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T3450

Sigma-Aldrich

Thiolutin

from Streptomyces luteosporeus, ≥95% (HPLC)

Synonyme(s) :

Farcinicin, N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl), Propiopyvothine

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About This Item

Formule empirique (notation de Hill):
C8H8N2O2S2
Numéro CAS:
87-11-6
Poids moléculaire :
228.29
Numéro MDL:
MFCD07370147
Code UNSPSC :
12352105
ID de substance PubChem :
329826766
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces luteosporeus

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

solid

Solubilité

DMSO: 0.90 - 1.10 mg/ml, clear, yellow

Spectre d'activité de l'antibiotique

fungi

Mode d’action

enzyme | inhibits

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

UGZYFXMSMFMTSM-UHFFFAOYSA-N

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300

Classification des risques

Acute Tox. 2 Oral

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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A Joshi et al.
Antimicrobial agents and chemotherapy, 22(4), 541-547 (1982-10-01)
Spontaneous mutants of Salmonella typhimurium isolated in our laboratory from thiolutin-containing tryptone agar plates are partially resistant to thiolutin in enriched media. In minimal media, they are not resistant. The mutants are not temperature sensitive but fail to support the
A O'Neill et al.
Antimicrobial agents and chemotherapy, 44(11), 3163-3166 (2000-10-19)
A collection of rifampin-resistant mutants of Staphylococcus aureus with characterized RNA polymerase beta-subunit (rpoB) gene mutations was cross-screened against a number of other RNA polymerase inhibitors to correlate susceptibility with specific rpoB genotypes. The rpoB mutants were cross-resistant to streptolydigin
K Minamiguchi et al.
International journal of cancer, 93(3), 307-316 (2001-07-04)
Recent studies have shown that integrin alpha v beta 3, a receptor for vitronectin, plays an important role in tumor-induced angiogenesis and tumor growth and that antagonists of alpha v beta 3 inhibit angiogenic processes including endothelial cell adhesion and
J Abrahão-Neto et al.
Biochemistry, 34(33), 10456-10462 (1995-08-22)
We examined the effects of inhibition of mitochondrial functions on the expression of two nuclear genes encoding the extracellular cellobiohydrolase I (cbh1) and endoglucanase I (egl1) of the cellulase system of the filamentous fungus Trichoderma reesei. The cbh1 and egl1
Jörg Grigull et al.
Molecular and cellular biology, 24(12), 5534-5547 (2004-06-01)
Using DNA microarrays, we compared global transcript stability profiles following chemical inhibition of transcription to rpb1-1 (a temperature-sensitive allele of yeast RNA polymerase II). Among the five inhibitors tested, the effects of thiolutin and 1,10-phenanthroline were most similar to rpb1-1.
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