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444152

MDM2 Antagonist IV, Nutlin-3a

Name: MDM2 Antagonist IV, Nutlin-3a
Brand: MM

The MDM2 Antagonist IV, Nutlin-3a, also referenced under CAS 675576-98-4, controls the biological activity of MDM2. This small molecule/inhibitor is primarily used for Cancer applications.

Synonym(s):

MDM2 Antagonist IV, Nutlin-3a, (-)-4-(4,5- bis-(4-Chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carbonyl)piperazine-2-one, (-)-4-(4,5-bis-(4-Chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carbonyl)piperazine-2-one

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About This Item

Empirical Formula (Hill Notation):

C₃₀H₃₀Cl₂N₄O₄

CAS Number:

675576-98-4

Molecular Weight:

581.49

UNSPSC Code:

12352200

MDL number:

MFCD14636430

Assay:

≥98% (HPLC)

Form:

powder

Storage condition:

OK to freeze, protect from light

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Properties

Quality Segment

100

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

−20°C

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+/m0/s1

InChI key

BDUHCSBCVGXTJM-WUFINQPMSA-N

Description

General description

A cell-permeable and highly potent active enantiomer of Nutlin-3 (Cat. No. 444143) that binds to the p53-binding pocket and blocks the interaction of p53 and MDM2 (IC₅₀ = 90 nM). Exhibits over 150-fold greater affinity for MDM2 than its less active enantiomer, Nutlin-3b. Induces p53 mediated apoptosis by both transcription-dependent and independent mechanisms. Shown to greatly potentiate the cytotoxic effects of chemotherapeutic agents and reduce tumor burden in vivo. Also shown to overcome ATM-mediated resistance to fludarabine in chronic lymphocyte leukemia. Cells treated with Nutlin-3a permanently lose their ability to proliferate and enter into a pattern of permanent senescence. Mouse embryonic fibroblasts with p53^+/+MEFs show significantly reduced reprogramming capabilities following Nutlin-3a treatment.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Ohnstad, H.O., et al. 2011. BMC Cancer11, 211.
Shen, H. and Maki, C.G., 2010. J. Biol. Chem.285, 23105.
Kawamura, T., et al. 2009. Nature460, 1140.
Kojima, K., et al. 2006. Blood108, 993.
Laurie, N.A., et al. 2006. Nature444, 61.
Tovar, C., et al. 2006. Proc. Natl. Acad. Sci. USA103, 1888.
Vassilev, L.T. 2006. Trends Mol Med.13, 23.
Thompson, T., et al. 2004. J. Biol. Chem.279, 53015.
Vassilev, L.T., et al. 2004. Science303, 844.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c