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Thiolutin

Thiolutin structure

CAS No:
87-11-6
Formula:
C8H8N2O2S2
Chemical Name:
Thiolutin
Synonyms:
Acetamide,N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-;1,2-Dithiolo[4,3-b]pyrrol-5(4H)-one,6-acetamido-4-methyl-;1,2-Dithiolo[4,3-b]pyrrole,acetamide deriv.;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;NSC 3927
Categories:
Active Pharmaceutical Ingredients > Antibiotics

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].

Solid

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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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 derives from a holomycin.

Thiolutin Basic Attributes

Molecular Weight：

228.29

Exact Mass：

228.29

UNII：

02C005Q20B

NSC Number：

3927

DSSTox ID：

DTXSID0040624

HScode：

2933990090

Characteristics

PSA：

100

XLogP3：

0.99

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Melting Point：

256-257 °C (decomp)

Boiling Point：

200 °C

Flash Point：

243.3±28.7 °C

Refractive Index：

1.721

Water Solubility：

DMSO: 5 mg/mL

Storage Conditions：

−20°C

Toxicity：

Oral-Mouse LD50: 25 mg/kg

Flammability characteristics：

Flammable; decomposes by heating to release toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

JP1355000

Marks：

T+,T

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P264-P301 + P310

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH Entry Terms：

acetopyrrothine

Thiolutin Use and Manufacturing

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

Computed Properties

Molecular Weight:228.3
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:228.00271985
Monoisotopic Mass:228.00271985
Topological Polar Surface Area:100
Heavy Atom Count:14
Complexity:387
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes