THIOLUTIN

Product Name: THIOLUTIN
CAS No.: 87-11-6
Chemical Name: THIOLUTIN
Synonyms: T-00098;NSC 3927;THIOLUTIN;Acetopyrrothin;Thiolutin ,80%;acetopyrrothine;THIOLUTIN USP/EP/BP;THIOLUTIN (ACETOPYRROTHIN);Thiolutin, from Streptomyces;Thiolutin NSC 3927
CBNumber: CB3435551
Molecular Formula: C8H8N2O2S2
Formula Weight: 228.29
MOL File: 87-11-6.mol

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THIOLUTIN Property

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
form: Yellow crystalline solid.
pka: 10.54±0.20(Predicted)
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 System: Thiolutin (87-11-6)

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Safety

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
Toxicity: LD50 in mice (mg/kg): 25 s.c.; 25 orally (Seneca)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T3450
Product name: Thiolutin
Purity: from Streptomyces luteosporeus, ≥95% (HPLC)
Packaging: 1mg
Price: $394
Updated: 2024/03/01

Cayman Chemical

Product number: 11350
Product name: Thiolutin
Purity: ≥97%
Packaging: 1mg
Price: $77
Updated: 2024/03/01

Cayman Chemical

Product number: 11350
Product name: Thiolutin
Purity: ≥97%
Packaging: 5mg
Price: $228
Updated: 2024/03/01

Cayman Chemical

Product number: 11350
Product name: Thiolutin
Purity: ≥97%
Packaging: 10mg
Price: $416
Updated: 2024/03/01

Tocris

Product number: 1567
Product name: Thiolutin
Purity: ≥98%(HPLC)
Packaging: 1
Price: $167
Updated: 2021/12/16

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THIOLUTIN Chemical Properties,Usage,Production

Description

Thiolutin 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 Properties

Yellow solid

Uses

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

Uses

Thiolutin is an antibiotic isolated from several strains of Streptomyces albus. Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases.

Uses

Thiolutin 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.

Definition

ChEBI: 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 Activity

Antibiotic; 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 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.

Safety Profile

Poison by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx and SOx.

References

Jing 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

Raw materials

Preparation Products

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THIOLUTIN Suppliers

Canada 1 China 67 India 1 South Korea 1 Switzerland 1 United Kingdom 9 United States 16 Global 96

EMMX Biotechnology LLC

Tel: 888-539-0666
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TargetMol Chemicals Inc.

Tel: +1-781-999-5354 +1-00000000000
Email: marketing@targetmol.com
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BOC Sciences

Tel: 16314854226; +16314854226
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InvivoChem

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Email: sales@invivochem.cn
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Aladdin Scientific

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ProdList: 57505
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ApexBio Technology

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Focus Biomolecules

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Cayman Chemical Company

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United States Biological

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Aagile Labs Division of Tyger Scientific

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Chemiplus Corporation

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View Lastest Price from THIOLUTIN manufacturers

Dideu Industries Group Limited

Product: THIOLUTIN 87-11-6
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons Min
Release date: 2021-06-24

Career Henan Chemical Co

Product: THIOLUTIN 87-11-6
Price: US $1.00/KG
Min. Order: 100KG
Purity: 99.0%
Supply Ability: 1000kg
Release date: 2020-03-11

87-11-6, THIOLUTINRelated Search:

NORFLUOXETINE HYDROCHLORIDE N-Eicosanoyl Serotonin AZ20 Acalabrutinib RHODODENDRI MOLLIS FLOS L-carnitine Gentamicin sulfate Chondroitin sulfate THIOLUTIN STREPTOMYCES LUTEOSPOREUS THIOLUTIN aureothricin holomycin

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%

Acetopyrrothin

NSC 3927

Thiolutin NSC 3927

6-acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5-one

Aureothricin, Farcinicin, Propiopyvothine

Thiolutin from Streptomyces luteosporeus

4-Methyl-6-(acetylamino)-1,2-dithiolo[4,3-b]pyrrole-5(4H)-one

4-Methyl-6-(acetylamino)-4,5-dihydro-1,2-dithiolo[4,3-b]pyrrole-5-one

T-00098

N-(4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl)ethanamide

N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide

6-(acetylamino)-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4h)-one

6-acetamido-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4h)-one

6-acetamido-4-methyl-2-dithiolo(4.3-b)pyrrol-5(4h)-one

acetopyrrothine

Acetamide, N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-

Thiolutin, from Streptomyces

THIOLUTIN USP/EP/BP

87-11-6

1987-11-6

C8H8N2S2O2

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