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T3450

Thiolutin

Name: Thiolutin
Brand: SIGMA

from Streptomyces luteosporeus, ≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):

C₈H₈N₂O₂S₂

Número de CAS:

87-11-6

Peso molecular:

228.29

Número MDL:

MFCD07370147

Código UNSPSC:

12352105

ID de la sustancia en PubChem:

329826766

NACRES:

NA.77

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Sigma-Aldrich

K6000

α-Keto-γ-(methylthio)butyric acid sodium salt

origen biológico

Streptomyces luteosporeus

Nivel de calidad

200

Análisis

≥95% (HPLC)

formulario

solid

solubilidad

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

espectro de actividad antibiótica

fungi

Modo de acción

enzyme | inhibits

Condiciones de envío

wet ice

temp. de almacenamiento

−20°C

cadena 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)

Clave InChI

UGZYFXMSMFMTSM-UHFFFAOYSA-N

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

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

Pictogramas

GHS06

Palabra de señalización

Danger

Frases de peligro

H300

Consejos de prudencia

P264 - P270 - P301 + P310 - P405 - P501

Clasificaciones de peligro

Acute Tox. 2 Oral

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Thiolutin-resistant mutants of Salmonella typhimurium.

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

RNA polymerase inhibitors with activity against rifampin-resistant mutants of Staphylococcus aureus.

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

Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis.

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

Mitochondrial functions mediate cellulase gene expression in Trichoderma reesei.

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

Genome-wide analysis of mRNA stability using transcription inhibitors and microarrays reveals posttranscriptional control of ribosome biogenesis factors.

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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