5.00503

CDC42 Inhibitor III, ZCL278

• Synonym(s): CDC42 Inhibitor III, ZCL278, CDC42 GTPase Inhibitor III, 4-(3-(2-(4-Bromo-2-chloro-phenoxy)-acetyl)-thioureido)-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide, 2-(4-Bromo-2-chlorophenoxy)-N-((4-((4,6-dimethyl-2-pyrimidinyl)sulfamoyl)phenyl)carbamothioyl)acetamide
• Empirical Formula (Hill Notation): C₂₁H₁₉BrClN₅O₄S₂
• CAS Number: 587841-73-4
• Molecular Weight: 584.89
• MDL number: MFCD03623090
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥94% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• assay: ≥94% (HPLC)
• Quality Segment: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: light beige
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: [S](=O)(=O)(Nc3nc(cc(n3)C)C)c1ccc(cc1)NC(=S)NC(=O)COc2c(cc(cc2)Br)Cl
• InChI: 1S/C21H19BrClN5O4S2/c1-12-9-13(2)25-20(24-12)28-34(30,31)16-6-4-15(5-7-16)26-21(33)27-19(29)11-32-18-8-3-14(22)10-17(18)23/h3-10H,11H2,1-2H3,(H,24,25,28)(H2,26,27,29,33)
• InChI key: XKZDWYDHEBCGCG-UHFFFAOYSA-N

Description

General description

A cell-permeable, non-cytotoxic, aqueous soluble (181 µM in PBS, pH 7.4, containing 0.33% DMSO) pyrimidinylthiourea compound that targets Cdc42 GEF ITSN/intersectin and adjacent GTP/GDP binding site (K_d = 6.4 and 11.4 µM by fluorescence titration and SPR, respectively) and effectively inhibits EGF-stimulated Cdc42 activity (by 100% with 1 h pretreatment of 50 µM ZCL278) and Cdc42-dependent microspike/filopodia formation in serum-starved Swiss 3T3 fibroblast cultures without affecting RhoA-dependent cellular processes or Rac1-dependent lamellipodia formation. Short-term ZCL278 exposure in 5 d-cultured primary neonatal cortical neurons from 1 d postnatal mice is shown to dramatically abolish neurite branching (Ave branches per neurite = 21, 7.8, and 6.4, respectively, with 0, 5, and 10 min exposure to 50 µM ZCL278).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
CDC42

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze 9-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Friesland, A., et al. 2013. Proc. Natl. Acad. Sci. USA110, 1261.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable