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About This Item
Empirical Formula (Hill Notation):
C13H19NO
CAS Number:
Molecular Weight:
205.30
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Assay
≥99% (HPLC)
Quality Level
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
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 (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.
Rico-Bautista, E., et al. 2010. BMC Biol.8, 153.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Certificates of Analysis (COA)
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