N6287

Sigma-Aldrich

Nutlin-3

≥98% (HPLC), powder

Synonym(s):
(±)-4-[4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one
Empirical Formula (Hill Notation):
C30H30Cl2N4O4
CAS Number:
Molecular Weight:
581.49
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

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

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 Eeugeniae
  • 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

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

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

Features and Benefits

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

Other Notes

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

Analysis Note

relative stereochemistry

Legal Information

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

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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)
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)
HDM2 antagonist Nutlin-3 disrupts p73-HDM2 binding and enhances p73 function
Lau LMS, et al.
Oncogene, 27(7), 997-997 (2008)
Sirtuin 7 promotes cellular survival following genomic stress by attenuation of DNA damage, SAPK activation and p53 response
Kiran S, et al.
Experimental Cell Research, 331(1), 123-141 (2015)

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