Home Other Building Blocks S-ETHYLGLUTATHIONE

S-ETHYLGLUTATHIONE

CAS No.:
24425-52-3
Catalog Number:
AG00C2NP
Molecular Formula:
C12H21N3O6S
Molecular Weight:
335.3766
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Product Description
Catalog Number:
AG00C2NP
Chemical Name:
S-ETHYLGLUTATHIONE
CAS Number:
24425-52-3
Molecular Formula:
C12H21N3O6S
Molecular Weight:
335.3766
MDL Number:
MFCD07357274
IUPAC Name:
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-ethylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
InChI:
InChI=1S/C12H21N3O6S/c1-2-22-6-8(11(19)14-5-10(17)18)15-9(16)4-3-7(13)12(20)21/h7-8H,2-6,13H2,1H3,(H,14,19)(H,15,16)(H,17,18)(H,20,21)/t7-,8-/m0/s1
InChI Key:
HMFDVPSBWOHOAP-YUMQZZPRSA-N
SMILES:
CCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
UNII:
7W95D60F4J
Properties
Complexity:
418  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
335.115g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
335.375g/mol
Monoisotopic Mass:
335.115g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
184A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.8  
Literature
Title Journal
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Involvement of oxidative stress in the regulation of NPY/CART-mediated appetite control in amphetamine-treated rats. Neurotoxicology 20150501
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. Chemico-biological interactions 20150225
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control. Archives of toxicology 20150101
Glycogen synthase kinase 3 regulates cell death and survival signaling in tumor cells under redox stress. Neoplasia (New York, N.Y.) 20140901
Diethyl maleate inhibits MCA+TPA transformed cell growth via modulation of GSH, MAPK, and cancer pathways. Chemico-biological interactions 20140805
Regulation of death induction and chemosensitizing action of 3-bromopyruvate in myeloid leukemia cells: energy depletion, oxidative stress, and protein kinase activity modulation. The Journal of pharmacology and experimental therapeutics 20140201
The molecular mechanisms and gene expression profiling for shikonin-induced apoptotic and necroptotic cell death in U937 cells. Chemico-biological interactions 20130925
[Effects of glutathione ethyl ester on smoke inhalation lung injury]. Zhongguo wei zhong bing ji jiu yi xue = Chinese critical care medicine = Zhongguo weizhongbing jijiuyixue 20121001
Redox state alters anti-cancer effects of wedelolactone. Environmental and molecular mutagenesis 20120801
Glutathione ethylester, a novel protein refolding reagent, enhances both the efficiency of refolding and correct disulfide formation. The protein journal 20120801
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Negative regulation of abscisic acid-induced stomatal closure by glutathione in Arabidopsis. Journal of plant physiology 20111115
Reversible time-dependent inhibition of cytochrome P450 enzymes by duloxetine and inertness of its thiophene ring towards bioactivation. Toxicology letters 20111030
Nitric oxide and DOPAC-induced cell death: from GSH depletion to mitochondrial energy crisis. Molecular and cellular neurosciences 20110901
Modulation of intracellular glutathione affects adipogenesis in 3T3-L1 cells. Journal of cellular physiology 20110801
GSH monoethyl ester rescues mitochondrial defects in cystic fibrosis models. Human molecular genetics 20110715
Redox-responsive polyphosphate nanosized assemblies: a smart drug delivery platform for cancer therapy. Biomacromolecules 20110613
In vitro developmental potential of macaque oocytes, derived from unstimulated ovaries, following maturation in the presence of glutathione ethyl ester. Human reproduction (Oxford, England) 20101001
Exposure to mycotoxins increases the allergic immune response in a murine asthma model. American journal of respiratory and critical care medicine 20100601
The critical role of the cellular thiol homeostasis in cadmium perturbation of the lung extracellular matrix. Toxicology 20100112
Developmental potential of bovine oocytes following IVM in the presence of glutathione ethyl ester. Reproduction, fertility, and development 20100101
Inhibition of IFN-gamma-dependent antiviral airway epithelial defense by cigarette smoke. Respiratory research 20100101
Chronic oxidative stress sensitizes hepatocytes to death from 4-hydroxynonenal by JNK/c-Jun overactivation. American journal of physiology. Gastrointestinal and liver physiology 20091101
Manganese inhibits the ability of astrocytes to promote neuronal differentiation. Toxicology and applied pharmacology 20091015
Suppression of acrylamide toxicity by carboxyfullerene in human neuroblastoma cells in vitro. Archives of toxicology 20090901
Mitochondrial cholesterol loading exacerbates amyloid beta peptide-induced inflammation and neurotoxicity. The Journal of neuroscience : the official journal of the Society for Neuroscience 20090520
The redox state of glutathione regulates the hypoxic induction of HIF-1. European journal of pharmacology 20090315
Screening and characterization of reactive metabolites using glutathione ethyl ester in combination with Q-trap mass spectrometry. Journal of mass spectrometry : JMS 20090101
Involvement of hydrogen peroxide in the manganese-induced myocytes mitochondrial membrane potential loss. Toxicology mechanisms and methods 20090101
Participation of glutathione in the elimination of Porphyromonas gingivalis in vivo. Oral microbiology and immunology 20081201
15-deoxy-delta12,14-PGJ2 enhances platelet production from megakaryocytes. Blood 20081115
Hydrogen peroxide potentiates the EDHF phenomenon by promoting endothelial Ca2+ mobilization. Arteriosclerosis, thrombosis, and vascular biology 20081001
Regulation of plant cytosolic glyceraldehyde 3-phosphate dehydrogenase isoforms by thiol modifications. Physiologia plantarum 20080601
Proteasome activation by hepatitis C core protein is reversed by ethanol-induced oxidative stress. Gastroenterology 20080601
Age-associated alterations of lipofuscin, membrane-bound ATPases and intracellular calcium in cortex, striatum and hippocampus of rat brain: protective role of glutathione monoester. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20080401
Cyclooxygenase-2 independent effects of cyclooxygenase-2 inhibitors on oxidative stress and intracellular glutathione content in normal and malignant human B-cells. Cancer immunology, immunotherapy : CII 20080301
Autophagy is increased after traumatic brain injury in mice and is partially inhibited by the antioxidant gamma-glutamylcysteinyl ethyl ester. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20080301
Rescue from neonatal death in the murine model of hereditary tyrosinemia by glutathione monoethylester and vitamin C treatment. Molecular genetics and metabolism 20080301
Activation of Nrf2-mediated oxidative stress response in macrophages by hypochlorous acid. Toxicology and applied pharmacology 20080201
Effects of N-acetylcysteine and glutathione ethyl ester drops on streptozotocin-induced diabetic cataract in rats. Molecular vision 20080101
Bovine in vitro oocyte maturation as a model for manipulation of the gamma-glutamyl cycle and intraoocyte glutathione. Reproduction, fertility, and development 20080101
Modulatory role of glutathione monoester in augmenting age-associated neuronal antioxidant system. Experimental aging research 20080101
Thalidomide resistance is based on the capacity of the glutathione-dependent antioxidant defense. Molecular pharmaceutics 20080101
Glutathione levels modulate domoic acid induced apoptosis in mouse cerebellar granule cells. Toxicological sciences : an official journal of the Society of Toxicology 20071201
Cellular thiol status-dependent inhibition of tumor cell growth via modulation of p27(kip1) translocation and retinoblastoma protein phosphorylation by 1'-acetoxychavicol acetate. Amino acids 20070901
Uncoupling protein-2 up-regulation and enhanced cyanide toxicity are mediated by PPARalpha activation and oxidative stress. Toxicology and applied pharmacology 20070815
Age-associated oxidative macromolecular damages in rat brain regions: role of glutathione monoester. The journals of gerontology. Series A, Biological sciences and medical sciences 20070801
Human p53 is inhibited by glutathionylation of cysteines present in the proximal DNA-binding domain during oxidative stress. Biochemistry 20070703
Characterization of intracellular elevation of glutathione (GSH) with glutathione monoethyl ester and GSH in brain and neuronal cultures: relevance to Parkinson's disease. Experimental neurology 20070201
Structure-activity relationship and elucidation of the determinant factor(s) responsible for the mechanism-based inactivation of cytochrome P450 2B6 by substituted phenyl diaziridines. Drug metabolism and disposition: the biological fate of chemicals 20061201
Glutathione ester protects against hydroxynonenal-induced loss of auditory hair cells. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery 20061101
Inducible nitric oxide synthase up-regulation and mitochondrial glutathione depletion mediate cyanide-induced necrosis in mesencephalic cells. Journal of neuroscience research 20061001
Deferoxamine reduces tissue damage during endotoxin-induced mastitis in dairy cows. Journal of dairy science 20061001
Glutathione is required for efficient production of infectious picornavirus virions. Virology 20060930
Investigation of bioactivation and toxicity of styrene in CYP2E1 transgenic cells. Toxicology 20060921
Cigarette smoke induces proinflammatory cytokine release by activation of NF-kappaB and posttranslational modifications of histone deacetylase in macrophages. American journal of physiology. Lung cellular and molecular physiology 20060701
Co-administration of glutathione and nitric oxide enhances insulin sensitivity in Wistar rats. British journal of pharmacology 20060401
Cadmium-induced astroglial death proceeds via glutathione depletion. Journal of neuroscience research 20060201
LPS-induced ROS generation and changes in glutathione level and their relation to the maturation of human monocyte-derived dendritic cells. Life sciences 20060125
Ebselen attenuates oxidative stress in ischemic astrocytes depleted of glutathione. Comparison with glutathione precursors. Pharmacological reports : PR 20060101
Downregulation of lysyl oxidase and upregulation of cellular thiols in rat fetal lung fibroblasts treated with cigarette smoke condensate. Toxicological sciences : an official journal of the Society of Toxicology 20050201
Thimerosal neurotoxicity is associated with glutathione depletion: protection with glutathione precursors. Neurotoxicology 20050101
Glutathione monoethyl ester improves functional recovery, enhances neuron survival, and stabilizes spinal cord blood flow after spinal cord injury in rats. Neuroscience 20050101
The role of glutathione transferases in cadmium stress. Toxicology letters 20041201
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 of pharmaceutical and biomedical analysis 20040921
Regulation of cytoplasmic stress granules by apoptosis-inducing factor. Journal of cell science 20040901
Argininosuccinate synthetase is reversibly inactivated by S-nitrosylation in vitro and in vivo. The Journal of biological chemistry 20040827
Induction of the glucose-6-phosphate dehydrogenase gene expression by chronic hypoxia in PC12 cells. FEBS letters 20040702
Synchronized generation of reactive oxygen species with the cell cycle. Life sciences 20040604
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Modulation of rat erythrocyte antioxidant defense system by buthionine sulfoximine and its reversal by glutathione monoester therapy. Biochimica et biophysica acta 20040302
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Polymer-coated polyethylenimine/DNA complexes designed for triggered activation by intracellular reduction. The journal of gene medicine 20040301
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Glutathione monoethyl ester provides neuroprotection in a rat model of stroke. Neuroscience letters 20040109
Nrf2 regulates the sensitivity of death receptor signals by affecting intracellular glutathione levels. Oncogene 20031218
Cytosolic and mitochondrial ROS in staurosporine-induced retinal cell apoptosis. Free radical biology & medicine 20031201
Glutathione mediates LPS-stimulated COX-2 expression via early transient p42/44 MAPK activation. Journal of cellular physiology 20031001
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Hg2+ signaling in trout hepatoma (RTH-149) cells: involvement of Ca2+-induced Ca2+ release. Cell calcium 20030901
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 of immunology (Baltimore, Md. : 1950) 20030715
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Sulfate conjugating and transport functions of MDCK distal tubular cells. Kidney international 20030301
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Photoprotection by antioxidants against UVB-radiation-induced damage in pig skin organ culture. Radiation research 20030201
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In vivo and in vitro hepatotoxicity and glutathione interactions of N-methyldithiocarbamate and N,N-dimethyldithiocarbamate in the rat. Toxicological sciences : an official journal of the Society of Toxicology 20021201
Oxidative stress and inflammation contribute to lung toxicity after a common breast cancer chemotherapy regimen. American journal of physiology. Lung cellular and molecular physiology 20020801
Role of nitric oxide in the regulation of HIF-1alpha expression during hypoxia. American journal of physiology. Cell physiology 20020701
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Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 19900301
Properties