GLIOTOXIN
- CAS No.
- 67-99-2
- Chemical Name:
- GLIOTOXIN
- Synonyms
- S-82;GLIOTOXIN;s.n.12870;Nsc102866;Aids086418;aspergillin;Aids-086418;Gliotoxin solution;Aspergillin solution;Gliotoxin in Acetonitrile
- CBNumber:
- CB2745332
- Molecular Formula:
- C13H14N2O4S2
- Molecular Weight:
- 326.39
- MDL Number:
- MFCD00058534
- MOL File:
- 67-99-2.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| pka | 12.90±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. |
| InChI | InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1 |
| InChIKey | FIVPIPIDMRVLAY-RBJBARPLSA-N |
| SMILES | N12C(=O)[C@@]3(CO)SS[C@@]1(C(=O)N3C)CC1[C@@]2([H])[C@@H](O)C=CC=1 |
| FDA UNII | 5L648PH06K |
| UNSPSC Code | 12352200 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301 | |||||||||
| Precautionary statements | P301+P310 | |||||||||
| 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 | |||||||||
| F | 4.2-10-23 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29419090 | |||||||||
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
|||||||||
| Hazard Classifications | Acute Tox. 3 Oral | |||||||||
| Toxicity | LD50 oral in mouse: 67mg/kg | |||||||||
| NFPA 704 |
|
GLIOTOXIN price More Price(50)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 371715 | Gliotoxin from Gliocladium fimbriatum | 67-99-2 | 1mg | $167 | 2023-01-07 | Buy |
| Cayman Chemical | 11433 | Gliotoxin ≥98% | 67-99-2 | 1mg | $63 | 2026-04-30 | Buy |
| Cayman Chemical | 11433 | Gliotoxin ≥98% | 67-99-2 | 5mg | $279 | 2026-04-30 | Buy |
| Cayman Chemical | 11433 | Gliotoxin ≥98% | 67-99-2 | 10mg | $465 | 2026-04-30 | Buy |
| Usbiological | G3026-01 | Gliotoxin ~99%(HPLC) | 67-99-2 | 1mg | $333 | 2026-06-03 | Buy |
GLIOTOXIN Chemical Properties, Uses, Production
Description
Gliotoxin 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 Properties
White powder
Uses
Gliotoxin 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.
Uses
Gliotoxin 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.
Definition
ChEBI: A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi.
Hazard
Poison.
Biological Activity
Immunosuppressive 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 Profile
Poison by intraperitoneal andintravenous routes. When heated to decomposition itemits very toxic fumes such as SOx and NOx.
target
COX | Wnt/β-catenin | Antifection
storage
-20°C (desiccate)
Purification Methods
Purify 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.]
References
[1] PAUL WARING Joanne B. Gliotoxin and related epipolythiodioxopiperazines[J]. General Pharmacology-the Vascular System, 1996, 27 8: Pages 1311-1316. DOI:10.1016/s0306-3623(96)00083-3
[2] M KROLL. The secondary fungal metabolite gliotoxin targets proteolytic activities of the proteasome.[J]. Chemistry & biology, 1999, 6 10: 689-698. DOI:10.1016/s1074-5521(00)80016-2
[3] In vitro and in vivo effects of gliotoxin, a fungal metabolite: efficacy against dextran sodium sulfate-induced colitis in rats
[4] STEFANIE KÖNIG . Gliotoxin from Aspergillus fumigatus Abrogates Leukotriene B4 Formation through Inhibition of Leukotriene A4 Hydrolase[J]. Cell Chemical Biology, 2019, 26 4: Pages 524-534.e5. DOI:10.1016/j.chembiol.2019.01.001
[5] RAINER HUBMANN. Targeting Nuclear NOTCH2 by Gliotoxin Recovers a Tumor-Suppressor NOTCH3 Activity in CLL.[J]. Cells, 2020. DOI:10.3390/cells9061484
GLIOTOXIN Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Nanjing Shizhou Biology Technology Co.,Ltd | 025-85560043 13675144456 | sean.lv@synzest.com | China | 11432 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| BioBioPha Co., Ltd. | 0871-65217109 | y.liu@mail.biobiopha.com | China | 5641 | 65 |
| Chengdu Biopurify Phytochemicals Ltd. | +86-028-82633397 18982077548 | cwb1@biopurify.cn | China | 2376 | 60 |
| Shanghai Tauto Biotech Co., Ltd. | 021-51320588 | tauto@tautobiotech.com | China | 3984 | 66 |
| AdooQ BioScience, LLC | +1 (866) 930-6790 | info@adooq.com | United States | 2774 | 58 |
| Hangzhou J&H Chemical Co., Ltd. | 0571-87396432 | sales@jhechem.com | China | 14905 | 59 |
| Shanghai Yongye Biotechnology Co., Ltd. | 86-021-61559134 15921386130 | 3423497944@qq.com | China | 8135 | 55 |
