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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Glutathione acts as an antioxidant, a free radical scavenger and a detoxifying agent. It is a tripeptide comprised of three amino acids (cysteine, glutamic acid, and glycine) present in most mammalian tissue.
Synonyms: GSH; γ-L-Glutamyl-L-cysteinyl-glycine; Tathion
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Ievtukhov, Vladyslav ; Zadykowicz, Beata ; Blazheyevskiy, Mykola Ye. ; Krzyminski, Karol ;
Abstract: Biologically active compounds containing sulfhydryl groups (RSHs: N-acetyl-L-cysteine, D-penicillamine, glutathione and acetylthiocholine chloride) were used to develop a luminometric method for their quantification. The title substrate capable of chemiluminescence (CL) was isolated in a highly pure state as a chloride salt (99.9% using RP-HPLC) and identified using mass spectrometry (ESI Q-TOF) and 1H NMR spectroscopy. The cation included in the salt, 9-CMA+, underwent oxidation in an alk. environment containing RSHs by mol. oxygen, generating CL of various intensities, with no need for the use of hydrogen peroxide. The amount of produced light was linearly proportional to the content of investigated analytes in the system over the concentration range ∼0.2-2μM, with the detection limits in the range 0.19-1.73μM. The mechanism of chemiluminogenic oxidation of 9-CMA+ in the presence of RSHs and mol. oxygen is proposed, using computational methods at the d.-functional theory level. The presence of RSHs in an alk. medium seems to be crucial to produce hydroperoxide anions (-OOH), which initiate the 'light path' of 9-CMA+ transformations, ending with the excretion of electronically excited mols. of 10 methyl-acridan-9-one.
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Keywords: 9-cyano-10-methylacridinium cation ; chemiluminescence analysis ; DFT methods ; MS and NMR spectroscopy ; thiol nucleophiles
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CAS No. : | 70-18-8 |
Formula : | C10H17N3O6S |
M.W : | 307.32 |
SMILES Code : | O=C(O)[C@@H](N)CCC(N[C@@H](CS)C(NCC(O)=O)=O)=O |
Synonyms : |
GSH; γ-L-Glutamyl-L-cysteinyl-glycine; Tathion
|
MDL No. : | MFCD00065939 |
InChI Key : | RWSXRVCMGQZWBV-WDSKDSINSA-N |
Pubchem ID : | 124886 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; 77 Se; water; | EXAMPLE 1 S-(2-Phenylcarbamoyl-phenylselenyl)-L-glutathione 1,1 g L-glutathione (4 mmol) are dissolved in 20 ml water. A solution of 1 g <strong>[60940-34-3]2-phenyl-1,2-benzoisoselenazol-3(2H)-one</strong> (3,65 mmol) in 10 ml dimethylformamide is added slowly while stirring. The solution which is at first turbid, after completion of the addition becomes clear and yellow. Some minutes later, a precipitate appears. The suspension is stirred during the night. The precipitate is sucked off, washed with 50 ml water, then with 20 ml ethanol and dried. Yield: 1,95 g (92,8% of the theory), melting point (Fp.) 245-247 (decomposition). In a 77 Se NMR spectrum, a signal at 959 ppm (reference CH3 -Se-CH3) for 2-phenyl-1,2-benzoisoselenazole-3(2H)-one can be seen. This signal is no more contained in the reaction product. However, a new signal at 394 ppm appears. This chemical shift is characteristic for selenylsulfides. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 9The compound above was made by dissolving 2 -phenyl- 1,2- benzisoselenazol-3(2H)-one (0.779 g, 2.84 mmol) in 45 ml THF followed by addition of glutathione and 10 ml more THF. The following day 25 ml ethyl acetate was added followed by 25 ml methanol. Then 4 M HC1 in dioxane (1 ml) was added and the solution became transparent. The solution was evaporated to dryness, coevaporated twice from dichloromethane, transferred to a medium glass6119.1 frit, and rinsed 3 x with dichloromethane and dried to yield 1.747 g yellow solid characterized by HPLC-MS: m/z = 583.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In methanol; dichloromethane; at 0 - 20℃; for 16h; | [00178] To a suspension of N-(3-{5-fluoro-2-[4-(2-methoxy-ethoxy)-phenylamino]- pyrimidin-4-ylamino}-phenyl)-acrylamide 3 (0.1 g, 0.236 mmol) and glutathione (0.1 g, 0.325 mmol) in DCM (10 niL) and CH3OH (10 niL) was added TEA (0.1 g, 0.988 mmol) dropwise at 0 C. The resulting mixture was stirred at room temperature for 16 h and then concentrated. The residue was washed with H20 and dried to afford the title compound, (S)-2-amino-5-((R)-l- (carboxymethylamino)-3-(3-(3-(5-fluoro-2-(4-(2-methoxyethoxy)phenylamino)pyrimidin-4- ylamino)phenylamino)-3-oxopropylthio)-l-oxopropan-2-ylamino)-5-oxopentanoic acid (0.17 g, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. buffer; at 37℃;pH 7.3; | General procedure: <strong>[1236199-60-2]NL-101</strong> (0.03 g) was incubated with amino acids (0.02 g) and peptides (0.03 g) at 37 oC in a buffer solution, which pH was 5.3,7.3 and 9.3 respectively as the experimental surroundings. The pH of the samples was determined by a pH-meter (FE 20, MettlerToledo). All samples were kept at -20 oC until further analysis. The desalting step of the <strong>[1236199-60-2]NL-101</strong> adducts obtained under theexperimental conditions was not carried out before MS analysis. |