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Merck

SML0580

Nutlin-3a

≥98% (HPLC), MDM2 inhibitor, powder

Sinónimos:

(-)-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

Fórmula empírica (notación de Hill):
C30H30Cl2N4O4
Número CAS:
675576-98-4
Peso molecular:
581.49
UNSPSC Code:
12352200
PubChem Substance ID:
329825564
NACRES:
NA.77
MDL number:
MFCD14636430

Nombre del producto

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

Categorías relacionadas

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000473010
0000473010
0000464704
0000464704
0000452787

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Visite la Librería de documentos

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)
Conservation and Divergence of p53 Oscillation Dynamics across Species.
Jacob S O, et al.
Cell Systems, 5(4), 410-417 (2017)
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
CITED2 affects leukemic cell survival by interfering with p53 activation.
Mattes K, et al.
Cell Death & Disease, 8(10), e3132-e3132 (2017)
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)
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