T3450

Thiolutin

from Streptomyces luteosporeus, ≥95% (HPLC)

• Synonym(s): Farcinicin, N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl), Propiopyvothine
• Empirical Formula (Hill Notation): C₈H₈N₂O₂S₂
• CAS Number: 87-11-6
• Molecular Weight: 228.29
• MDL number: MFCD07370147
• UNSPSC Code: 12352105
• PubChem Substance ID: 329826766
• NACRES: NA.77

Properties

• biological source: Streptomyces luteosporeus
• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: solid
• solubility: DMSO: 0.90 - 1.10 mg/ml, clear, yellow
• antibiotic activity spectrum: fungi
• Mode of action: enzyme | inhibits
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: CCC(=O)NC1=C2SSC=C2N(C)C1=O
• InChI: 1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
• InChI key: UGZYFXMSMFMTSM-UHFFFAOYSA-N

Description

Application

Thiolutin has been used as a polymerase II inhibitor:

• to study its effects on yeast cells to calculate transcript half-life
• to study its effects on transcription during germination in budding yeast
• to study its effects on cell adhesion in zebrafish

Biochem/physiol Actions

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.

Preparation Note

Thiolutin dissolves in DMSO at 0.90 - 1.10 mg/ml to yield a clear, yellow solution.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves