Nutlin-3 Disrupts MDM2-p53 interaction, inducing apoptosis

Nutlin-3 (CAS 548472-68-0)

Nutlin-3 | CAS 548472-68-0 is rated 5.0 out of 5 by 1.
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Synonym: (±)-4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4, 5-dihydroimidazole-1-carbonyl]piperazin-2-one
Application: Disrupts MDM2-p53 interaction, inducing apoptosis
CAS Number: 548472-68-0
Purity: ≥98%
Molecular Weight: 581.49
Molecular Formula: C30H30Cl2N4O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Nutlin-3, the racemic and most commonly used form of nutlin, inhibits p53-MDM2 interaction. It has shown ability to induce the expression of p53-regulated genes and exhibits potent antiproliferative activity in cells with functional p53, but not in cells with mutated p53. When in combination with perifosine, anti-leukaemic activity has been observed. High N-MYC (MycN) expression has been induced in non-N-MYC-amplified neuroblastoma cells when treated with the combination of nutlin-3 and doxorubicin (sc-200923).


References

1. Shangary, S., et al. 2009. Annu. Rev. Pharmacol. Toxicol. 49: 223-241. PMID: 18834305
2. Tokalov, S.V., et al. 2010. BMC Cancer. 10: 57. PMID: 20178585
3. Cipriano, R., et al. 2010. Cell Cycle. PMID: 20305378
4. Vassilev, L.T., et al. 2004. Science. 303: 844-848. PMID: 14704432
5. Sarek, G., et al. 2007. J. Clin. Invest. 117: 1019-1028. PMID: 17364023
6. Wawrzynow, B., et al. 2009. J. Biol. Chem. 284: 11517-11530. PMID: 19188367
7. Voltan, R., et al. 2009. Br. J. Haematol. 148: 957-961. PMID: 19958355

Physical State :
Solid
Solubility :
Soluble in ethanol (25 mg/ml), DMSO (20 mg/ml), DMF, methanol, and acetonitrile. Insoluble in water. Sparingly soluble in ethanol:PBS pH 7.2 (1:10).
Storage :
Store at -20° C
Density :
1.36 g/cm3 (Predicted)
Refractive Index :
n20D 1.65 (Predicted)
IC50 :
p53/MDM2 interaction: IC50 = 0.09 µM; 1043SK: IC50 = 2.2 µM (human); NIH/3T3: IC50 = 1.3 µM (mouse)
Ki Data :
p53-Binding Protein MDM2: Ki= 36 nM (human)
pK Values :
pKb: 2.82 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
216345
MDL Number :
MFCD07784509
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

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Certificate of Analysis

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Nutlin-3  Product Citations

See how others have used Nutlin-3. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 10 total

PMID: # 28528573  Riegel, E. et al. 2017. BioTechniques. 62: 206-214.

PMID: # 26728659  Cortes, CL. et al. 2016. Mol. Cancer. 15: 1.

PMID: # 27362806  Hallenborg, P. et al. 2016. Cell Death Dis. 7: e2289.

PMID: # 25511924  Katzman, B. et al. 2015. Biotechnology journal. 10: 379-85.

PMID: # 25449786  El-Khattouti, A. et al. 2015. Cancer Lett. 357: 83-104.

PMID: # 24831529  Bouafia, A. et al. 2014. PLoS Genet. 10: e1004309.

PMID: # 22705848  Fortini, P. et al. 2012. Cell death and differentiation. 19: 1741-9.

PMID: # 17080083  Laurie, N.A. et al. 2006. Nature. 444(7115): 61-66.

PMID: # 16443686  Tovar, C. et al. 2006. Proc. Natl. Acad. Sci. U.S.A. 103: 1888-1893.

PMID: # 15753391  Carvajal, D. et al. 2005. Cancer Res. 65: 1918-1924.

Citations 1 to 10 of 10 total

What is the shipping temperature for this product?

Asked by: hawkeye11
This chemical, Nutlin-3 (CAS 548472-68-0), ships ambient.
Answered by: Chemical Support 1
Date published: 2017-04-07
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Rated 5 out of 5 by from Tokalov et al Tokalov et al. (PubMed ID 20178585) found that Nutlin-3 protected normal cells from Taxol while selectively targeting p53-deficient cells for apoptosis. -SCBT Publication Review
Date published: 2015-01-30
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