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E8405

EB-47

Name: EB-47
Brand: SIGMA

≥98% (HPLC), solid

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About This Item

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

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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
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
to study chromosomal aberrations in response to ionizing radiation (IR) and PARPi in BRCA1-deficient cells that overcome growth arrest (BOGA) cells

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. 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.

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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