| Size | Price | |
|---|---|---|
| 5mg | ||
| Other Sizes |
Purity: ≥98%
Thiolutin (formerly Acetopyrrothin and NSC-3927), is a potent and naturally occusinrg disulfide-containing antibiotic and anti-angiogenic agent isolated from Streptomyces, it acts as a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases, also inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation.
| References |
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| Additional Infomation |
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antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively.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.
Thiolutin has been reported in Streptomyces celluloflavus, Saccharothrix algeriensis, and Streptomyces kasugaensis with data available. |
| Molecular Formula |
C8H8N2O2S2
|
|---|---|
| Molecular Weight |
228.29132
|
| Exact Mass |
228.002
|
| Elemental Analysis |
C, 42.09; H, 3.53; N, 12.27; O, 14.02; S, 28.09
|
| CAS # |
87-11-6
|
| PubChem CID |
6870
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
478.6±45.0 °C at 760 mmHg
|
| Melting Point |
273-276℃
|
| Flash Point |
243.3±28.7 °C
|
| Vapour Pressure |
0.0±1.2 mmHg at 25°C
|
| Index of Refraction |
1.721
|
| LogP |
0.99
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
14
|
| Complexity |
387
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C(C)NC1=C2C(=CSS2)N(C)C1=O
|
| InChi Key |
MHMRAFONCSQAIA-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
|
| Chemical Name |
N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
|
| Synonyms |
Thiolutin; Acetopyrrothin; NSC 3927; NSC-3927; NSC3927
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~6.25 mg/mL (~27.38 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 1.25 mg/mL (5.48 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: 1.25 mg/mL (5.48 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3804 mL | 21.9020 mL | 43.8039 mL | |
| 5 mM | 0.8761 mL | 4.3804 mL | 8.7608 mL | |
| 10 mM | 0.4380 mL | 2.1902 mL | 4.3804 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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