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24425-52-3,MFCD07357274
Catalog No.:AA00C2KX

24425-52-3 | S-ETHYLGLUTATHIONE

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C2KX
Chemical Name:
S-ETHYLGLUTATHIONE
CAS Number:
24425-52-3
Molecular Formula:
C12H21N3O6S
Molecular Weight:
335.3766
MDL Number:
MFCD07357274
SMILES:
CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
Properties
Computed Properties
 
Complexity:
418  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
11  
XLogP3:
-3.8  

Literature

Title: Deregulation of NR2E3, an orphan nuclear receptor, by benzo(a)pyrene-induced oxidative stress is associated with histone modification status change of the estrogen receptor gene promoter.

Journal: Toxicology letters 20150917

Title: Involvement of oxidative stress in the regulation of NPY/CART-mediated appetite control in amphetamine-treated rats.

Journal: Neurotoxicology 20150501

Title: 6-Shogaol enhances renal carcinoma Caki cells to TRAIL-induced apoptosis through reactive oxygen species-mediated cytochrome c release and down-regulation of c-FLIP(L) expression.

Journal: Chemico-biological interactions 20150225

Title: Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.

Journal: Archives of toxicology 20150101

Title: Glycogen synthase kinase 3 regulates cell death and survival signaling in tumor cells under redox stress.

Journal: Neoplasia (New York, N.Y.) 20140901

Title: Diethyl maleate inhibits MCA+TPA transformed cell growth via modulation of GSH, MAPK, and cancer pathways.

Journal: Chemico-biological interactions 20140805

Title: Regulation of death induction and chemosensitizing action of 3-bromopyruvate in myeloid leukemia cells: energy depletion, oxidative stress, and protein kinase activity modulation.

Journal: The Journal of pharmacology and experimental therapeutics 20140201

Title: The molecular mechanisms and gene expression profiling for shikonin-induced apoptotic and necroptotic cell death in U937 cells.

Journal: Chemico-biological interactions 20130925

Title: [Effects of glutathione ethyl ester on smoke inhalation lung injury].

Journal: Zhongguo wei zhong bing ji jiu yi xue = Chinese critical care medicine = Zhongguo weizhongbing jijiuyixue 20121001

Title: Redox state alters anti-cancer effects of wedelolactone.

Journal: Environmental and molecular mutagenesis 20120801

Title: Glutathione ethylester, a novel protein refolding reagent, enhances both the efficiency of refolding and correct disulfide formation.

Journal: The protein journal 20120801

Title: Glutathione-mediated neuroprotection against methylmercury neurotoxicity in cortical culture is dependent on MRP1.

Journal: Neurotoxicology 20120601

Title: Negative regulation of abscisic acid-induced stomatal closure by glutathione in Arabidopsis.

Journal: Journal of plant physiology 20111115

Title: Reversible time-dependent inhibition of cytochrome P450 enzymes by duloxetine and inertness of its thiophene ring towards bioactivation.

Journal: Toxicology letters 20111030

Title: Nitric oxide and DOPAC-induced cell death: from GSH depletion to mitochondrial energy crisis.

Journal: Molecular and cellular neurosciences 20110901

Title: Modulation of intracellular glutathione affects adipogenesis in 3T3-L1 cells.

Journal: Journal of cellular physiology 20110801

Title: GSH monoethyl ester rescues mitochondrial defects in cystic fibrosis models.

Journal: Human molecular genetics 20110715

Title: Redox-responsive polyphosphate nanosized assemblies: a smart drug delivery platform for cancer therapy.

Journal: Biomacromolecules 20110613

Title: In vitro developmental potential of macaque oocytes, derived from unstimulated ovaries, following maturation in the presence of glutathione ethyl ester.

Journal: Human reproduction (Oxford, England) 20101001

Title: Exposure to mycotoxins increases the allergic immune response in a murine asthma model.

Journal: American journal of respiratory and critical care medicine 20100601

Title: The critical role of the cellular thiol homeostasis in cadmium perturbation of the lung extracellular matrix.

Journal: Toxicology 20100112

Title: Developmental potential of bovine oocytes following IVM in the presence of glutathione ethyl ester.

Journal: Reproduction, fertility, and development 20100101

Title: Inhibition of IFN-gamma-dependent antiviral airway epithelial defense by cigarette smoke.

Journal: Respiratory research 20100101

Title: Chronic oxidative stress sensitizes hepatocytes to death from 4-hydroxynonenal by JNK/c-Jun overactivation.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20091101

Title: Manganese inhibits the ability of astrocytes to promote neuronal differentiation.

Journal: Toxicology and applied pharmacology 20091015

Title: Suppression of acrylamide toxicity by carboxyfullerene in human neuroblastoma cells in vitro.

Journal: Archives of toxicology 20090901

Title: Mitochondrial cholesterol loading exacerbates amyloid beta peptide-induced inflammation and neurotoxicity.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090520

Title: The redox state of glutathione regulates the hypoxic induction of HIF-1.

Journal: European journal of pharmacology 20090315

Title: Screening and characterization of reactive metabolites using glutathione ethyl ester in combination with Q-trap mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20090101

Title: Involvement of hydrogen peroxide in the manganese-induced myocytes mitochondrial membrane potential loss.

Journal: Toxicology mechanisms and methods 20090101

Title: Participation of glutathione in the elimination of Porphyromonas gingivalis in vivo.

Journal: Oral microbiology and immunology 20081201

Title: 15-deoxy-delta12,14-PGJ2 enhances platelet production from megakaryocytes.

Journal: Blood 20081115

Title: Hydrogen peroxide potentiates the EDHF phenomenon by promoting endothelial Ca2+ mobilization.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20081001

Title: Regulation of plant cytosolic glyceraldehyde 3-phosphate dehydrogenase isoforms by thiol modifications.

Journal: Physiologia plantarum 20080601

Title: Proteasome activation by hepatitis C core protein is reversed by ethanol-induced oxidative stress.

Journal: Gastroenterology 20080601

Title: Age-associated alterations of lipofuscin, membrane-bound ATPases and intracellular calcium in cortex, striatum and hippocampus of rat brain: protective role of glutathione monoester.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20080401

Title: Cyclooxygenase-2 independent effects of cyclooxygenase-2 inhibitors on oxidative stress and intracellular glutathione content in normal and malignant human B-cells.

Journal: Cancer immunology, immunotherapy : CII 20080301

Title: Autophagy is increased after traumatic brain injury in mice and is partially inhibited by the antioxidant gamma-glutamylcysteinyl ethyl ester.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20080301

Title: Rescue from neonatal death in the murine model of hereditary tyrosinemia by glutathione monoethylester and vitamin C treatment.

Journal: Molecular genetics and metabolism 20080301

Title: Activation of Nrf2-mediated oxidative stress response in macrophages by hypochlorous acid.

Journal: Toxicology and applied pharmacology 20080201

Title: Effects of N-acetylcysteine and glutathione ethyl ester drops on streptozotocin-induced diabetic cataract in rats.

Journal: Molecular vision 20080101

Title: Bovine in vitro oocyte maturation as a model for manipulation of the gamma-glutamyl cycle and intraoocyte glutathione.

Journal: Reproduction, fertility, and development 20080101

Title: Modulatory role of glutathione monoester in augmenting age-associated neuronal antioxidant system.

Journal: Experimental aging research 20080101

Title: Thalidomide resistance is based on the capacity of the glutathione-dependent antioxidant defense.

Journal: Molecular pharmaceutics 20080101

Title: Glutathione levels modulate domoic acid induced apoptosis in mouse cerebellar granule cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20071201

Title: Cellular thiol status-dependent inhibition of tumor cell growth via modulation of p27(kip1) translocation and retinoblastoma protein phosphorylation by 1'-acetoxychavicol acetate.

Journal: Amino acids 20070901

Title: Uncoupling protein-2 up-regulation and enhanced cyanide toxicity are mediated by PPARalpha activation and oxidative stress.

Journal: Toxicology and applied pharmacology 20070815

Title: Age-associated oxidative macromolecular damages in rat brain regions: role of glutathione monoester.

Journal: The journals of gerontology. Series A, Biological sciences and medical sciences 20070801

Title: Human p53 is inhibited by glutathionylation of cysteines present in the proximal DNA-binding domain during oxidative stress.

Journal: Biochemistry 20070703

Title: Characterization of intracellular elevation of glutathione (GSH) with glutathione monoethyl ester and GSH in brain and neuronal cultures: relevance to Parkinson's disease.

Journal: Experimental neurology 20070201

Title: Structure-activity relationship and elucidation of the determinant factor(s) responsible for the mechanism-based inactivation of cytochrome P450 2B6 by substituted phenyl diaziridines.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20061201

Title: Glutathione ester protects against hydroxynonenal-induced loss of auditory hair cells.

Journal: Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery 20061101

Title: Inducible nitric oxide synthase up-regulation and mitochondrial glutathione depletion mediate cyanide-induced necrosis in mesencephalic cells.

Journal: Journal of neuroscience research 20061001

Title: Deferoxamine reduces tissue damage during endotoxin-induced mastitis in dairy cows.

Journal: Journal of dairy science 20061001

Title: Glutathione is required for efficient production of infectious picornavirus virions.

Journal: Virology 20060930

Title: Investigation of bioactivation and toxicity of styrene in CYP2E1 transgenic cells.

Journal: Toxicology 20060921

Title: Cigarette smoke induces proinflammatory cytokine release by activation of NF-kappaB and posttranslational modifications of histone deacetylase in macrophages.

Journal: American journal of physiology. Lung cellular and molecular physiology 20060701

Title: Co-administration of glutathione and nitric oxide enhances insulin sensitivity in Wistar rats.

Journal: British journal of pharmacology 20060401

Title: Cadmium-induced astroglial death proceeds via glutathione depletion.

Journal: Journal of neuroscience research 20060201

Title: LPS-induced ROS generation and changes in glutathione level and their relation to the maturation of human monocyte-derived dendritic cells.

Journal: Life sciences 20060125

Title: Ebselen attenuates oxidative stress in ischemic astrocytes depleted of glutathione. Comparison with glutathione precursors.

Journal: Pharmacological reports : PR 20060101

Title: Downregulation of lysyl oxidase and upregulation of cellular thiols in rat fetal lung fibroblasts treated with cigarette smoke condensate.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20050201

Title: Thimerosal neurotoxicity is associated with glutathione depletion: protection with glutathione precursors.

Journal: Neurotoxicology 20050101

Title: Glutathione monoethyl ester improves functional recovery, enhances neuron survival, and stabilizes spinal cord blood flow after spinal cord injury in rats.

Journal: Neuroscience 20050101

Title: The role of glutathione transferases in cadmium stress.

Journal: Toxicology letters 20041201

Title: The development of a higher throughput reactive intermediate screening assay incorporating micro-bore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent.

Journal: Journal of pharmaceutical and biomedical analysis 20040921

Title: Regulation of cytoplasmic stress granules by apoptosis-inducing factor.

Journal: Journal of cell science 20040901

Title: Argininosuccinate synthetase is reversibly inactivated by S-nitrosylation in vitro and in vivo.

Journal: The Journal of biological chemistry 20040827

Title: Induction of the glucose-6-phosphate dehydrogenase gene expression by chronic hypoxia in PC12 cells.

Journal: FEBS letters 20040702

Title: Synchronized generation of reactive oxygen species with the cell cycle.

Journal: Life sciences 20040604

Title: Effect of ozone exposure on intracellular glutathione redox state in cultured human airway epithelial cells.

Journal: Inflammation 20040401

Title: Modulation of rat erythrocyte antioxidant defense system by buthionine sulfoximine and its reversal by glutathione monoester therapy.

Journal: Biochimica et biophysica acta 20040302

Title: Intracellular glutathione in stretch-induced cytokine release from alveolar type-2 like cells.

Journal: Respirology (Carlton, Vic.) 20040301

Title: Polymer-coated polyethylenimine/DNA complexes designed for triggered activation by intracellular reduction.

Journal: The journal of gene medicine 20040301

Title: Glutathione monoethylester prevents mitochondrial glutathione depletion during focal cerebral ischemia.

Journal: Neurochemistry international 20040201

Title: Glutathione monoethyl ester provides neuroprotection in a rat model of stroke.

Journal: Neuroscience letters 20040109

Title: Nrf2 regulates the sensitivity of death receptor signals by affecting intracellular glutathione levels.

Journal: Oncogene 20031218

Title: Cytosolic and mitochondrial ROS in staurosporine-induced retinal cell apoptosis.

Journal: Free radical biology & medicine 20031201

Title: Glutathione mediates LPS-stimulated COX-2 expression via early transient p42/44 MAPK activation.

Journal: Journal of cellular physiology 20031001

Title: Mitochondrial glutathione content determines the rate of liver regeneration after partial hepatectomy in eu- and hypothyroid rats.

Journal: Journal of hepatology 20031001

Title: Hg2+ signaling in trout hepatoma (RTH-149) cells: involvement of Ca2+-induced Ca2+ release.

Journal: Cell calcium 20030901

Title: c-Jun N-terminal kinase negatively regulates lipopolysaccharide-induced IL-12 production in human macrophages: role of mitogen-activated protein kinase in glutathione redox regulation of IL-12 production.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030715

Title: Mechanisms for sensitization to TNF-induced apoptosis by acute glutathione depletion in murine hepatocytes.

Journal: Hepatology (Baltimore, Md.) 20030601

Title: Noise-induced hearing loss in chinchillas pre-treated with glutathione monoethylester and R-PIA.

Journal: Hearing research 20030501

Title: Oxidant regulation of gene expression and neural tube development: Insights gained from diabetic pregnancy on molecular causes of neural tube defects.

Journal: Diabetologia 20030401

Title: Glutathione ester but not glutathione protects against cisplatin-induced ototoxicity in a rat model.

Journal: Journal of the American Academy of Audiology 20030401

Title: Sulfate conjugating and transport functions of MDCK distal tubular cells.

Journal: Kidney international 20030301

Title: Modulation of airway hyperresponsiveness by thiols in a murine in vivo model of allergic asthma.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20030301

Title: Photoprotection by antioxidants against UVB-radiation-induced damage in pig skin organ culture.

Journal: Radiation research 20030201

Title: Mediation of cadmium-induced oxidative damage and glucose-6-phosphate dehydrogenase expression through glutathione depletion.

Journal: Journal of biochemical and molecular toxicology 20030101

Title: 8-iso-prostaglandin F(2alpha), a product of noise exposure, reduces inner ear blood flow.

Journal: Audiology & neuro-otology 20030101

Title: In vivo and in vitro hepatotoxicity and glutathione interactions of N-methyldithiocarbamate and N,N-dimethyldithiocarbamate in the rat.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20021201

Title: Oxidative stress and inflammation contribute to lung toxicity after a common breast cancer chemotherapy regimen.

Journal: American journal of physiology. Lung cellular and molecular physiology 20020801

Title: Role of nitric oxide in the regulation of HIF-1alpha expression during hypoxia.

Journal: American journal of physiology. Cell physiology 20020701

Title: Reduced glutathione depletion causes necrosis and sensitization to tumor necrosis factor-alpha-induced apoptosis in cultured mouse hepatocytes.

Journal: Hepatology (Baltimore, Md.) 20020701

Title: Chemical chaperones reduce aggregate formation and cell death caused by the truncated Machado-Joseph disease gene product with an expanded polyglutamine stretch.

Journal: Neurobiology of disease 20020701

Title: Activation of the antioxidant response element in primary cortical neuronal cultures derived from transgenic reporter mice.

Journal: Journal of neurochemistry 20020601

Title: The systems V(IV)O(2+)-glutathione and related ligands: a potentiometric and spectroscopic study.

Journal: Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20020301

Title: Glutathione redox regulates lipopolysaccharide-induced IL-12 production through p38 mitogen-activated protein kinase activation in human monocytes: role of glutathione redox in IFN-gamma priming of IL-12 production.

Journal: Journal of leukocyte biology 20020201

Title: Neurotoxic mechanisms triggered by Alzheimer's disease-linked mutant M146L presenilin 1: involvement of NO synthase via a novel pertussis toxin target.

Journal: Journal of neurochemistry 20020201

Title: Microsomal glutathione S-transferase A1-1 with glutathione peroxidase activity from sheep liver: molecular cloning, expression and characterization.

Journal: The Biochemical journal 20011201

Title: Kainic acid induces selective mitochondrial oxidative phosphorylation enzyme dysfunction in cerebellar granule neurons: protective effects of melatonin and GSH ethyl ester.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20010801

Title: Secreted Abeta does not mediate neurotoxicity by antibody-stimulated amyloid precursor protein.

Journal: Biochemical and biophysical research communications 20010330

Title: IL-4 gene expression up-regulated by mercury in rat mast cells: a role of oxidant stress in IL-4 transcription.

Journal: International immunology 20010301

Title: Effect of in vitro ischemic or hypoxic treatment on mitochondrial electron transfer activity in rat brain slices assessed by gas-tissue autoradiography using.

Journal: Brain research 20010126

Title: Decreased levels of total and reduced glutathione in CD4+ lymphocytes in common variable immunodeficiency are associated with activation of the tumor necrosis factor system: possible immunopathogenic role of oxidative stress.

Journal: Blood 19950815

Title: Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 19900301

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Tags:24425-52-3 Molecular Formula|24425-52-3 MDL|24425-52-3 SMILES|24425-52-3 S-ETHYLGLUTATHIONE