Art. -Nr.: HY-N6727

Gliotoxin

(Synonyms: Aspergillin)

2 Cited Publications

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Based on 2 publication(s) in Google Scholar

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 . Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis. Gliotoxin activates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cells. Gliotoxin is a potent NOTCH2 transactivation inhibitor, can effectively induce apoptosis of chronic lymphocytic leukemia (CLL) cells.

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Reinheit: 99.50%
CAS. Nr.: 67-99-2
Formel: C₁₃H₁₄N₂O₄S₂
Molecular Weight:326.39

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Gliotoxin Chemical Structure

CAS. Nr.: 67-99-2

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (2)
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

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]. Gliotoxin is a potent NOTCH2 transactivation inhibitor, can effectively induce apoptosis of chronic lymphocytic leukemia (CLL) cells^[4].

Alle PKA Isoform-spezifische Produkte anzeigen :

Alle NF-κB Isoform-spezifische Produkte anzeigen :

Alle Antibiotic Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	0.003 μM Compound: 10	Cytotoxicity against human A549 cells Cytotoxicity against human A549 cells	[PMID: 20303767]
CCRF-CEM	IC₅₀	0.15 μM Compound: gliotoxin	Cytotoxicity against human CEM cells after 96 hrs Cytotoxicity against human CEM cells after 96 hrs	[PMID: 16124785]
HCT-116	IC₅₀	0.41 μM Compound: 311	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 38181652]
HCT-116	IC₅₀	1.24 μM Compound: 311	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 38181652]
HEK293	IC₅₀	1.58 μM Compound: 311	Cytotoxicity against HEK293 cells assessed as cell growth inhibition Cytotoxicity against HEK293 cells assessed as cell growth inhibition	[PMID: 38181652]
HeLa	IC₅₀	2.45 μM Compound: 10	Cytotoxicity against human HeLa cells Cytotoxicity against human HeLa cells	[PMID: 20303767]
HepG2	IC₅₀	0.21 μM Compound: 311	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
HepG2	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
HUVEC	IC₅₀	0.123 μM Compound: 10	Cytotoxicity against HUVEC Cytotoxicity against HUVEC	[PMID: 20303767]
Jurkat	IC₅₀	<1 μM Compound: 10	Cytotoxicity against human Jurkat cells after 40 hrs bioluminescence assay Cytotoxicity against human Jurkat cells after 40 hrs bioluminescence assay	[PMID: 20303767]
Macrophage	ED₅₀	0.104 μM Compound: 10	Immunomodulatory activity in macrophage assessed as inhibition of phagocytosis Immunomodulatory activity in macrophage assessed as inhibition of phagocytosis	[PMID: 20303767]
MCF7	IC₅₀	0.08 μM Compound: 311	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
MCF7	IC₅₀	0.08 μM Compound: 311	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
NCI-H460	IC₅₀	0.21 μM Compound: 311	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
NCI-H460	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
P388	IC₅₀	0.024 μM Compound: 6	Cytotoxicity against mouse P388 cells after 96 hrs by MTT assay Cytotoxicity against mouse P388 cells after 96 hrs by MTT assay	[PMID: 22148349]
P815	ED₅₀	2 μM Compound: Gliotoxin	Compound was evaluated for Thymidine incorporation in P815 cell lines Compound was evaluated for Thymidine incorporation in P815 cell lines	10.1016/S0960-894X(97)10052-X
PC-3	IC₅₀	0.39 μM Compound: 311	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability Cytotoxicity against human PC-3 cells assessed as reduction in cell viability	[PMID: 38181652]
PC-3	IC₅₀	15.87 μM Compound: 311	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay Cytotoxicity against human PC-3 cells assessed as reduction in cell viability measured after 72 hrs by MTT assay	[PMID: 38181652]
RKO	IC₅₀	0.8 μM Compound: 311	Cytotoxicity against human RKO cells assessed as inhibition of cell growth measured after 48 hrs by MTT assay Cytotoxicity against human RKO cells assessed as inhibition of cell growth measured after 48 hrs by MTT assay	[PMID: 38181652]
SF-268	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 48 hrs by SRB assay	[PMID: 38181652]
SF-268	IC₅₀	0.24 μM Compound: 311	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay Cytotoxicity against human SF-268 cells assessed as reduction in cell growth incubated for 72 hrs by SRB assay	[PMID: 38181652]
U-937	IC₅₀	0.2 μM Compound: 311	Cytotoxicity against human U-937 cells assessed as reduction in cell viability Cytotoxicity against human U-937 cells assessed as reduction in cell viability	[PMID: 38181652]
U-937	IC₅₀	0.52 μM Compound: 311	Cytotoxicity against human U-937 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human U-937 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 38181652]

In Vitro

Gliotoxin (50 ng/ml, 48 hours) promotes the internalization of Aspergillus fumigatus by A549 type II human pneumocytes through inducing cofilin phosphorylation and actin cytoskeleton rearrangement^[3].
Gliotoxin (2.5%, 5%, 10%, 20% culture filtrates of Aspergillus fumigatus containing Gliotoxin, 16 hours) induces apoptosis in EL4 thymoma cells through Bak-dependent mechanisms and activation of caspase 3, leading to phosphatidylserine translocation and cell death^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[3]

Cell Line:

A549 type II human pneumocytes
Concentration:

50 ng/ml
Incubation Time:

48 hours
Result:

Induced cofilin phosphorylation, promoting actin cytoskeleton rearrangement and facilitating internalization of Aspergillus fumigatus.

In Vivo

Gliotoxin (50 ng/ml, Intranasal administration, single dose) enhances the invasiveness of Aspergillus fumigatus in Hydrocortisone (HY-N0583)-induced immunosuppressed C57BL/6 mouse models by promoting lung tissue invasion and increasing fungal burden^[3].
Gliotoxin (Intranasal administration, single dose) significantly increases fungal burden in the lungs and mortality in Hydrocortisone (HY-N0583)-induced immunosuppressed BALB/c and 129/Sv mouse models, contributing to the virulence of Aspergillus fumigatus^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Hydrocortisone (HY-N0583)-induced immunosuppressed C57BL/6 mice^[3]

Dosage:

50 ng/ml

Administration:

Intranasal administration, single dose

Result:

Helped the gliP mutant strain (which cannot produce Gliotoxin) invade lung tissues, leading to increased fungal burden in the lungs of immunosuppressed mice.

Animal Model:

Hydrocortisone (HY-N0583)-induced immunosuppressed BALB/c and 129/Sv mouse models [4]
Dosage:

Gliotoxin concentration not explicitly mentioned, present in Aspergillus fumigatus culture filtrates
Administration:

Intranasal administration of culture filtrates containing gliotoxin, single dose
Result:

Increased lung tissue fungal burden and mortality in immunosuppressed mice. The gliP deletion strain, which cannot produce gliotoxin, showed reduced virulence.

Chemical Information

CAS. Nr. 67-99-2
Appearance Solid
Molecular Weight 326.39
Formel C₁₃H₁₄N₂O₄S₂
Color White to off-white
SMILES

O=C1N([C@]2(C(N3[C@]1(CC4=CC=C[C@@H]([C@@]34[H])O)SS2)=O)CO)C
Synonyms

Aspergillin
Structure Classification
- Antibiotics
- Other Antibiotics
Initial Source
- Microorganisms
Aspergillus fumigatus
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (2)

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Journal Impact Factor

J Biol Chem

Mitotic spindle-organizing protein 2A (MZT2A) promotes cisplatin resistance through NEMO ubiquitination and NF-κB activation in lung adenocarcinoma. [Abstract]

2026 Apr;302(4):111330. PMID: 41763311
J Nat Prod

Production of ETP-Type (Epipolythiodioxopiperazine) Mycotoxins in Clinical Fungal Isolates. [Abstract]

2026 Jan 23;89(1):322-328. PMID: 41485188

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 5 mg/mL (15.32 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

DMF : 5 mg/mL (15.32 mM; Need ultrasonic and warming)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.0638 mL

15.3191 mL

30.6382 mL

5 mM

0.6128 mL

3.0638 mL

6.1276 mL

10 mM

0.3064 mL

1.5319 mL

3.0638 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (285 KB)
SDS (419 KB)
- English - EN (419 KB)
- Français - FR (419 KB)
- Deutsch - DE (419 KB)
- Norwegian - NO (419 KB)
- Español - ES (419 KB)
- Swedish - SV (419 KB)
- Italian - IT (419 KB)
- Korean - KR (419 KB)
- Portuguese - PT (419 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[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. [Content Brief]

[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. [Content Brief]

[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. [Content Brief]

[4]. Hubmann R, et al. Gliotoxin is a potent NOTCH2 transactivation inhibitor and efficiently induces apoptosis in chronic lymphocytic leukaemia (CLL) cells. Br J Haematol. 2013 Mar;160(5):618-29. [Content Brief]

[5]. Sugui JA, et al. Gliotoxin is a virulence factor of Aspergillus fumigatus: gliP deletion attenuates virulence in mice immunosuppressed with hydrocortisone. Eukaryot Cell. 2007 Sep;6(9):1562-9. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO / DMF	1 mM	3.0638 mL	15.3191 mL	30.6382 mL	76.5955 mL
	5 mM	0.6128 mL	3.0638 mL	6.1276 mL	15.3191 mL
	10 mM	0.3064 mL	1.5319 mL	3.0638 mL	7.6595 mL
	15 mM	0.2043 mL	1.0213 mL	2.0425 mL	5.1064 mL

Keywords

Gliotoxin

2 Cited Publications

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Gliotoxin

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Publications Citing Use of MedChemExpress (MCE) Gliotoxin

Alle PKA Isoform-spezifische Produkte anzeigen

Alle NF-κB Isoform-spezifische Produkte anzeigen

Alle Antibiotic Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (2)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Gliotoxin

MCE Bioactive Compound Library

Natural Product Library Plus

Biotoxin Library

Publications Citing Use of MedChemExpress (MCE) Gliotoxin

Alle PKA Isoform-spezifische Produkte anzeigen

Alle NF-κB Isoform-spezifische Produkte anzeigen

Alle Antibiotic Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (2)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Gliotoxin Related Classifications

HY-N6727 Related Classifications