2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Struktur

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

Bezeichnung:2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

CAS-Nr5291-32-7

Englisch Name:2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

CBNumberCB52518928

SummenformelC10H17NO3

Molgewicht199.25

MOL-Datei5291-32-7.mol

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one physikalisch-chemischer Eigenschaften

Schmelzpunkt	115-116 °C
Siedepunkt	313.8±17.0 °C(Predicted)
Dichte	1.20±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO (up to 20 mg/ml)
Aggregatzustand	powder
pka	13.99±0.10(Predicted)
Farbe	white to beige
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

Gefahreninformationscode (GHS)

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
PRIMA-1MET?(5291-32-7) reactivates mutant p53, an important tumor suppressor gene, in cancer cells.1?It induces p53-dependent mitochondrial apoptosis?via?activation of caspase-2.2?PRIMA-1MET?showed significant antitumor activity in multiple myeloma?via?activation of p733?and had previously been shown to target p53 family members p63 and p734. Tumor cell death by PRIMA-1MET?has been also shown to be caused by glutathione depletion and induced ROS production in a p53 independent manner.5-7?PRIMA-1MET?probably induces tumor cell death by both reactivating mutant p53 and inhibiting cellular thiol-dependent redox systems.8
Verwenden
2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one is a small molecule that has shown promising preclinical activity in various cancer types. 2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one shows antitumor activity in multiple myeloma by induction of p73 and Noxa.
Biochem/physiol Actions
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.
Lager
Store at +4°C
Einzelnachweise
1) Bykov?et al.?(2005),?PRIMA-1MET?synergizes with cisplatin to induce tumor cell apoptosis;?Oncogene?24?3484 2) Shen?et al.?(2008),?PRIMA-1MET induces mitochondrial apoptosis through activation of caspase-2; Oncogene?27?6571 3) Saha?et al.?(2013),?PRIMA-1MET/APR-246 displays high antitumor in multiple myeloma by induction of p73 and Noxa; Mol. Cancer Ther.?12?2331 4) Rokaeus?et al.?(2010),?PRIMA-1(MET)/APR-246 targets mutant forms of p53 family members p63 and p73; Oncogene?29?6442 5) Tessoulin?et al.?(2014),?PRIMA-1Met induces myeloma cell death independent of p53 by impairing GSH/ROS balance; Blood?124?1626 6) Liu?et al.?(2017),?Inhibiting the system xc-/glutathione axis selectively targets cancers with mutant-p53 accumulation; Nat. Commun.?28?14844 7) Synnott?et al.?(2018),?The Mutant p53-Targeting Compound APR-246 Induces ROS-modulating Genes in Breast Cancer Cells; Transl. Oncol.?11?1343 8) Haffo?et al.?(2018),?Inhibition of the glutaredoxin and thioredoxin systems and ribonucleotide reductase by mutant p53-targeting compound APR-246; Oncogene?24?3484

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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