87-11-6 Usage
Description
Thiolutin is a natural dithiol that exhibits potent inhibitory effects on bacterial and yeast RNA polymerases, with an IC50 value of 3 μg/ml. This property allows it to be utilized for analyzing mRNA stability. Additionally, Thiolutin demonstrates the ability to inhibit endothelial cell adhesion with an IC50 of less than 1 μM and suppresses tumor-induced angiogenesis in mice by interfering with Hsp27 interactions with cytoskeletal elements.
Uses
Used in Pharmaceutical Industry:
Thiolutin is employed as an antibiotic, first described in 1950 by Tanner and co-workers. Its selective antitumor activity has garnered significant interest, making it a valuable compound in the development of treatments for various cancers. It acts as a potent inhibitor of RNA polymerases in bacteria and yeast and also hinders the formation of mannan and glucan in fungi, which are essential components of the fungal cell wall.
Used in Research Applications:
Thiolutin serves as a polymerase II inhibitor, which is instrumental in various research applications. It is used to study the effects on yeast cells, allowing researchers to calculate transcript half-life. Additionally, it is utilized to investigate its impact on transcription during germination in budding yeast and to examine its influence on cell adhesion in zebrafish models. These applications contribute to a deeper understanding of cellular processes and the development of potential therapeutic strategies.
Biological Activity
Antibiotic; inhibits bacterial RNA polymerase. Inhibits adhesion of HUVEC cells to vitronectin (IC 50 = 0.83 mM) and subsequently reduces paxillin levels. Suppresses tumor cell-induced angiogenesis.
Biochem/physiol Actions
Sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases. It was found to inhibit in vitro RNA synthesis directed by all three yeast RNA polymerases (I, II, and III). Thiolutin is also an inhibitor of mannan and glucan formation in Saccharomyces cerevisiae and used for the analysis of mRNA stability. Studies have shown that thiolutin inhibits adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin and thus suppresses tumor cell-induced angiogenesis in vivo.
Safety Profile
Poison by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx and SOx.
References
Jing et al. (2021), Blockade of deubiquitinating enzyme PSMD14 overcomes chemoresistance in head and neck squamous cell carcinoma by antagonizing E2F1/Akt/SOX2-mediated stemness; Theranostics, 11 2655
Jia et al. (2010), Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton; Cell Stress Chaperones 15 165
Minamiguchi et al. (2001), Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis; Int. J. Cancer, 93 307
Check Digit Verification of cas no
The CAS Registry Mumber 87-11-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 87-11:
(4*8)+(3*7)+(2*1)+(1*1)=56
56 % 10 = 6
So 87-11-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
87-11-6Relevant articles and documents
Ring-Fused 1,2-Dithioles, I. - Synthesis of Thiolutine and Related Compounds
Stachel, Hans-Dietrich,Nienaber, Juliane,Zoukas, Thomas
, p. 473 - 480 (2007/10/02)
The 1,2-dithiolopyrrole 1 (thiolutine) has been obtained on two different routes.Firstly, by synthesis of the dithiolopyrrole 6a and introduction of the acetamino function into compound 6d by nitration followed by ester saponification and decarboxylation.
