Basic information
- CAS
87-11-6- Standard SMILES
CC(=O)Nc1c2sscc-2n(C)c1=O- InChIKey
MHMRAFONCSQAIA-UHFFFAOYSA-N- Molecular formula
- C8H8N2O2S2
- Average molar mass
- 228.3 g/mol
- Monoisotopic mass
- 228.00271985
Overview
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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 a toxin, an antibacterial agent, an antineoplastic agent, an antifungal agent, an EC 2.7.7.6 (RNA polymerase) inhibitor, a chelator, a protein synthesis inhibitor, an angiogenesis inhibitor, a marine metabolite and a bacterial metabolite. It is a dithiolopyrrolone antibiotic and a member of acetamides. It is functionally related to a holomycin.
Names & identifiers
- Preferred name
- Thiolutin
- IUPAC
- N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide
- English name
- Thiolutin
- Molecular formula
- C8H8N2O2S2
- Molecular weight
- 228.29
Names & synonyms
Thiolutin87-11-6AcetopyrrothinAcetopyrrothineN-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide3-Acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithioleNSC-392702C005Q20BN-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo(4,3-b)pyrrol-6-yl)acetamideN-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamideDTXSID00406246-Acetamido-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one
Show more names
T-00098NSC 3927Thiolutin ,80%THIOLUTIN USP/EP/BPThiolutin, 10 mM in DMSOTHIOLUTIN (ACETOPYRROTHIN)Thiolutin, antibiotic agent
CHEBI:156450N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamideN-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide6-Acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneN-(4-Methyl-5-oxodithiolo(4,3-b)pyrrol-6-yl)acetamideN-(4-methyl-5-oxo-4,5-dihydro(1,2)dithiolo(4,3-b)pyrrol-6-yl)acetamideN-(4-methyl-5-oxo-4H,5H-(1,2)dithiolo(4,3-b)pyrrol-6-yl)acetamideRefChem:189553
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 100 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 387
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Solubility0.21 mg/mL
Boiling Point152.00 to 156.00 °C. @ 17.00 mm Hg
Melting Point273 - 276 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 273 · 273-276℃
- Boiling point
- 200 °C · 200°C (rough estimate)
- Density
- 1.4614 · 1.4614 (rough estimate)
- refractive index
- 1.569 · 1.5690 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 5 mg/mL · DMSO: 5 mg/mL
- form
- Yellow crystalline solid.
- pka
- 10.54 · 10.54±0.20(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- JP1355000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29419090
- Toxicity
- LD50 in mice (mg/kg): 25 s.c.; 25 orally (Seneca)
- risk_code
- 28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+,T
- safety_code
- 45
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard statements
- H300
- Hazard Classifications
- Acute Tox. 2 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
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 induced angiogenesis in mice by inhibiting Hsp27 interactions with cytoskeletal elements.
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
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 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.
Suppliers46 total
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Syntechem Co.,Ltd[email protected]
Related reactions
0 records
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Compound notes
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