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T3450

Sigma-Aldrich

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

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$384.75

About This Item

Empirical Formula (Hill Notation):
C8H8N2O2S2
CAS Number:
Molecular Weight:
228.29
MDL number:
UNSPSC Code:
12352105
PubChem Substance ID:
NACRES:
NA.77

$384.75

List Price$405.00Save 5%

In StockDetails


Request a Bulk Order

biological source

Streptomyces luteosporeus

Quality Level

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

Application

Thiolutin has been used as a polymerase II inhibitor:
  • to study its effects on yeast cells to calculate transcript half-life [1]
  • to study its effects on transcription during germination in budding yeast [2]
  • to study its effects on cell adhesion in zebrafish [3]

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.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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N Sivasubramanian et al.
Molecular & general genetics : MGG, 180(3), 609-615 (1980-01-01)
Two mutations in Escherichia coli conferring resistance to the transcription initiation inhibitor, thiolutin, have been mapped. One of these mutations (tln-I)( maps at 10.2 min on the genetic map and is cotransducible with dnaZ at a frequency of approximately 50%.
Vicent Pelechano et al.
Yeast (Chichester, England), 25(2), 85-92 (2007-10-05)
Thiolutin is commonly used as a general inhibitor of transcription in yeast. It has been used to calculate mRNA decay rates by stopping the transcription and then determining the relative abundance of individual mRNAs at different times after inhibition. We
Nutritional and meiotic induction of transiently heritable stress resistant states in budding yeast
Gutierrez H, et al.
Microbial cell, 5(11), 511-511 (2018)
Jeff Coller
Methods in enzymology, 448, 267-284 (2008-12-30)
Much of our understanding of eukaryotic mRNA decay has come from studies in budding yeast, Saccharomyces cerevisiae. The facile nature of genetic and biochemical manipulations in yeast has allowed detailed investigations into the mRNA decay pathway and the identification of
T Kadowaki et al.
The Journal of cell biology, 126(3), 649-659 (1994-08-01)
To understand the mechanisms of mRNA transport in eukaryotes, we have isolated Saccharomyces cerevisiae temperature-sensitive (ts) mutants which accumulate poly(A)+ RNA in the nucleus at the restrictive temperature. A total of 21 recessive mutants were isolated and classified into 16

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