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534-25-8,MFCD00961788
Catalog No.:AA01E4LS

534-25-8 | 3H-1,2-Dithiole-3-thione

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA01E4LS
Chemical Name:
3H-1,2-Dithiole-3-thione
CAS Number:
534-25-8
Molecular Formula:
C3H2S3
Molecular Weight:
134.2430
MDL Number:
MFCD00961788
SMILES:
S=c1ccss1
Properties
Properties
 
Form:
Solid  
MP:
79-83°C  
Storage:
-20 ℃;Inert atmosphere;  

Computed Properties
 
Complexity:
94.2  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
3  
XLogP3:
1.2  

Literature

Title: Induction of complementary function reductase enzymes in colon cancer cells by dithiole-3-thione versus sodium selenite.

Journal: Journal of biochemical and molecular toxicology 20150101

Title: Up-regulation of human prostaglandin reductase 1 improves the efficacy of hydroxymethylacylfulvene, an antitumor chemotherapeutic agent.

Journal: The Journal of pharmacology and experimental therapeutics 20121101

Title: Involvement of the Nrf2-proteasome pathway in the endoplasmic reticulum stress response in pancreatic β-cells.

Journal: Toxicology and applied pharmacology 20121101

Title: Fyn inhibition by cycloalkane-fused 1,2-dithiole-3-thiones enhances antioxidant capacity and protects mitochondria from oxidative injury.

Journal: Molecular pharmacology 20120701

Title: Nrf2-mediated resistance to oxidant-induced redox disruption in embryos.

Journal: Birth defects research. Part B, Developmental and reproductive toxicology 20120601

Title: The lipid peroxidation by-product 4-hydroxy-2-nonenal (4-HNE) induces insulin resistance in skeletal muscle through both carbonyl and oxidative stress.

Journal: Endocrinology 20120501

Title: Induction of phase 2 antioxidant enzymes by broccoli sulforaphane: perspectives in maintaining the antioxidant activity of vitamins a, C, and e.

Journal: Frontiers in genetics 20120101

Title: Alternative strategy for Alzheimer's disease: stress response triggers.

Journal: International journal of Alzheimer's disease 20120101

Title: The antioxidant 3H-1,2-dithiole-3-thione potentiates advanced glycation end-product-induced oxidative stress in SH-SY5Y cells.

Journal: Experimental diabetes research 20120101

Title: Induction of human fetal hemoglobin via the NRF2 antioxidant response signaling pathway.

Journal: Blood 20110602

Title: Stabilization of Nrf2 protein by D3T provides protection against ethanol-induced apoptosis in PC12 cells.

Journal: PloS one 20110101

Title: Apoptosis modulation as a promising target for treatment of systemic sclerosis.

Journal: International journal of rheumatology 20110101

Title: Screening for active small molecules in mitochondrial complex I deficient patient's fibroblasts, reveals AICAR as the most beneficial compound.

Journal: PloS one 20110101

Title: Inactivation of protein tyrosine phosphatases by oltipraz and other cancer chemopreventive 1,2-dithiole-3-thiones.

Journal: Bioorganic & medicinal chemistry 20100815

Title: Synthesis, biological evaluation, and structure-activity relationships of dithiolethiones as inducers of cytoprotective phase 2 enzymes.

Journal: Journal of medicinal chemistry 20100624

Title: Involvement of pregnane X receptor in the regulation of CYP2B6 gene expression by oltipraz in human hepatocytes.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20100301

Title: HPLC determination of novel dithiolethione containing drugs and its application for in vivo studies in rats.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100201

Title: Up- and down-modulation of liver cytochrome P450 activities and associated events in two murine malaria models.

Journal: Malaria journal 20100101

Title: Effects of tert-butylhydroquinone on intestinal inflammatory response and apoptosis following traumatic brain injury in mice.

Journal: Mediators of inflammation 20100101

Title: Induced expression of drug metabolizing enzymes by preventive agents: role of the antioxidant response element.

Journal: Chemico-biological interactions 20091110

Title: Cruciferous nutraceutical 3H-1,2-dithiole-3-thione protects human primary astrocytes against neurocytotoxicity elicited by MPTP, MPP(+), 6-OHDA, HNE and acrolein.

Journal: Neurochemical research 20091101

Title: Hydrogen peroxide is a second messenger in phase 2 enzyme induction by cancer chemopreventive dithiolethiones.

Journal: Chemical research in toxicology 20090817

Title: Evidence for the involvement of xenobiotic-responsive nuclear receptors in transcriptional effects upon perfluoroalkyl acid exposure in diverse species.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20090601

Title: Transgenic expression of aflatoxin aldehyde reductase (AKR7A1) modulates aflatoxin B1 metabolism but not hepatic carcinogenesis in the rat.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20090501

Title: Cruciferous dithiolethione-mediated coordinated induction of total cellular and mitochondrial antioxidants and phase 2 enzymes in human primary cardiomyocytes: cytoprotection against oxidative/electrophilic stress and doxorubicin toxicity.

Journal: Experimental biology and medicine (Maywood, N.J.) 20090401

Title: Chemical genomics of cancer chemopreventive dithiolethiones.

Journal: Carcinogenesis 20090301

Title: Inhibition of arachidonic acid and iron-induced mitochondrial dysfunction and apoptosis by oltipraz and novel 1,2-dithiole-3-thione congeners.

Journal: Molecular pharmacology 20090101

Title: Upregulation of cellular glutathione by 3H-1,2-dithiole-3-thione as a possible treatment strategy for protecting against acrolein-induced neurocytotoxicity.

Journal: Neurotoxicology 20090101

Title: Phosphorylation of Nrf2 at multiple sites by MAP kinases has a limited contribution in modulating the Nrf2-dependent antioxidant response.

Journal: PloS one 20090101

Title: A Model for NAD(P)H:Quinoneoxidoreductase 1 (NQO1) Targeted Individualized Cancer Chemotherapy.

Journal: Drug target insights 20090101

Title: Nrf2-mediated transcriptional induction of antioxidant response in mouse embryos exposed to ethanol in vivo: implications for the prevention of fetal alcohol spectrum disorders.

Journal: Antioxidants & redox signaling 20081201

Title: Induction of sulfiredoxin expression and reduction of peroxiredoxin hyperoxidation by the neuroprotective Nrf2 activator 3H-1,2-dithiole-3-thione.

Journal: Journal of neurochemistry 20081001

Title: Renal protection by 3H-1,2-dithiole-3-thione against cisplatin through the Nrf2-antioxidant pathway.

Journal: Biochemical pharmacology 20080901

Title: Oridonin confers protection against arsenic-induced toxicity through activation of the Nrf2-mediated defensive response.

Journal: Environmental health perspectives 20080901

Title: The neuroprotective potential of phase II enzyme inducer on motor neuron survival in traumatic spinal cord injury in vitro.

Journal: Cellular and molecular neurobiology 20080801

Title: Effect of glutathione depletion on Leydig cell steroidogenesis in young and old brown Norway rats.

Journal: Endocrinology 20080501

Title: Abrogation of hyperosmotic impairment of insulin signaling by a novel class of 1,2-dithiole-3-thiones through the inhibition of S6K1 activation.

Journal: Molecular pharmacology 20080501

Title: Antioxidants and phase 2 enzymes in macrophages: regulation by Nrf2 signaling and protection against oxidative and electrophilic stress.

Journal: Experimental biology and medicine (Maywood, N.J.) 20080401

Title: Potent induction of total cellular GSH and NQO1 as well as mitochondrial GSH by 3H-1,2-dithiole-3-thione in SH-SY5Y neuroblastoma cells and primary human neurons: protection against neurocytotoxicity elicited by dopamine, 6-hydroxydopamine, 4-hydroxy-2-nonenal, or hydrogen peroxide.

Journal: Brain research 20080304

Title: Generation of superoxide from reaction of 3H-1,2-dithiole-3-thione with thiols: implications for dithiolethione chemoprotection.

Journal: Molecular and cellular biochemistry 20080101

Title: Nuclear factor E2-related factor 2-dependent myocardiac cytoprotection against oxidative and electrophilic stress.

Journal: Cardiovascular toxicology 20080101

Title: In situ real-time chemiluminescence imaging of reactive oxygen species formation from cardiomyocytes.

Journal: International journal of biomedical imaging 20080101

Title: Induction of Nrf2-regulated genes by 3H-1, 2-dithiole-3-thione through the ERK signaling pathway in murine keratinocytes.

Journal: European journal of pharmacology 20071222

Title: Glutathione and glutathione-linked enzymes in normal human aortic smooth muscle cells: chemical inducibility and protection against reactive oxygen and nitrogen species-induced injury.

Journal: Molecular and cellular biochemistry 20070701

Title: Tissue specific increase of the catalytic subunits of the 26S proteasome by indirect antioxidant dithiolethione in mice: enhanced activity for degradation of abnormal protein.

Journal: Life sciences 20070606

Title: The thiol antioxidant 1,2-dithiole-3-thione stimulates the expression of heat shock protein 70 in dopaminergic PC12 cells.

Journal: Neuroscience letters 20070406

Title: Upregulation of endogenous glutathione system by 3H-1,2-dithiole-3-thione in pancreatic RINm5F beta-cells as a novel strategy for protecting against oxidative beta-cell injury.

Journal: Free radical research 20070201

Title: The highly expressed and inducible endogenous NAD(P)H:quinone oxidoreductase 1 in cardiovascular cells acts as a potential superoxide scavenger.

Journal: Cardiovascular toxicology 20070101

Title: In vivo modulation of the Parkinsonian phenotype by Nrf2.

Journal: Neurotoxicology 20061201

Title: Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase.

Journal: The Journal of biological chemistry 20060908

Title: Antioxidants and phase 2 enzymes in cardiomyocytes: Chemical inducibility and chemoprotection against oxidant and simulated ischemia-reperfusion injury.

Journal: Experimental biology and medicine (Maywood, N.J.) 20060901

Title: Nrf2 controls bone marrow stromal cell susceptibility to oxidative and electrophilic stress.

Journal: Free radical biology & medicine 20060701

Title: 3H-1,2-dithiole-3-thione targets nuclear factor kappaB to block expression of inducible nitric-oxide synthase, prevents hypotension, and improves survival in endotoxemic rats.

Journal: The Journal of pharmacology and experimental therapeutics 20060401

Title: Structure-activity relationships in the induction of Phase II enzymes by derivatives of 3H-1,2-dithiole-3-thione in rats.

Journal: Chemico-biological interactions 20060325

Title: Synthesis of 1,3-dithiin dithioortho esters from the reaction of Fischer carbenes and 3H-1,2-dithiole-3-thiones.

Journal: The Journal of organic chemistry 20060120

Title: Identification of novel transcriptional networks in response to treatment with the anticarcinogen 3H-1,2-dithiole-3-thione.

Journal: Physiological genomics 20060112

Title: Modulation of apoptosis by cancer chemopreventive agents.

Journal: Mutation research 20051211

Title: Differential roles of 3H-1,2-dithiole-3-thione-induced glutathione, glutathione S-transferase and aldose reductase in protecting against 4-hydroxy-2-nonenal toxicity in cultured cardiomyocytes.

Journal: Archives of biochemistry and biophysics 20050701

Title: Role of Nrf2 signaling in regulation of antioxidants and phase 2 enzymes in cardiac fibroblasts: protection against reactive oxygen and nitrogen species-induced cell injury.

Journal: FEBS letters 20050606

Title: log P estimation of 1,2-dithiole-3-thiones and 1,2-dithiole-3-ones: a comparison of experimental and calculative approaches.

Journal: Pharmaceutical research 20050601

Title: QSAR studies on 1,2-dithiole-3-thiones: modeling of lipophilicity, quinone reductase specific activity, and production of growth hormone.

Journal: Bioorganic & medicinal chemistry letters 20050215

Title: The transcriptional response to a peroxisome proliferator-activated receptor alpha agonist includes increased expression of proteome maintenance genes.

Journal: The Journal of biological chemistry 20041210

Title: Oltipraz, 3H-1,2-dithiole-3-thione, and sulforaphane induce overlapping and protective antioxidant responses in murine microglial cells.

Journal: Toxicology letters 20041128

Title: Mimetics of caloric restriction include agonists of lipid-activated nuclear receptors.

Journal: The Journal of biological chemistry 20041029

Title: Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo.

Journal: British journal of cancer 20041018

Title: Induction of phase II enzymes by 3H-1,2-dithiole-3-thione: dose-response study in rats.

Journal: Carcinogenesis 20040901

Title: The chemical inducibility of mouse cardiac antioxidants and phase 2 enzymes in vivo.

Journal: Biochemical and biophysical research communications 20040514

Title: Induction of endogenous glutathione by the chemoprotective agent, 3H-1,2-dithiole-3-thione, in human neuroblastoma SH-SY5Y cells affords protection against peroxynitrite-induced cytotoxicity.

Journal: Biochemical and biophysical research communications 20040416

Title: Effects of 3H-1,2-dithiole-3-thione, 1,4-phenylenebis(methylene)selenocyanate, and selenium-enriched yeast individually and in combination on benzo[a]pyrene-induced mutagenesis in oral tissue and esophagus in lacZ mice.

Journal: Mutation research 20040411

Title: In vitro-in vivo antifungal evaluation and structure-activity relationships of 3H-1,2-dithiole-3-thione derivatives.

Journal: Farmaco (Societa chimica italiana : 1989) 20040401

Title: Protecting against peroxynitrite-mediated cytotoxicity in vascular smooth muscle cells via upregulating endogenous glutathione biosynthesis by 3H-1,2-dithiole-3-thione.

Journal: Cardiovascular toxicology 20040101

Title: Mass spectrometric identification of cyclic polysulfides in sediment of the Eastern Gulf of Finland. II.

Journal: European journal of mass spectrometry (Chichester, England) 20040101

Title: Evaluation of the cancer chemopreventive potency of dithiolethione analogs of oltipraz.

Journal: Carcinogenesis 20031201

Title: Modulation of gene expression by cancer chemopreventive dithiolethiones through the Keap1-Nrf2 pathway. Identification of novel gene clusters for cell survival.

Journal: The Journal of biological chemistry 20030307

Title: Induction of cellular glutathione and glutathione S-transferase by 3H-1,2-dithiole-3-thione in rat aortic smooth muscle A10 cells: protection against acrolein-induced toxicity.

Journal: Atherosclerosis 20030201

Title: Use of transgenic and mutant animal models in the study of heterocyclic amine-induced mutagenesis and carcinogenesis.

Journal: Journal of biochemistry and molecular biology 20030131

Title: Nrf2 mediates the induction of ferritin H in response to xenobiotics and cancer chemopreventive dithiolethiones.

Journal: The Journal of biological chemistry 20030124

Title: Modulation of cigarette smoke-related end-points in mutagenesis and carcinogenesis.

Journal: Mutation research 20030101

Title: The role of chemically induced glutathione and glutathione S-transferase in protecting against 4-hydroxy-2-nonenal-mediated cytotoxicity in vascular smooth muscle cells.

Journal: Cardiovascular toxicology 20030101

Title: Transcriptional induction of CYP1A1 by oltipraz in human Caco-2 cells is aryl hydrocarbon receptor- and calcium-dependent.

Journal: The Journal of biological chemistry 20020705

Title: Induction of cellular glutathione-linked enzymes and catalase by the unique chemoprotective agent, 3H-1,2-dithiole-3-thione in rat cardiomyocytes affords protection against oxidative cell injury.

Journal: Pharmacological research 20020601

Title: Lack of NQO1 induction in human tumor cells is not due to changes in the promoter region of the gene.

Journal: International journal of oncology 20020401

Title: Chemical induction of cellular antioxidants affords marked protection against oxidative injury in vascular smooth muscle cells.

Journal: Biochemical and biophysical research communications 20020322

Title: Effect of chemopreventive agents on DNA adduction induced by the potent mammary carcinogen dibenzo[a,l]pyrene in the human breast cells MCF-7.

Journal: Mutation research 20010901

Title: Role of phase 2 enzyme induction in chemoprotection by dithiolethiones.

Journal: Mutation research 20010901

Title: Kinetic constraints for the thiolysis of 4-methyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (oltipraz) and related dithiole-3-thiones in aqueous solution.

Journal: Chemical research in toxicology 20010801

Title: Formation of DNA adducts in the aorta of smoke-exposed rats, and modulation by chemopreventive agents.

Journal: Mutation research 20010725

Title: Factors influencing the induction of DT-diaphorase activity by 1,2-dithiole-3-thione in human tumor cell lines.

Journal: Biochemical pharmacology 20010415

Title: Modulation of biomarkers by chemopreventive agents in smoke-exposed rats.

Journal: Cancer research 20010315

Title: Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the cancer chemoprotective agent, 3H-1, 2-dimethiole-3-thione.

Journal: Molecular medicine (Cambridge, Mass.) 20010201

Title: 1,2-dithiole-3-thione and its structural analogue oltipraz are potent inhibitors of dibenz.

Journal: International journal of cancer 20010101

Title: Feeding thiol-containing compounds, derived from vegetables, fails to inhibit N-methylnitrosourea-induced mammary tumorigenesis.

Journal: Cancer detection and prevention 20010101

Title: Modulation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mutation in the cecum and colon of big blue rats by conjugated linoleic acid and 1,2-dithiole-3-thione.

Journal: Nutrition and cancer 20010101

Title: Inhibition of human cytochrome P450 enzymes by 1,2-dithiole-3-thione, oltipraz and its derivatives, and sulforaphane.

Journal: Chemical research in toxicology 20000401

Title: Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.

Journal: Anticancer research 20000101

Title: Inhibition of human immunodeficiency virus type 1 long terminal repeat-driven transcription by an in vivo metabolite of oltipraz: implications for antiretroviral therapy.

Journal: Biochemical and biophysical research communications 19960425

Title: Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE).

Journal: Molecular medicine (Cambridge, Mass.) 19951101

Title: Differences in xenobiotic detoxifying activities between bone marrow stromal cells from mice and rats: implications for benzene-induced hematotoxicity.

Journal: Journal of toxicology and environmental health 19951001

Title: Electrophile and antioxidant regulation of enzymes that detoxify carcinogens.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19950912

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