CAS Number188011-69-0
Synonyms4-[(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; Bikinin
Molecular FormulaC9H9BrN2O3
Molecular Weight273.08
Purity≥98 (HPLC)%
Density1.7±0.1 g/cm3
Boiling Point521.6±45.0 °C at 760 mmHg
Melting Point144°C(lit.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 188011-69-0 |
| Catalog No. | 2A-9093274 |
| Chinese Name | 4-[(5-溴吡啶-2-基)氨基]-4-氧代丁酸 |
| Synonyms | 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; Bikinin |
| Molecular Formula | C9H9BrN2O3 |
| Molecular Weight | 273.08 |
| Purity | ≥98 (HPLC) |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 521.6±45.0 °C at 760 mmHg |
| Melting Point | 144°C(lit.) |
| Appearance | powder |
| Water Solubility | DMSO: ≥5mg/mL |
| Storage Condition | 2-8°C |
| Application | Bikinin is a nonsteroidal, plant-based ATP competitive inhibitor of GSK-3/Shaggy-like kinases that activates the BR signaling pathway. |
| HTC | 2933399090 |
| PubChem ID | 329825152 |
| MDL Number | MFCD00116442 |
| SMILES | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/93274_1_188011_69_0.pdf |
| Bioactivity | 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. 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 InChIKey XFYYQDHEDOXWGA-UHFFFAOYSA-N SMILES O=C(O)CCC(=O)Nc1ccc(Br)cn1 Storage condition 2-8°C Water Solubility DMSO: ≥5mg/mL |
| Use of | Properties Name 4-[(5-bromopyridin-2-yl)amino]-4-oxobutanoic acid Synonym More Synonyms Bikinin Biological Activity Related Catalog Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Others 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. [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. Chemical & Physical Properties Molecular Formula C9H9BrN2O3 Exact Mass 271.979645 PSA 79.29000 Appearance of Characters white to tan Index of Refraction 1.635 InChIKey XFYYQDHEDOXWGA-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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