WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H407403
CAS#: 1906920-28-2 (BAY598 R-isomer)
Description: BAY-598 R-isomer is the R-isomer of BAY589. BAY-598 R-isomer may be used as a reference compound. BAY-598 is a potent, peptide-competitive chemical probe for SMYD2. BAY-598 has a unique chemotype relative to the current SMYD2 chemical probe LLY-507. BAY-598 inhibits in vitro methylation of p53K370 with IC50 = 27 nM and has more than 100-fold selectivity over other histone methyltransferases and other non-epigenetic targets. BAY-598 inhibits the methylation of p53K370 in cells with IC50 < 1 µM. (Further to this, BAY-598 has properties that are compatible with in vivo experiments.) A control compound, BAY-369, has also been developed. BAY-369 inhibits the in vitro methylation of p53K370 with IC50 > 70 micromolar.
Hodoodo Cat#: H407403
Name: BAY-598 R-isomer
CAS#: 1906920-28-2 (BAY598 R-isomer)
Chemical Formula: C22H20Cl2F2N6O3
Exact Mass: 524.09
Molecular Weight: 525.338
Elemental Analysis: C, 50.30; H, 3.84; Cl, 13.50; F, 7.23; N, 16.00; O, 9.14
Related CAS #: 1906920-28-2 (BAY598 R-isomer) 1906919-67-2 (BAY598) 1906920-07-7 (BAY598 recamic mixture)
Synonym: BAY-598 R-isomer; BAY 598 R-isomer; BAY598 R-isomer
IUPAC/Chemical Name: (R,E)-N-(1-(N'-cyano-N-(3-(difluoromethoxy)phenyl)carbamimidoyl)-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl)-N-ethyl-2-hydroxyacetamide
InChi Key: OTTJIRVZJJGFTK-GOSISDBHSA-N
InChi Code: InChI=1S/C22H20Cl2F2N6O3/c1-2-31(19(34)11-33)18-10-32(30-20(18)13-6-7-16(23)17(24)8-13)22(28-12-27)29-14-4-3-5-15(9-14)35-21(25)26/h3-9,18,21,33H,2,10-11H2,1H3,(H,28,29)/t18-/m1/s1
SMILES Code: CCN([C@@H]1CN(N=C1C2=CC(Cl)=C(C=C2)Cl)/C(NC3=CC=CC(OC(F)F)=C3)=N/C#N)C(CO)=O
Appearance: Beige 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
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 525.34 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.
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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Eggert E, Hillig RC, Koehr S, Stöckigt D, Weiske J, Barak N, Mowat J, Brumby T, Christ CD, Ter Laak A, Lang T, Fernandez-Montalvan AE, Badock V, Weinmann H, Hartung IV, Barsyte-Lovejoy D, Szewczyk M, Kennedy S, Li F, Vedadi M, Brown PJ, Santhakumar V, Arrowsmith CH, Stellfeld T, Stresemann C. Discovery and Characterization of a Highly Potent and Selective Aminopyrazoline-Based in Vivo Probe (BAY-598) for the Protein Lysine Methyltransferase SMYD2. J Med Chem. 2016 May 26;59(10):4578-600. doi: 10.1021/acs.jmedchem.5b01890. PubMed PMID: 27075367; PubMed Central PMCID: PMC4917279.
2: Ahmed H, Duan S, Arrowsmith CH, Barsyte-Lovejoy D, Schapira M. An Integrative Proteomic Approach Identifies Novel Cellular SMYD2 Substrates. J Proteome Res. 2016 Jun 3;15(6):2052-9. doi: 10.1021/acs.jproteome.6b00220. PubMed PMID: 27163177.