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;2-(Hydroxymethyl)-2-(methoxymethyl)-3-quinuclidinone;2-(Hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one
- CBNumber
- CB52518928
- Molecular Formula
- C10H17NO3
- Formula Weight
- 199.25
- MOL File
- 5291-32-7.mol
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.
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.
N-Bromosuccinimide Price
- Product number
- SML1789
- Product name
- PRIMA-1Met
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $114
- Updated
- 2024/03/01
- Product number
- SML1789
- Product name
- PRIMA-1Met
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $464
- Updated
- 2024/03/01
- Product number
- 9000487
- Product name
- PRIMA-1MET
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $68
- Updated
- 2024/03/01
- Product number
- 9000487
- Product name
- PRIMA-1MET
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $109
- Updated
- 2024/03/01
- Product number
- 9000487
- Product name
- PRIMA-1MET
- Purity
- ≥95%
- Packaging
- 25mg
- Price
- $219
- Updated
- 2024/03/01
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
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View Lastest Price from 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one manufacturers
- 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
- 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