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N6287

Nutlin-3

Name: Nutlin-3
Brand: SIGMA

≥98% (HPLC), powder, Mdm2 antagonist

Synonym(s):

(±)-4-[4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one

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About This Item

Empirical Formula (Hill Notation):

C₃₀H₃₀Cl₂N₄O₄

CAS Number:

548472-68-0

Molecular Weight:

581.49

UNSPSC Code:

12352200

PubChem Substance ID:

24724554

NACRES:

NA.77

MDL number:

MFCD07784509

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Nutlin-3, ≥98% (HPLC), powder

ligand

nutlin-3

Quality Level

100

assay

≥98% (HPLC)

form

powder

reaction suitability

reagent type: ligand

solubility

DMSO: 20 mg/mL, H₂O: insoluble

originator

Roche

shipped in

wet ice

storage temp.

−20°C

SMILES string

O=C(N1CC(NCC1)=O)N2C(C3=CC=C(Cl)C=C3)C(C4=CC=C(Cl)C=C4)N=C2C5=C(OC(C)C)C=C(OC)C=C5

InChI

1S/C30H30Cl2N4O4/c1-18(2)40-25-16-23(39-3)12-13-24(25)29-34-27(19-4-8-21(31)9-5-19)28(20-6-10-22(32)11-7-20)36(29)30(38)35-15-14-33-26(37)17-35/h4-13,16,18,27-28H,14-15,17H2,1-3H3,(H,33,37)/t27-,28+/m1/s1

InChI key

BDUHCSBCVGXTJM-IZLXSDGUSA-N

Description

Application

Nutlin-3 has been used:

as a drug to stimulate p53 functions in gene transfer experiment
to inject worms to verify the prevalent role of translationally controlled tumor protein (TCTP) in posterior amputated E. eugeniae
as a p53 activator in cyclotherapy studies
as an mdm2 inhibitor to know its effect on p53 levels, cleaved caspase 3 and Poly (ADP-ribose) polymerase (PARP) cleavage

Biochem/physiol Actions

Nutlin-3 is a Mdm2 (mouse double minute 2) antagonist, p53 pathway activator, and apoptosis inducer.

Nutlin-3, an antagonist of a human homolog of murine double minute 2 (HDM2). It has the ability to inhibit the HDM2-directed degradation of p53. Nutlin-3 can also enhance the transcriptional activities of p73.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Analysis Note

relative stereochemistry

Other Notes

Relative stereochemistry; racemic mixture of (4R, 5S) and (4S, 5R) enantiomers.

Legal Information

Sold under license from Hoffman-La Roche, Inc. US patent 6,734,302.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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p53 requires the stress sensor USF1 to direct appropriate cell fate decision.

Amine Bouafia et al.

PLoS genetics, 10(5), e1004309-e1004309 (2014-05-17)

Genomic instability is a major hallmark of cancer. To maintain genomic integrity, cells are equipped with dedicated sensors to monitor DNA repair or to force damaged cells into death programs. The tumor suppressor p53 is central in this process. Here

Activation of endogenous p53 by combined p19Arf gene transfer and nutlin-3 drug treatment modalities in the murine cell lines B16 and C6

Merkel CA, et al.

BMC Cancer, 10(1), 316-316 (2010)

Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis

Lee DM, et al.

Experimental & Molecular Medicine, 49(8), e365-e365 (2017)

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