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GLIOTOXIN

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Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
Email: ivan@atkchemical.com
Products Intro: CAS:67-99-2
Company Name: Chengdu GLP biotechnology Co Ltd
Tel: 028-87075086 13350802083
Email: scglp@glp-china.com
Products Intro: Product Name:Gliotoxin
CAS:67-99-2
Purity:98% Package:1g;5g;10g
Company Name: Chengdu Biopurify Phytochemicals Ltd.
Tel: +8618080483897
Email: sales@biopurify.com
Products Intro: Product Name:Gliotoxin
CAS:67-99-2
Purity:0.98 Package:10mg;20mg;50mg;100mg;500mg Remarks:Can Be Customized in Bulk
Company Name: Shaanxi Pioneer Biotech Co., Ltd .
Tel: +8613259417953
Email: sales@pioneerbiotech.com
Products Intro: Product Name:Gliotoxin
CAS:67-99-2
Purity:0.99 Package:1g;25g;1kg;25kg;100kg
Company Name: career henan chemical co
Tel: +86-0371-86658258 15093356674;
Email: factory@coreychem.com
Products Intro: Product Name:GLIOTOXIN
CAS:67-99-2
Purity:99% Package:1g;1USD

GLIOTOXIN manufacturers

  • GLIOTOXIN
  • GLIOTOXIN pictures
  • $1.00 / 1g
  • 2020-01-13
  • CAS:67-99-2
  • Min. Order: 1g
  • Purity: 99%
  • Supply Ability: 200kg
GLIOTOXIN Basic information
Product Name:GLIOTOXIN
Synonyms:GLIOTOXIN;GLIOTOXIN, GLADIOCLADIUM FIMBRIATUM;2,3,5A,6-TETRAHYDRO-6-HYDROXY-3(HYROXYMETHYL)-2-METHYL-10H-3A, 10A-EPIDITHIO-PYRAZINOL[1,2ALPHA]INDOLE-1,4-DIONE;(3r-(3-alpha,5a-beta,6-beta,10a-alpha))-ymethyl)-2-methyl;10h-3,10a-epidithiopyrazino(1,2-a)indole-1,4-dione,2,3,5a,6-hydroxy-3-(hydrox;aspergillin;s.n.12870;gliotoxin from gliocladium fimbriatum
CAS:67-99-2
MF:C13H14N2O4S2
MW:326.39
EINECS:636-170-3
Product Categories:antibiotic
Mol File:67-99-2.mol
GLIOTOXIN Structure
GLIOTOXIN Chemical Properties
Melting point 221°C (rough estimate)
Boiling point 699.7±55.0 °C(Predicted)
alpha D25 -290° (c = 0.08 in ethanol)
density 1.4069 (rough estimate)
refractive index 1.6510 (estimate)
Fp 2℃
storage temp. 2-8°C
solubility chloroform: 10 mg/mL, clear, colorless
form White solid
pka12.90±0.40(Predicted)
color Monoclinic crystals from MeOH
Merck 13,4454
BRN 50675
Stability:Stable for 2 yeara as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
Safety Information
Hazard Codes T,Xn,F
Risk Statements 25-36-20/21/22-11
Safety Statements 36/37/39-45-36/37-16
RIDADR UN 3462 6.1/PG 3
WGK Germany 3
RTECS KB4725000
4.2-10-23
HazardClass 6.1(b)
PackingGroup III
HS Code 29419090
ToxicityLD50 oral in mouse: 67mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
GLIOTOXIN Usage And Synthesis
DescriptionGliotoxin is an immunosuppressive mycotoxin produced by pathogenic strains of Aspergillus and other fungi with diverse biological activities. It inhibits 20S proteasomal chymotrypsin activity (IC50 = 10 μM), blocking the degradation of IκBα and preventing the activation of NF-κB. Gliotoxin induces apoptosis in monocytes and dendritic cells and reduces phagocytosis by neutrophils. It suppresses viral infection by Nipah and Hendra virus in HEK293T cells (IC50s = 149 and 579 nM, respectively). Under reducing conditions, gliotoxin inhibits leukotriene A4 hydrolase (LTA4H; ) epoxide hydrolase activity, but not aminopeptidase activity, and leukotriene B4 (LTB4; ) synthesis in neutrophils and monocytes. In vivo, gliotoxin (5 mg/kg) reduces LTB4 plasma levels and blocks peritoneal neutrophil infiltration in a mouse model of peritonitis induced by zymosan A . It also inhibits geranylgeranyltransferase I and farnesyltransferase (IC50s = 17 and 80 μM, respectively).
Chemical PropertiesWhite powder
UsesGliotoxin is a potent epithiodioxopiperazine mycotoxin produced by species of Gliocladium, Aspergillus and Penicillium. At the cellular level gliotoxin inhibits a broad range of unrelated mechanisms, including inhibition of chymotrypsin-like activity of the 20S proteasome and Ca2+ release from mitochondria, activation of transcription factor NF-κB in response to a variety of stimuli in T and B cells, anti-inflammatory activity, and inhibition of farnesyltransferase and geranylgeranyltransferase. The mode of action appears to be via covalent interaction with proteins through mixed disulphide formation. Gliotoxin inhibits a number of thiol-requiring enzymes and also displays antioxidant and immunomodulatory activity.
UsesGliotoxin is a sulfur-containing mycotoxin produced by species of fungi and pathogens of humans. Gliotoxin exhibits inhibitory activities against histone H3K9 methyltransferase, a key enzyme in the re gulation of transcriptional activity by writing epigenetic marks. Gliotoxin also exhibits immunosuppressive properties by causing apoptosis of cells of the immune system. In addition, various studies suggests Gliotoxin may also be a potential anti-inflammatory, antibiotic, antifungal and antiviral agent.
DefinitionChEBI: A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.
HazardPoison.
Biological ActivityImmunosuppressive agent; blocks phagocytosis, cytokine production and proliferation of T and B cells. Non-competitively inhibits chymotrypsin-like activity of 20S proteasome; prevents degradation of I κ B α , an endogenous blocker of NF- κ B. Also inhibits farnesyltransferase and geranylgeranyltransferase I (IC 50 values are 80 and 17 μ M respectively) and displays antitumor activity against breast cancer in vivo .
Safety ProfilePoison by intraperitoneal andintravenous routes. When heated to decomposition itemits very toxic fumes such as SOx and NOx.
targetCOX | Wnt/β-catenin | Antifection
storage-20°C (desiccate)
Purification MethodsPurify gliotoxin by recrystallisation from MeOH. Its solubility in CHCl3 is 1%. The dibenzoyl derivative has m 202o (from CHCl3/MeOH). [Glister & Williams Nature 153 651 1944, Elvidge & Spring J Chem Soc Suppl 135 1949, Johnson et al. J Am Chem Soc 65 2005 1943, Bracken & Raistrick Biochem J 41 569 1947.]
ReferencesWaring & Beaver (1996), Gliotoxin and related epipolythiodioxopiperazines; Gen. Pharmacol., 27 1311 Kroll et al. (1999), The secondary fungal metabolite gliotoxin targets proteolytic activities of the proteasome; Chem. Biol., 6 689 Fitzpatrick et al. (2000), In vitro and in vivo effects of gliotoxin, a fungal metabolite: efficacy against dextran sodium sulfate-induced colitis in rats; Dig. Dis. Sci., 45 2327 Konig et al. (2019), Gliotoxin from Aspergillus fumigatus Abrogates Leukotriene B4 Formation through Inhibition of Leukotriene A4 Hydrolase ; Cell Chem. Biol., 26 524 Hubmann et al. (2020), Targeting Nuclear NOTCH2 by Gliotoxin Recovers a Tumor-Suppressor NOTCH3 Activity in CLL; Cells, 9 1484
Tag:GLIOTOXIN(67-99-2) Related Product Information
BUTYL ETHYL DISULPHIDE 1,5-HEXADIEN-3-OL 1,3-CYCLOHEXADIENE 1-ALLYLPIPERAZINE 2-Piperazinone 2,5-Dimethylpiperazine CYCLO(-ALA-ALA) (R)-(-)-1-OCTEN-3-OL, 99 1,2,4-TRIMETHYLDIETHYLENEDIAMINE N,N'-Diisopropylethylenediamine isopropyl methyl disulphide 2-Aminoethyldiisopropylamine METHYL PENTYL DISULPHIDE (S)-(+)-2-Methylpiperazine (R)-2-ETHYL-PIPERAZINE GLIOTOXIN 1-ETHYLPIPERAZIN-2-ONE HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE