An inhibitor of Hsp27 and RNA polymerases
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Thiolutin

Item No. 11350

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-acetamide
CAS Number
87-11-6
Synonyms
  • Acetopyrrothin
  • NSC 3927
Molecular Formula
C8H8N2O2S2
Formula Weight
228.3
Purity
≥97%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 1 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
310, 390 nm
SMILES
CC(NC1=C2C(N(C)C1=O)=CSS2)=O
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)
InChi Key
MHMRAFONCSQAIA-UHFFFAOYSA-N
Origin
Bacterium/Streptomyces luteosporeus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases (IC50 = 3 μg/ml).1,2,3 Because of this, it can be used for the analysis of mRNA stability. Thiolutin also inhibits endothelial cell adhesion (IC50 < 1 μM) and S180 tumor-induced angiogenesis in mice by inhibiting Hsp27 interactions with cytoskeletal elements.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jimenez, A., Tipper, D.J., and Davies, J. Mode of action of thiolutin, an inhibitor of macromolecular synthesis in Saccharomyces cerevisiae. Antimicrob. Agents Chemother. 3(6), 729-738 (1973).

    2. Tipper, D.J. Inhibition of yeast ribonucleic acid polymerases by thiolutin. J. Bacteriol. 116(1), 245-256 (1973).

    3. Khachatourians, G.G., and Tipper, D.J. Inhibition of messenger ribonucleic acid synthesis in Escherichia coli by thiolutin. J. Bacteriol. 119(3), 795-804 (1974).

    4. Dai, S., Jia, Y., Wu, S.L., et al. Comprehensive characterization of heat shock protein 27 phosphorylation in human endothelial cells stimulated by the microbial dithiole thiolutin. J. Proteome Res. 7(10), 4384-4395 (2008).

    5. Jia, Y., Wu, S.L., Isenberg, J.S., et al. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones 15, 165-181 (2010).