Bikinin

Names

[ Name ]:
Bikinin

[Synonym ]:
4-[(5-bromopyridin-2-yl)amino]-4-oxobutanoic acid
4-[(5-bromo-2-pyridyl)amino]-4-oxobutanoic acid
4-[(5-Bromo-2-pyridinyl)amino]-4-oxobutanoic acid
Butanoic acid, 4-[(5-bromo-2-pyridinyl)amino]-4-oxo-
Butanoic acid,4-[(5-bromo-2-pyridinyl)amino]-4-oxo-
Bikinin

Biological Activity

[Description]:

Bikinin is a non-steroidal, ATP-competitive inhibitor of plant GSK-3/Shaggy-like kinases and activates BR (brassinosteroids) signaling.

[Related Catalog]:

Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3

Signaling Pathways >> Stem Cell/Wnt >> GSK-3

Research Areas >> Others

[Target]

GSK-3

[In Vitro]

Bikinin reduces transcript levels of NbRBOHB and BR-induced NbRBOHB expression in TRV:00, TRV:NbDWARF, TRV:NbBRI1, TRV:NbBSK1, TRV:NbBAK1, TRV:NbBIK1 and TRV:NbBSU1 plants. Bikinin largely inhibits BR-increased ROS accumulation. Moreover, Bikinin decreases the transcripts of these six genes in all plants, but fails to down-regulate transcripts of these genes in NbBES1/BZR1-silenced plants. Bikinin also inhabits BR-induced up-regulation of the six genes, and the inhibition effects are compromised in NbBES1/BZR1-silenced plants[1]. Bikinin is a potent inhibitor of group I and group II ASKs[2]. Bikinin directly binds the GSK3 BIN2 and acts as an ATP competitor. Furthermore, bikinin inhibits the activity of six other Arabidopsis GSK3s[3].

[Kinase Assay]

ASKs are expressed as GST-fusion proteins in Escherichia coli BL21. In vitro kinase assays are performed by incubating 50 ng GST-fusion protein, 10 μg myelin basic protein (MBP) as a substrate and 0.15 MBq γ-[32P]-ATP as co-substrate at 25°C for 30 min. The reaction buffer consists of 20 mM HEPES/KOH pH 7.4, 15 mM MgCl2, 5 mM EGTA, 1 mM dithiothreitol and 1 μM cold ATP. The reaction products are separated by SDS-PAGE and the amount of radioactivity incorporated into MBP quantified using an Amersham storage phosphor imager screen and a Biorad Molecular Imager FX[2].

[References]

[1]. Deng XG, et al. Role of brassinosteroid signaling in modulating Tobacco mosaic virus resistance in Nicotiana benthamiana. Sci Rep. 2016 Feb 3;6:20579.

[2]. Rozhon W, et al. Bikinin-like inhibitors targeting GSK3/Shaggy-like kinases: characterisation of novel compounds and elucidation of their catabolism in planta. BMC Plant Biol. 2014 Jun 19;14:172.

[3]. De Rybel B, et al. Chemical inhibition of a subset of Arabidopsis thaliana GSK3-like kinases activates brassinosteroid signaling. Chem Biol. 2009 Jun 26;16(6):594-604.

[Related Small Molecules]

CHIR-99021 (CT99021) | SB216763 | TWS119 | LY2090314 | Tideglusib | BIO | Kenpaullone | AR-A014418 | AZD1080 | CHIR-98014 | AZD2858 | Indirubin-3'-monoxime | SB 415286 | RGB-286638 | TDZD-8

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
521.6±45.0 °C at 760 mmHg

[ Melting Point ]:
144°C(lit.)

[ Molecular Formula ]:
C₉H₉BrN₂O₃

[ Molecular Weight ]:
273.083

[ Flash Point ]:
269.2±28.7 °C

[ Exact Mass ]:
271.979645

[ PSA ]:
79.29000

[ LogP ]:
1.73

[ Appearance of Characters ]:
white to tan

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.635

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: ≥5mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933399090

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

BR-dependent phosphorylation modulates PIF4 transcriptional activity and shapes diurnal hypocotyl growth.

Genes Dev. 28(15) , 1681-94, (2014)

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 tempera...

Chemical inhibition of a subset of Arabidopsis thaliana GSK3-like kinases activates brassinosteroid signaling.

Chem. Biol. 16 , 594-604, (2009)

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 ...