Thiolutin

Modify Date: 2024-01-04 16:12:29

Thiolutin structure	Common Name	Thiolutin
	CAS Number	87-11-6	Molecular Weight	228.291
	Density	1.6±0.1 g/cm3	Boiling Point	478.6±45.0 °C at 760 mmHg
	Molecular Formula	C₈H₈N₂O₂S₂	Melting Point	273-276℃
	MSDS	Chinese USA	Flash Point	243.3±28.7 °C
	Symbol	GHS06	Signal Word	Danger

Use of Thiolutin

Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2].

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

Description	Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2].
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Metabolic Disease
References	[1]. Lauinger L, et al. Thiolutin is a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases. Nat Chem Biol. 2017 Jul;13(7):709-714. [2]. Jia Y, et al. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones. 2010 Mar;15(2):165-81.

Description

Related Catalog

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

References

[1]. Lauinger L, et al. Thiolutin is a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases. Nat Chem Biol. 2017 Jul;13(7):709-714.

[2]. Jia Y, et al. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones. 2010 Mar;15(2):165-81.

Density	1.6±0.1 g/cm3
Boiling Point	478.6±45.0 °C at 760 mmHg
Melting Point	273-276℃
Molecular Formula	C₈H₈N₂O₂S₂
Molecular Weight	228.291
Flash Point	243.3±28.7 °C
Exact Mass	228.002716
PSA	107.58000
LogP	0.99
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.721
Water Solubility	DMSO: 5 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JP1355000

CHEMICAL NAME :: 1,2-Dithiolo(4.3-b)pyrrol-5(4H)-one, 6-acetamido-4-methyl-

CAS REGISTRY NUMBER :: 87-11-6

BEILSTEIN REFERENCE NO. :: 0209485

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C8-H8-N2-O2-S2

MOLECULAR WEIGHT :: 228.30

WISWESSER LINE NOTATION :: T55 BNV FSSJ B1 DMV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 4 mg/L

REFERENCE :: AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 3,729,1973

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300
Precautionary Statements	P264-P301 + P310
Personal Protective Equipment	Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T+: Very toxic;T: Toxic;
Risk Phrases	28
Safety Phrases	S45
RIDADR	UN 2811 6.1/PG 2
WGK Germany	3
RTECS	JP1355000
HS Code	2933990090

Precursor 7
CAS#:139102-08-2 Methyl-6-acetam... CAS#:142705-66-6 N-(5,6-Dihydro-... CAS#:139101-74-9 Methyl-4,5-dihy... CAS#:139101-96-5 5-Methyl-2,2-di...
CAS#:139101-98-7 7-Acetyl-5-meth... CAS#:139102-00-4 7-(1-Hydroxyimi... CAS#:139101-81-8 5,6,7,7a-Tetrah...
DownStream 0

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Condensin targets and reduces unwound DNA structures associated with transcription in mitotic chromosome condensation.

Nat. Commun. 6 , 7815, (2015)

Chromosome condensation is a hallmark of mitosis in eukaryotes and is a prerequisite for faithful segregation of genetic material to daughter cells. Here we show that condensin, which is essential for...

Thiophene-degrading Escherichia coli mutants possess sulfone oxidase activity and show altered resistance to sulfur-containing antibiotics.

Appl. Environ. Microbiol. 56(10) , 3179-85, (1990)

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...

Mapping of two transcription mutations (tlnI and tlnII) conferring thiolutin resistance, adjacent to dnaZ and rho in Escherichia coli.

Mol. Gen. Genet. 180(3) , 609-15, (1980)

Two mutations in Escherichia coli conferring resistance to the transcription initiation inhibitor, thiolutin, have been mapped. One of these mutations (tln-I)( maps at 10.2 min on the genetic map and ...

acetopyrrothine

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

N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[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)-on

Acetopyrrothin

6-Acetamido-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

MFCD07370147

3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole

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

Thiolutin

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

3-Acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithiole

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

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Thiolutin
Price: ￥488.0/1mg ￥6718.0/25mg ￥1618.0/5mg
Purity: 95.0%
Stocking Period: Inquiry
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Thiolutin
Price: ￥Inquiry/1g
Purity: 98.9%
Stocking Period: 1 Day
Contact: Tony Cao

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Thiolutin

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