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SML0580

Sigma-Aldrich

Nutlin-3a

≥98% (HPLC)

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
MDL number:
MFCD14636430
UNSPSC Code:
12352200
PubChem Substance ID:
329825564
NACRES:
NA.77

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

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

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

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 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.

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
CITED2 affects leukemic cell survival by interfering with p53 activation.
Mattes K, et al.
Cell Death & Disease, 8(10), e3132-e3132 (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
View All Related Papers

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