CAS 87-11-6|Thiolutin
| 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 | ChineseUSA | Flash Point | 243.3±28.7 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide |
|---|---|
| Synonym | More Synonyms |
Thiolutin BiologicalActivity
| 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 >>OthersResearch 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. |
Chemical & Physical Properties
| 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 |
| InChIKey | MHMRAFONCSQAIA-UHFFFAOYSA-N |
| SMILES | CC(=O)Nc1c2sscc-2n(C)c1=O |
| Water Solubility | DMSO: 5 mg/mL |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
- 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
Safety Information
| 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 |
Customs
| 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% |
Articles27
More Articles| 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 ... |
Synonyms
| 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 |
