5.00519

SKP2 E3 Ligase Inhibitor I, C1

• Synonym(e): 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
• Empirische Formel (Hill-System): C₁₈H₁₃BrN₂O₄S₂
• CAS-Nummer: 432001-69-9
• Molekulargewicht: 465.34
• MDL-Nummer: MFCD03705291
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Assay: ≥99% (HPLC)
• Qualitätsniveau: 100
• Form: powder
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; protect from light
• Farbe: orange-brown
• Löslichkeit: DMSO: 10 mg/mL
• Lagertemp.: 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-
• InChIKey: IYCJJVVXEHZJHE-CHHVJCJISA-N

Beschreibung

Allgemeine Beschreibung

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. Wirkung

Cell permeable: yes

Primary Target
disrupts p27-Skp2 interaction

Reversible: yes

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Standard Handling (A)

Rekonstituierung

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.

Sonstige Hinweise

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

Rechtliche Hinweise

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

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 2
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable