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Nutlin-3a — Datasheet

CAT. NO. DC8454

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ParameterValue
Chemical NameNutlin-3A
CAS No.675576-98-4
SynonymsNutlin-3a;(-)-Nutlin-3;2-​Piperazinone, 4-​[[(4S,​5R)​-​4,​5-​bis(4-​chlorophenyl)​-​4,​5-​dihydro-​2-​[4-​methoxy-​2-​(1-​methylethoxy)​phenyl]​-​1H-​imidazol-​1-​yl]​carbonyl]​-;Nutlin (3a);Nutlin-3a chiral;(-)-4-(4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one;4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydroimidazol-1-yl]carbonyl]piperazin-2-one;4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imidazol-1-yl]carbonyl]-2-Piperazinone;Nutlin 3a;L7C92IOE65;4-((4S,5R)-4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one;C30H30Cl2N4O4;Nutlin3a;Nutlin-3a (chiral);4j3e;4hg7;(?)-Nutlin-3;Nutlin-3, (-)-;(4S,5R)-Nutlin-3;BDUHCSBCVGXTJ;4-[(4s,5r)-4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one;4-[(4s,5r)-4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one;675576-98-4;675576-98-4;Nutlin 3b;Nutlin 3b;4-[cis-4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl]piperazin-2-one;4-[cis-4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl]piperazin-2-one;BDBM50229787;BDBM50229787;53IA0V845C;53IA0V845C;s8059;s8059;548472-68-0 (4R5S, and 4S5R);548472-68-0 (4R5S, and 4S5R);UNII-53IA0V845C;UNII-53IA0V845C;2-Piperazinone, 4-(((4S,5R)-4,5-bis(4-chlorophenyl)-4,5-dihydro-2-(4-methoxy-2-(1-methylethoxy)phenyl)-1H-imidazol-1-yl)carbonyl)-;2-Piperazinone, 4-(((4S,5R)-4,5-bis(4-chlorophenyl)-4,5-dihydro-2-(4-methoxy-2-(1-methylethoxy)phenyl)-1H-imidazol-1-yl)carbonyl)-;UNII-L7C92IOE65;UNII-L7C92IOE65;NSC756875;NSC756875;SML-0580;SML-0580;4-[(4S,5R)-4,5-bis(4-chlorophenyl)-2-[4-methoxy-2-(propan-2-yloxy)phenyl]-4,5-dihydro-1H-imidazole-1-carbonyl]piperazin-2-one;4-[(4S,5R)-4,5-bis(4-chlorophenyl)-2-[4-methoxy-2-(propan-2-yloxy)phenyl]-4,5-dihydro-1H-imidazole-1-carbonyl]piperazin-2-one;AKOS027422740;AKOS027422740;MFCD14636430;MFCD14636430;BDUHCSBCVGXTJM-WUFINQPMSA-N;BDUHCSBCVGXTJM-WUFINQPMSA-N;NSC-756876;NSC-756876;nutlin-3A;nutlin-3A;NSC 732664;NSC 732664;Nutlin-3;Nutlin-3;Z2037279564;Z2037279564;REBEMADLIN;REBEMADLIN;SR-01000946691-1;SR-01000946691-1;CHEMBL191334;CHEMBL191334;NSC-756875;NSC-756875;4-[(4S,5R)-4,5-Bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one;4-[(4S,5R)-4,5-Bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one;SCHEMBL1155752;SCHEMBL1155752;2-PIPERAZINONE, 4-(((4R,5S)-4,5-BIS(4-CHLOROPHENYL)-4,5-DIHYDRO-2-(4-METHOXY-2-(1-METHYLETHOXY)PHENYL)-1H-IMIDAZOL-1-YL)CARBONYL)-, REL-;2-PIPERAZINONE, 4-(((4R,5S)-4,5-BIS(4-CHLOROPHENYL)-4,5-DIHYDRO-2-(4-METHOXY-2...
FormulaC30H30Cl2N4O4
M.Wt581.4896
SMILESClC1C([H])=C([H])C(=C([H])C=1[H])[C@]1([H])[C@]([H])(C2C([H])=C([H])C(=C([H])C=2[H])Cl)N=C(C2C([H])=C([H])C(=C([H])C=2OC([H])(C([H])([H])[H])C([H])([H])[H])OC([H])([H])[H])N1C(N1C([H])([H])C(N([H])C([H])([H])C1([H])[H])=O)=O
Purity>98%
Storage2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO

Biological Activity

Nutlin 3a is an active enantiomer of Nutlin-3, acts as a murine double minute (MDM2) antagonist that inhibits MDM2-p53 interactions and stabilizes the p53 protein, and thereby induces cell cycle arrest and apoptosis.

In Vitro

Nutlin 3a (Nutlin-3a) is a therapeutic which inhibits MDM2, activates wild-type p53, and induces apoptosis-as a therapeutic compound for TP53 wild-type ovarian carcinomas. Three cell lines (HOC-7, OVCA429 and A2780) with wild-type TP53 are highly sensitive to Nutlin 3a (IC50=4 to 6 μM). SKOV3 cells have an IC50 of 38 μM to Nutlin 3a. The two remaining ovarian clear cell lines (TOV21G and OVAS), both with TP53 wild-type, are relatively more sensitive to growth inhibition with Nutlin 3a (IC50=14 and 25 μm respectively) than the TP53 mutant cell lines[1]. Nutlin 3a (Nutlin-3a) is the active enantiomer of Nutlin-3. Nutlin 3a is a highly selective MDM2 antagonist and p53 inducer. Seven days of incubation with 10 μM Nutlin 3a leads to >90% inhibition of NIH/3T3 cells’growth but does not affect the proliferation of MEF in which both targets of the drug are eliminated. Nutlin 3a effectively arrestes cell-cycle progression in all cell lines, depleting the S-phase compartment to 0.2-2% and increasing the G1- and G2/M-phase compartments, indicating G1 and G2 arrest. The p53 targets p21 and MDM2 are elevated significantly 3 h after Nutlin 3a addition and reach maximal levels at 8 h. Nutlin 3a induces apoptosis in ≈60% of SJSA-1 and MHM cells after 40 h, which increase further after 60 h (85% and 65%, respectively)[2].

In Vivo

Nutlin 3a (Nutlin-3a) is efficacious in all models with average tumor growth inhibition ≥98%. Nutlin 3a suppresses xenograft growth in a dose-dependent fashion with the highest dose (200 mg/kg) showing a substantial tumor shrinkage (eight partial and one full regressions). The established SJSA-1 and MHM osteosarcoma xenografts with Nutlin 3a causes extensive tumor regression[2].

References & source

DC Chemicals original product information

Published experimental findings depend on the model and assay conditions. They do not guarantee equivalent performance in every application. For laboratory research use only.

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