Vialinin AUSP/isopeptidase T (IsoT)/UCH-L1 DUB inhibitor CAS# 858134-23-3 |
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| Cas No. | 858134-23-3 | SDF | Download SDF |
| PubChem ID | 11563133 | Appearance | Powder |
| Formula | C34H26O8 | M.Wt | 562.57 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 20 mM in DMSO | ||
| Chemical Name | [3,4-dihydroxy-2,5-bis(4-hydroxyphenyl)-6-(2-phenylacetyl)oxyphenyl] 2-phenylacetate | ||
| SMILES | C1=CC=C(C=C1)CC(=O)OC2=C(C(=C(C(=C2C3=CC=C(C=C3)O)O)O)C4=CC=C(C=C4)O)OC(=O)CC5=CC=CC=C5 | ||
| Standard InChIKey | NOJUKCRPSUMHQQ-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C34H26O8/c35-25-15-11-23(12-16-25)29-31(39)32(40)30(24-13-17-26(36)18-14-24)34(42-28(38)20-22-9-5-2-6-10-22)33(29)41-27(37)19-21-7-3-1-4-8-21/h1-18,35-36,39-40H,19-20H2 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Inhibitor of ubiquitin-specific peptidase 4 (USP4), USP5/isopeptidase T (IsoT) and UCH-L1 deubiquitinating enzyme (DUB) activity (IC50 values are 1.5, 5.9 and 22.3 μM, respectively). Shows no significant inhibition of UCH-L3, USP2, and USP8 activities. Decreases release of TNF-α (IC50 = 0.09 nM) from RBL-2H3 mast cells. Displays anti-cancer activity decreasing viability in human colonic carcinoma cells. |
Vialinin A Dilution Calculator
Vialinin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.7776 mL | 8.8878 mL | 17.7756 mL | 35.5511 mL | 44.4389 mL |
| 5 mM | 0.3555 mL | 1.7776 mL | 3.5551 mL | 7.1102 mL | 8.8878 mL |
| 10 mM | 0.1778 mL | 0.8888 mL | 1.7776 mL | 3.5551 mL | 4.4439 mL |
| 50 mM | 0.0356 mL | 0.1778 mL | 0.3555 mL | 0.711 mL | 0.8888 mL |
| 100 mM | 0.0178 mL | 0.0889 mL | 0.1778 mL | 0.3555 mL | 0.4444 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Vialinin A is a potent inhibitor of ubiquitin-specific peptidases with IC50 values of 1.5, 5.9 and 22.3 μM for ubiquitin-specific peptidase 4 (USP4), USP5/isopeptidase T (IsoT) and UCH-L1 deubiquitinating enzyme (DUB), respectively [1].
Ubiquitin-specific peptidases (USPs) are a series of proteases that deubiquitinate target proteins. The dynamic modification of a protein with ubiquitin can modify its function, localization and fate in the cell. Ubiquitin hydrolase plays an important role in immunology and infection [2].
In RBL-2H3 cells, vialinin A inhibited TNF-ɑ production and release and inhibited USP5 enzymatic activity. In USP5 siRNA-knockdown RBL-2H3 cells, vialinin A inhibited TNF-ɑ production and release in a dose dependent way. Also, the mRNA expression of TNF-ɑ was decreased significantly [2]. In RBL-2H3 cells, Vialinin A inhibited TNF-ɑ production with IC50 value of 0.09 nM. Also, it inhibited the release of interleukin 4, β-hexosaminidase and monocyte chemotactic protein 1, which suggested Vialinin A had anti-allergic activities [3].
References:
[1]. Okada K, Ye YQ, Taniguchi K, et al. Vialinin A is a ubiquitin-specific peptidase inhibitor. Bioorg Med Chem Lett, 2013, 23(15): 4328-4331.
[2]. Yoshioka Y, Ye YQ, Okada K, et al. Ubiquitin-specific peptidase 5, a target molecule of vialinin A, is a key molecule of TNF-α production in RBL-2H3 cells. PLoS One, 2013, 8(12): e80931.
[3]. Onose J, Xie C, Ye YQ, et al. Vialinin A, a novel potent inhibitor of TNF-alpha production from RBL-2H3 cells. Biol Pharm Bull, 2008, 31(5): 831-833.
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Ubiquitin-specific peptidase 5, a target molecule of vialinin A, is a key molecule of TNF-alpha production in RBL-2H3 cells.[Pubmed:24349023]
PLoS One. 2013 Dec 4;8(12):e80931.
Tumor necrosis factor alpha (TNF-alpha), a central mediator of the inflammatory response, is released from basophilic cells and other cells in response to a variety of proinflammatory stimuli. Vialinin A is a potent inhibitor of TNF-alpha production and is released from RBL-2H3 cells. Ubiquitin-specific peptidase 5 (USP5), a deubiquitinating enzyme, was identified as a target molecule of Vialinin A and its enzymatic activity was inhibited by Vialinin A. Here we report production of TNF-alpha is decreased in USP5 siRNA-knockdown RBL-2H3 cells, compared with control cells. The finding of the present study strongly suggests that USP5 is one of the essential molecules for the production of TNF-alpha in RBL-2H3.
Structural elucidation and synthesis of vialinin C, a new inhibitor of TNF-alpha production.[Pubmed:24679673]
Bioorg Med Chem. 2014 Apr 15;22(8):2442-6.
A new inhibitor of TNF-alpha production (IC50=0.89 muM) named vialinin C (1) was isolated from dry fruiting bodies of an edible Chinese mushroom, Thelephora vialis. The structure of 1 was determined by high-resolution MS, NMR spectroscopic analysis, and confirmed by synthesis. Synthesis of ganbajunin B (5) obtained from the same origin was also described.
Vialinin A is a ubiquitin-specific peptidase inhibitor.[Pubmed:23791076]
Bioorg Med Chem Lett. 2013 Aug 1;23(15):4328-31.
Vialinin A, a small compound isolated from the Chinese mushroom Thelephora vialis, exhibits more effective anti-inflammatory activity than the widely used immunosuppressive drug tacrolimus (FK506). Here, we show that ubiquitin-specific peptidase 5/isopeptidase T (USP5/IsoT) is a target molecule of Vialinin A, identified by using a beads-probe method. Vialinin A inhibited the peptidase activity of USP5/IsoT and also inhibited the enzymatic activities of USP4 among deubiquitinating enzymes tested. Although USPs are a member of thiol protease family, Vialinin A exhibited no inhibitions for other thiol proteases, such as calpain and cathepsin.
Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-alpha production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity.[Pubmed:27491710]
Bioorg Med Chem Lett. 2016 Sep 1;26(17):4237-40.
Several p-terphenyl compounds have been isolated from the edible Chinese mushroom Thelephora vialis. Vialinin A, a p-terphenyl compound, strongly inhibits tumor necrosis factor-alpha production and release. Vialinin A inhibits the enzymatic activity of ubiquitin-specific peptidase 5, one of the target molecules in RBL-2H3 cells. Here we examined the inhibitory effect of p-terphenyl compounds, including Vialinin A, against sentrin/SUMO-specific protease 1 (SENP1) enzymatic activity. The half maximal inhibitory concentration values of Vialinin A and thelephantin G against full-length SENP1 were 1.64+/-0.23muM and 2.48+/-0.02muM, respectively. These findings suggest that p-terphenyl compounds are potent SENP1 inhibitors.
Inhibitory effects of vialinin A and its analog on tumor necrosis factor-alpha release and production from RBL-2H3 cells.[Pubmed:23246504]
Cell Immunol. 2012 Oct;279(2):140-4.
Vialinin A is an extremely potent inhibitor of tumor necrosis factor (TNF)-alpha release from RBL-2H3 cells. The present study investigated in detail the inhibitory effects of Vialinin A and its analog, 5',6'-dimethyl-1,1':4',1''-terphenyl-2',3',4,4''-tetraol (DMT), on TNF-alpha. Vialinin A and DMT inhibited the release of TNF-alpha from RBL-2H3 cells in a dose-dependent manner, but had no effect on beta-hexosaminidase activity. Also, vialinins had little effect on TNF-alpha mRNA levels. Intriguingly, vialinins inhibited TNF-alpha production at low concentrations, but not shown a dose-dependency. The potent inhibitory activities of vialinins against TNF-alpha production and release suggest promising new candidate pathways for anti-inflammatory agents.
Anticancer activities of thelephantin O and vialinin A isolated from Thelephora aurantiotincta.[Pubmed:21630659]
J Agric Food Chem. 2011 Jul 13;59(13):6974-9.
Thelephora aurantiotincta is an edible mushroom belonging to the genus Thelephora; it grows in symbiosis with pine trees. Recently, phytochemical investigations have revealed that the genus Thelephora is an abundant source of p-terphenyl derivatives. However, their bioactivity has not yet been well characterized. In screening for natural materials with anticancer activity, a T. aurantiotincta ethanol extract (TAE) was found to decrease cell viability in human hepatocellular carcinoma cells (HepG2). In this study, a new p-terphenyl derivative, thelephantin O, and a known compound, Vialinin A, were isolated as the principal bioactive components of TAE. These compounds decreased cell viability in HepG2 and human colonic carcinoma cells (Caco2), but not in noncancerous human hepatocytes. This is the first report of the isolation from T. aurantiotincta of selective cytotoxic agents against cancer cells.
