5291-32-7 Usage
Uses
Used in Pharmaceutical Industry:
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one is used as an anticancer agent for its ability to reactivate mutant p53 in cancer cells. It is particularly effective in inducing p53-dependent apoptosis and has shown significant antitumor activity in multiple myeloma via activation of p73 and Noxa.
Used in Cancer Research:
In the field of cancer research, 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one is used as a tool to study the mechanisms of p53 reactivation and its role in tumor suppression. This helps in understanding the potential of 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one in developing targeted cancer therapies.
Used in Drug Development:
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one is utilized in drug development for its potential to be formulated into various drug delivery systems. These systems aim to improve the bioavailability, delivery, and therapeutic outcomes of the compound in treating cancer.
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.
References
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
Check Digit Verification of cas no
The CAS Registry Mumber 5291-32-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,9 and 1 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5291-32:
(6*5)+(5*2)+(4*9)+(3*1)+(2*3)+(1*2)=87
87 % 10 = 7
So 5291-32-7 is a valid CAS Registry Number.
5291-32-7Relevant academic research and scientific papers
QUINUCLIDINONE ANALOGUES AS ANTICANCER AGENTS
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Page/Page column 72-74; 83-84; 89-91, (2021/08/13)
The disclosure includes compounds of Formula (I) and Formula(A) wherein R1, R2, R3, m, n, k, and L are defined herein. Also disclosed are methods for treating a neoplastic disease, autoimmune disease, or an inflammatory disorder with these compounds.
