| Identification | Back Directory | [Name]
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 | [CAS]
675576-98-4 | [Synonyms]
CS-391
Nutlin 3a
(ndash)-Nutlin-3
Nutlin-3a (chiral)
Nutlin 3a USP/EP/BP
Nutlin-3a - Nutlin-3, (-)-
MDM2 Antagonist IV, Nutlin-3a
4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-4,5-dihydro-2-MDM2 Antagonist IV, Nutlin-3a - CAS 675576-98-4 - Calbiochem
4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imid
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)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one
4-[(4S,5R)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-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
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
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]-2-piperazinone Nutlin 3a | [Molecular Formula]
C30H30Cl2N4O4 | [MDL Number]
MFCD14636430 | [MOL File]
675576-98-4.mol | [Molecular Weight]
581.497 |
| Chemical Properties | Back Directory | [density ]
1.36 | [storage temp. ]
?20°C | [solubility ]
DMSO: soluble5mg/mL, clear | [form ]
White powder | [pka]
14.35±0.20(Predicted) | [color ]
white to beige | [optical activity]
[α]/D -140 to -155° (c=0.5, CDCl3) | [InChIKey]
BDUHCSBCVGXTJM-WUFINQPMSA-N |
| Hazard Information | Back Directory | [Description]
Nutlin-3 is a novel small-molecule antagonist of the human homolog of mouse double minute (MDM2) that binds MDM2 in the p53-binding pocket and activates the p53 signaling pathway. | [Uses]
(ndash)-Nutlin-3 is an inhibitor of p-53-MDM2 interaction. Anti-cancer agent. | [Definition]
ChEBI: 4-[[(4S,5R)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-oxomethyl]-2-piperazinone is a stilbenoid. | [reaction suitability]
reagent type: ligand | [Biological Activity]
nutlin-3 is a small-molecule inhibitor of mdm2 (mouse double minute 2) with ic50 value of 0.09μm [1].nutlin-3 binds mdm2 in the tp53-bindingpocket, thereby interfering with mdm2-directed tp53 degradation. this has been shown to cause cell cycle arrest, growth inhibitionand apoptosis in both solid tumors and lymphoid neoplasms.in mantle cell lymphoma(mcl), it is reported that nutlin-3 can inhibit cell growth and activate apoptosis in bothwt-tp53(ic50 of 1 to 10μm) and mt-tp53(ic50 of 22.5μm) cells [2].nutlin-3 can also effectcell cycle in gastric cancer cell lines. it induces g1 arrest inmkn-45 and snu-1 cell lines. in vitro assay shows nutlin-3can enhance the antitumoreffects of conventional chemotherapeutic agents in several gastric cancer cell lines. and in in vivo assay, nutlin-3 significantly inhibits the growth of xenograft tumors [3]. | [Biochem/physiol Actions]
Nutlin-3a is a potent nongenotoxic drug. It acts as a tumor suppressor p53 (TP53) activator and stabilizer. | [target]
MDM2 | [storage]
Store at -20°C | [Mode of action]
Nutlin-3 binds to the p53 binding pocket in MDM2 and inhibits the p53/MDM2 interaction, leading to stabilization of p53 and induction of p53-dependent cell cycle arrest or apoptosis. Nutlin-3 can also inhibit cancer cell migration and invasion in a p53-dependent manner, most likely through inhibition of RhoA and Rac1 activity. In addition to p53, Nutlin-3 also blocks the interaction of MDM2 with p73, E2F1, HIF-1α, resulting in increased apoptosis (p73, E2F1) and decreased VEGF production and decreased angiogenesis (HIF-1α). Nutlin-3 is predicted to block the interaction of MDM2 and Numb.
Molecular Mechanisms of the actions of Nutlin-3 | [References]
[1] lyubomir t.vassilev et al. in vivo activation of the p53 pathway by small-molecule antagonists of mdm2.science.2004, 303: 844-848.
[2] yoko tabe, denise sebasigari, linhua jin, et al.mdm2 antagonist nutlin-3 displays antiproliferative andproapoptotic activity in mantle cell lymphoma. clin cancer res. 2009, 15:933-942.
[3] shinji endo,kenji yamato,sachiko hirai,toshikazu moriwaki,kuniaki fukuda,hideo suzuki,masato abei,ichiro nakagawa and ichinosukehyodo.potent in vitro and in vivo antitumor effects ofmdm2 inhibitor nutlin-3 in gastric cancer cells.cancer science. 2011, 102 (3): 605-613. |
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