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AB144426

(+)-Nutlin-3, p53-MDM2 binding inhibitor

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MW 581.5 Da, Purity >98%. p53-MDM2 binding inhibitor (IC50 = 13 μM). Less potent enantiomer of (-)-Nutlin-3 (Asc-4428). Shows antiproliferative effects (IC50 values are 2.2 and 1.3 μM for human skin and murine fibroblasts respectively). Shows antitumor effects in vivo. Orally active.
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Chemical Structure - (+)-Nutlin-3, p53-MDM2 binding inhibitor (AB144426)
  • Chemical Structure

Lab

Chemical Structure - (+)-Nutlin-3, p53-MDM2 binding inhibitor (AB144426)

2D chemical structure image of ab144426, (+)-Nutlin-3, p53-MDM2 binding inhibitor

Key facts

CAS number

675576-97-3

Purity

>98%

Molecular weight

581.5 Da

Molecular formula

C<sub>3</sub><sub>0</sub>H<sub>3</sub><sub>0</sub>Cl<sub>2</sub>N<sub>4</sub>O<sub>4</sub>

PubChem

16755649

Nature

Synthetic

Solubility

Soluble in DMSO

Biochemical name

nutlin-3B

Biological description

p53-MDM2 binding inhibitor (IC50 = 13 μM). Less potent enantiomer of (-)-Nutlin-3 (Asc-4428). Shows antiproliferative effects (IC50 values are 2.2 and 1.3 μM for human skin and murine fibroblasts respectively). Shows antitumor effects in vivo. Orally active.

Canonical smiles

CC(C)OC1=C(C=CC(=C1)OC)C2=NC(C(N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl

Isomeric smiles

CC(C)OC1=C(C=CC(=C1)OC)C2=N[C@@H]([C@@H](N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl

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

IUPAC Name

4-[(4R,5S)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one

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Complementary Products

Biochemicals

AB120646

(±)-Nutlin-3, MDM2 antagonist

Chemical Structure - (±)-Nutlin-3, MDM2 antagonist (AB120646)

  • 0
  • 0
Secondary Antibodies

AB150077

Goat Anti-Rabbit IgG H&L (Alexa Fluor® 488)

Immunocytochemistry/ Immunofluorescence - Goat Anti-Rabbit IgG H&L (Alexa Fluor® 488) (AB150077)

  • 5
  • 20
Primary Antibodies

AB259265

Anti-MDM2 antibody [EPR22256-98]

20ul selling size|RabMAb|Recombinant

Immunocytochemistry/ Immunofluorescence - Anti-MDM2 antibody [EPR22256-98] (AB259265)

  • 5
  • 5
Primary Antibodies

AB15580

Anti-Ki67 antibody

BOND RX™ Validated|KO Validated

Immunohistochemistry (Formalin/PFA-fixed paraffin-embedded sections) - Anti-Ki67 antibody (AB15580)

  • 5
  • 230
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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

MDM2 also known as murine double minute 2 is an important regulator of the p53 tumor suppressor protein. It functions as an E3 ubiquitin ligase targeting p53 for proteasomal degradation. The MDM2 protein has a molecular weight of approximately 55 kDa. It is expressed in various human tissues with higher levels in rapidly dividing cells. MDM2 interacts through its N-terminal domain with the transactivation domain of p53 inhibiting its transcriptional activity.
Biological function summary

The MDM2 protein plays a central role in cell cycle control and apoptosis regulation. It forms a complex with p53 which modulates p53's stability and activity. By binding to p53 MDM2 prevents p53 from inducing cell cycle arrest or apoptosis in response to DNA damage or oncogenic signals. Its interaction allows cells to proliferate even in the presence of potential growth-arrest signals maintaining homeostasis under normal physiological conditions.

Pathways

MDM2 and p53 form a critical axis within the DNA damage response and tumorigenesis pathways. The p53-MDM2 feedback loop is a well-studied mechanism that balances cell survival and death. When DNA damage occurs p53 gets activated and in turn upregulates MDM2 expression creating a feedback loop. Other proteins like ARF also interact with MDM2 inhibiting its activity towards p53 and thereby enhancing p53 function during cellular stress.

Mutations or overexpression of the MDM2 protein are often associated with various cancers including sarcoma and breast cancer. In these cancers MDM2 amplification leads to enhanced degradation of p53 resulting in unchecked cell proliferation. MDM2's involvement in these pathologies highlights its potential as a therapeutic target with inhibitors like Nutlin-3 being developed to disrupt the MDM2-p53 interaction. The relationship between MDM2 and other proteins such as HDM201 in the context of p53 alterations further highlights its importance in cancer biology.
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Product protocols

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