200980-M

Bikinin

A cell-permeable nonsteroidal pyridinylamido compound that acts as an ATP-competitive inhibitor.

• Synonym(s): Bikinin, Arabidopsis GSK-3 Inhibitor, Arabidopsis SHAGGY-related Kinase Inhibitor, GSK-3-like Kinase BIN2 Inhibitor, 4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid
• Empirical Formula (Hill Notation): C₉H₉BrN₂O₃
• CAS Number: 188011-69-0
• Molecular Weight: 273.08
• MDL number: MFCD00116442
• UNSPSC Code: 12352200

Properties

• Assay: ≥90% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: Brc1cnc(cc1)NC(=O)CCC(=O)O
• InChI: 1S/C9H9BrN2O3/c10-6-1-2-7(11-5-6)12-8(13)3-4-9(14)15/h1-2,5H,3-4H2,(H,14,15)(H,11,12,13)
• InChI key: XFYYQDHEDOXWGA-UHFFFAOYSA-N

Description

General description

A cell-permeable nonsteroidal pyridinylamido compound that acts as an ATP-competitive inhibitor against 7 of the 10 Arabidopsis thaliana GSK3′s, BIN2 & ASKα/ γ/ε/ζ/ι/θ, but not ASKβ/δ or three other Arabidopsis Ser/Thr kinases, AtMPK4, AtMPK6, and AtAURORA1. The inhibitory activity is plant species-selective, as Bikinin exhibits much reduced activity against human Gsk-3β, Aurora B, Aurora C (45.6%, 69.4%, and 42.8% inhibition, respectively, with 10 µM Bikinin), and little or no activity against 74 other human kinases, nor does it affect GSK-3β-mediated dorsoventral axis formation during Xenopus embryo development. Bikinin at 30 µM is shown to bypass brassinolide (BL) and BRI1 and effectively activate brassinosteroid (BR) signaling responses in Arabidopsis thaliana seedings, including decreased BES1 phosphorylation, increased hypocotyl length, long and bending petioles, blade-shaped, pale-green leaves, as well as reduced lateral root density.

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

Rybel, B.D., et al. 2009. Chem. Biol.16, 594.

Legal Information

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3