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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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About This Item

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

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

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton
Jia Y, et al.
Cell Stress & Chaperones, 15(2), 165-181 (2010)
M J Juhl et al.
Applied and environmental microbiology, 56(10), 3179-3185 (1990-10-01)
We have previously isolated mutants of Escherichia coli which show increased oxidation of heterocyclic furan and thiophene substrates. We have now found that strains carrying the thdA mutation express a novel enzyme activity which oxidizes a variety of substrates containing
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
Qiaoning Guan et al.
PLoS genetics, 2(11), e203-e203 (2006-12-15)
Nonsense-mediated mRNA decay (NMD) is a eukaryotic mechanism of RNA surveillance that selectively eliminates aberrant transcripts coding for potentially deleterious proteins. NMD also functions in the normal repertoire of gene expression. In Saccharomyces cerevisiae, hundreds of endogenous RNA Polymerase II
Size-dependent expression of the mitotic activator Cdc25 suggests a mechanism of size control in fission yeast
Keifenheim D, et al.
Current Biology, 27(10), 1491-1497 (2017)
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