5.00517

SKP2 E3 Ligase Inhibitor II, SMIP004

• Synonyme(s) : 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
• Formule empirique (notation de Hill): C₁₃H₁₉NO
• Numéro CAS: 143360-00-3
• Poids moléculaire : 205.30
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥99% (HPLC)
• Niveau de qualité: 100
• Forme: solid
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: white
• Solubilité: DMSO: 100 mg/mL
• Température de stockage: 2-8°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)
• Clé InChI: ZFVMECVBUGMWIX-UHFFFAOYSA-N

Description

Description générale

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 (40 µM for 24 h) with a concomitant downregulation of the F-box E3 ubiquitin ligase Skp2 and a delayed G1-to-S cell cycle transition, 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 with cytotoxicity observed only in LNCaP cultures at high concentrations (IC₅₀ = 40 µM in 72 h), but not PC3 or DU145 even at concentrations as high as 80 µM and for up to 96 h.

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

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.

Actions biochimiques/physiologiques

Cell permeable: yes

Reversible: yes

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Reconstitution

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

Autres remarques

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

Informations légales

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

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2