Thiolutin

Thiolutin

Systematic (IUPAC) name
N-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
Identifiers
CAS Number	87-11-6
ATC code	none
PubChem	CID 6870
ChemSpider	6608
ChEMBL	CHEMBL507026
Synonyms	N-(8-methyl-7-oxo-3,4-dithia-8-azabicyclo[3.3.0]octa-1,5-dien-6-yl)acetamide, farcinicin, propiopyvothine, acetopyrrothine
Chemical data
Formula	C8H8N2O2S2
Molar mass	228.293 g/mol
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) Key:MHMRAFONCSQAIA-UHFFFAOYSA-N
(what is this?)  (verify)

Thiolutin is a sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases.^[1] 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.^[2]

References

1. Kebaara BW, Nielsen LE, Nickerson KW, Atkin AL (Aug 2006). "Determination of mRNA half-lives in Candida albicans using thiolutin as a transcription inhibitor". Genome 49 (8): 894–9. doi:10.1139/g06-046. PMID 17036064.
2. Fermentek product page