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P0069

Sigma-Aldrich

PRIMA-1

≥98% (HPLC), solid

Synonym(s):

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

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$105.00
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$414.00

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5 MG
$105.00
25 MG
$414.00

About This Item

Empirical Formula (Hill Notation):
C9H15NO3
CAS Number:
5608-24-2
Molecular Weight:
185.22
MDL number:
MFCD04974196
UNSPSC Code:
12352200
PubChem Substance ID:
329820004
NACRES:
NA.77

$105.00

Available to ship onApril 29, 2025Details

Request a Bulk Order

Quality Level

100

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.[1][2] PRIMA-1 stimulates cytotoxic effects in human cancer cells.[2] It induces eryptosis.[3]

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.
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
GHS08,GHS07

signalword

Danger

hcodes

H302,H334

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000277200
0000277200
100M4614V
078K46124
078K46123

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Federica Eduati et al.
Molecular systems biology, 16(2), e8664-e8664 (2020-02-20)
Mechanistic modeling of signaling pathways mediating patient-specific response to therapy can help to unveil resistance mechanisms and improve therapeutic strategies. Yet, creating such models for patients, in particular for solid malignancies, is challenging. A major hurdle to build these models
PRIMA-1 as a cancer therapy restoring mutant p53: A review
Lewis EJ
Bioscience Horizons, 8 (2015)
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)
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)
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