About A public-private partnership that supports the discovery of new medicines through open access research. About SGC Partners Research Laboratories SGC-Toronto SGC-UNC SGC-Frankfurt SGC-Karolinska SGC-Neuro Governance Collaborators Open Science Equity, Diversity and Inclusion Impact Science and Resources Proteins Structure Gallery Expression Vectors Plasmids Constructs Production Protocols ChromoHub Phylogenetic Trees UbiHub Phylogenetic Trees ChemBioPort Chemical Probes Program CHEMICAL PROBES Donated chemical probes Chemical Handles Human Kinase Chemical Probe Program ANTIBODIES TARGET ENABLING PACKAGES (TEPs) TISSUE PLATFORM Open Lab Notebooks Open Chemistry Network PUBLICATIONS People Global Aled Edwards, CEO Susan McCormick, CFO Max Morgan, General Counsel and Public Policy Director SGC Toronto Cheryl Arrowsmith Dalia Barsyte-Lovejoy Takis Prinos Matthieu Schapira Levon Halabelian Rachel Harding SGC UNC Tim Willson Alison Axtman David Drewry Peter J. Brown Rafael M. Couñago SGC UCL Mat Todd SGC Karolinska Michael Sundström Opher Gileadi SGC Frankfurt Stefan Knapp Susanne Müller-Knapp Thomas Hanke Vladimir Rogov Krishnal Saxena Andreas Joerger Václav Němec Andreas Krämer Sandra Röhm SGC Neuro Edward Fon Thomas Durcan Jean-François Trempe Ziv Gan-Or Peter McPherson Carl Laflamme Roxanne Lariviere News & Outreach News & Events News from SGC Press Releases Events Blog Tweets by thesgconline Careers
A public-private partnership that supports the discovery of new medicines through open access research.
BAY-850 A chemical probe for ATAD2AThis probe is available from Sigma For any inquiries please contact proberequests@thesgc.org.group newOverview BAY-850 BAY-460 (negative control) ATAD2 and ATAD2B are epigenetic regulators known to function as co-factors for oncogenic transcription factors. ATAD2 overexpression correlates with poor outcomes in several cancers. The bromodomain module of ATAD2 has been shown to be essential for its association with acetylated chromatin and presumable function. BAY-850 is a chemical probe for the ATAD2A bromodomain which displaces acetylated H4 peptide from the ATAD2 bromodomain with an IC50 value of 20 nM (HTRF). MST and BROMOscan measurements indicate a Kd of 84.9 nM and 120 nM, respectively. BAY-850 displays exquisite selectivity over all other bromodomains (no hits in BROMOscan at 10 µM) and displaces full-length ATAD2 from chromatin in live cells at a concentration of 1 µM as determined by FRAP. To avoid potential unspecific off-target effects concentrations of ≥ 5 µM are not recommended. BAY-460 is a companion control compound with strongly reduced potency against ATAD2 (HTRF IC50 = 16 µM, no activity in BROMOscan at 10 µM test concentration). Properties ATAD2H4AcK5/8/12/16 IC50 (HTRF) 0.02 μM LLElogD 2.6 ATAD2 TSA ΔT(100μM) 13.9°C BRD4 BD1 IC50 (HRTF) >20 μM BRD4BD2 IC50 (HTRF) >20 μM DiscoverX BromoScan ATAD2A @ 10 μM DiscoverX ATAD2A KD 0.12 μM MST KD 0.08 μM Sw pH 6.5 [mg/L] >500* log D (pH 7.5) 2.9 *HCl salt Properties BAY-850 BAY-460 (negative control) Physical and chemical properties for BAY-850 Molecular weight 653.3 Molecular formula C38H44ClN5O3 IUPAC name 4-(3-(4-amino-cyclohexylamino)-2-((2-chloro-4-methoxy-5-(5-((1-p-tolyl-ethylamino)-methyl)-furan-2-yl)-phenyl)-formylamino)-propyl)-benzonitrile MollogP 6.17 PSA 98.59 No. of chiral centres 2 No. of rotatable bonds 15 No. of hydrogen bond acceptors 8 No. of hydrogen bond donors 5 Physical and chemical properties for BAY-460 (Negative Control) Molecular weight 568.2 Molecular formula C33H33ClN4O3 IUPAC name 4-(2-((2-chloro-5-(5-((1-p-tolyl-ethylamino)-methyl)-furan-2-yl)-phenyl)-formylamino)-4-methylamino-4-oxo-butyl)-benzonitrile MollogP 5.533 PSA 84.53 No. of chiral centres 2 No. of rotatable bonds 14 No. of hydrogen bond acceptors 7 No. of hydrogen bond donors 3 SMILES: BAY-850: Cc1ccc(cc1)[C@@H](C)NCc1ccc(c2cc(C(N[C@H](Cc3ccc(C#N)cc3)CN[C@@H]3CC[C@@H](CC3)N)=O)c(cc2OC)[Cl])o1 BAY-460: Cc1ccc(cc1)[C@@H](C)NCc1ccc(c2ccc(c(c2)C(N[C@H](CC(NC)=O)Cc2ccc(C#N)cc2)=O)[Cl])o1 InChI: BAY-850: InChI=1S/C38H44ClN5O3/c1-24-4-10-28(11-5-24)25(2)42-23-32-16-17-36(47-32)34-19-33(35(39)20-37(34)46-3)38(45)44-31(18-26-6-8-27(21-40)9-7-26)22-43-30-14-12-29(41)13-15-30/h4-11,16-17,19-20,25,29-31,42-43H,12-15,18,22-23,41H2,1-3H3,(H,44,45)/t25-,29-,30+,31-/m1/s1 BAY-460: InChI=1S/C33H33ClN4O3/c1-21-4-10-25(11-5-21)22(2)37-20-28-13-15-31(41-28)26-12-14-30(34)29(17-26)33(40)38-27(18-32(39)36-3)16-23-6-8-24(19-35)9-7-23/h4-15,17,22,27,37H,16,18,20H2,1-3H3,(H,36,39)(H,38,40)/t22-,27+/m1/s1 InChIKey: BAY-850: BSISGUIVBKDTQO-QIKYYPRYSA-N BAY-460: HBEUJCCOUJWRIC-AMGIVPHBSA-N ReferencesFernández-Montalván, A., Berger, M., Kuropka, B., Koo, S., Badock, V., & Weiske, J. et al. (2017). Isoform-Selective ATAD2 Chemical Probe with Novel Chemical Structure and Unusual Mode of Action. ACS Chemical Biology. http://dx.doi.org/10.1021/acschembio.7b00708