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MedKoo Cat#: 522391 | Name: Bikinin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bikinin is a GSK-3 inhibitor. Bikinin directly binds the GSK3 BIN2 and acts as an ATP competitor. Bikinin inhibits the activity of six other Arabidopsis GSK3s. Glycogen synthase kinase 3 (GSK3) is a key regulator in signaling pathways in both animals and plants. 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.

Chemical Structure

Bikinin
Bikinin
CAS#188011-69-0

Theoretical Analysis

MedKoo Cat#: 522391

Name: Bikinin

CAS#: 188011-69-0

Chemical Formula: C9H9BrN2O3

Exact Mass: 271.9797

Molecular Weight: 273.09

Elemental Analysis: C, 39.58; H, 3.32; Br, 29.26; N, 10.26; O, 17.58

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
200mg USD 700.00 2 Weeks
500mg USD 1,050.00 2 Weeks
1g USD 1,650.00 2 Weeks
2g USD 2,450.00 2 Weeks
5g USD 4,050.00 2 Weeks
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Related CAS #
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Synonym
Bikinin; Abrasin
IUPAC/Chemical Name
4-((5-bromopyridin-2-yl)amino)-4-oxobutanoic acid
InChi Key
XFYYQDHEDOXWGA-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
BrC1=CN=C(NC(CCC(O)=O)=O)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 273.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rozhon W, Wang W, Berthiller F, Mayerhofer J, Chen T, Petutschnig E, Sieberer T, Poppenberger B, Jonak C. 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. doi: 10.1186/1471-2229-14-172. PMID: 24947596; PMCID: PMC4078015. 2: Groszyk J, Przyborowski M. Inhibition of the Glycogen Synthase Kinase 3 Family by the Bikinin Alleviates the Long-Term Effects of Salinity in Barley. Int J Mol Sci. 2022 Oct 1;23(19):11644. doi: 10.3390/ijms231911644. PMID: 36232941; PMCID: PMC9569769. 3: Lu Q, Houbaert A, Ma Q, Huang J, Sterck L, Zhang C, Benjamins R, Coppens F, Van Breusegem F, Russinova E. Adenosine monophosphate deaminase modulates BIN2 activity through hydrogen peroxide-induced oligomerization. Plant Cell. 2022 Sep 27;34(10):3844-3859. doi: 10.1093/plcell/koac203. PMID: 35876813; PMCID: PMC9520590. 4: Rozhon W, Akter S, Fernandez A, Poppenberger B. Inhibitors of Brassinosteroid Biosynthesis and Signal Transduction. Molecules. 2019 Nov 29;24(23):4372. doi: 10.3390/molecules24234372. PMID: 31795392; PMCID: PMC6930552. 5: De Rybel B, Audenaert D, Vert G, Rozhon W, Mayerhofer J, Peelman F, Coutuer S, Denayer T, Jansen L, Nguyen L, Vanhoutte I, Beemster GT, Vleminckx K, Jonak C, Chory J, Inzé D, Russinova E, Beeckman T. Chemical inhibition of a subset of Arabidopsis thaliana GSK3-like kinases activates brassinosteroid signaling. Chem Biol. 2009 Jun 26;16(6):594-604. doi: 10.1016/j.chembiol.2009.04.008. PMID: 19549598; PMCID: PMC4854203. 6: Yamazaki K, Kondo Y, Kojima M, Takebayashi Y, Sakakibara H, Fukuda H. Suppression of DELLA signaling induces procambial cell formation in culture. Plant J. 2018 Apr;94(1):48-59. doi: 10.1111/tpj.13840. Epub 2018 Mar 9. PMID: 29383774. 7: Min HJ, Cui LH, Oh TR, Kim JH, Kim TW, Kim WT. OsBZR1 turnover mediated by OsSK22-regulated U-box E3 ligase OsPUB24 in rice BR response. Plant J. 2019 Aug;99(3):426-438. doi: 10.1111/tpj.14332. Epub 2019 May 7. PMID: 30920691. 8: Bittner T, Nadler S, Schulze E, Fischer-Iglesias C. Two homolog wheat Glycogen Synthase Kinase 3/SHAGGY--like kinases are involved in brassinosteroid signaling. BMC Plant Biol. 2015 Oct 13;15:247. doi: 10.1186/s12870-015-0617-z. PMID: 26458871; PMCID: PMC4604091. 9: Lu Q, Zhang Y, Hellner J, Giannini C, Xu X, Pauwels J, Ma Q, Dejonghe W, Han H, Van de Cotte B, Impens F, Gevaert K, De Smet I, Friml J, Molina DM, Russinova E. Proteome-wide cellular thermal shift assay reveals unexpected cross-talk between brassinosteroid and auxin signaling. Proc Natl Acad Sci U S A. 2022 Mar 15;119(11):e2118220119. doi: 10.1073/pnas.2118220119. Epub 2022 Mar 7. PMID: 35254915; PMCID: PMC8931322. 10: Sasaki T, Oda Y. Imaging of Developing Metaxylem Vessel Elements in Cultured Hypocotyls. Methods Mol Biol. 2019;1992:351-358. doi: 10.1007/978-1-4939-9469-4_23. PMID: 31148050. 11: Xiao Y, Zhang G, Liu D, Niu M, Tong H, Chu C. GSK2 stabilizes OFP3 to suppress brassinosteroid responses in rice. Plant J. 2020 Jun;102(6):1187-1201. doi: 10.1111/tpj.14692. Epub 2020 Feb 13. PMID: 31950543. 12: Deng XG, Zhu T, Peng XJ, Xi DH, Guo H, Yin Y, Zhang DW, Lin HH. Role of brassinosteroid signaling in modulating Tobacco mosaic virus resistance in Nicotiana benthamiana. Sci Rep. 2016 Feb 3;6:20579. doi: 10.1038/srep20579. PMID: 26838475; PMCID: PMC4738339. 13: Kondo Y, Fujita T, Sugiyama M, Fukuda H. A novel system for xylem cell differentiation in Arabidopsis thaliana. Mol Plant. 2014 Oct 25:ssu122. doi: 10.1093/mp/ssu122. Epub ahead of print. PMID: 25344955. 14: Furuya T, Nishihama R, Ishizaki K, Kohchi T, Fukuda H, Kondo Y. A glycogen synthase kinase 3-like kinase MpGSK regulates cell differentiation in Marchantia polymorpha. Plant Biotechnol (Tokyo). 2022 Mar 25;39(1):65-72. doi: 10.5511/plantbiotechnology.21.1219a. PMID: 35800965; PMCID: PMC9200085. 15: Kim YW, Youn JH, Roh J, Kim JM, Kim SK, Kim TW. Brassinosteroids enhance salicylic acid-mediated immune responses by inhibiting BIN2 phosphorylation of clade I TGA transcription factors in Arabidopsis. Mol Plant. 2022 Jun 6;15(6):991-1007. doi: 10.1016/j.molp.2022.05.002. Epub 2022 May 6. PMID: 35524409. 16: Kondo Y, Fujita T, Sugiyama M, Fukuda H. A novel system for xylem cell differentiation in Arabidopsis thaliana. Mol Plant. 2015 Apr;8(4):612-21. doi: 10.1016/j.molp.2014.10.008. Epub 2014 Dec 13. PMID: 25624147. 17: Groszyk J, Szechyńska-Hebda M. Brassinazole Resistant 1 Activity Is Organ- Specific and Genotype-Dependent in Barley Seedlings. Int J Mol Sci. 2021 Dec 17;22(24):13572. doi: 10.3390/ijms222413572. PMID: 34948366; PMCID: PMC8706524. 18: Minami A, Takahashi K, Inoue SI, Tada Y, Kinoshita T. Brassinosteroid Induces Phosphorylation of the Plasma Membrane H+-ATPase during Hypocotyl Elongation in Arabidopsis thaliana. Plant Cell Physiol. 2019 May 1;60(5):935-944. doi: 10.1093/pcp/pcz005. PMID: 30649552. 19: Bjornson M, Dandekar AM, Chory J, Dehesh K. Brassinosteroid's multi-modular interaction with the general stress network customizes stimulus-specific responses in Arabidopsis. Plant Sci. 2016 Sep;250:165-177. doi: 10.1016/j.plantsci.2016.06.007. Epub 2016 Jun 16. PMID: 27457993. 20: Yang C, Shen W, He Y, Tian Z, Li J. OVATE Family Protein 8 Positively Mediates Brassinosteroid Signaling through Interacting with the GSK3-like Kinase in Rice. PLoS Genet. 2016 Jun 22;12(6):e1006118. doi: 10.1371/journal.pgen.1006118. Erratum in: PLoS Genet. 2017 Aug 22;13(8):e1006970. PMID: 27332964; PMCID: PMC4917237.