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Nutlin 3a

 Nutlin 3a Structure
CAS No.
675576-98-4
Chemical Name:
Nutlin 3a
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;(-)-Nutlin-3|||Nutlin-3a chiral|||(?)-Nutlin-3;4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-4,5-dihydro-2-
CBNumber:
CB32473892
Molecular Formula:
C30H30Cl2N4O4
Molecular Weight:
581.49
MOL File:
675576-98-4.mol
MSDS File:
SDS
Modify Date:
2024/2/25 14:10:47

Nutlin 3a Properties

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

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
NFPA 704
0
2 0

Nutlin 3a price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) SML0580 Nutlin-3a ≥98% (HPLC) 675576-98-4 5MG ₹30169.8 2022-06-14 Buy
Sigma-Aldrich(India) SML0580 Nutlin-3a ≥98% (HPLC) 675576-98-4 25MG ₹122444.1 2022-06-14 Buy
Product number Packaging Price Buy
SML0580 5MG ₹30169.8 Buy
SML0580 25MG ₹122444.1 Buy

Nutlin 3a Chemical Properties,Uses,Production

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.

Definition

ChEBI: Nutlin-3 is a stilbenoid. It is a small molecule inhibitor that targets p53-Mdm2 interaction.

Biochem/physiol Actions

Nutlin-3a is a potent nongenotoxic drug. It acts as a tumor suppressor p53 (TP53) activator and stabilizer.

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.
Mechanisms of the actions of Nutlin-3
Molecular Mechanisms of the actions of Nutlin-3

References

[1] LYUBOMIR T. VASSILEV. In Vivo Activation of the p53 Pathway by Small-Molecule Antagonists of MDM2[J]. Science, 2004, 303 5659. DOI:10.1126/science.1092472.
[2] YOKO TABE. MDM2 antagonist nutlin-3 displays antiproliferative and proapoptotic activity in mantle cell lymphoma.[J]. Clinical Cancer Research, 2009, 15 3: 933-942. DOI:10.1158/1078-0432.CCR-08-0399.
[3] SHINJI ENDO. Potent in vitro and in vivo antitumor effects of MDM2 inhibitor nutlin-3 in gastric cancer cells[J]. Cancer Science, 2010, 102 3: 605-613. DOI:10.1111/j.1349-7006.2010.01821.x.
[4] HONG SHEN  Carl G M. Pharmacologic activation of p53 by small-molecule MDM2 antagonists.[J]. Current pharmaceutical design, 2011, 17 6: 560-568. DOI:10.2174/138161211795222603.

Nutlin 3a Preparation Products And Raw materials

Raw materials

Preparation Products

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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 Nutlin-3a (chiral) 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]- 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 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)-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- (ndash)-Nutlin-3 4-[[(4S,5R)-4,5-Bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imid MDM2 Antagonist IV, Nutlin-3a 4-((4S,5R)-4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one Nutlin-3a - Nutlin-3, (-)- CS-391 MDM2 Antagonist IV, Nutlin-3a - CAS 675576-98-4 - Calbiochem Nutlin 3a USP/EP/BP 4-[(4S,5R)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one (-)-Nutlin-3|||Nutlin-3a chiral|||(?)-Nutlin-3 675576-98-4 677576-98-4 Inhibitors