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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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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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