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    Natural Products
    Gliotoxin
    Gliotoxin
    Information
    CAS No. 67-99-2 Price
    Catalog No.CFN93993Purity>=98%
    Molecular Weight326.4Type of CompoundMiscellaneous
    FormulaC13H14N2O4S2Physical DescriptionPowder
    Download     COA    MSDS    SDFSimilar structuralComparison (Web)  (SDF)
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    According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
    Size /Price /Stock 10 mM * 1 mL in DMSO / Inquiry
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    Gliotoxin

    Gliotoxin
    Product Name Gliotoxin
    CAS No.: 67-99-2
    Catalog No.: CFN93993
    Molecular Formula: C13H14N2O4S2
    Molecular Weight: 326.4 g/mol
    Purity: >=98%
    Type of Compound: Miscellaneous
    Physical Desc.: Powder
    Targets: COX | Wnt/尾-catenin | Antifection | NOTCH2
    Source: From Gliocladium fimbriatum
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price:
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  • Korean J. of Food Sci. and Tech2016, 172-177
  • Antioxidants (Basel).2020, 9(2):E99
  • J.Acta Agriculturae Scandinavica2017, 571-575
  • Toxins (Basel).2019, 11(10):E575
  • Exp Parasitol.2017, 183:160-166
  • Enzyme Microb Technol.2019, 122:64-73
  • Oncology Letters2018, 4690-4696
  • J Chromatogr B Analyt Technol Biomed Life Sci.2020, 1149:122123.
  • JPC-Journal of Planar Chromatography 2017, 30(2)
  • Chinese Medicine2019, 14(1)
  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
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  • Biological Activity
    Description: Gliotoxin, a Wnt signaling pathway inhibitor, induces growth inhibition and apoptosis in multiple colorectal cancer cell lines with mutations of the Wnt signaling pathway. Gliotoxin targets nuclear NOTCH2 in human solid tumor derived cell lines in vitro and inhibits melanoma growth in xenograft mouse model. Gliotoxin exhibits very strong anti-tuberculosis activity towards Mycobacterium tuberculosis with the the prominent MIC50 value of <0.03 uM. Gliotoxin also suppresses macrophage immune function by subverting phosphatidylinositol 3,4,5-trisphosphate homeostasis.
    Targets: COX | Wnt/β-catenin | Antifection | NOTCH2
    In vitro:
    Nat Prod Res. 2017 Aug;31(16):1958-1962.
    Antituberculosis compounds from a deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01.[Pubmed: 28068839 ]
    Eleven diketopiperazine and fumiquinazoline alkaloids (1-11) together with a tetracyclic triterpenoid helvolic acid (12) were obtained from the cultures of a deep-sea derived fungus Aspergillus sp. SCSIO Ind09F01.
    METHODS AND RESULTS:
    The structures of these compounds (1-12) were determined mainly by the extensive NMR, ESIMS spectra data and by comparison with previously described compounds. Besides, anti-tuberculosis, cytotoxic, antibacterial, COX-2 inhibitory and antiviral activities of these compounds were evaluated.
    CONCLUSIONS:
    Gliotoxin (3), 12,13-dihydroxy-fumitremorgin C (11) and helvolic acid (12) exhibited very strong anti-tuberculosis activity towards Mycobacterium tuberculosis with the prominent MIC50 values of <0.03, 2.41 and 0.894 μM, respectively, which was here reported for the first time. Meanwhile Gliotoxin also displayed significant selective cytotoxicities against K562, A549 and Huh-7 cell lines with the IC50 values of 0.191, 0.015 and 95.4 μM, respectively.
    Front Pharmacol. 2017 Jul 7;8:319.
    Gliotoxin Targets Nuclear NOTCH2 in Human Solid Tumor Derived Cell Lines In Vitro and Inhibits Melanoma Growth in Xenograft Mouse Model.[Pubmed: 28736522 ]

    METHODS AND RESULTS:
    The effect of Gliotoxin on cell viability and its clinical relevance was evaluated in vitro and in a melanoma xenograft mouse model. Cell lines derived from melanoma (518A2), hepatocellular carcinoma (SNU398, HCC-3, Hep3B), and pancreas carcinoma (PANC1) express high amounts of nuclear NOTCH2. Gliotoxin efficiently induced apoptosis in these cell lines whereas the GSI DAPT was ineffective. The specificity of Gliotoxin was demonstrated in the well differentiated nuclear NOTCH negative cell line Huh7, which was resistant to Gliotoxin treatment in vitro. In xenotransplanted 518A2 melanomas, a single day dosing schedule of Gliotoxin was well tolerated without any study limiting side effects. Gliotoxin significantly reduced the tumor volume in early (83 mm3 vs. 115 mm3, p = 0.008) as well as in late stage (218 mm3 vs. 576 mm3, p = 0.005) tumor models.
    CONCLUSIONS:
    In conclusion, NOTCH2 appears to be a key target of Gliotoxin in human neoplasias and Gliotoxin deserves further evaluation as a potential therapeutic agent in cancer management.
    Gliotoxin Description
    Source: From Gliocladium fimbriatum
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.0637 mL 15.3186 mL 30.6373 mL 61.2745 mL 76.5931 mL
    5 mM 0.6127 mL 3.0637 mL 6.1275 mL 12.2549 mL 15.3186 mL
    10 mM 0.3064 mL 1.5319 mL 3.0637 mL 6.1275 mL 7.6593 mL
    50 mM 0.0613 mL 0.3064 mL 0.6127 mL 1.2255 mL 1.5319 mL
    100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6127 mL 0.7659 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    MBio. 2016 Apr 5;7(2):e02242.
    Gliotoxin Suppresses Macrophage Immune Function by Subverting Phosphatidylinositol 3,4,5-Trisphosphate Homeostasis.[Pubmed: 27048806]
    Aspergillus fumigatus, an opportunistic fungal pathogen, spreads in the environment by releasing numerous conidia that are capable of reaching the small alveolar airways of mammalian hosts. In otherwise healthy individuals, macrophages are responsible for rapidly phagocytosing and eliminating these conidia, effectively curbing their germination and consequent invasion of pulmonary tissue. However, under some circumstances, the fungus evades phagocyte-mediated immunity and persists in the respiratory tree.
    METHODS AND RESULTS:
    Here, we report thatA. fumigatusescapes macrophage recognition by strategically targeting phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] metabolism through Gliotoxin, a potent immunosuppressive mycotoxin. Time-lapse microscopy revealed that, in response to the toxin, macrophages cease to ruffle, undergo abrupt membrane retraction, and fail to phagocytose large targets effectively. Gliotoxin was found to prevent integrin activation and interfere with actin dynamics, both of which are instrumental for phagocytosis; similar effects were noted in immortalized and primary phagocytes. Detailed studies of the underlying molecular mechanisms of toxicity revealed that inhibition of phagocytosis is attributable to impaired accumulation of PtdIns(3,4,5)P3and the associated dysregulation of downstream effectors, including Rac and/or Cdc42.
    CONCLUSIONS:
    Strikingly, in response to the diacylglycerol mimetic phorbol 12-myristate 13-acetate, Gliotoxin-treated macrophages reactivate beta integrins, reestablish actin dynamics, and regain phagocytic capacity, despite the overt absence of plasmalemmal PtdIns(3,4,5)P3 Together, our findings identify phosphoinositide metabolism as a critical upstream target of Gliotoxin and also indicate that increased diacylglycerol levels can bypass the requirement for PtdIns(3,4,5)P3signaling during membrane ruffling and phagocytosis.
    Mar Drugs. 2015 Oct 2;13(10):6259-73.
    Gliotoxin Inhibits Proliferation and Induces Apoptosis in Colorectal Cancer Cells.[Pubmed: 26445050 ]
    The discovery of new bioactive compounds from marine natural sources is very important in pharmacological research.
    METHODS AND RESULTS:
    Here we developed a Wnt responsive luciferase reporter assay to screen small molecule inhibitors of cancer associated constitutive Wnt signaling pathway. We identified that Gliotoxin (GTX) and some of its analogues, the secondary metabolites from marine fungus Neosartorya pseufofischeri, acted as inhibitors of the Wnt signaling pathway. In addition, we found that GTX downregulated the β-catenin levels in colorectal cancer cells with inactivating mutations of adenomatous polyposis coli (APC) or activating mutations of β-catenin. Furthermore, we demonstrated that GTX induced growth inhibition and apoptosis in multiple colorectal cancer cell lines with mutations of the Wnt signaling pathway.
    CONCLUSIONS:
    Together, we illustrated a practical approach to identify small-molecule inhibitors of the Wnt signaling pathway and our study indicated that GTX has therapeutic potential for the prevention or treatment of Wnt dependent cancers and other Wnt related diseases.
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