ChemicalBook Product Catalog Biochemical Engineering Inhibitors Ubiquitin DUB inhibitors 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone

1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone

Product Name1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone
CAS314245-33-5
MFC18H21FN2O
MW300.37
EINECS232-983-9
MOL File314245-33-5.mol

Chemical Properties

Boiling point	437.0±45.0 °C(Predicted)
Density	1.16±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: >10mg/mL
pka	8.20±0.20(Predicted)
form	powder
color	off-white to light brown
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChI	1S/C18H21FN2O/c1-13-11-17(18(22)12-20-9-3-4-10-20)14(2)21(13)16-7-5-15(19)6-8-16/h5-8,11H,3-4,9-10,12H2,1-2H3
InChIKey	JUWDSDKJBMFLHE-UHFFFAOYSA-N
SMILES	FC1=CC=C(N2C(C)=CC(C(CN3CCCC3)=O)=C2C)C=C1

Safety Information

Hazard Codes	Xi
Risk Statements	41
Safety Statements	61
WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

IU1 (314245-33-5) is a selective inhibitor of USP14 (IC50<4 μM). Enhances proteasome activity and substrate proteolysis.1,2 Inhibits Dengue virus replication.3 In prion-infected CAD5 cells activation of the ubiquitin proteasome system by IU1 is sufficient to induce clearance of polyubiquitinated substrates and reduce misfolded prion protein load.4 Attenuates ischemia/reperfusion-induced neuronal injury in a mouse model.5 Cell permeable.

Uses

IU1 has been used for the inhibition of Ubiquitin Specific Peptidase 14 (USP14) in human neuroblastoma cells (SH-SY5Y) and in ubiquitin-rhodamine hydrolysis plate assay.

Biochem/physiol Actions

IU1 is an inhibitor of USP14, a deubiquitinating enzyme associated with the proteasome. The proteasome mediates the cellular degradation of oxidized, damaged and misfolded proteins which, if not removed, accumulate and become toxic to cells. Proteins targeted for proteasomal degradation are first ubiquitinated, with longer length ubiquitin chains interacting more strongly with the proteasome. Deubiquitinating enzymes (DUBs) such as USP14 interfere with the degradation process. IU1 inhibits USP14-mediated ubiquitin "chain-trimming" thereby enhancing substrate degradation by the proteasome. The compound may help to eliminate toxic proteins more effectively by enhancing their degradation.

References

[1] BYUNG-HOON LEE. Enhancement of proteasome activity by a small-molecule inhibitor of USP14[J]. Nature, 2010, 467 7312: 179-184. DOI:10.1038/nature09299
[2] MIN JAE LEE. Trimming of ubiquitin chains by proteasome-associated deubiquitinating enzymes.[J]. Molecular & cellular proteomics : MCP, 2011: R110.003871. DOI:10.1074/mcp.r110.003871
[3] DILIP K. NAG Daniel F. A small-molecule inhibitor of deubiquitinating enzyme USP14 inhibits Dengue virus replication[J]. Virus research, 2012, 165 1: Pages 103-106. DOI:10.1016/j.virusres.2012.01.009
[4] CHRIS MCKINNON. Prion-mediated neurodegeneration is associated with early impairment of the ubiquitin–proteasome system[J]. Acta Neuropathologica, 2015, 131 3: 411-425. DOI:10.1007/s00401-015-1508-y
[5] JIA-WEI MIN. USP14 inhibitor attenuates cerebral ischemia/reperfusion-induced neuronal injury in mice[J]. Journal of Neurochemistry, 2016, 140 5: 826-833. DOI:10.1111/jnc.13941
[6] TAKUJIRO HOMMA. Ubiquitin-specific protease 14 modulates degradation of cellular prion protein.[J]. Scientific Reports, 2015: 11028. DOI:10.1038/srep11028

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