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  3. Gliotoxin

Gliotoxin  (Synonyms: Aspergillin)

Cat. No.: HY-N6727 Purity: 98.76%
SDS COA Handling Instructions

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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Gliotoxin Chemical Structure

Gliotoxin Chemical Structure

CAS No. : 67-99-2

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5 mg USD 420 In-stock
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Based on 1 publication(s) in Google Scholar

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

Cellular Effect
Cell Line Type Value Description References
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]
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]
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]
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.
Molecular Weight

326.39

Formula

C13H14N2O4S2

CAS No.
Appearance

Solid

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

Structure Classification
Initial Source

Aspergillus fumigatus

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
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)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.0638 mL 15.3191 mL 30.6382 mL
5 mM 0.6128 mL 3.0638 mL 6.1276 mL
View the Complete Stock Solution Preparation Table

* 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.

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Purity & Documentation

Purity: 99.51%

References

Complete Stock Solution Preparation Table

* 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.

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
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Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Gliotoxin
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