All Photos(1)
Synonym(s):
2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one, APR-246
Empirical Formula (Hill Notation):
C10H17NO3
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
InChI
1S/C10H17NO3/c1-14-7-10(6-12)9(13)8-2-4-11(10)5-3-8/h8,12H,2-7H2,1H3
InChI key
BGBNULCRKBVAKL-UHFFFAOYSA-N
Biochem/physiol Actions
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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)
The mutant p53-targeting compound APR-246 induces ROS-modulating genes in breast cancer cells
Synnott N, et al.
Translational Oncology, 11(6) (2018)
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
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
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
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