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Submit ReviewSMIP 004
Description: SKP2 (S-phase kinase-associated protein 2) inhibitor; upregulates p27 and arrests cell cycle in G1 phase
Chemical Name: N-(4-Butyl-2-methylphenyl)acetamide
Purity: ≥98% (HPLC)
Biological Activity for SMIP 004
SMIP 004 is an SKP2 (S-phase kinase-associated protein 2) inhibitor. Upregulates p27 and activates the unfolded protein response (UPR) in LNCaP prostate cancer cells overexpressing SKP2. Also induces oxidative stress. Induces proteasomal degradation of cyclin D1 and acts as CDK2 inhibitor. Arrests cell cycle in G1 phase and induces apoptosis in prostate cancer cells, but not normal cells in vitro. Inhibits growth of breast and prostate cancer xenografts in mice. Also induces autophagy and reduces replication of MERS-CoV in VeroB4 cells.
Compound Libraries for SMIP 004
SMIP 004 is also offered as part of the Tocriscreen Epigenetics Library. Find out more about compound libraries available from Tocris.
Technical Data for SMIP 004
| M. Wt | 205.3 |
| Formula | C13H19NO |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 143360-00-3 |
| PubChem ID | 2747581 |
| InChI Key | ZFVMECVBUGMWIX-UHFFFAOYSA-N |
| Smiles | CCCCC1=CC(C)=C(NC(C)=O)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for SMIP 004
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 20.53 | 100 |
Preparing Stock Solutions for SMIP 004
The following data is based on the product molecular weight 205.3. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 4.87 mL | 24.35 mL | 48.71 mL |
| 5 mM | 0.97 mL | 4.87 mL | 9.74 mL |
| 10 mM | 0.49 mL | 2.44 mL | 4.87 mL |
| 50 mM | 0.1 mL | 0.49 mL | 0.97 mL |
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Product Datasheets for SMIP 004
References for SMIP 004
References are publications that support the biological activity of the product.
Rico-Bautista et al (2010) Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells. BMC Biol. 8 153 PMID: 21182779
Rico-Bautista et al (2013) Small molecule-induced mitochondrial disruption directs prostate cancer inhibition via UPR signaling. Oncotarget 4 1212 PMID: 23902736
Gassen et al (2019) SKP2 attenuates autophagy through Beclin1-ubiquitination and its inhibition reduces MERS-Coronavirus infection. Nat.Commun. 10 5770 PMID: 31852899
If you know of a relevant reference for SMIP 004, please let us know.
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Keywords: SMIP 004, SMIP 004 supplier, SMIP004, S-phase, kinase-associated, protein, 2, SKP2, E3, ligase, inhibitors, inhibits, p27, upregulates, MERS-CoV, unfolded, response, UPR, activates, activators, CDK2, CKI, cyclin, dependent, kinase, ubiquitin, Ubiquitin, Ligases, Coronavirus, Other, ER, stress/UPR, CDK1, Subfamily, 7192, Tocris Bioscience
Citations for SMIP 004
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TPD and Induced Proximity Research Product GuideUpdated
This brochure highlights the tools and services available from Bio-Techne to support your Targeted Protein Degradation and Induced Proximity research, including:
- Active Degraders
- TAG Degradation Platform
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- Assays for Protein Degradation
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Programmed Cell Death Poster
There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.
Targeted Protein Degradation Poster
Degraders (e.g. PROTACs) are bifunctional small molecules, that harness the Ubiquitin Proteasome System (UPS) to selectively degrade target proteins within cells. They consist of three covalently linked components: an E3 ubiquitin ligase ligand, a linker and a ligand for the target protein of interest. Authored in-house, this poster outlines the generation of a toolbox of building blocks for the development of Degraders. The characteristics and selection of each of these components are discussed. Presented at EFMC 2018, Ljubljana, Slovenia