Dephostatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01831 |
| CAS | 151606-30-3 |
| Molecular Weight | 168.15 |
| Molecular Formula | C7H8N2O3 |
| Purity | ≥90% |
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Description
It is produced by the strain of Streptomyces sp. MJ7420NF5. Dephostatin inhibits the activity of protein tyrosine phosphatase, has an IC50 of 7.7 moL/L against PTPase prepared from human tumor T cell lines, and it inhibits the growth of Jokat cells, and has a weak antibacterial activity (MIC 50~ 100 μg/mL).
Specification
| Synonyms | 1,4-Benzenediol,2-(methylnitrosoamino); 2-(Methylnitrosoamino)-1,4-benzenediol; 2-[(hydroxyamino)-methylamino]cyclohexa-2,5-diene-1,4-dione |
| IUPAC Name | N-(2,5-dihydroxyphenyl)-N-methylnitrous amide |
| Canonical SMILES | CN(C1=C(C=CC(=C1)O)O)N=O |
| InChI | InChI=1S/C7H8N2O3/c1-9(8-12)6-4-5(10)2-3-7(6)11/h2-4,10-11H,1H3 |
| InChI Key | HCJOLYFWJWJPTJ-UHFFFAOYSA-N |
Properties
| Appearance | Brown Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 104-107°C |
| Density | 1.41 g/cm3 |
Reference Reading
1. Targeting Two-Component Systems Uncovers a Small-Molecule Inhibitor of Salmonella Virulence
Caressa N Tsai, Craig R MacNair, My P T Cao, Jordyn N Perry, Jakob Magolan, Eric D Brown, Brian K Coombes Cell Chem Biol. 2020 Jul 16;27(7):793-805.e7. doi: 10.1016/j.chembiol.2020.04.005. Epub 2020 May 14.
Salmonella serovars are leading causes of gastrointestinal disease and have become increasingly resistant to fluoroquinolone and cephalosporin antibiotics. Overcoming this healthcare crisis requires new approaches in antibiotic discovery and the identification of unique bacterial targets. In this work, we describe a chemical genomics approach to identify inhibitors of Salmonella virulence. From a cell-based, promoter reporter screen of ~50,000 small molecules, we identified dephostatin as a non-antibiotic compound that inhibits intracellular virulence factors and polymyxin resistance genes. Dephostatin disrupts signaling through both the SsrA-SsrB and PmrB-PmrA two-component regulatory systems and restores sensitivity to the last-resort antibiotic, colistin. Cell-based experiments and mouse models of infection demonstrate that dephostatin attenuates Salmonella virulence in vitro and in vivo, suggesting that perturbing regulatory networks is a promising strategy for the development of anti-infectives.
2. Dual actions of dephostatin on the nitric oxide/cGMP-signalling pathway in porcine iliac arteries
Anna Asplund Persson, Peter Gunnarsson, Eva Lindström, Magnus Grenegård Eur J Pharmacol. 2005 Oct 3;521(1-3):124-32. doi: 10.1016/j.ejphar.2005.08.023. Epub 2005 Sep 22.
We examined the effects of the nitrosoamine dephostatin on the nitric oxide (NO)/cyclic guanosine 3',5'-monophosphate (cGMP)-signalling in porcine iliac arteries. Dephostatin has been characterised as a tyrosine phosphatase inhibitor, but Western blot analyses showed that dephostatin did not augment tyrosine phosphorylation of arterial proteins. However, dephostatin relaxed pre-contracted arteries, and this effect was antagonised by the soluble guanylyl cyclase inhibitor 1H[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ). Furthermore, dephostatin increased the cGMP content and the serine phosphorylation of vasodilator-stimulated phosphoprotein. Dephostatin also inhibited the relaxation induced by acetylcholine and the NO-donor S-nitroso-N-acetyl-penicillamine (SNAP). In contrast, dephostatin did not affect the NO-dependent actions of 1,2,3,4-Oxatriazolium, 3-(3-chloro-2-metylphenyl)-5-[[(4methylphenyl)sulfonyl]amino]-hydroxide inner salt (GEA 3175). Measurement of NO revealed that dephostatin accelerated the consumption of NO. In conclusion, dephostatin exerts dual effects on the NO/cGMP-signalling pathway in iliac arteries. The drug actions included scavenging of NO, but also stimulation of cGMP production. These effects were not related to inhibition of tyrosine phosphatases.
3. Inhibition of dual-specificity phosphatase 26 by ethyl-3,4-dephostatin: Ethyl-3,4-dephostatin as a multiphosphatase inhibitor
Huiyun Seo, Sayeon Cho Pharmazie. 2016 Apr;71(4):196-200.
Protein tyrosine phosphatases (PTPs) regulate protein function by dephosphorylating phosphorylated proteins in many signaling cascades and some of them have been targets for drug development against many human diseases. There have been many reports that some chemical inhibitors could regulate particular phosphatases. However, there was no extensive study on specificity of inhibitors towardss phosphatases. We investigated the effects of ethyl-3,4-dephostatin, a potent inhibitor of five PTPs including PTP-1B and Src homology-2-containing protein tyrosine phosphatase-1 (SHP-1), on thirteen other PTPs using in vitro phosphatase assays. Of them, dual-specificity protein phosphatase 26 (DUSP26), which inhibits mitogen-activated protein kinase (MAPK) and p53 tumor suppressor and is known to be overexpressed in anaplastic thyroid carcinoma, was inhibited by ethyl-3,4-dephostatin in a concentration-dependent manner. Kinetic studies with ethyl-3,4-dephostatin and DUSP26 revealed competitive inhibition, suggesting that ethyl-3,4-dephostatin binds to the catalytic site of DUSP26 like other substrate PTPs. Moreover, ethyl-3,4-dephostatin protects DUSP26-mediated dephosphorylation of p38, a member of the MAPK family, and p53. Taken together, these results suggest that ethyl-3,4-dephostatin functions as a multiphosphatase inhibitor and is useful as a therapeutic agent for cancers overexpressing DUSP26.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
