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PRIMA-1

CAS No.:
5608-24-2
Catalog Number:
AG00D7Z8
Molecular Formula:
C9H15NO3
Molecular Weight:
185.2203
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$76
- +
5mg
≥95%
1 week
United States
$135
- +
10mg
98%
1 week
United States
$173
- +
25mg
98%
1 week
United States
$307
- +
50mg
98%
1 week
United States
$423
- +
100mg
98%
1 week
United States
$723
- +
200mg
98%
1 week
United States
$1257
- +
Product Description
Catalog Number:
AG00D7Z8
Chemical Name:
PRIMA-1
CAS Number:
5608-24-2
Molecular Formula:
C9H15NO3
Molecular Weight:
185.2203
MDL Number:
MFCD04974196
IUPAC Name:
2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one
InChI:
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
SMILES:
OCC1(CO)N2CCC(C1=O)CC2
UNII:
GHC34M30BG
NSC Number:
281668
Properties
Complexity:
217  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
185.105g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
185.223g/mol
Monoisotopic Mass:
185.105g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
60.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.6  
Literature
Title Journal
Reactivation of p53 mutants by prima-1 [corrected] in thyroid cancer cells. International journal of cancer 20120515
Transient transfection of a wild-type p53 gene triggers resveratrol-induced apoptosis in cancer cells. PloS one 20120101
Curcumin, but not Prima-1, decreased tumor cell proliferation in the syngeneic murine orthotopic bladder tumor model. Clinics (Sao Paulo, Brazil) 20111201
An inverse docking approach for identifying new potential anti-cancer targets. Journal of molecular graphics & modelling 20110401
APR-246 exhibits anti-leukemic activity and synergism with conventional chemotherapeutic drugs in acute myeloid leukemia cells. European journal of haematology 20110301
Targeting mutant p53 protein and the tumor vasculature: an effective combination therapy for advanced breast tumors. Breast cancer research and treatment 20110101
p53-Reactivating small molecules induce apoptosis and enhance chemotherapeutic cytotoxicity in head and neck squamous cell carcinoma. Oral oncology 20110101
E6 and E7 proteins from different beta-papillomaviruses types do not interfere in UVB-induced apoptosis of HaCaT keratinocytes. Experimental dermatology 20110101
PRIMA-1 cytotoxicity correlates with nucleolar localization and degradation of mutant p53 in breast cancer cells. Biochemical and biophysical research communications 20101112
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
A molecular signature of normal breast epithelial and stromal cells from Li-Fraumeni syndrome mutation carriers. Oncotarget 20101001
Pharmacological reactivation of mutant p53: from protein structure to the cancer patient. Oncogene 20100729
The p53 tumor suppressor: a master regulator of diverse cellular processes and therapeutic target in cancer. Biochemical and biophysical research communications 20100521
PRIMA-1 inhibits growth of breast cancer cells by re-activating mutant p53 protein. International journal of oncology 20091101
PRIMA-1 reactivates mutant p53 by covalent binding to the core domain. Cancer cell 20090505
Regression of progestin-accelerated 7,12-dimethylbenz[a]anthracene-induced mammary tumors in Sprague-Dawley rats by p53 reactivation and induction of massive apoptosis: a pilot study. Endocrine-related cancer 20090301
PRIMA-1MET induces mitochondrial apoptosis through activation of caspase-2. Oncogene 20081120
PRIMA-1 synergizes with adriamycin to induce cell death in non-small cell lung cancer cells. Journal of cellular biochemistry 20080815
In vitro and in vivo cytotoxic effects of PRIMA-1 on hepatocellular carcinoma cells expressing mutant p53ser249. Carcinogenesis 20080701
A novel p53 rescue compound induces p53-dependent growth arrest and sensitises glioma cells to Apo2L/TRAIL-induced apoptosis. Cell death and differentiation 20080401
PRIMA-1(met) radiosensitizes prostate cancer cells independent of their MTp53-status. Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20080301
Restoration of p53 to limit tumor growth. Current opinion in oncology 20080101
PRIMA-1MET inhibits growth of mouse tumors carrying mutant p53. Cellular oncology : the official journal of the International Society for Cellular Oncology 20080101
Progestin-dependent progression of human breast tumor xenografts: a novel model for evaluating antitumor therapeutics. Cancer research 20071015
Re-activation of the p53 pathway inhibits in vivo and in vitro growth of hormone-dependent human breast cancer cells. International journal of oncology 20071001
PRIMA-1(MET) induces nucleolar accumulation of mutant p53 and PML nuclear body-associated proteins. Oncogene 20070215
PRIMA-1 induces apoptosis by inhibiting JNK signaling but promoting the activation of Bax. Biochemical and biophysical research communications 20070105
Expression proteomics to p53 mutation reactivation with PRIMA-1 in breast cancer cells. Biochemical and biophysical research communications 20061027
Dissecting p53-dependent apoptosis. Cell death and differentiation 20060601
Strategies for therapeutic targeting of the p53 pathway in cancer. Cell death and differentiation 20060601
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
PRIMA-1 induces apoptosis in acute myeloid leukaemia cells with p53 gene deletion. British journal of haematology 20060101
Effects of PRIMA-1 on wild-type L1210 cells expressing mutant p53 and drug-resistant L1210 cells lacking expression of p53: necrosis vs. apoptosis. Anticancer research 20060101
Selective induction of apoptosis in mutant p53 premalignant and malignant cancer cells by PRIMA-1 through the c-Jun-NH2-kinase pathway. Molecular cancer therapeutics 20050601
A new family of small molecules to probe the reactivation of mutant p53. Journal of the American Chemical Society 20050504
p53-dependent inhibition of progestin-induced VEGF expression in human breast cancer cells. The Journal of steroid biochemistry and molecular biology 20050201
Proteomic identification of heat shock protein 90 as a candidate target for p53 mutation reactivation by PRIMA-1 in breast cancer cells. Breast cancer research : BCR 20050101
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis. Bioorganic & medicinal chemistry letters 20041115
Effects of PRIMA-1 on chronic lymphocytic leukaemia cells with and without hemizygous p53 deletion. British journal of haematology 20041101
Targeting p53 by PTD-mediated transduction. Trends in biotechnology 20040901
[Tumor suppressor gene p53 and molecular targeting therapy]. Gan to kagaku ryoho. Cancer & chemotherapy 20040901
Pharmacologic activation of p53 elicits Bax-dependent apoptosis in the absence of transcription. Cancer cell 20031101
Small molecules that reactivate mutant p53. European journal of cancer (Oxford, England : 1990) 20030901
Restoring p53-dependent tumor suppression. Cancer biology & therapy 20030101
Mutant p53-dependent growth suppression distinguishes PRIMA-1 from known anticancer drugs: a statistical analysis of information in the National Cancer Institute database. Carcinogenesis 20021201
Restoration of the tumor suppressor function to mutant p53 by a low-molecular-weight compound. Nature medicine 20020301
Properties