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N6287

Sigma-Aldrich

Nutlin-3

≥98% (HPLC), powder

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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

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

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This Item
SML0580SML3406N6664
Nutlin-3 ≥98% (HPLC), powder

N6287

Nutlin-3

Nutlin-3a ≥98% (HPLC)

SML0580

Nutlin-3a

Nutlin-3b ≥98% (HPLC)

SML3406

Nutlin-3b

Neurodazine ≥98% (HPLC)

N6664

Neurodazine

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: 20 mg/mL, H2O: insoluble

solubility

DMSO: 5 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: >20 mg/mL

shipped in

wet ice

shipped in

wet ice

shipped in

-

shipped in

-

originator

Roche

originator

-

originator

-

originator

-

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

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 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.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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
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)
HDM2 antagonist Nutlin-3 disrupts p73-HDM2 binding and enhances p73 function
Lau LMS, et al.
Oncogene, 27(7), 997-997 (2008)
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

Articles

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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