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E8405

Sigma-Aldrich

EB-47

≥98% (HPLC), solid

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About This Item

Formule empirique (notation de Hill):
C24H29N9O6Cl2
Numéro CAS:
366454-36-6
Poids moléculaire :
610.45
Numéro MDL:
MFCD06411565
Code UNSPSC :
12352200
ID de substance PubChem :
329799078
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Solubilité

H2O: soluble 10 mg/mL

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

DDFLFKTXUWPNMV-UAKAABGRSA-N

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

Actions biochimiques/physiologiques

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Wei Qiu et al.
Acta crystallographica. Section D, Biological crystallography, 70(Pt 10), 2740-2753 (2014-10-08)
The poly(ADP-ribose) polymerase (PARP) family represents a new class of therapeutic targets with diverse potential disease indications. PARP1 and PARP2 inhibitors have been developed for breast and ovarian tumors manifesting double-stranded DNA-repair defects, whereas tankyrase 1 and 2 (TNKS1 and
Teemu Haikarainen et al.
ACS medicinal chemistry letters, 5(1), 18-22 (2014-06-06)
Tankyrases, an enzyme subfamily of human poly(ADP-ribosyl)polymerases, are potential drug targets especially against cancer. We have evaluated inhibition of tankyrases by known PARP inhibitors and report five cocrystal structures of the most potent compounds in complex with human tankyrase 2.
Anubha Joshi et al.
Reproduction (Cambridge, England), 147(6), 765-780 (2014-02-12)
Pregnancy requires successful implantation of an embryo, which occurs during a restricted period defined as 'receptivity of the endometrium' and is influenced by the ovarian steroids progesterone and oestradiol. The role of poly(ADP-ribose)polymerase-1 (PARP1) in apoptosis is well established. However

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