Chemistry:Thiolutin

Short description: Chemical compound

Thiolutin

Clinical data
Other names	N-(8-methyl-7-oxo-3,4-dithia-8-azabicyclo[3.3.0]octa-1,5-dien-6-yl)acetamide, farcinicin, propiopyvothine, acetopyrrothine
ATC code	none
Identifiers
IUPAC name N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
CAS Number	87-11-6 N
PubChem CID	6870
ChemSpider	6608 Y
UNII	02C005Q20B
ChEBI	CHEBI:156450
ChEMBL	ChEMBL507026 Y
Chemical and physical data
Formula	C8H8N2O2S2
Molar mass	228.28 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(NC/2=C/1\SS\C=C\1N(C\2=O)C)C
InChI InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11) Y Key:MHMRAFONCSQAIA-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Thiolutin is a sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases. It was found to inhibit in vitro RNA synthesis directed by all three yeast RNA polymerases (I, II, and III). Thiolutin is also an inhibitor of mannan and glucan formation in Saccharomyces cerevisiae and used for the analysis of mRNA stability. Studies have shown that thiolutin inhibits adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin and thus suppresses tumor cell-induced angiogenesis in vivo.

Thiolutin is formed in submerged fermentation by several strains of Streptomycetes luteosporeus. Some sources erroneously specify "aureothricin" as a synonym of thiolutin. Aureothricin is an antibiotic very similar to thiolutin, and is created as a by-product during the thiolutin fermentation.