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5.00519

SKP2 E3 Ligase Inhibitor I, C1

Name: SKP2 E3 Ligase Inhibitor I, C1
Brand: MM

Synonym(s):

SKP2 E3 Ligase Inhibitor I, C1, p21/Cip1/Waf1 Activator I; p27/Kip1 Activator I, S-phase Kinase-associated Protein 2 Inhibitor I; SCF ^SKP2 Inhibitor I, CRL1 ^SKP2 Inhibitor I, ( Z)-2-(4-Bromo-2-((4-oxo-3-(pyridin-3-ylmethyl)-2-thioxothiazolidin-5-ylidene)met

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₃BrN₂O₄S₂

CAS Number:

432001-69-9

Molecular Weight:

465.34

MDL number:

MFCD03705291

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥99% (HPLC)

Form:

powder

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥99% (HPLC)

Quality Segment

100

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

orange-brown

solubility

DMSO: 10 mg/mL

storage temp.

2-8°C

SMILES string

S1\C(=C/c3c(ccc(c3)Br)OCC(=O)O)\C(=O)N(C1=S)Cc2cnccc2

InChI

1S/C18H13BrN2O4S2/c19-13-3-4-14(25-10-16(22)23)12(6-13)7-15-17(24)21(18(26)27-15)9-11-2-1-5-20-8-11/h1-8H,9-10H2,(H,22,23)/b15-7-

InChI key

IYCJJVVXEHZJHE-CHHVJCJISA-N

Description

General description

A cell-permeable rhodanine compound that upregulates cellular p21^Cip1/Waf1 and p27^Kip1 protein levels (10 µM for 16 h in 501 Mel cultures) by preventing Skp2-Cks1-mediated substrate recruitment without affecting the F-box E3 ubiquitin ligase Skp2 interaction with Cks1 or the SCF (Skp1-cullin1-F-box) complex. Shown to inhibit the proliferation of human breast cancer MCF-7 and melanoma 501 Mel cells (IC₅₀ = 8 and 30 µM, respectively; 16 h incubation). Unlike SMIP004, C1 does not affect cellular Cyclin E/CDK2 kinase activity or Skp2 level.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.

Biochem/physiol Actions

Primary Target
disrupts p27-Skp2 interaction

Reversible: yes

Cell permeable: 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.

Use only fresh DMSO for reconstitution.

Other Notes

Rico-Bautista, E., and Wolf, D.A. 2012. Chem. Biol.19, 1497.
Wu, L., et al. 2012. Chem. Biol.19, 1515.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c