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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

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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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