662140

DUB Inhibitor IV, b-AP15

The DUB Inhibitor IV, b-AP15 controls the biological activity of DUB. This small molecule/inhibitor is primarily used for Protease Inhibitors applications.

• Synonym(s): DUB Inhibitor IV, b-AP15, NSC687852, 3,5- bis((4-Nitrophenyl)methylidene)-1-prop-2-enoylpiperidin-4-one, (3 E,5 E)-1-Acryloyl-3,5- bis(4-nitrobenzylidene)piperidin-4-one, USP14 Inhibitor III, UCH-L5/UCH37 Inhibitor II, NSC687852, 3,5-bis((4-Nitrophenyl)methylidene)-1-prop-2-enoylpiperidin-4-one, (3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one, USP14 Inhibitor III, UCH-L5/UCH37 Inhibitor II
• Empirical Formula (Hill Notation): C₂₂H₁₇N₃O₆
• CAS Number: 1009817-63-3
• Molecular Weight: 419.39
• MDL number: MFCD26142662
• UNSPSC Code: 12352200

Properties

• assay: ≥97% (HPLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: yellow
• solubility: DMSO: 100 mg/mL, clear, yellow
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: O=C(/C(CN(C(C=C)=O)C/1)=C/C(C=C2)=CC=C2[N+]([O-])=O)C1=C\C3=CC=C(C=C3)[N+]([O-])=O
• InChI: 1S/C22H17N3O6/c1-2-21(26)23-13-17(11-15-3-7-19(8-4-15)24(28)29)22(27)18(14-23)12-16-5-9-20(10-6-16)25(30)31/h2-12H,1,13-14H2/b17-11+,18-12+
• InChI key: GFARQYQBWJLZMW-JYFOCSDGSA-N

Description

General description

A cell-permeable bis-nitrobenzylidene-piperidinone that inhibits 19S deubiquitinase (DUB) activity (IC₅₀ = 2.1 µM against Ub-AMC hydrolysis) in a reversible manner by directly targeting UCH37/UCH-L5 and USP14, while exhibiting little or no activity toward BAP1, UCH-L1, UCH-L3, USP2, USP7, USP8 (IC₅₀ >100 µM), or POH1/PRN11. Dual UCH37 and USP14 inhibition by a-AP15 results in increased bulk cellular protein ubiquitination level and a blockage of protein proteasomal degradation (Effective conc. ≥770 nM in HCT-116 cells), exactly opposite to the effects seen with USP14 inhibition alone by IU1 (Cat. No. 662210). Effectively suppresses the growth of various tumors in mice (2.5 to 5 mg/kg, i.p. or s.c.) in vivo.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

D′Arcy, P., et al. 2011. Nat. Med.17, 1636.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable