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Nutlin 3a

Product Name
Nutlin 3a
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-<W;MDM2 Antagonist IV, Nutlin-3a - CAS 675576-98-4 - Calbiochem
CBNumber
CB32473892
Molecular Formula
C30H30Cl2N4O4
Formula Weight
581.49
MOL File
675576-98-4.mol
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Nutlin 3a Property

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
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0580
Product name
Nutlin-3a
Purity
≥98% (HPLC)
Packaging
5mg
Price
$295
Updated
2024/03/01
Sigma-Aldrich
Product number
444152
Product name
MDM2 Antagonist IV, Nutlin-3a
Packaging
5mg
Price
$272
Updated
2022/05/15
Cayman Chemical
Product number
18585
Product name
(-)-Nutlin-3
Purity
≥98%
Packaging
1mg
Price
$93
Updated
2024/03/01
Cayman Chemical
Product number
18585
Product name
(-)-Nutlin-3
Purity
≥98%
Packaging
5mg
Price
$230
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0580
Product name
Nutlin-3a
Purity
≥98% (HPLC)
Packaging
25mg
Price
$1180
Updated
2024/03/01
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Nutlin 3a Chemical Properties,Usage,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.

Uses

Nutlin-3a has been used as a tumor suppressor p53(TP53) stabilizer and as an inhibitor of the mouse double minute 2 homolog (MDM2)–p53 interaction.

Definition

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

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. 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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Nutlin 3a Suppliers

Alsachim SAS
Tel
--
Fax
--
Email
sales@alsachim.com
Country
France
ProdList
424
Advantage
0
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View Lastest Price from Nutlin 3a manufacturers

Career Henan Chemical Co
Product
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 675576-98-4
Price
US $1.00/g
Min. Order
100g
Purity
99%
Supply Ability
G /kg/t
Release date
2019-12-20

675576-98-4, Nutlin 3aRelated Search:


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  • 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-<W
  • (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