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Documentos Principais

SML1789

Sigma-Aldrich

PRIMA-1Met

≥98% (HPLC)

Sinônimo(s):

2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one, APR-246

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About This Item

Fórmula empírica (Notação de Hill):
C10H17NO3
Número CAS:
5291-32-7
Peso molecular:
199.25
Código UNSPSC:
12352200
NACRES:
NA.77

Nível de qualidade

100

Ensaio

≥98% (HPLC)

Formulário

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

N21CCC(CC2)C(=O)C1(COC)CO

InChI

1S/C10H17NO3/c1-14-7-10(6-12)9(13)8-2-4-11(10)5-3-8/h8,12H,2-7H2,1H3

chave InChI

BGBNULCRKBVAKL-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

PRIMA-1Met (APR-246) is a re-activator of mutant p53 activity. It′s the methylated, more potent derivative of PRIMA-1. PRIMA-1Met covalently modifies the core domain of mutated p53 restoring the wild-type conformation and activty of p53 in tumor cells, leading to cell cycle arrest and apoptosis. PRIMA-1Met has also been shown to increase intracellular levels of reactive oxygen species (ROS), which may contribute to its anti-tumor activity.
PRIMA-1Met, also called APR-246, is converted to methylene quinuclidinone (MQ), a Michael acceptor. It interacts with p53 through the cysteine (Cys) residue. It blocks the thioredoxin reductase (TrxR1) enzyme. It is under clinical investigation and well-studied. PRIMA-1Met effect is tested on breast cancer specific gene expression.
Re-activator of mutant p53 activity

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319

Classificações de perigo

Eye Irrit. 2 - Skin Irrit. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number

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APR-246/PRIMA-1 MET inhibits thioredoxin reductase 1 and converts the enzyme to a dedicated NADPH oxidase
Peng X, et al.
Cell Death & Disease, 4(10), e881-e881 (2013)
Christophe Deben et al.
Cancer letters, 375(2), 313-322 (2016-03-16)
APR-246 (PRIMA-1(Met)) is able to bind mutant p53 and restore its normal conformation and function. The compound has also been shown to increase intracellular ROS levels. Importantly, the poly-[ADP-ribose] polymerase-1 (PARP-1) enzyme plays an important role in the repair of
The mutant p53-targeting compound APR-246 induces ROS-modulating genes in breast cancer cells
Synnott N, et al.
Translational Oncology, 11(6) (2018)
Nobuhisa Yoshikawa et al.
Oncology reports, 35(5), 2543-2552 (2016-03-18)
There is an intensive need for the development of novel drugs for the treatment of epithelial ovarian cancer (EOC), the most lethal gynecologic malignancy due to the high recurrence rate. TP53 mutation is a common event in EOC, particularly in
Vladimir J N Bykov et al.
Frontiers in oncology, 6, 21-21 (2016-02-13)
TP53 is the most frequently mutated gene in cancer. The p53 protein activates transcription of genes that promote cell cycle arrest or apoptosis, or regulate cell metabolism, and other processes. Missense mutations in TP53 abolish specific DNA binding of p53
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