VLX1570 is an inhibitor of 19S proteasomal deubiquitinases
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VLX1570

Item No. 29721

Technical Information
Formal Name
3,5-bis[(4-fluoro-3-nitrophenyl)methylene]hexahydro-1-(1-oxo-2-propen-1-yl)-4H-azepin-4-one
CAS Number
1431280-51-1
Molecular Formula
C23H17F2N3O6
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 16 mg/mlEthanol: Partially soluble
λmax
296 nm
SMILES
O=C(/C(CCN(C(C=C)=O)C/1)=C/C2=CC([N+]([O-])=O)=C(F)C=C2)C1=C\C3=CC=C(F)C([N+]([O-])=O)=C3
InChi Code
InChI=1S/C23H17F2N3O6/c1-2-22(29)26-8-7-16(9-14-3-5-18(24)20(11-14)27(31)32)23(30)17(13-26)10-15-4-6-19(25)21(12-15)28(33)34/h2-6,9-12H,1,7-8,13H2/b16-9+,17-10+
InChi Key
SCKXBVLYWLLALY-CZCYGEDCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    VLX1570 is an inhibitor of 19S proteasomal deubiquitinases with IC50 values of 6.4 and 13 μM for deubiquitinase activity in vitro using Ub-rhodamine and Ub-AMC, respectively, as substrates.1,2 It is selective for proteasomal deubiquitinases over a panel of deubiquitinases at 20 μM, but inhibits USP5 by greater than 50%, and over a panel of 211 kinases at 10 μM, but inhibits Cdk4 by 77%.1 VLX1570 binds to and inhibits recombinant ubiquitin-specific protease 14 (USP14) and ubiquitin carboxyl-terminal hydrolase isozyme L5 (UCHL5) in vitro, and inhibits the USP14 and UCHL5 activity of purified 19S proteasomes when used at a concentration of 50 μM.1,2 It inhibits the proliferation of KMS-11, RPMI-8226, OPM-2, and OPM-2-BZR multiple myeloma cells (IC50s = 43, 74, 126, and 191 nM, respectively), as well as induces apoptosis and increases the accumulation of polyubiquitinated proteins.2 VLX1570 (3 mg/kg per day for 10 days) increases survival and reduces tumor growth in KMS-11-LUC2 and RPMI-8226 mouse xenograft models, respectively.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, X., D'Arcy, P., Caulfield, T.R., et alSynthesis and evaluation of derivatives of the proteasome deubiquitinase inhibitor b-AP15. Chem. Biol. Drug Des. 86(5), 1036-1048 (2015).

    2. Wang, X., Mazurkiewicz, M., Hillert, E.-K., et alThe proteasome deubiquitinase inhibitor VLX1570 shows selectivity for ubiquitin-specific protease-14 and induces apoptosis of multiple myeloma cells. Sci. Rep. 6:26979, (2016).

    Product Citations

    Cho, C.-C., Li, S.G., Lalonde, T.J., et alDrug repurposing for the SARS-CoV-2 papain-like protease. ChemMedChem 17(1), e202100455 (2022).