ChemicalBook > Product Catalog > Analytical Chemistry > Standard > Food and cosmetics standards > GLIOTOXIN
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)
- Flash point:2℃
- storage temp. 2-8°C
- solubility chloroform: 10 mg/mL, clear, colorless
- form White solid
- color Monoclinic crystals from MeOH
- Merck 13,4454
- BRN 50675
GLIOTOXIN Usage And Synthesis
- Chemical PropertiesWhite powder
- 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.
- 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.
- DefinitionChEBI: A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.
- Hazard Poison.
- 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.
- 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.]
- 5-Methyl-1,5-hexadien-3-ol isopropyl propyl disulphide (R)-2-ETHYL-PIPERAZINE GLIOTOXIN 1-ETHYLPIPERAZIN-2-ONE HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE CYCLO(-ALA-ALA) CYCLO(-ALA-GLY) 1-ISOPROPYL-PIPERAZIN-2-ONE (+/-)-1,4-DIAZABICYCLO[4.4.0]DECANE 1-(3-PENTYL)-PIPERAZINE (S)-1-ISOPROPYL-2-METHYL-PIPERAZINE 2-Piperazinone 2,5-Dimethylpiperazine N,N,N',N'-TETRAMETHYL-1,2-DIAMINOPROPANE N,N-Dipropylpropionamide BUTYL ETHYL DISULPHIDE 1,5-HEXADIEN-3-OL
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