THIOLUTIN

THIOLUTIN Basic information
Product Name:THIOLUTIN
Synonyms:THIOLUTIN;N-(4,5-DIHYDRO-4-METHYL-5-OXO-1,2-DITHIOLO[4,3-B]PYRROL-6-YL)ACETAMIDE;3-acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithiole;THIOLUTIN (ACETOPYRROTHIN);N-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetaMide;N-acetylpyrrothine, Farcinicine, Acetopyrrothine;N-(5-keto-4-methyl-dithiolo[4,3-b]pyrrol-6-yl)acetamide;Thiolutin ,80%
CAS:87-11-6
MF:C8H8N2O2S2
MW:228.29
EINECS:635-840-2
Product Categories:antibiotic;Heterocycles;Antibiotics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;pharmacetical
Mol File:87-11-6.mol
THIOLUTIN Structure
THIOLUTIN Chemical Properties
Melting point 273-276℃
Boiling point 200°C (rough estimate)
density 1.4614 (rough estimate)
refractive index 1.5690 (estimate)
storage temp. −20°C
solubility DMSO: 5 mg/mL
pka10.54±0.20(Predicted)
form Yellow crystalline solid.
color Brilliant-yellow needles from 1-butanol
Stability:Stable for 3 years as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
EPA Substance Registry SystemThiolutin (87-11-6)
Safety Information
Hazard Codes T+,T
Risk Statements 28
Safety Statements 45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS JP1355000
HS Code 29419090
ToxicityLD50 in mice (mg/kg): 25 s.c.; 25 orally (Seneca)
MSDS Information
THIOLUTIN Usage And Synthesis
DescriptionThiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases (IC50 = 3 μg/ml). Because of this, it can be used for the analysis of mRNA stability. Thiolutin also inhibits endothelial cell adhesion (IC50 < 1 μM) and S180 tumor-induced angiogenesis in mice by inhibiting Hsp27 interactions with cytoskeletal elements.
Chemical PropertiesYellow solid
UsesThiolutin is an antibiotic first described by Tanner and co-workers in 1950. Resurgent interest in this class of microbial metabolites was stimulated by the discovery of their selective antitumour activity. Thiolutin is a potent inhibitor of bacterial and yeast RNA polymerases, and also inhibits mannan and glucan formation in fungi. Thiolutin suppresses tumour cell-induced angiogenesis in vivo.
UsesThiolutin is an antibiotic isolated from several strains of Streptomyces albus. Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases.
UsesThiolutin 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

DefinitionChEBI: Thiolutin is a dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases. It has a role as an angiogenesis inhibitor, a chelator, a protein synthesis inhibitor, an EC 2.7.7.6 (RNA polymerase) inhibitor, an antibacterial agent, a toxin, a marine metabolite, a bacterial metabolite, an antifungal agent and an antineoplastic agent. It is a dithiolopyrrolone antibiotic and a member of acetamides. It is functionally related to a holomycin.
Biological ActivityAntibiotic; inhibits bacterial RNA polymerase. Inhibits adhesion of HUVEC cells to vitronectin (IC 50 = 0.83 mM) and subsequently reduces paxillin levels. Suppresses tumor cell-induced angiogenesis.
Biochem/physiol ActionsSulfur-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.
Safety ProfilePoison by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx and SOx.
ReferencesJing et al. (2021), Blockade of deubiquitinating enzyme PSMD14 overcomes chemoresistance in head and neck squamous cell carcinoma by antagonizing E2F1/Akt/SOX2-mediated stemness; Theranostics, 11 2655 Jia et al. (2010), Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton; Cell Stress Chaperones 15 165 Minamiguchi et al. (2001), Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis; Int. J. Cancer, 93 307
THIOLUTIN Preparation Products And Raw materials
NORFLUOXETINE HYDROCHLORIDE Chondroitin sulfate Acalabrutinib Gentamicin sulfate AZ20 L-carnitine N-Eicosanoyl Serotonin RHODODENDRI MOLLIS FLOS THIOLUTIN STREPTOMYCES LUTEOSPOREUS THIOLUTIN aureothricin holomycin

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