N6287

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

Properties

• 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, 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.

Safety Information

• 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