Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

P0069

Sigma-Aldrich

PRIMA-1

≥98% (HPLC), solid

Synonym(s):

2,2-Bishydroxymethyl-1-aza-bicyclo[2.2.2]octan-3-one

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C9H15NO3
CAS Number:
Molecular Weight:
185.22
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

OCC1(CO)N2CC[C@@H](CC2)C1=O

InChI

1S/C9H15NO3/c11-5-9(6-12)8(13)7-1-3-10(9)4-2-7/h7,11-12H,1-6H2

InChI key

RFBVBRVVOPAAFS-UHFFFAOYSA-N

General description

P53-dependent reactivation and induction of massive apoptosis (PRIMA-1) is a low molecular weight compound and has a role in cancer therapy. PRIMA-1 stimulates cytotoxic effects in human cancer cells. It induces eryptosis.

Biochem/physiol Actions

PRIMA-1 is a selective re-activator of mutant p53 activity in tumor cells, and an inducer of apoptosis and inhibitor of growth of human tumors with mutant p53. Mutations in the tumor suppressor p53 take place in >50% tumor cells. PRIMA-1 selectively restores sequence-specific DNA binding and transactivational activity to mutant p53 proteins at μM concentrations. PRIMA-1 works as a re-activator of the apoptotic function of mutant p53 via conformational modulation of function-specific epitopes.

pictograms

Health hazardExclamation mark

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Effects of PRIMA-1 on chronic lymphocytic leukaemia cells with and without hemizygous p53 deletion
Nahi H, et al.
British Journal of Haematology, 127(3), 285-291 (2004)
Masashi Idogawa et al.
Oncotarget, 5(17), 7540-7548 (2014-10-04)
p53 transduction is a potentially effective cancer therapy but does not result in a good therapeutic response in all human cancers due to resistance to apoptosis. To discover factors that overcome resistance to p53-induced apoptosis, we attempted to identify RNAi
Stimulation of suicidal erythrocyte death by PRIMA-1
Faggio C, et al.
Cellular Physiology and Biochemistry, 35(2), 529-540 (2015)
Joana Soares et al.
Oncotarget, 7(4), 4326-4343 (2016-01-07)
Restoration of the p53 pathway, namely by reactivation of mutant (mut) p53, represents a valuable anticancer strategy. Herein, we report the identification of the enantiopure tryptophanol-derived oxazoloisoindolinone SLMP53-1 as a novel reactivator of wild-type (wt) and mut p53, using a
PRIMA-1 as a cancer therapy restoring mutant p53: A review
Lewis EJ
Bioscience Horizons, 8 (2015)

Articles

We present an article about how proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service