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Merck

N6287

Nutlin-3

≥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

Key Documents

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Product Name

Nutlin-3, ≥98% (HPLC), powder

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

ligand

nutlin-3

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

Quality Level

100

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

N6287-5MG: + N6287-1MG: + N6287-BULK: + N6287-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
0000492659
0000465128
0000465128
0000447732
0000447730

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HDM2 antagonist Nutlin-3 disrupts p73-HDM2 binding and enhances p73 function
Lau LMS, et al.
Oncogene, 27(7), 997-997 (2008)
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)
A Quintás-Cardama et al.
Leukemia, 31(6), 1296-1305 (2016-11-26)
TP53 mutations are associated with the lowest survival rates in acute myeloid leukemia (AML). In addition to mutations, loss of p53 function can arise via aberrant expression of proteins that regulate p53 stability and function. We examined a large AML
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
Christian A Merkel et al.
BMC cancer, 10, 316-316 (2010-06-24)
Reactivation of p53 by either gene transfer or pharmacologic approaches may compensate for loss of p19Arf or excess mdm2 expression, common events in melanoma and glioma. In our previous work, we constructed the pCLPG retroviral vector where transgene expression is
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