188011-69-0

Basic information

• Product Name: Bikinin
• Synonyms: Butanoic acid, 4-[(5-bromo-2-pyridinyl)amino]-4-oxo-;Bikinin;4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid;4-[(5-Bromo-2-pyridinyl)amino]-4-oxo-butanoic acid;Abrasin;Bikinin(Abrasin)
• CAS NO: 188011-69-0
• Molecular Formula: C9H9BrN2O3
• Molecular Weight: 273
• Product Categories: Inhibitors
• Mol File: 188011-69-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 144°C(lit.)
• Appearance: white to tan/
• Density: 1.711
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥5mg/mL
• CAS DataBase Reference: Bikinin(CAS DataBase Reference)
• NIST Chemistry Reference: Bikinin(188011-69-0)
• EPA Substance Registry System: Bikinin(188011-69-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 188011-69-0(Hazardous Substances Data)

Usage

Uses

Bikinin has been used: as a glycogen synthase kinase-3 (GSK3) inhibitor in Arabidopsis Col-0 seedlings to test its effect on gene expressionas a component of induction medium and as a GSK3 inhibitor to test its effect on mesophyll cells in Arabidopsis leaf discs or cotyledonsas a brassinosteroid agonist to test its effect on the leaf index of R. trichophyllus terrestrial leaves

Biochem/physiol Actions

Bikinin is a strong activator of brassinosteroid (BR) signaling. It is an Arabidopsis GSK-3 Inhibitor, an Arabidopsis SHAGGY-related Kinase Inhibitor, and a GSK-3-like Kinase BIN2 Inhibitor. Bikinin directly inhibits BIN2 (group II GSK3s) by interfering with ATP binding. Bikinin is specific toward a subset of Arabidopsis GSK3 kinases including BIN2 and ASK α, γ, ε, ι, and θ.

Enzyme inhibitor

This ATP-competitive Arabidopsis GSK-3 inhibitor, (FW = 273.08 g/mol; CAS 188011-69-0), also named 4-(5-bromopyridin-2-ylamino)-4- oxobutanoic acid, is a strong activator of brassinosteroid (BR) signaling. Bikinin directly binds the GSK3 BIN2 and also inhibits the activity of six other Arabidopsis GSK3s. Genome-wide transcript analyses demonstrate that simultaneous inhibition of seven GSK3s is sufficient to activate BR responses. inhibited the SnRK2.3 kinase activity and its T180 phosphorylation in vivo by blocking BIN2 phosphorylation of SnRK2.3 on Thr-180.

Upstream product

• 108-30-5 succinic acid anhydride 
• 1072-97-5 5-bromo-2-pyridylamine 

Downstream Products

• 1443415-55-1 4,4,4-trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate 

Relevant articles and documents

Inhibitors for brassinosteroid signalling

The invention describes a compound having the formula (I): wherein X is F, Cl, Br, or I; R1 is CH3, C2H5, C2H4R3, C2H3R3R4, C3H7, C3H6R3 or C3H5R3R4; R2 is H, CH3, C2H5, C2H4R3, C2H3R3R4; and R3 and R4 are, independently, X, OH or NH2. Compounds are used for increasing plant growth.