 636-58-8 ]

References: [1]Agricultural and Biological Chemistry,1981,vol. 45,p. 2839 - 2846.
[2]Biochemical Journal,2013,vol. 449,p. 783 - 794.

3
[ 2799-07-7 ]
[ 52-90-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 2339 - 2347.

4
[ 2799-07-7 ]
[ 52-90-4 ]
[ 519-73-3 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 2739 - 2742.

5
[ 147214-63-9 ]
[ 56-41-7 ]
[ 56-45-1 ]
[ 52-90-4 ]
[ 567-35-1 ]