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67-99-2

67-99-2 structure
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: 2025-08-22 23:52:42
  • 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
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
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
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