5.00517

SKP2 E3 Ligase Inhibitor II, SMIP004

• Synonym(e): SKP2 E3 Ligase Inhibitor II, SMIP004, CRL1 ^SKP2 Inhibitor II, p21/Cip1/CKI/Waf1 Activator II, p27/Kip1 Activator II, S-phase Kinase-associated Protein 2 Inhibitor II, SCF ^SKP2 Inhibitor II, Small Molecule Inhibitor of p27 Depletion 004, N-(4-Butyl-2-methylphenyl)acetami, CRL1^SKP2 Inhibitor II, p21/Cip1/CKI/Waf1 Activator II, p27/Kip1 Activator II, S-phase Kinase-associated Protein 2 Inhibitor II, SCF^SKP2 Inhibitor II, Small Molecule Inhibitor of p27 Depletion 004, N-(4-Butyl-2-methylphenyl)acetamide
• Empirische Formel (Hill-System): C₁₃H₁₉NO
• CAS-Nummer: 143360-00-3
• Molekulargewicht: 205.30
• MDL number: MFCD00277686
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥99% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Eigenschaften

• assay: ≥99% (HPLC)
• Quality Segment: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 100 mg/mL
• storage temp.: 2-8°C
• SMILES string: N(c1c(cc(cc1)CCCC)C)C(=O)C
• InChI: 1S/C13H19NO/c1-4-5-6-12-7-8-13(10(2)9-12)14-11(3)15/h7-9H,4-6H2,1-3H3,(H,14,15)
• InChI key: ZFVMECVBUGMWIX-UHFFFAOYSA-N

Beschreibung

General description

A cell-permeable phenylacetamide compound that is shown to upregulate p21^Cip1/Waf1 and/or p27^Kip1 in prostate cancer LNCaP, PC3, DU145, but not HeLa, cultures (Fold of control p21/27 levels = 2.7/2.1, 1.7/1,1, 1.7/1.3, and 1.1/1.1, respectively; 24 h 40 µM treatment) with a concomitant downregulation of the F-box E3 ubiquitin ligase Skp2 and a delayed G1-to-S cell cycle transition (G1 population with/ without 24 h 40 µM drug treatment = 81.7%/70.8%, 58.5%/42.2%, 75.7%/40.5%, respectively; S population with/ without 24 h 40 µM drug treatment = 7.9%/18.0%, 14.3%/26.7%, 14.1%/44.0%, respectively), displaying no apparent effect toward cell cycle progression or p21 and p27 levels in non-cancer human fibroblast IMR90. SMIP004 antiproliferative activity against LNCaP, PC3, DU145 soft agar colony formation is mainly cytostatic in nature and SMIP004 cytotoxic effect is observed only in LNCaP cultures at high concentrations (IC₅₀ = 40 and 2.4 µM, respectively, with 72 h or 96 h treatment), but not PC3 or DU145 even at concentrations as high as 80 µM and for up to 96 h.

Biochem/physiol Actions

Cell permeable: yes

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Rico-Bautista, E., and Wolf, D.A. 2012. Chem. Biol.19, 1497.
Rico-Bautista, E., et al. 2010. BMC Biol.8, 153.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 2