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

ChemicalBook > CAS DataBase List > 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

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

Product Name: 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
CAS No.: 5291-32-7
Chemical Name: 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
Synonyms: PRIMA-1MET;APR-246;Eprenetapopt;APR246;APR 246;PRIMA-1MET(APR-246);APR-246 (PRIMA-1MET);Eprenetapopt (APR246;PRIMA-1MET;PRIMA-1MET, p53 activity;Eprenetapopt, 10 mM in DMSO
CBNumber: CB52518928
Molecular Formula: C10H17NO3
Formula Weight: 199.25
MOL File: 5291-32-7.mol

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

Melting point:: 115-116 °C
Boiling point:: 313.8±17.0 °C(Predicted)
Density: 1.20±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: Soluble in DMSO (up to 20 mg/ml)
form: powder
pka: 13.99±0.10(Predicted)
color: white to beige
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML1789
Product name: PRIMA-1Met
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $114
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML1789
Product name: PRIMA-1Met
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $464
Updated: 2024/03/01

Cayman Chemical

Product number: 9000487
Product name: PRIMA-1MET
Purity: ≥95%
Packaging: 5mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 9000487
Product name: PRIMA-1MET
Purity: ≥95%
Packaging: 10mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 9000487
Product name: PRIMA-1MET
Purity: ≥95%
Packaging: 25mg
Price: $219
Updated: 2024/03/01

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2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Chemical Properties,Usage,Production

Description

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

Uses

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.

storage

Store at +4°C

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

2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: APR-246 (PRIMA-1MET) 5291-32-7
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

Hubei XinRunde Chemical Co., Ltd.

Product: APR-246 (PRIMA-1MET) 5291-32-7
Price: US $10.00/KG
Min. Order: 10KG
Purity: 99
Supply Ability: 10MT
Release date: 2018-06-19

5291-32-7, 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-oneRelated Search:

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

PRIMA-1MET

APR-246

PRIMA-1<sup>MET</sup>

APR-246 (PRIMA-1MET)

PRIMA-1MET(APR-246)

APR246;APR 246

PRIMA-1MET 2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one APR-246

2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one

1-Azabicyclo[2.2.2]octan-3-one, 2-(hydroxymethyl)-2-(methoxymethyl)-

2-(Hydroxymethyl)-2-(methoxymethyl)-3-quinuclidinone

Eprenetapopt

Eprenetapopt (APR246

PRIMA-1MET, p53 activity

Eprenetapopt, 10 mM in DMSO

5291-32-7