E8405

EB-47

≥98% (HPLC), solid

• Empirical Formula (Hill Notation): C₂₄H₂₉N₉O₆Cl₂
• CAS Number: 366454-36-6
• Molecular Weight: 610.45
• NACRES: NA.77
• PubChem Substance ID: 329799078
• UNSPSC Code: 12352200
• MDL number: MFCD06411565
• Assay: ≥98% (HPLC)
• Form: solid

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: solid
• solubility: H₂O: soluble 10 mg/mL
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)C(=O)N4CCN(CC4)CC(=O)Nc5cccc6C(=O)NCc56
• InChI: 1S/C24H27N9O6/c25-20-16-21(28-10-27-20)33(11-29-16)24-18(36)17(35)19(39-24)23(38)32-6-4-31(5-7-32)9-15(34)30-14-3-1-2-12-13(14)8-26-22(12)37/h1-3,10-11,17-19,24,35-36H,4-9H2,(H,26,37)(H,30,34)(H2,25,27,28)/t17-,18+,19-,24+/m0/s1
• InChI key: DDFLFKTXUWPNMV-UAKAABGRSA-N

Description

Application

EB-47 has been used as a poly [ADP-ribose] polymerase 1 (PARP/PARP1/PARPi) inhibitor:

• to investigate its effect on the activity of matrix metalloproteinase-2 (MMP-2) and compare its inhibitory potencies with the MMP inhibitors[1]
• in treating human acute monocytic leukemia cells to confirm if PARP1 is responsible for the decrease in high mobility group box protein 1 (HMGB1) supernatant levels[1]
• to study chromosomal aberrations in response to ionizing radiation (IR) and PARPi in BRCA1-deficient cells that overcome growth arrest (BOGA) cells[2]

Biochem/physiol Actions

1-piperazineacetamide-4-[1-(6-amino-9H-purin-9-yl)-1-deoxy-d-ribofuranuron]-N-(2,3-dihydro-1H-isoindol-4-yl)-1-one (EB-47) can mimic the substrate NAD⁺ binding.[3][4] This inhibitor targets the nicotinamide (NI) and adenosine (AD)-subsite within the tankyrase 2 (TNKS2) catalytic domain. EB-47 is one of the most effective TNKS2 inhibitors, with an IC50 of 32 nM, in the presence of piperazine and succinyl linkers that connect the adenosine and isoindolinone cores.[5]

Potent inhibitor of poly (ADP-ribose) polymerase (PARP).

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)