Gliotoxin-13C13

Gliotoxin-13C13 is intended for use as an internal standard for the quantification of gliotoxin (Cay-11433) by GC- or LC-MS. 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: (3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl-13C)-2-(methyl-13C)-2,3,5a,6-tetrahydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione-1,3,4,5a,6,7,8,9,9a,10,10a-13C11. Synonyms: Aspergillin-13C13. Molecular Formula: [13C]13H14N2O4S2. Formula Weight: 339.3. Purity: >95%. Formulation: (Request formulation change), A solution in acetonitrile. Solubility: Acetonitrile: 3 mg/ml. lambdamax: 265 nm. SMILES: O=[13C]([13C@]1(SS2)[13CH2][13C]3=[13CH][13CH]=[13CH][13C@H](O)[13C@H]3N14)N([13CH3])[13C@@]2([13CH2]O)[13C]4=O. 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/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1,11+1,12+1,13+1. InChi Key: FIVPIPIDMRVLAY-DKOZNSHBSA-N.