Bikinin

• CAT Number: I002424
• CAS Number: 188011-69-0
• Molecular Formula: C₉H₉BrN₂O₃
• Molecular Weight: 273.08
• Purity: ≥95%
• Synonyms: 4-((5-bromopyridin-2-yl)amino)-4-oxobutanoic acid
• Target: GSK-3
• Solubility: DMSO: ≥ 42 mg/mL
• Storage: Store at -20°C
• InChI: 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)
• InChIKey: XFYYQDHEDOXWGA-UHFFFAOYSA-N
• SMILES: C1=CC(=NC=C1Br)NC(=O)CCC(=O)O

Bikinin(Abrasin) is a potent inhibitor of plant GSK-3/Shaggy-like kinase; activates BR signaling downstream of the BR receptor.IC50 value:Target: GSK-3/Shaggy-like kinase inhibitorin vitro: Bikinin is a potent inhibitor of group I and group II ASKs. ASKθ, a group III ASK is moderately inhibited. The second kinase of this class, ASKβ, and the group IV kinase ASKδ are not inhibited. plants treated with the ASK inhibitor bikinin show the typical signs of constitutive BR response including elongated hypocotyls and light-green leaves indicating that most or all ASKs crucial for BR signalling are inhibited [1]. Bikinin directly binds the GSK3 BIN2 and acts as an ATP competitor. Furthermore, bikinin inhibits the activity of six other Arabidopsis GSK3s [3].in vivo: Bikinin, a GSK3 kinase inhibitor, inhibited the SnRK2.3 kinase activity and its T180 phosphorylation in vivo [2].

Reference

1:BMC Plant Biol. 2014 Jun 19;14:172. doi: 10.1186/1471-2229-14-172. Bikinin-like inhibitors targeting GSK3/Shaggy-like kinases: characterisation of novel compounds and elucidation of their catabolism in planta.Rozhon W,Wang W,Berthiller F,Mayerhofer J,Chen T,Petutschnig E,Sieberer T,Poppenberger B,Jonak C, PMID: 24947596 PMCID: PMC4078015 DOI: 10.1186/1471-2229-14-172 Abstract: BACKGROUND: Plant GSK-3/Shaggy-like kinases are key players in brassinosteroid (BR) signalling which impact on plant development and participate in response to wounding, pathogens and salt stress. Bikinin was previously identified in a chemical genetics screen as an inhibitor targeting these kinases. To dissect the structural elements crucial for inhibition of GSK-3/Shaggy-like kinases by bikinin and to isolate more potent compounds we synthesised a number of related substances and tested their inhibitory activity in vitro and in vivo using Arabidopsis thaliana.RESULTS: A pyridine ring with an amido succinic acid residue in position 2 and a halogen in position 5 were crucial for inhibitory activity. The compound with an iodine substituent in position 5, denoted iodobikinin, was most active in inhibiting BIN2 activity in vitro and efficiently induced brassinosteroid-like responses in vivo. Its methyl ester, methyliodobikinin, showed improved cell permeability, making it highly potent in vivo although it had lower activity in vitro. HPLC analysis revealed that the methyl residue was rapidly cleaved off in planta liberating active iodobikinin. In addition, we provide evidence that iodobikinin and bikinin are inactivated in planta by conjugation with glutamic acid or malic acid and that the latter process is catalysed by the malate transferase SNG1.CONCLUSION: Brassinosteroids participate in regulation of many aspects of plant development and in responses to environmental cues. Thus compounds modulating their action are valuable tools to study such processes and may be an interesting opportunity to modify plant growth and performance in horticulture and agronomy. Here we report the development of bikinin derivatives with increased potency that can activate BR signalling and mimic BR action. Methyliodobikinin was 3.4 times more active in vivo than bikinin. The main reason for the superior activity of methyliodobikinin, the most potent compound, is its enhanced plant tissue permeability. Inactivation of bikinin and its derivatives in planta involves SNG1, which constitutes a novel pathway for modification of xenobiotic compounds.