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67-99-2

67-99-2 structure

Name: Gliotoxin
Chemical Name: gliotoxin
CAS Number: 67-99-2
Molecular Formula: C₁₃H₁₄N₂O₄S₂
Molecular Weight: 326.391
Catalog: analytical chemistry Standard Food and cosmetics standards
Create Date: 2018-03-31 08:00:00
Modify Date: 2024-01-03 10:02:50
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
Synonyms	(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 10H-3,10a-(Iminomethano)[1,2,4]dithiazino[4,3-a]indole-4,11(3H)-dione, 5a,6-dihydro-6-hydroxy-3-(hydroxymethyl)-12-methyl-, (3R,5aS,6S,10aR)- Gliotoxin

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.

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

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
1402592-69-1 1402592-87-3
DownStream 2
19079-11-9 74149-38-5

67-99-2	101623-21-6
29762-25-2	74149-38-5
61378-02-7