ChemicalBook > CAS DataBase List > GLIOTOXIN

GLIOTOXIN

Product Name: 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
Formula Weight: 326.39
MOL File: 67-99-2.mol

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GLIOTOXIN Property

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

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Safety

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
Toxicity: LD50 oral in mouse: 67mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger
Hazard statements: H301Toxic if swalloed
Precautionary statements: P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 371715
Product name: Gliotoxin from Gliocladium fimbriatum
Packaging: 1mg
Price: $167
Updated: 2023/01/07

Cayman Chemical

Product number: 11433
Product name: Gliotoxin
Purity: ≥98%
Packaging: 1mg
Price: $57
Updated: 2024/03/01

Cayman Chemical

Product number: 11433
Product name: Gliotoxin
Purity: ≥98%
Packaging: 5mg
Price: $253
Updated: 2024/03/01

Sigma-Aldrich

Product number: G9893
Product name: Gliotoxin from Gliocladium fimbriatum
Packaging: 5mg
Price: $262
Updated: 2025/07/31

Sigma-Aldrich

Product number: G9893
Product name: Gliotoxin from Gliocladium fimbriatum
Packaging: 25mg
Price: $824
Updated: 2025/07/31

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GLIOTOXIN Chemical Properties,Usage,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

Raw materials

Preparation Products

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GLIOTOXIN Suppliers

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View Lastest Price from GLIOTOXIN manufacturers

Career Henan Chemical Co

Product: GLIOTOXIN 67-99-2
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 200kg
Release date: 2020-01-10

67-99-2, GLIOTOXINRelated Search:

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

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

Gliotoxin, Gladiocladium fimbriatum - CAS 67-99-2 - Calbiochem

Gliotoxin, 99%, from Gliocladium fimbriatum

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

GLIOTOXIN FROM GLIOCLADIUM VIRENS

10H-3,10a-Epidithiopyrazino1,2-aindole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R,5aS,6S,10aR)-

(3R)-2-Methyl-3-(hydroxymethyl)-6β-hydroxy-3α,10aα-epidithio-1,2,3,4,5aβ,6,10,10a-octahydropyrazino[1,2-a]indole-1,4-dione

2,3,5aβ,6-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione

S-82

6-Hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5ah-3,10A-epidithiopyrazino[1,2-A]indole-1,4-dione

Aids086418

Aids-086418

Nsc102866

(3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione

Aspergillin, SN 12879, SN 12870

Aspergillin solution

Gliotoxin solution

Gliotoxin, 98%, from Gliocladium fimbriatum

GliotoxinQ: What is Gliotoxin Q: What is the CAS Number of Gliotoxin Q: What is the storage condition of Gliotoxin Q: What are the applications of Gliotoxin

Gliotoxin in Acetonitrile

Gliotoxin, NF-kappaB inhibitor

Gliotoxin, <i>Gladiocladium fimbriatum</i>

67-99-2

C13H14N2O4S2

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