Gliotoxin

• CAT Number: R040030
• CAS Number: 67-99-2
• Molecular Formula: C13H14N2O4S2
• Molecular Weight: 326.385
• Purity: ≥95%
• Synonyms: (3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
• Target: Proteasome
• Solubility: Soluble in DMSO > 10 mM
• Storage: Desiccate at -20°C
• IUPAC Name: (1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione
• InChI: 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
• InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N
• SMILES: CN1C(=O)C23CC4=CC=CC(C4N2C(=O)C1(SS3)CO)O

Gliotoxin(CAS67-99-2) is a fungal antibiotic mycotoxin with antiphagycytic and immunomodulatory activities.Gliotoxin is an antibiotic that is toxic to higher animals as well as to animal and plant pathogens and that is produced by various fungi (as of the genera Gliocladium, Aspergillus, andPenicillium).

Overview of Clinical Research

Gliotoxin is an immunosuppressant. The Preclinical study for Cancer discontinused in Germany (unspecified route) in Feb, 2007. 

Reference

1.Gliotoxin, the antibiotic principle of Gliocladium fimbriatum. I. Production, physical and biological properties. Johnson D. et al. JACS 1943, 65, 2005.

2.The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis. Gardiner D. M. et al. Microbiology 2005, 151, 1021.

3.Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with antitumor activity against breast cancer in vivo. Vigushin D. M. et al. Med. Oncol. 2004, 21, 21.

4.The secondary fungal metabolite gliotoxin targets proteolytic activities of the proteasome. Kroll M, et al. Chem. Biol. 1999, 6, 689.

5.The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kappaB. Pahl, H. L. et al. J.Exp. Med. 1996, 183, 1829.

6.Gliotoxin stimulates Ca2+ release from intact rat liver mitochondria. Schweizer M. & Richter C. Biochemistry 1994, 33, 13401.