SMIP 004

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Cat.No. 7192 - SMIP 004 | C13H19NO | CAS No. 143360-00-3
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)
Datasheet
Citations
Reviews
Literature (3)

Biological Activity for SMIP 004

SMIP 004 is a 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.

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.

Select a batch to recalculate based on the batch molecular weight:
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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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


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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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Literature in this Area

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