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Gliotoxin

Gliotoxin structure

CAS No:
67-99-2
Formula:
C13H14N2O4S2
Chemical Name:
Gliotoxin
Synonyms:
10H-3,10a-Epidithiopyrazino[1,2-a]indole-1,4-dione,2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-,(3R,5aS,6S,10aR)-;Gliotoxin;10H-3,10a-Epidithiopyrazino[1,2-a]indole-1,4-dione,2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-,[3R-(3α,5aβ,6β,10aα)]-;(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;S. N. 12870;11000-18-3;11000-32-1
Categories:
Analytical Chemistry > Standard

Description

Gliotoxin is a secondary metabolite, the most abundant mycotoxin secreted by A. fumigatus, inhibits the phagocytosis of macrophages and the immune functions of other immune cells [1]. Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis[2]. Gliotoxin activates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cel

Gliotoxin is a pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. It has a role as a mycotoxin, an immunosuppressive agent, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor, a proteasome inhibitor and an antifungal agent. It is an organic disulfide, a pyrazinoindole, an organic heterotetracyclic compound and a dipeptide.|A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.

Gliotoxin Basic Attributes

Molecular Weight：

326.39

Exact Mass：

326.39

EC Number：

200-835-2

UNII：

5L648PH06K

HScode：

29419090

Characteristics

PSA：

132

XLogP3：

0.52

Density：

1.8±0.1 g/cm3

Melting Point：

195 °C

Boiling Point：

699.7±55.0 °C at 760 mmHg

Flash Point：

2℃

Refractive Index：

1.814

Water Solubility：

chloroform: 10 mg/mL, clear, colorless

Storage Conditions：

2-8°C

Toxicity：

Oral-Mouse LD50: 67 mg/kg; Abdominal cavity-mouse LDL0: 45 mg/kg

Flammability characteristics：

Combustible; burning produces toxic sulfur oxides and nitrogen oxide gases

Specific rotation：

D25 -290° (c = 0.08 in ethanol)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 3462 6.1/PG 3

wgk germany：

hazard class code：

25-36-20/21/22-11

safety instructions：

36/37/39-45-36/37-16

RTECS Number：

KB4725000

Marks：

T,Xn,F

Storage features：

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Precautionary statement(s)：

P210-P280-P305 + P351 + P338

Hazard Statements：

H225-H302-H312-H319-H332

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

MeSH Entry Terms：

Aspergillin

Gliotoxin Use and Manufacturing

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.

Computed Properties

Molecular Weight:326.4
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:326.03949928
Monoisotopic Mass:326.03949928
Topological Polar Surface Area:132
Heavy Atom Count:21
Complexity:621
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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