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N6287 Sigma-Aldrich

Nutlin-3

≥98% (HPLC), powder

Synonym: (±)-4-[4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one

  • CAS Number 548472-68-0

  • Empirical Formula (Hill Notation) C30H30Cl2N4O4

  • Molecular Weight 581.49

  •  MDL number MFCD07784509

  •  PubChem Substance ID 24724554

  •  NACRES NA.77

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Properties

Related Categories Apoptosis Inducers, Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
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

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 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 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 & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Apoptosis

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...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Peer-Reviewed Papers
15

References

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