Anguizole

Inhibitor of HCV replication CAS# 442666-98-0

Anguizole

Catalog No. BCC1365----Order now to get a substantial discount!

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Chemical structure

Anguizole

3D structure

Chemical Properties of Anguizole

Cas No. 442666-98-0 SDF Download SDF
PubChem ID 1046082 Appearance Powder
Formula C17H11ClF2N4O2S M.Wt 408.81
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (122.31 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 7-[chloro(difluoro)methyl]-5-(furan-2-yl)-N-(thiophen-2-ylmethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide
SMILES C1=COC(=C1)C2=NC3=CC(=NN3C(=C2)C(F)(F)Cl)C(=O)NCC4=CC=CS4
Standard InChIKey GBNREAYNZPJROB-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H11ClF2N4O2S/c18-17(19,20)14-7-11(13-4-1-5-26-13)22-15-8-12(23-24(14)15)16(25)21-9-10-3-2-6-27-10/h1-8H,9H2,(H,21,25)
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.
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.
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.

Biological Activity of Anguizole

DescriptionAnguizole is a small molecule inhibitor of HCV replication and alters NS4B's subcellular distribution.
TargetsHCV    

Anguizole Dilution Calculator

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Anguizole Molarity Calculator

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Preparing Stock Solutions of Anguizole

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4461 mL 12.2306 mL 24.4612 mL 48.9225 mL 61.1531 mL
5 mM 0.4892 mL 2.4461 mL 4.8922 mL 9.7845 mL 12.2306 mL
10 mM 0.2446 mL 1.2231 mL 2.4461 mL 4.8922 mL 6.1153 mL
50 mM 0.0489 mL 0.2446 mL 0.4892 mL 0.9784 mL 1.2231 mL
100 mM 0.0245 mL 0.1223 mL 0.2446 mL 0.4892 mL 0.6115 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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Background on Anguizole

Anguizole is a selective inhibitor of NS4B with IC50 value of 310 nM [1].

NS4B (nonstructural protein 4B) is a viral protein which was found in hepatitis C virus and was a key regulator in HCV replication complex formation. It is reported that NS4B plays a pivotal role in HCV replication via inducing a specific membrane rearrangement and designating membranous web. NS4B-AH2, comprising amino acid 42 to 66, is identified as a major regulator for NS4B oligomerization [2].

Anguizole is a potent NS4B inhibitor and targets the second amphipathic helix of NS4B (NS4B-AH2). When tested with HCV virus, anguizole treatment significantly disrupted NS4B-AH2-mediated biological functions of NS4B which played an important role in HCV life cycle [3]. In Huh7.5 cells transferring a plasmid expressing NS4B fused in frame with GFP, 5μM anguizole treatment (48 hours) altered the distribution of NS4B MAF pattern which inhibited HCV life cycle [1].

References:
[1].  Bryson, P.D., et al., A small molecule inhibits HCV replication and alters NS4B's subcellular distribution. Antiviral Res, 2010. 87(1): p. 1-8.
[2].  Gouttenoire, J., et al., Aminoterminal amphipathic alpha-helix AH1 of hepatitis C virus nonstructural protein 4B possesses a dual role in RNA replication and virus production. PLoS Pathog, 2014. 10(10): p. e1004501.
[3].  Choi, M., et al., A hepatitis C virus NS4B inhibitor suppresses viral genome replication by disrupting NS4B's dimerization/multimerization as well as its interaction with NS5A. Virus Genes, 2013. 47(3): p. 395-407.

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References on Anguizole

A hepatitis C virus NS4B inhibitor suppresses viral genome replication by disrupting NS4B's dimerization/multimerization as well as its interaction with NS5A.[Pubmed:23868571]

Virus Genes. 2013 Dec;47(3):395-407.

Chronic hepatitis C virus (HCV) infection is responsible for severe liver diseases including liver cirrhosis and hepatocellular carcinoma. An HCV non-structural protein 4B (NS4B) plays an essential role in viral RNA genome replication by building multi-vesicular structures around endoplasmic reticulum membranes. Especially, the second amphipathic helix of NS4B (NS4B-AH2) was shown to be essential for this process. By screening compounds against a membrane-aggregating activity of NS4B-AH2, several anti-HCV replication small molecules targeting NS4B-AH2 were discovered. However, little is known about detailed molecular mechanism of action for these NS4B-AH2 inhibitors. In this report, we provide evidences that NS4B-AH2 is required for NS4B's dimerization/multimerization, its proper subcellular localization, as well as its interaction with NS5A. More importantly, one of NS4B-AH2 inhibitors called "Anguizole" was found to be able to disrupt all of these NS4B-AH2-mediated biological functions of NS4B. This newly elucidated mechanism of action will enable us not only to better understand a central role of NS4B-AH2 in HCV life cycle but also to develop a more safe and effective new class of NS4B-AH2 inhibitors of HCV replication in the future.

Description

Anguizole is a small molecule inhibitor of HCV replication and alters NS4B's subcellular distribution.

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