BAY-850

BAY-850 A chemical probe for ATAD2A

This probe is available from Sigma

  • overview
  • properties
  • references
overview
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
LLElogD2.6
ATAD2 TSA ΔT(100μM)13.9°C
BRD4 BD1 IC50 (HRTF)>20 μM
BRD4BD2 IC50 (HTRF)>20 μM
DiscoverX BromoScanATAD2A @ 10 μM
DiscoverX ATAD2A KD0.12 μM
MST KD0.08 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 weight653.3
Molecular formulaC38H44ClN5O3
IUPAC name4-(3-(4-amino-cyclohexylamino)-2-((2-chloro-4-methoxy-5-(5-((1-p-tolyl-ethylamino)-methyl)-furan-2-yl)-phenyl)-formylamino)-propyl)-benzonitrile
MollogP6.17
PSA98.59
No. of chiral centres2
No. of rotatable bonds15
No. of hydrogen bond acceptors8
No. of hydrogen bond donors5



 

Physical and chemical properties for BAY-460 (Negative Control)
Molecular weight

568.2

 

Molecular formulaC33H33ClN4O3
IUPAC name4-(2-((2-chloro-5-(5-((1-p-tolyl-ethylamino)-methyl)-furan-2-yl)-phenyl)-formylamino)-4-methylamino-4-oxo-butyl)-benzonitrile
MollogP5.533
PSA84.53
No. of chiral centres2
No. of rotatable bonds14
No. of hydrogen bond acceptors7
No. of hydrogen bond donors3
  • 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

     

selectivity profile
in vitro potency
cell based assay data
references

Fernández-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

pk properties
co-crystal structures
synthetic schemes
materials and methods
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