Gliotoxin

Gliotoxin is an immunosuppressive mycotoxin produced by pathogenic strains of Aspergillus and other fungi with diverse biological activities. It inhibits 20S proteasomal chymotrypsin activity (IC50 = 10 µM), blocking the degradation of IkappaBalpha and preventing the activation of NF-kappaB. Gliotoxin induces apoptosis in monocytes and dendritic cells and reduces phagocytosis by neutrophils. It suppresses viral infection by Nipah and Hendra virus in HEK293T cells (IC50s = 149 and 579 nM, respectively). Under reducing conditions, gliotoxin inhibits leukotriene A4 hydrolase (LTA4H, Cay-10007817) epoxide hydrolase activity, but not aminopeptidase activity, and leukotriene B4 (LTB4, Cay-20110) synthesis in neutrophils and monocytes. In vivo, gliotoxin (5 mg/kg) reduces LTB4 plasma levels and blocks peritoneal neutrophil infiltration in a mouse model of peritonitis induced by zymosan A (Cay-21175). It also inhibits geranylgeranyltransferase I and farnesyltransferase (IC50s = 17 and 80 µM, respectively).Formal Name: 2,3R,5aS,6S-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10aR-epidithiopyrazino[1,2-a]indole-1,4-dione. CAS Number: 67-99-2. Synonyms: Aspergillin. Molecular Formula: C13H14N2O4S2. Formula Weight: 326.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 5 mg/ml, DMSO:PBS (pH 7.2)(1:5): 0.5 mg/ml. lambdamax: 202, 269 nm. SMILES: O[C@H]1C=CC=C2[C@@H]1N(C([C@]3(CO)N(C)C4=O)=O)[C@@]4(SS3)C2. InChi Code: InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13?/m0/s1. InChi Key: FIVPIPIDMRVLAY-ZKVOIBSNSA-N.