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Quality Control of [ 52-90-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 52-90-4 ]

Product Citations Expand+

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

Purchased 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.

from AmBeed: class="">2251-65-2 ; class="">90098-04-7 ; class="">4876-14-6 ; class="">90098-08-1 ; class="">874-60-2 ; class="">4876-10-2 ; class="">7158-32-9 ; class="">5271-67-0 ; class="">118-45-6 ; class="">73-22-3 ; class="">56-41-7 ; class="">34893-92-0 ; class="">403-43-0 ; class="">58757-38-3 ; class="">76903-88-3 ; class="span_more span_less">52-90-4 ; class="span_more span_less">6068-72-0 ; class="span_more span_less">2243-83-6 ; class="span_more span_less">38818-50-7 ; class="span_more span_less">16331-45-6 ; class="span_more span_less">36823-88-8 ; class="span_more span_less">90098-06-9 ; class="span_more span_less">90098-05-8 ; class="span_more span_less">3024-72-4 ; class="span_more span_less">618-46-2 ; class="span_more span_less">63024-43-1 ; class="span_more span_less">4122-68-3 ; class="span_more span_less">22980-09-2 ; class="span_more span_less">681806-75-7 ; class="span_more span_less">39544-74-6 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

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	MDL No. :	MFCD00064306
Formula :	C₃H₇NO₂S	Boiling Point :	-
Linear Structure Formula :	H₂NCH(CH₂SH)CO₂H	InChI Key :	XUJNEKJLAYXESH-REOHCLBHSA-N
M.W :	121.16	Pubchem ID :	5862
Synonyms :	Cysteine;L-Cys;Cysteinum;FEMA No. 3263;NSC 8746;(R)-Cysteine;L-(+)-Cysteine	Chemical Name :	(R)-2-Amino-3-mercaptopropanoic acid

Calculated chemistry of [ 52-90-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	28.94
TPSA :	102.12 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.37
Log Po/w (XLOGP3) :	-2.49
Log Po/w (WLOGP) :	-0.67
Log Po/w (MLOGP) :	-3.06
Log Po/w (SILICOS-IT) :	-0.69
Consensus Log Po/w :	-1.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.11
Solubility :	1560.0 mg/ml ; 12.9 mol/l
Class :	Highly soluble
Log S (Ali) :	0.89
Solubility :	936.0 mg/ml ; 7.73 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.59
Solubility :	470.0 mg/ml ; 3.88 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 52-90-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 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 ]

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

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

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

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

Reference： [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 ]

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

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

Reference： [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 ]

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

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

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

[ 52-90-4 ] Synthesis Path-Downstream 1~10

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

Reference： [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
[ 2799-07-7 ]
[ 52-90-4 ]

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

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

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

4
[ 52-90-4 ]
[ 5780-66-5 ]
(R)-2-Pyrazin-2-yl-thiazolidine-4-carboxylic acid [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 1468 - 1473

5
[ 52-90-4 ]
[ 76-83-5 ]
[ 2799-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	magnesium bromide; In acetonitrile; at 40 - 50℃;Product distribution / selectivity;	Example 16: H-Cys(Tr)-OH (S-trityl cysteine) by selective S- tritylation of cysteine.Method A.; 0.20 g of cysteine (1.7 mmol) are dissolved in a solution of 0.46 g of triphenylmethyl chloride (1.7 mmol) and 0.31 g of MgBr2 (1.7 mmol) in 4 mL of MeCN, kept under stirring at 40 - 50°. The clear, yellow solution loses its colour when its temperature is lowered at room temperature. An equal volume of water containing 0.32 g (1.7 mmol) of citric acid is added to the final mixture and TEA is added until the pH is about 5. The evaporation under vacuum of MeCN gives rise to a suspension. The solid, isolated by filtration and washings with water, is thoroughly washed with Ac and the organic washings are added to a second portion of the water solution of citric acid, and treated as previously described, obtaining a second portion of the solid insoluble in Ac. The amount of solid, chromatographically pure H-Cys (Tr) -OH recovered in the two successive EPO <DP n="33"/>treatments is 0.28 g (th. 0.60 g, 46.67percent; mp 182 - 84 dec; an. C 72.63 (72.70), H 6.11 (5.87), N 3.85 (3.85), S 8.55 (8.82) .
	zinc(II) chloride; In acetonitrile; at 20℃; for 0.166667h;Product distribution / selectivity;	Method B.; 0.10 g of cysteine (0.8 mmol) , on dissolving under stirring in 4 piiL of hot MeCN containing 0.11 g of ZnC12 (0.8 mmol) and 0.23 g of TrCl (0.8 mmol), gives rise to complete dissolution and loss of colour in about 5 min. After further 5 min at room temperature, the liquid becomes turbid. The reaction mixture is poured into 100 mL of water and kept under vigorous stirring after the pH is adjusted to 5, the suspension was filtered off, the solid washed with water. The dried solid is dissolved in 4 mL of Ac and mixed with an equal volume of water containing citric acid in a molar ratio 8:1. The mixture, alkalinised to pH 6 with TEA becomes clear. Ac is distilled under vacuum and 4 mL of water are added to the remaining suspension. Filtration leads to the isolation of a solid only partially soluble in Ac. After washing with this solvent, 0.23 g of chromatographically pure H-Cys (Tr) -OH are obtained. The treatment of the organic filtrate, reunited with washings, with citric acid, according to the procedure described above, produces further product (0.18 g) with analogous features (th. 0.60 g, 68.33percent; mp 183 - 84° dec; an.: C 72.65 (72.70), H 6.05 (5.82), N 3.83 (3.85), S 8.72 (8.82) .

Reference： [1]Patent: WO2007/9944,2007,A1 .Location in patent: Page/Page column 31-32
[2]Patent: WO2007/9944,2007,A1 .Location in patent: Page/Page column 30-31

6
[ 7724-12-1 ]
[ 52-90-4 ]
[ 5571-98-2 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9658 - 9662

7
[ 76-84-6 ]
[ 52-90-4 ]
[ 2799-07-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; acetic acid; at 20℃; for 5h;	To a solution of l-cysteine (1.0 g, 5.69 mmol) in acetic acid (15 mL) was added triphenyl methanol (1.64 g, 6.30 mmol), followed by adding trifluoroboron ethylether (720 muL, 5.69 mmol) dropwise and the reaction was stirred at room temperature. After 5 h, the reaction mixture was neutralized with saturated sodium acetate. The resulting precipitate was washed with ethylether and collected to give the desired compound 3 (1.87 g, 90percent) as a white solid. 1H NMR (300 MHz, acetone-d6): delta = 7.46-7.23 (m, 15H), 3.64 (dd, J = 8.10 Hz, 4.20 Hz, 1H), 2.67-2.52 (m, 2H). 13C NMR (75 MHz, DMSO-d6): delta = 169.89, 144.42, 129.25, 128.11, 126.78, 65.95, 53.64, 34.39. MALDI-TOF-MS: Calcd for C22H20NO2S 362.1. Found 362.1 [M-H]-.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3465 - 3469

8
[ 52-90-4 ]
[ 4016-63-1 ]
[ 1439388-74-5 ]
[ 118-00-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3864 - 3867

9
[ 52-90-4 ]
[ 6574-97-6 ]
C₁₀H₇Cl₂NO₂S [ No CAS ]

Reference： [1]Biochemical Pharmacology,2015,vol. 96,p. 93 - 106

10
[ 52-90-4 ]
[ 939-69-5 ]
C₁₂H₁₀N₂O₂S₂ [ No CAS ]

Reference： [1]ChemistryOpen,2018,vol. 7,p. 256 - 261

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Isomers

Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 52-90-4 ] {[proInfo.proName]}

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