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Merck

SML0580

Nutlin-3a

≥98% (HPLC), MDM2 inhibitor, powder

Synonym(s):

(-)-4-(4,5-Bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-2-one, (-)-Nutlin-3, 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-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imidazol-1-yl]carbonyl]-2-Piperazinone, Nutlin 3a

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About This Item

Empirical Formula (Hill Notation):
C30H30Cl2N4O4
CAS Number:
675576-98-4
Molecular Weight:
581.49
UNSPSC Code:
12352200
PubChem Substance ID:
329825564
NACRES:
NA.77
MDL number:
MFCD14636430
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

Nutlin-3a, ≥98% (HPLC)

SMILES string

O=C(N1CC(NCC1)=O)N2[C@H](C3=CC=C(Cl)C=C3)[C@H](C4=CC=C(Cl)C=C4)N=C2C5=CC=C(OC)C=C5OC(C)C

InChI key

BDUHCSBCVGXTJM-WUFINQPMSA-N

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

ligand

nutlin-3a

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -130 to -154° (c=0.5, CDCl3)

reaction suitability

reagent type: ligand

color

white to beige

solubility

DMSO: 5 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Related Categories

Application

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.

Biochem/physiol Actions

Nutlin-3a [(-)-Nutlin] is a more potent diastereoisomer of racemic MDM2 antagonist Nutlin-3. It was called enantiomer-a since it elutes as the first peak from chiral purification of racemic nutlin-3. Nutlin-3a is a potent inhibitor of MDM2 (mouse double minute 2) binding to p53 that induces the expression of p53 regulated genes, and shows potent antiproliferative activity in cells expressing functional p53. Nutlin-3a is 150 times more potent than Nutlin-3b.
Nutlin-3a [(-)-Nutlin] is a potent inhibitor of MDM2 (mouse double minute 2) binding to p53; Mdm2 antagonist.
Nutlin-3a is a potent nongenotoxic drug. It acts as a tumor suppressor p53 (TP53) activator and stabilizer.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML0580-25MG: + SML0580-VAR: + SML0580-5MG: + SML0580-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000473010
0000473010
0000464704
0000464704
0000452787

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Long non-coding RNA NEAT1-modulated abnormal lipolysis via ATGL drives hepatocellular carcinoma proliferation.
Liu X, et al.
Molecular Cancer, 17(1), 90-90 (2018)
Manasi Das et al.
Nanomedicine : nanotechnology, biology, and medicine, 11(2), 379-389 (2014-09-23)
The promising proposition of multifunctional nanoparticles for cancer diagnostics and therapeutics has inspired the development of theranostic approach for improved cancer therapy. Moreover, active targeting of drug carrier to specific target site is crucial for providing efficient delivery of therapeutics
Conservation and Divergence of p53 Oscillation Dynamics across Species.
Jacob S O, et al.
Cell Systems, 5(4), 410-417 (2017)
Multiplex detection of protein?protein interactions using a next generation luciferase reporter.
Verhoef L G G C, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1863(2), 284-292 (2016)
Joana Soares et al.
Molecular oncology, 11(6), 612-627 (2017-03-16)
The transcription factor p53 plays a crucial role in cancer development and dissemination, and thus, p53-targeted therapies are among the most encouraging anticancer strategies. In human cancers with wild-type (wt) p53, its inactivation by interaction with murine double minute (MDM)2
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