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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

Pricing and availability is not currently available.

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Properties

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).

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This Item	B0936	S4443	P0080
Sigma-Aldrich E8405 EB-47	Sigma-Aldrich B0936 BRL 50481	Sigma-Aldrich S4443 SCH-28080	Sigma-Aldrich P0080 Pranlukast hemihydrate
form solid	form solid	form solid	form solid
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. −20°C
solubility H₂O: soluble 10 mg/mL	solubility DMSO: >10 mg/mL, H₂O: insoluble	solubility DMSO: soluble >10 mg/mL, H₂O: insoluble	solubility DMSO: ≥10 mg/mL, H₂O: insoluble
shipped in dry ice	shipped in -	shipped in -	shipped in -

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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Certificates of Analysis (COA)

Lot/Batch Number

044K4708

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Insights into the binding of PARP inhibitors to the catalytic domain of human tankyrase-2.

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

Evaluation and Structural Basis for the Inhibition of Tankyrases by PARP Inhibitors.

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.

Inhibition of matrix metalloproteinase-2 by PARP inhibitors.

Adrian C Nicolescu et al.

Biochemical and biophysical research communications, 387(4), 646-650 (2009-07-22)

Matrix metalloproteinase-2 (MMP-2), a ubiquitously expressed zinc-dependent endopeptidase, and poly(ADP-ribosyl) polymerase (PARP), a nuclear enzyme regulating DNA repair, are activated by nitroxidative stress associated with various pathologies. As MMP-2 plays a detrimental role in heart injuries resulting from enhanced nitroxidative

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Global Trade Item Number

SKU	GTIN
E8405-5MG	04061833270882
E8405-1MG	04061826674710

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