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5mg |
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25mg |
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Purity: ≥98%
BAY-598 (BAY598 S-isomer) is novel, potent, selective and peptide-competitive small molecule inhibitor of lysine methyltransferase SMYD2 with potential antitumor activity. SMYD2 is overexpressed in various cancers. BAY-598 is a chemical probe that 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.
ln Vitro |
Treatment with BAY-598 prevents SMYD2 from methylating MAPKAPK3 in vitro, but it has no effect on the KMT SMYD2-associated SMYD2. After nine days in culture, BAY-598 administration inhibited the growth of Kras;p53 mutant PDAC cells, but had no effect on the growth of Kras;p53;Smyd2 mutant cells [1].
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References |
[1]. Reynoird N, et al. Coordination of stress signals by the lysine methyltransferase SMYD2 promotes pancreaticcancer. Genes Dev. 2016 Apr 1;30(7):772-85.
[2]. Eggert E, et al. 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 |
Molecular Formula |
C22H20CL2F2N6O3
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Molecular Weight |
525.335409164429
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Exact Mass |
524.09
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Elemental Analysis |
C, 50.30; H, 3.84; Cl, 13.50; F, 7.23; N, 16.00; O, 9.14
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CAS # |
1906919-67-2
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Related CAS # |
1906919-67-2 (S-isomer);1906920-28-2 (BAY598 R-isomer);1906920-07-7 (BAY598 recamic mixture);
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Appearance |
Beige Solid powder
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SMILES |
CCN(C(CO)=O)[C@H]1CN(/C(NC2=CC=CC(OC(F)F)=C2)=N/C#N)N=C1C3=CC(Cl)=C(Cl)C=C3
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InChi Key |
OTTJIRVZJJGFTK-SFHVURJKSA-N
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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-/m0/s1
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Chemical Name |
(S,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
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Synonyms |
BAY598; BAY 598; BAY-598 S-isomer
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO : ~125 mg/mL (~237.94 mM)
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.96 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.96 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 1.9035 mL | 9.5176 mL | 19.0353 mL | |
5 mM | 0.3807 mL | 1.9035 mL | 3.8071 mL | |
10 mM | 0.1904 mL | 0.9518 mL | 1.9035 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
MAPKAPK3 is methylated in PDAC cells and regulates PDAC-associated phenotypes.Genes Dev. 2016 Apr 1;30(7):772-85. td> |
SMYD2 inhibition enhances PDAC chemosensitivity in vitro and in vivo. (A) BAY-598 inhibits SMYD2.Genes Dev. 2016 Apr 1;30(7):772-85. td> |
SMYD2 promotes Ras-driven pancreatic cancer.Genes Dev. 2016 Apr 1;30(7):772-85. td> |