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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:
548472-68-0
Molecular Weight:
581.49
MDL number:
MFCD07784509
UNSPSC Code:
12352200
PubChem Substance ID:
24724554
NACRES:
NA.77

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

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, 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.

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WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
Laura G Caller et al.
Journal of virology, 93(16) (2019-05-31)
BK polyomavirus (BKPyV) is a small DNA virus that establishes a life-long persistent infection in the urinary tract of most people. BKPyV is known to cause severe morbidity in renal transplant recipients and can lead to graft rejection. The simple
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