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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Moritz Graeff et al.
Current biology : CB, 30(9), 1626-1638 (2020-03-30)
The plant vasculature is an essential adaptation to terrestrial growth. Its phloem component permits efficient transfer of photosynthates between source and sink organs but also transports signals that systemically coordinate physiology and development. Here, we provide evidence that developing phloem
Stella Bernardo-García et al.
Genes & development, 28(15), 1681-1694 (2014-08-03)
Signaling by the hormones brassinosteroid (BR) and gibberellin (GA) is critical to normal plant growth and development and is required for hypocotyl elongation in response to dark and elevated temperatures. Active BR signaling is essential for GA promotion of hypocotyl

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