Gliotoxin

Modify Date: 2025-08-22 23:52:42

Gliotoxin structure	Common Name	Gliotoxin
	CAS Number	67-99-2	Molecular Weight	326.391
	Density	1.8±0.1 g/cm3	Boiling Point	699.7±55.0 °C at 760 mmHg
	Molecular Formula	C₁₃H₁₄N₂O₄S₂	Melting Point	153.5ºC
	MSDS	Chinese USA	Flash Point	377.0±31.5 °C
	Symbol	GHS02, GHS07	Signal Word	Danger

Use of Gliotoxin

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 cells[3].

Name	gliotoxin
Synonym	More Synonyms

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 cells[3].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA Signaling Pathways >> Stem Cell/Wnt >> PKA Research Areas >> Inflammation/Immunology
References	[1]. Schlam D, et al. Gliotoxin Suppresses Macrophage Immune Function by Subverting Phosphatidylinositol 3,4,5-Trisphosphate Homeostasis. MBio. 2016 Apr 5;7(2):e02242. [2]. Coméra C, et al. Gliotoxin from Aspergillus fumigatus affects phagocytosis and the organization of the actin cytoskeleton by distinct signalling pathways in human neutrophils. Microbes Infect. 2007 Jan;9(1):47-54. Epub 2006 Dec 12. [3]. Zhang C, et al. Gliotoxin Induces Cofilin Phosphorylation to Promote Actin Cytoskeleton Dynamics and Internalization of Aspergillus fumigatus Into Type II Human Pneumocyte Cells. Front Microbiol. 2019 Jun 18;10:1345.

Description

Related Catalog

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA

Signaling Pathways >> Stem Cell/Wnt >> PKA

Research Areas >> Inflammation/Immunology

References

[1]. Schlam D, et al. Gliotoxin Suppresses Macrophage Immune Function by Subverting Phosphatidylinositol 3,4,5-Trisphosphate Homeostasis. MBio. 2016 Apr 5;7(2):e02242.

[2]. Coméra C, et al. Gliotoxin from Aspergillus fumigatus affects phagocytosis and the organization of the actin cytoskeleton by distinct signalling pathways in human neutrophils. Microbes Infect. 2007 Jan;9(1):47-54. Epub 2006 Dec 12.

[3]. Zhang C, et al. Gliotoxin Induces Cofilin Phosphorylation to Promote Actin Cytoskeleton Dynamics and Internalization of Aspergillus fumigatus Into Type II Human Pneumocyte Cells. Front Microbiol. 2019 Jun 18;10:1345.

Density	1.8±0.1 g/cm3
Boiling Point	699.7±55.0 °C at 760 mmHg
Melting Point	153.5ºC
Molecular Formula	C₁₃H₁₄N₂O₄S₂
Molecular Weight	326.391
Flash Point	377.0±31.5 °C
Exact Mass	326.039490
PSA	131.68000
LogP	0.52
Vapour Pressure	0.0±5.0 mmHg at 25°C
Index of Refraction	1.814
InChIKey	FIVPIPIDMRVLAY-RBJBARPLSA-N
SMILES	CN1C(=O)C23CC4=CC=CC(O)C4N2C(=O)C1(CO)SS3

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KB4725000

CHEMICAL NAME :: 10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-hydroxy-3- (hydroxymethyl)-2-methyl-, (3R-(3-alpha,5a-beta,6-beta,10a-alpha))-

CAS REGISTRY NUMBER :: 67-99-2

BEILSTEIN REFERENCE NO. :: 0050675

LAST UPDATED :: 199709

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C13-H14-N2-O4-S2

MOLECULAR WEIGHT :: 326.41

WISWESSER LINE NOTATION :: T C6 B566/JO A 2BJ O AVN JXSS NNV EU GU MHTT&&J DQ M1Q N

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 67 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 32 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA repair

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 250 mg/L

REFERENCE :: MYCPAH Mycopathologia. (Kluwer Academic Pub. Group, Distribution Centre, POB 322, 3300 AH Dordrecht, Netherlands) V.1- 1938- Volume(issue)/page/year: 87,43,1984

Symbol	GHS02, GHS07
Signal Word	Danger
Hazard Statements	H225-H302-H312-H319-H332
Precautionary Statements	P210-P280-P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T
Risk Phrases	25
Safety Phrases	S45;S36/S37/S39
RIDADR	UN 3462 6.1/PG 3
WGK Germany	3
RTECS	KB4725000
Packaging Group	III
Hazard Class	6.1(b)
HS Code	29419090

Precursor 2
CAS#:1402592-69-1 (3aS,5S,6aR,7S,... CAS#:1402592-87-3 (2S,7S,7aS)-1-t...
DownStream 2
CAS#:19079-11-9 Pyrazino[1,2-a]... CAS#:74149-38-5 Bisdethiobis(me...

The MAP kinase MpkA controls cell wall integrity, oxidative stress response, gliotoxin production and iron adaptation in Aspergillus fumigatus.

Mol. Microbiol. 82(1) , 39-53, (2011)

The saprophytic fungus Aspergillus fumigatus is the most important air-borne fungal pathogen. The cell wall of A. fumigatus has been studied intensively as a potential target for development of effect...

Single-pot derivatisation strategy for enhanced gliotoxin detection by HPLC and MALDI-ToF mass spectrometry.

Anal. Bioanal. Chem 401(8) , 2519-29, (2011)

Gliotoxin is produced by non-ribosomal peptide synthesis and secreted from certain fungi, including Aspergillus fumigatus. It is an epipolythiodioxopiperazine that contains an intact disulphide bridge...

Individual and combined effects of mycotoxins from typical indoor moulds.

Toxicol. In Vitro 27(6) , 1970-8, (2013)

The mycotoxins patulin, gliotoxin and sterigmatocystin can be produced by common indoor moulds and enter the human body via inhalation of mycotoxin containing spores and particulates. There are variou...

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in YKL0...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262461

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in MEF2...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262460

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in CYS3...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262459

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in YGL0...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262458

Name: USP8 deubiquitinase inhibition: Primary qHTS
Source: 24642
Target: ubiquitin specific peptidase 8
External Id: USP8 FAST DUB HTS Primary

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in YLR4...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262457

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in YOR3...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262456

Name: USP17 deubiquitinase inhibition: Primary qHTS
Source: 24642
Target: ubiquitin specific peptidase 17 like family member 5
External Id: USP17 FAST DUB HTS Primary

Name: Antimicrobial activity against Saccharomyces cerevisiae containing disruption in YGL2...
Source: ChEMBL
Target: Saccharomyces cerevisiae
External Id: CHEMBL1262455

Name: Antimicrobial activity against fluconazole-resistant Cryptococcus gattii serotype C i...
Source: ChEMBL
Target: Cryptococcus gattii
External Id: CHEMBL1261944

Total 86, Current Page 1 of 9

(1R,7S,8S,11R)-7-Hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0.0]pentadeca-3,5-diene-10,14-dione

epithiodiketopiperazine

Gliotoxin,(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

MFCD00058534

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

[3R-(3a,5ab,6b,10aa)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione

Gliotoxin

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Gliotoxin

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CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

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Precursor & DownStream

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Synonyms

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