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5.06305

SKP2 E3 Ligase Inhibitor III

Synonym(s):

SKP2 E3 Ligase Inhibitor III, 3-(1,3-Benzothiazol-2-yl)-6-ethyl-7-hydroxy-8-(1-piperidinylmethyl)-4H-chromen-4-one, 3-(Benzo[d]thiazol-2-yl)-6-ethyl-7-hydroxy-8-(piperidin-1-ylmethyl)-4H-chromen-4-one, 3-Benzothiazol-2-yl-6-ethyl-7-hydroxy-8-(piperidylmethyl)chromen-4-one, p21/Cip1/CKI/Waf1 Activator III, CRL1SKP2 Inhibitor III, p27/Kip1 Activator III, S-phase Kinase-associated Protein 2 Inhibitor III, SCFSKP2 Inhibitor III, SZL-P1-41, p21/Cip1/CKI/Waf1 Activator III, CRL1SKP2 Inhibitor III, p27/Kip1 Activator III, S-phase Kinase-associated Protein 2 Inhibitor III, SCFSKP2 Inhibitor III, SZL-P1-41, 3-(1,3-Benzothiazol-2-yl)-6-ethyl-7-hydroxy-8-(1-piperidinylmethyl)

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About This Item

Empirical Formula (Hill Notation):
C24H24N2O3S
Molecular Weight:
420.52
NACRES:
NA.77
UNSPSC Code:
12352202
Assay:
≥98% (HPLC)
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assay

≥98% (HPLC)

Quality Segment

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

beige

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

General description

A cell-permeable benzothiazolylchromenone compound that disrupts Skp2-Skp1 interaction via direct Skp2 affinity binding and selectively prevents Skp2-, but not Fbw7- or β-TrCP-, Skp1-Cullin-1-F-box (SFC) complex-mediated substrates ubiquitination both in cell-free systems and in cultures, effectively preventing ubiquitination-dependent activation (Akt) and degradation (p21 & p27) of Skp2 substrates with concomitant down-regulation of cellular Skp2 protein level (10 to 20 µM in HEK293T & PC3 cultures). Exhibits antiproliferation activity toward a panel of 8 cancer (IC50 from 1.22 to 10.5 µM), but not normal PNT1A epithelial or IMR90 fibroblast, lines and effectively reduces ALDH+ cancer stem cell (CSC; Cancer Initiating Cell) population in prostate cancer PC3 cultures (10 to 20 µM) by promoting p53-independent senescence and blocking Akt-dependent aerobic glycolysis. Exhibits good pharmacokinetic property (tmax = 1 h; t1/2 >6 h; Cmax >1 µM/plasma and >4 µM/tumor in 200 mm3 PC3 tumor-bearing mice; 80 mg/kg i.p.) and is efficacious in suppressing A549 and PC3 tumor growth in mice (40 to 80 mg/kg/d i.p.) in vivo.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Skp2
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Use only fresh DMSO for reconstitution.

Other Notes

Chan, C.H., et al. 2013 Cell154, 556.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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