PRIMA-1
Synonym(s):2,2-Bis(hydroxymethyl)-1-azabicyclo[2,2,2]octan-3-one, p53 Reactivation and Induction of Massive Apoptosis;2,2-Bishydroxymethyl-1-aza-bicyclo[2.2.2]octan-3-one;PRIMA-1 - CAS 5608-24-2 - Calbiochem
- CAS NO.:5608-24-2
- Empirical Formula: C9H15NO3
- Molecular Weight: 185.22
- MDL number: MFCD19199989
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-09 21:40:10
What is PRIMA-1?
The Uses of PRIMA-1
PRIMA-1 is a reactivator of p53 and inducer of apoptosis.
What are the applications of Application
PRIMA-1 is a reactivator of p53 and inducer of apoptosis
Definition
ChEBI: 2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one is a member of quinuclidines and a cyclic ketone.
Biological Activity
Selectively restores mutant p53 activity in tumor cells via activation of Bax and PUMA. Induces apoptosis and inhibits growth of human tumors with mutant p53.
in vitro
the substantial increase in saos-2-his-273-cells death could be noticed after being treated with 125 μm prima-1 for 48 hours. tunel staining revealed that such tumor-cell death was primarily triggered by apoptosis. prima-1 could also restore the transcriptional transactivation function to mutant p53 in vitro. [2]
in vivo
to assess the effect of prima-1 on human tumor xenografts, mice were inoculated with saos-2-his-273 cells expressing mutant p53. the mice then received prima-1 treatment at intra-tumor does of 20 mg/kg or i.v. doses of 20 and 100 mg/kg twice a day for three days. compared with the control group, the average tumor volume decreased from 555.7 mm3 to 11.7 (100 mg/kg) and 53 (20 mg/kg) mm3 after i.v. injections of prima-1. intra-tumor injections of prima-1 also decreased the average tumor volume to 5.3 mm3. [2]
storage
Store at +4°C
References
[1] bykov v, issaeva n, zache n, shilov a, hultcrantz m, bergman j, selivanova g, wiman kg. reactivation of mutant p53 and induction of apoptosis in human tumor cells by maleimide analogs. j biol chem. 2005 aug; 280(34): 30384–91.
[2] bykov v, issaeva n, shilov a, hultcrantz m, pugacheva e, chumakov p, bergman j, wiman kg, selivanova g. restoration of the tumor suppressor function to mutant p53 by a low-molecular-weight compound. nat med. 2002 mar; 8(3):282-8.
[3] lehmann s, bykov v, ali d, andren o, cherif h, tidefelt u, uggla b, yachnin j, juliusson g, moshfegh a, paul c, wiman kg, andersson po. targeting p53 in vivo: a first-in-human study with p53-targeting compound apr-246 in refractory hematologic malignancies and prostate cancer. j clin oncol. 2012. doi: 10.1200/jco.2011.40.7783.
Properties of PRIMA-1
Melting point: | 146-147 °C |
Boiling point: | 353.7±17.0 °C(Predicted) |
Density | 1.32±0.1 g/cm3(Predicted) |
storage temp. | Inert atmosphere,2-8°C |
solubility | H2O: >10mg/mL |
pka | 13.68±0.10(Predicted) |
form | solid |
color | white to off-white |
Water Solubility | Soluble in water at 10mg/ml |
Sensitive | Light Sensitive |
Safety information for PRIMA-1
Signal word | Danger |
Pictogram(s) |
Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H302:Acute toxicity,oral H334:Sensitisation, respiratory |
Computed Descriptors for PRIMA-1
New Products
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