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SML0094

Sigma-Aldrich

Bikinin

≥98% (HPLC)

Synonym(s):

4-((5-Bromo-2-pyridinyl)amino)-4-oxobutanoic acid, 4-[(5-Bromo-2-pyridinyl)amino]-4-oxo-butanoic acid, Abrasin

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About This Item

Empirical Formula (Hill Notation):
C9H9BrN2O3
CAS Number:
188011-69-0
Molecular Weight:
273.08
MDL number:
MFCD00116442
UNSPSC Code:
12352200
PubChem Substance ID:
329825152
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥5 mg/mL

application(s)

agriculture

storage temp.

2-8°C

SMILES string

OC(=O)CCC(=O)Nc1ccc(Br)cn1

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

Application

Bikinin has been used:
  • as a glycogen synthase kinase-3 (GSK3) inhibitor in Arabidopsis Col-0 seedlings to test its effect on gene expression
  • as a component of induction medium and as a GSK3 inhibitor to test its effect on mesophyll cells in Arabidopsis leaf discs or cotyledons
  • as 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.

WGK

WGK 3

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Bert De Rybel et al.
Chemistry & biology, 16(6), 594-604 (2009-06-25)
Glycogen synthase kinase 3 (GSK3) is a key regulator in signaling pathways in both animals and plants. Three Arabidopsis thaliana GSK3s are shown to be related to brassinosteroid (BR) signaling. In a phenotype-based compound screen we identified bikinin, a small
Wei Lin et al.
Science advances, 6(26), eaaz2963-eaaz2963 (2020-07-09)
DNA demethylation is important for the erasure of DNA methylation. The role of DNA demethylation in plant development remains poorly understood. Here, we found extensive DNA demethylation in the CHH context around pericentromeric regions and DNA demethylation in the CG
Ami N Saito et al.
Plant direct, 3(9), e00172-e00172 (2019-09-25)
Casein kinase 1 (CK1) is an evolutionarily conserved protein kinase family among eukaryotes. Studies in non-plants have shown CK1-dependent divergent biological processes, but the collective knowledge regarding the biological roles of plant CK1 lags far behind other members of the
Yunshuai Huang et al.
Journal of integrative plant biology, 64(10), 1883-1900 (2022-07-30)
Grain size is a key agronomic trait that determines the yield in plants. Regulation of grain size by brassinosteroids (BRs) in rice has been widely reported. However, the relationship between the BR signaling pathway and grain size still requires further
Jinyu Luo et al.
Plant communications, 3(6), 100419-100419 (2022-08-06)
High temperature adversely affects plant growth and development. The steroid phytohormones brassinosteroids (BRs) are recognized to play important roles in plant heat stress responses and thermotolerance, but the underlying mechanisms remain obscure. Here, we demonstrate that the glycogen synthase kinase
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