Walrycin B

WalR inhibitor CAS# 878419-78-4

Walrycin B

Catalog No. BCC5156----Order now to get a substantial discount!

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Chemical structure

Walrycin B

3D structure

Chemical Properties of Walrycin B

Cas No. 878419-78-4 SDF Download SDF
PubChem ID 3164070 Appearance Powder
Formula C14H10F3N5O2 M.Wt 337.26
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 11.5 mg/mL (34.10 mM; Need ultrasonic and warming)
Chemical Name 1,6-dimethyl-3-[4-(trifluoromethyl)phenyl]pyrimido[5,4-e][1,2,4]triazine-5,7-dione
SMILES CN1C2=NC(=O)N(C(=O)C2=NC(=N1)C3=CC=C(C=C3)C(F)(F)F)C
Standard InChIKey XRVMPTWWKLKLPB-UHFFFAOYSA-N
Standard InChI InChI=1S/C14H10F3N5O2/c1-21-12(23)9-11(19-13(21)24)22(2)20-10(18-9)7-3-5-8(6-4-7)14(15,16)17/h3-6H,1-2H3
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 Walrycin B

DescriptionWalrycin B is a novel antibacterial compound specifically targeting the essential WalR response regulator. IC50 value: 0.39 ug/ml (MIC for B. subtilis 168); 3.13 ug/ml (MIC for S. aureus N315) [1] Target: bacterial WalR response regulator; Antibacterial Walrycin B is known as an analog of toxoflavin (a phytotoxin from Burkholderia glumae), which has been shown to have a strong MIC for B. subtilis and S. aureus but whose mode of action is not clear. The compound could also interact with WalR to cause bactericidal effects. Walrycins are a new class of potent small molecule compounds that kill bacterial cells by targeting the RR WalR and inhibiting this essential signal transduction pathway. They not only have therapeutic potential but will also prove to be useful reagents for the further study of the WalK/WalR TCS. Walrycin B target WalR and lead to cell death in both B. subtilis and S. aureus.

References:
[1]. Gotoh Y, et al. Novel antibacterial compounds specifically targeting the essential WalR response regulator. J Antibiot (Tokyo). 2010 Mar;63(3):127-34.

Walrycin B Dilution Calculator

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Walrycin B Molarity Calculator

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Preparing Stock Solutions of Walrycin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9651 mL 14.8254 mL 29.6507 mL 59.3014 mL 74.1268 mL
5 mM 0.593 mL 2.9651 mL 5.9301 mL 11.8603 mL 14.8254 mL
10 mM 0.2965 mL 1.4825 mL 2.9651 mL 5.9301 mL 7.4127 mL
50 mM 0.0593 mL 0.2965 mL 0.593 mL 1.186 mL 1.4825 mL
100 mM 0.0297 mL 0.1483 mL 0.2965 mL 0.593 mL 0.7413 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 Walrycin B

Walrycin B is an inhibitor of WalR [1].

Walrycin B is screened out from a chemical library. It is proved to be a selective WalR inhibitor by measuring EGFP fluorescence intensity. In this assay, it is found to strongly increase fluorescence intensity in strain JM109/pFI014 but has no significant effect on the strain JM109/pFI001. Walrycin B shows effects on the expression of WalR regulon genes in the in vivo assay. The addition of it lowers the expression of ydjM, yocH and yvcE and increases the expression of yoeB and yjeA rapidly. These effects caused by Walrycin B are opposite with which caused by WalR suggesting that Walrycin B specifically affects the WalK/WalR system. Since WalK/WalR plays a regulating role in cell wall metabolism and cell division in Bacillus subtilis and Staphylococcus aureus, Walrycin B is found to cause cell death in both of them with strong MICs through targeting WalR [1].

References:
[1] Gotoh Y, Doi A, Furuta E, Dubrac S, Ishizaki Y, Okada M, Igarashi M, Misawa N, Yoshikawa H, Okajima T, Msadek T, Utsumi R. Novel antibacterial compounds specifically targeting the essential WalR response regulator. J Antibiot (Tokyo). 2010 Mar;63(3):127-34.

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References on Walrycin B

NH125 kills methicillin-resistant Staphylococcus aureus persisters by lipid bilayer disruption.[Pubmed:26910612]

Future Med Chem. 2016;8(3):257-69.

BACKGROUND: NH125, a known WalK inhibitor kills MRSA persisters. However, its precise mode of action is still unknown. METHODS & RESULTS: The mode of action of NH125 was investigated by comparing its spectrum of antimicrobial activity and its effects on membrane permeability and giant unilamellar vesicles (GUVs) with Walrycin B, a WalR inhibitor and benzyldimethylhexadecylammonium chloride (16-BAC), a cationic surfactant. NH125 killed persister cells of a variety of Staphylococcus aureus strains. Similar to 16-BAC, NH125 killed MRSA persisters by inducing rapid membrane permeabilization and caused the rupture of GUVs, whereas Walrycin B did not kill MRSA persisters or induce membrane permeabilization and did not affect GUVs. CONCLUSION: NH125 kills MRSA persisters by interacting with and disrupting membranes in a detergent-like manner.

Novel antibacterial compounds specifically targeting the essential WalR response regulator.[Pubmed:20111065]

J Antibiot (Tokyo). 2010 Mar;63(3):127-34.

The WalK/WalR (YycG/YycF) two-component system, which is essential for cell viability, is highly conserved and specific to low-GC percentage of Gram-positive bacteria, making it an attractive target for novel antimicrobial compounds. Recent work has shown that WalK/WalR exerts an effect as a master regulatory system in controlling and coordinating cell wall metabolism with cell division in Bacillus subtilis and Staphylococcus aureus. In this paper, we develop a high-throughput screening system for WalR inhibitors and identify two novel inhibitors targeting the WalR response regulator (RR): walrycin A (4-methoxy-1-naphthol) and Walrycin B (1,6-dimethyl-3-[4-(trifluoromethyl)phenyl]pyrimido[5,4-e][1,2,4]triazine-5,7-dio ne). Addition of these compounds simultaneously affects the expression of WalR regulon genes, leading to phenotypes consistent with those of cells starved for the WalK/WalR system and having a bactericidal effect. B. subtilis cells form extremely long aseptate filaments and S. aureus cells form large aggregates under these conditions. These results show that walrycins A and B are the first antibacterial agents targeting WalR in B. subtilis and S. aureus.

Description

Walrycin B is a novel antibacterial compound specifically targeting the essential WalR response regulator.

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