| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H14N2O4S2 |
| Molecular Weight | 326.391 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@@H](O)C=CC=C1C[C@@]34SS[C@@](CO)(N(C)C3=O)C(=O)N24
InChI
InChIKey=FIVPIPIDMRVLAY-RBJBARPLSA-N
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
| Molecular Formula | C13H14N2O4S2 |
| Molecular Weight | 326.391 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Gliotoxin is a potent crystalline antibiotic substance produced during the growth of the imperfect fungus Gliocladium jimbriatum. It is a natural mycotoxin with immunosuppressive and antimicrobial activity. Gliotoxin acts as NOTCH2 transactivation inhibitor in human neoplasias. It induced growth inhibition and apoptosis in multiple colorectal cancer cell lines with mutations of the Wnt signaling pathway. Gliotoxin stimulates the apoptosis of human and rat hepatic stellate cells and enhances the resolution of liver fibrosis in rats. Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with pronounced antitumor activity and favorable toxicity profile against breast cancer in vitro and in vivo.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Culture-activated (14-day) rat Hepatic stellate cells (HSCs) and Culture-activated (24-day) human (H2) HSCs cells were treated for 4 hours with 1.5 umol/L gliotoxin. Rat and human HSCs resulted in striking morphologic alterations within 1 hour as judged by light microscopy. HSCs changed from a flattened fibroblastic phenotype with distinct cell-cell interfaces to a substratum-detached, rounded, and blebbed morphology.