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Nutlin-3b
- (+)-Nutlin-3
- Optical Purity: Optically pure
- Soluble in DMSO
- MF: C30H30Cl2N4O4
- MW: 581.49
Description
Nutlin-3b is the less active (+)-enantiomer of Nutlin-3 (1585) and is reported to be about 150-fold less potent than its opposite (-)-enantiomer, Nutlin-3a (Axon 1880), as an MDM2-p53 antagonist.
Because Nutlin-3b has much weaker activity at the MDM2-p53 interface, it is useful as a stereochemical control for distinguishing p53-dependent pharmacology from nonspecific compound effects in Nutlin-related studies.
Key Features
- Less active Nutlin-3 enantiomer
- Approximately 150-fold weaker than Nutlin-3a in MDM2-p53 antagonism
- Useful stereochemical control compound
- Supports validation of p53-dependent cellular responses
Applications
- MDM2-p53 interaction control experiments
- Nutlin enantiomer comparison studies
- p53 pathway assay validation
- Off-target and stereochemical specificity assessment
More Information
| Parent CAS No. | 675576-97-3 |
|---|---|
| Chemical Name | 4-((4R,5S)-4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one |
| SMILES | [C@@]1([H])(C2C=CC(Cl)=CC=2)N=C(C2C(OC(C)C)=CC(OC)=CC=2)N(C(=O)N2CC(=O)NCC2)[C@@]1([H])C1C=CC(Cl)=CC=1 |&1:0,33,r| |
| MFCD | N.A. |
| InChi | 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 |
| InChiKey | BDUHCSBCVGXTJM-IZLXSDGUSA-N |
| CID | 16755649 |
| Short Description | MDM2 inhibitor |
References
- V Manfé et al. MDM2 Inhibitor Nutlin-3a Induces Apoptosis and Senescence in Cutaneous T-Cell Lymphoma: Role of p53. J. Invest. Dermatol. 2012, 132, 1487-1496.
- E Drakos et al. Activation of the p53 pathway by the MDM2 inhibitor nutlin-3a overcomes BCL2 overexpression in a preclinical model of diffuse large B-cell lymphoma associated with t(14;18)(q32;q21). Leukemia 2011, 25, 856–867.
- F Zhang et al. MDM2 antagonist nutlin-3a reverses mitoxantrone resistance by inhibiting breast cancer resistance protein mediated drug transport. Biochem. Pharmacol. 2011, 82(1), 24-34.
- H Hasegawa et al. Activation of p53 by Nutlin-3a, an antagonist of MDM2, induces apoptosis and cellular senescence in adult T-cell leukemia cells. Leukemia 2009, 23, 2090–2101.
- TA Davis and JN Johnston. Catalytic, enantioselective synthesis of stilbene cis-diamines: A concise preparation of (-)-Nutlin-3, a potent p53/MDM2 inhibitor. Chem. Sci. 2011, 2, 1076-1079.
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