Replaces Prod. #: ALX-350-239
Immunomodulating mycotoxin which acts by blocking membrane thiol groups. Inhibits the chymotrypsin-like activity of the 20S proteasome in a non-competitive manner. Causes apoptotic cell death in macrophages and thymocytes. Induces Ca2+ release from intact rat liver mitochondria. Inhibits the activation of transcription factor NF-κB in response to a variety of stimuli in T and B cells. Displays anti-inflammatory activity in vivo. Antioxidant. Inhibitor of farnesyltransferase and geranylgeranyltransferase I. A negative control analog is available (Prod. No. BML-L122). Displays anti-tumor activity against breast cancer in vivo.
Product Details
| Alternative Name: | [3R-(3α, 5aβ,6β,10aα)]-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epi-dithiopyrazino[1,2-a]indole-1,4-dione |
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| Formula: | C13H14N2O4S2 |
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| MW: | 326.4 |
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| Source: | Isolated from Gliocladium fimbriatum |
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| CAS: | 67-99-2 |
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| MI: | 14: 4441 |
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| RTECS: | KB4725000 |
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| Purity: | ≥97% (HPLC, TLC) |
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| Appearance: | White to yellow crystalline solid. |
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| Solubility: | Soluble in DMSO or methanol (10mg/ml). |
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| Shipping: | Ambient Temperature |
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| Long Term Storage: | -20°C |
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| Use/Stability: | Stock solutions are stable for up to 3 months when stored at -20°C. |
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| Regulatory Status: | RUO - Research Use Only |
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Product Literature References
Lipo-Chitooligosaccharides Induce Specialized Fungal Metabolite Profiles That Modulate Bacterial Growth: T.A. Rush, et al.; mSystems
7, e0105222 (2022),
Abstract;
Discovery of gliotoxin as a new small molecule targeting thioredoxin redox system: H.S. Choi, et al.; BBRC
359, 523 (2007),
Abstract;
Aspergillus fumigatus suppresses the human cellular immune response via gliotoxin-mediated apoptosis of monocytes: M. Stanzani, et al.; Blood
105, 2258 (2005),
Abstract;
Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with antitumor activity against breast cancer in vivo: D.M. Vigushin, et al.; Med. Oncol.
21, 21 (2004),
Abstract;
Nuclear factor-kappa B activity and intestinal inflammation in dextran sulphate sodium (DSS)-induced colitis in mice is suppressed by gliotoxin: H. Herfarth, et al.; Clin. Exp. Immunol.
120, 59 (2000),
Abstract;
NF-kappaB activation is a critical regulator of human granulocyte apoptosis in vitro: C. Ward, et al.; J. Biol. Chem.
274, 4309 (1999),
Abstract;
The secondary fungal metabolite gliotoxin targets proteolytic activities of the proteasome: M. Kroll, et al.; Chem. Biol.
6, 689 (1999),
Abstract;
Gliotoxin and related epipolythiodioxopiperazines: P. Waring & J. Beaver; Gen. Pharmacol.
27, 1311 (1996), Review,
Abstract;
The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kappaB: H.L. Pahl, et al.; J. Exp. Med.
183, 1829 (1996),
Abstract;
Extracellular calcium is not required for gliotoxin or dexamethasone- induced DNA fragmentation: a reappraisal of the use of EGTA: P. Waring & A. Sjaarda; Int. J. Immunopharmacol.
17, 403 (1995),
Abstract;
Gliotoxin stimulates Ca2+ release from intact rat liver mitochondria: M. Schweizer & C. Richter; Biochemistry
33, 13401 (1994),
Abstract;
Mechanism of Gliotoxin Action and Factors Mediating Gliotoxin Sensitivity: R.W. Jones & J.G. Hancock; J. Gen. Microbiol.
134, 2067 (1988),
Abstract;
Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro: A. Müllbacher, et al.; J. Gen. Microbiol.
131, 1251 (1985),
Abstract;
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