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5.00517

Sigma-Aldrich

SKP2 E3 Ligase Inhibitor II, SMIP004

Synonym(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, CRL1SKP2 Inhibitor II, p21/Cip1/CKI/Waf1 Activator II, p27/Kip1 Activator II, S-phase Kinase-associated Protein 2 Inhibitor II, SCFSKP2 Inhibitor II, Small Molecule Inhibitor of p27 Depletion 004, N-(4-Butyl-2-methylphenyl)acetamide

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About This Item

Empirical Formula (Hill Notation):
C13H19NO
CAS Number:
143360-00-3
Molecular Weight:
205.30
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥99% (HPLC)

Quality Level

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

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

General description

A cell-permeable phenylacetamide compound that is shown to upregulate p21Cip1/Waf1 and/or p27Kip1 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 p21Cip1/Waf1 and/or p27Kip1 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

Warning

Toxicity: Standard Handling (A)

Reconstitution

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Elizabeth Rico-Bautista et al.
Chemistry & biology, 19(12), 1497-1498 (2012-12-25)
The cullin-RING ubiquitin ligase, CRL1(SKP2), directing the degradation of the tumor suppressor p27, is a well validated drug target in a wide variety of human cancers. In this issue of Chemistry & Biology, Wu and colleagues describe first-in-class small molecule
Elizabeth Rico-Bautista et al.
BMC biology, 8, 153-153 (2010-12-25)
The cyclin-dependent kinase (CDK) inhibitor p27(Kip)¹ is downregulated in a majority of human cancers due to ectopic proteolysis by the ubiquitin-proteasome pathway. The expression of p27 is subject to multiple mechanisms of control involving several transcription factors, kinase pathways and
Philip E D Chung et al.
Nature communications, 11(1), 1825-1825 (2020-04-15)
Pineoblastoma is a rare pediatric cancer induced by germline mutations in the tumor suppressors RB1 or DICER1. Presence of leptomeningeal metastases is indicative of poor prognosis. Here we report that inactivation of Rb plus p53 via a WAP-Cre transgene, commonly

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