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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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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
Pricing and availability is not currently available.

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

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1 of 4

This Item
04733W246905PHL80715
Acetyleugenol phyproof® Reference Substance

PHL82460

Acetyleugenol

Acetyleugenol analytical standard

04733

Acetyleugenol

Eugenyl acetate ≥98%, FCC, FG

W246905

Eugenyl acetate

Eugenol phyproof® Reference Substance

PHL80715

Eugenol

grade

primary reference standard

grade

analytical standard

grade

FG, Fragrance grade, Halal, Kosher

grade

primary reference standard

product line

phyproof® Reference Substance

product line

-

product line

-

product line

phyproof® Reference Substance

assay

≥90.0% (GC)

assay

≥98.0% (GC)

assay

≥98%

assay

≥95.0% (GC)

form

liquid

form

-

form

-

form

liquid

manufacturer/tradename

PhytoLab

manufacturer/tradename

-

manufacturer/tradename

-

manufacturer/tradename

PhytoLab

refractive index

n20/D 1.518 (lit.)

refractive index

n20/D 1.517-1.521, n20/D 1.518 (lit.)

refractive index

n20/D 1.518 (lit.)

refractive index

n20/D 1.541 (lit.)

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
100M4614V
078K46124
078K46123
078K46122
078K46121

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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)
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Articles

Oncogenes and Tumor Suppressors Reprogram Metabolism

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

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