67-99-2
67-99-2
Chemical Structure
Gliotoxin
Synonym(s): Aspergillin
- CAS No.: 67-99-2
- Formula:C13H14N2O4S2
- Molecular Weight:326.39
IUPAC Name: (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,5a,6-tetrahydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N
SMILES: O=C1N([C@]2(C(N3[C@]1(CC4=CC=C[C@@H]([C@@]34[H])O)SS2)=O)CO)C
Biological Activity: 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].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Gliotoxin | 99.50% | 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 . 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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Aranotin | Aranotin strongly binds to Nsp15 viral protein. Aranotin can be used as promising SARS-CoV-2 replication strong inhibitor. Aranotin has the potential for COVID-19 research. | |||||||||||||||||||||
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Acetylaranotin | Acetylaranotin is a metabolite produced by the fungus Arachniotus aureus, exhibiting antitumor activity. Acetylaranotin is utilized in research within the field of oncology for its potential in anti-cancer applications. | |||||||||||||||||||||
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Hyalodendrin | Hyalodendrin ((+)-Hyalodendrin) is a fungal growth inhibitor with inhibitory activity against wood decay fungi. Hyalodendrin has low phytotoxicity, with an acute toxicity (LD50) of 75 mg/kg in mice. | |||||||||||||||||||||
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Acetylgliotoxin | Acetylgliotoxin (Gliotoxin monoacetate) is a farnesyltransferase (FTase) inhibitor with an IC50 of 4.4 μM against human targets. Acetylgliotoxin inhibits the growth of fungal, bacterial, and viral pathogens; it binds to free protein thiols and induces ROS production. Acetylgliotoxin increases the survival rate of Caenorhabditis elegans infected with Candida albicans, but exhibits toxicity at higher concentrations. Acetylgliotoxin is applicable to research related to Candida albicans infections. | |||||||||||||||||||||
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Rostratin A | Rostratin A is a cytotoxic disulfide found in the marine-derived fungus Exserohilum rostratum. Rostratin A shows in vitro cytotoxicity against human colon carcinoma (HCT-116) with an IC50 of 8.5 μg/mL. | |||||||||||||||||||||
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Rostratin B | Rostratin B, a cytotoxic disulfide, shows in vitro cytotoxicity against human colon carcinoma (HCT-116) with IC50 of 1.9 μg/mL. | |||||||||||||||||||||
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Epicorazine A | Epicorazine A has activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococcus (VRE), MICs of 12.5-25 μg/mL. Epicorazine A also has effect on Candida albicans with a MIC of 25 μg/mL. | |||||||||||||||||||||
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Epicorazine B | Epicorazine B has activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococcus (VRE), MICs of 12.5-25 μg/mL. Epicorazine B also has effect on Candida albicans with a MIC of 25 μg/mL. | |||||||||||||||||||||
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Haematocin | Haematocin can inhibit the germination of Pyricularia oryzae spore. | |||||||||||||||||||||
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Bis(methylthio)gliotoxin | Bis(methylthio)gliotoxin is a more stable and reliable marker for invasive aspergillosis than gliotoxin and suitable for use in diagnosis. | |||||||||||||||||||||
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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. [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]
