2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one
![2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Structure](CAS/GIF/5291-32-7.gif)
- 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
- Molecular Weight:
- 199.25
- MDL Number:
- MFCD20620963
- MOL File:
- 5291-32-7.mol
- MSDS File:
- SDS
| 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. |
| FDA UNII | Z41TGB4080 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319 |
| Precautionary statements | P305+P351+P338 |
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one price More Price(28)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML1789 | PRIMA-1Met ≥98% (HPLC) | 5291-32-7 | 5mg | $114 | 2024-03-01 | Buy |
| Sigma-Aldrich | SML1789 | PRIMA-1Met ≥98% (HPLC) | 5291-32-7 | 25mg | $464 | 2024-03-01 | Buy |
| Cayman Chemical | 9000487 | PRIMA-1MET ≥95% | 5291-32-7 | 5mg | $68 | 2024-03-01 | Buy |
| Cayman Chemical | 9000487 | PRIMA-1MET ≥95% | 5291-32-7 | 10mg | $109 | 2024-03-01 | Buy |
| Cayman Chemical | 9000487 | PRIMA-1MET ≥95% | 5291-32-7 | 25mg | $219 | 2024-03-01 | Buy |
2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Chemical Properties,Uses,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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hubei XinRunde Chemical Co., Ltd. | +8615102730682 | bruce@xrdchem.cn | CHINA | 566 | 55 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| Career Henan Chemica Co | +86-0371-86658258 15093356674; | laboratory@coreychem.com | China | 30255 | 58 |
| Chemia Biotechnology（Shanghai） Co., Ltd | +8613816753574 | info@chemia-pharm.com | CHINA | 311 | 58 |
| Zhejiang J&C Biological Technology Co.,Limited | +1-2135480471 +1-2135480471 | sales@sarms4muscle.com | China | 10523 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| Nantong HI-FUTURE Biology Co., Ltd. | +undefined18051384581 | sales@chemhifuture.com | China | 3136 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 | support@targetmol.com | United States | 19973 | 58 |
| Wuhan Topule Biopharmaceutical Co., Ltd | +8618327326525 | masar@topule.com | China | 8474 | 58 |
| Aladdin Scientific | +1-833-552-7181 | sales@aladdinsci.com | United States | 57511 | 58 |
View Lastest Price from 2-(Hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2021-07-02 | APR-246 (PRIMA-1MET)
5291-32-7
|
US $15.00-10.00 / KG | 1KG | 99%+ HPLC | Monthly supply of 1 ton | Zhuozhou Wenxi import and Export Co., Ltd | |
 |
2019-01-15 | APR-246 (PRIMA-1MET)
5291-32-7
|
US $10.00 / KG | 10KG | 99 | 10MT | Hubei XinRunde Chemical Co., Ltd. |
-
- APR-246 (PRIMA-1MET)
5291-32-7
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd
-
- APR-246 (PRIMA-1MET)
5291-32-7
- US $10.00 / KG
- 99
- Hubei XinRunde Chemical Co., Ltd.