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MedKoo Cat#: 527080 | Name: Prima-1
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prima-1 is an inhibitor of the growth of cell lines derived from various human tumor types in a mutant p53-dependent manner. Prima-1 is a metabolite of Eprenetapopt (APR-246) and a potential potent anti-cancer drug. Prima-1 has been previously shown to restore function to the p53 mutants.

Chemical Structure

Prima-1
CAS#5608-24-2

Theoretical Analysis

MedKoo Cat#: 527080

Name: Prima-1

CAS#: 5608-24-2

Chemical Formula: C9H15NO3

Exact Mass: 185.1052

Molecular Weight: 185.22

Elemental Analysis: C, 58.36; H, 8.16; N, 7.56; O, 25.91

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
50mg USD 750.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,850.00 2 Weeks
2g USD 6,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Prima-1; APR 246 metalobite; APR246 metalobite; APR-246 metalobite; PRIMA-1MET metalobite; Eprenetapopt metalobite;
IUPAC/Chemical Name
2,2-Bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one
InChi Key
RFBVBRVVOPAAFS-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H15NO3/c11-5-9(6-12)8(13)7-1-3-10(9)4-2-7/h7,11-12H,1-6H2
SMILES Code
O=C1C(CO)(CO)N2CCC1CC2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
PRIMA-1 (NSC-281668) is a mutant p53 reactivator.
In vitro activity:
This study investigated the effects of PRIMA-1 on cell viability, cell cycle and expression of p53-regulated proteins in PANC-1 and BxPC-3 (mutant TP53), and CAPAN-2 (wild-type TP53) pancreatic cell lines. Treatment with PRIMA-1 selectively induced apoptosis and cell cycle arrest in p53 mutant cells compared to CAPAN-2 cells. The growth suppressive effect of PRIMA-1 was markedly reduced in p53 mutant cell lines transfected with p53 siRNA, supporting the role of mutant p53 in PRIMA-1 induced cell death. Reference: Invest New Drugs. 2014 Oct;32(5):783-94. https://pubmed.ncbi.nlm.nih.gov/24838627/
In vivo activity:
The authors studied chemopreventive effects of p53-modulating agents, namely, CP-31398 and Prima-1, on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung adenoma and adenocarcinoma formation in female A/J mice. 150 or 300 ppm Prima-1 significantly suppressed (P < .0001) lung adenocarcinoma formation by 56% and 62%, respectively, after 17 weeks and 39% and 56%, respectively, after 34 weeks. Importantly, these results suggest that both p53 modulators cause a delay in the progression of adenoma to adenocarcinoma. Reference: Neoplasia. 2013 Sep;15(9):1018-27. https://pubmed.ncbi.nlm.nih.gov/24027427/
Solvent mg/mL mM comments
Solubility
DMSO 39.0 210.56
Ethanol 23.5 126.87
PBS (pH 7.2) 50.0 269.94
Water 51.8 279.88
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 185.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Izetti P, Hautefeuille A, Abujamra AL, de Farias CB, Giacomazzi J, Alemar B, Lenz G, Roesler R, Schwartsmann G, Osvaldt AB, Hainaut P, Ashton-Prolla P. PRIMA-1, a mutant p53 reactivator, induces apoptosis and enhances chemotherapeutic cytotoxicity in pancreatic cancer cell lines. Invest New Drugs. 2014 Oct;32(5):783-94. doi: 10.1007/s10637-014-0090-9. Epub 2014 May 20. PMID: 24838627. 2. Lambert JM, Gorzov P, Veprintsev DB, Söderqvist M, Segerbäck D, Bergman J, Fersht AR, Hainaut P, Wiman KG, Bykov VJ. PRIMA-1 reactivates mutant p53 by covalent binding to the core domain. Cancer Cell. 2009 May 5;15(5):376-88. doi: 10.1016/j.ccr.2009.03.003. PMID: 19411067. 3. Cui B, Yang Q, Guan H, Shi B, Hou P, Ji M. PRIMA-1, a mutant p53 reactivator, restores the sensitivity of TP53 mutant-type thyroid cancer cells to the histone methylation inhibitor 3-Deazaneplanocin A. J Clin Endocrinol Metab. 2014 Jun;99(6):E962-70. doi: 10.1210/jc.2013-3147. Epub 2014 Feb 10. PMID: 24512488. 4. Rao CV, Patlolla JM, Qian L, Zhang Y, Brewer M, Mohammed A, Desai D, Amin S, Lightfoot S, Kopelovich L. Chemopreventive effects of the p53-modulating agents CP-31398 and Prima-1 in tobacco carcinogen-induced lung tumorigenesis in A/J mice. Neoplasia. 2013 Sep;15(9):1018-27. doi: 10.1593/neo.131256. PMID: 24027427; PMCID: PMC3769881.
In vitro protocol:
1. Izetti P, Hautefeuille A, Abujamra AL, de Farias CB, Giacomazzi J, Alemar B, Lenz G, Roesler R, Schwartsmann G, Osvaldt AB, Hainaut P, Ashton-Prolla P. PRIMA-1, a mutant p53 reactivator, induces apoptosis and enhances chemotherapeutic cytotoxicity in pancreatic cancer cell lines. Invest New Drugs. 2014 Oct;32(5):783-94. doi: 10.1007/s10637-014-0090-9. Epub 2014 May 20. PMID: 24838627. 2. Lambert JM, Gorzov P, Veprintsev DB, Söderqvist M, Segerbäck D, Bergman J, Fersht AR, Hainaut P, Wiman KG, Bykov VJ. PRIMA-1 reactivates mutant p53 by covalent binding to the core domain. Cancer Cell. 2009 May 5;15(5):376-88. doi: 10.1016/j.ccr.2009.03.003. PMID: 19411067.
In vivo protocol:
1. Cui B, Yang Q, Guan H, Shi B, Hou P, Ji M. PRIMA-1, a mutant p53 reactivator, restores the sensitivity of TP53 mutant-type thyroid cancer cells to the histone methylation inhibitor 3-Deazaneplanocin A. J Clin Endocrinol Metab. 2014 Jun;99(6):E962-70. doi: 10.1210/jc.2013-3147. Epub 2014 Feb 10. PMID: 24512488. 2. Rao CV, Patlolla JM, Qian L, Zhang Y, Brewer M, Mohammed A, Desai D, Amin S, Lightfoot S, Kopelovich L. Chemopreventive effects of the p53-modulating agents CP-31398 and Prima-1 in tobacco carcinogen-induced lung tumorigenesis in A/J mice. Neoplasia. 2013 Sep;15(9):1018-27. doi: 10.1593/neo.131256. PMID: 24027427; PMCID: PMC3769881.
1: Shukla P, Bera AK, Ghosh A, Kiranmai G, Pati F. Assessment and process optimization of high throughput biofabrication of immunocompetent breast cancer model for drug screening applications. Biofabrication. 2024 Jun 27;16(3). doi: 10.1088/1758-5090/ad586b. PMID: 38876096. 2: Gong K, Lin J, Chen X, Duan Y, Zhang J, Yu J, Wang J, Sun R, Li J, Duan Y. Thermosensitive gel-nano system against esophageal cancer via restoring p53 activity and boosting T-cell immunity. J Control Release. 2024 Jul;371:111-125. doi: 10.1016/j.jconrel.2024.05.040. Epub 2024 May 24. PMID: 38782064. 3: Wang S, Zou Z, Tang Z, Deng J. AMPK/MTOR/TP53 Signaling Pathway Regulation by Calcitonin Gene-Related Peptide Reduces Oxygen-Induced Lung Damage in Neonatal Rats through Autophagy Promotion. Inflammation. 2024 Aug;47(4):1083-1108. doi: 10.1007/s10753-023-01963-7. Epub 2024 Mar 19. PMID: 38502251. 4: Valenti GE, Roveri A, Venerando R, Menichini P, Monti P, Tasso B, Traverso N, Domenicotti C, Marengo B. PTC596-Induced BMI-1 Inhibition Fights Neuroblastoma Multidrug Resistance by Inducing Ferroptosis. Antioxidants (Basel). 2023 Dec 19;13(1):3. doi: 10.3390/antiox13010003. PMID: 38275623; PMCID: PMC10812464. 5: Li XL, Zhou J, Xia CJ, Min H, Lu ZK, Chen ZR. [Corrigendum] PRIMA‑1met induces autophagy in colorectal cancer cells through upregulation of the mTOR/AMPK‑ULK1‑Vps34 signaling cascade. Oncol Rep. 2024 Mar;51(3):44. doi: 10.3892/or.2024.8703. Epub 2024 Jan 19. Erratum for: Oncol Rep. 2021 May;45(5):86. doi: 10.3892/or.2021.8037. PMID: 38240099; PMCID: PMC10831212. 6: Zaza M, Rashed MH, Elrefaey H, Hassan MH, Abo-Salem OM, El-Sayed ESM. PRIMA-1 synergizes olaparib-induced cell death in p53 mutant triple negative human breast cancer cell line via restoring p53 function, arresting cell cycle, and inducing apoptosis. Can J Physiol Pharmacol. 2024 Jan 1;102(1):55-68. doi: 10.1139/cjpp-2023-0031. Epub 2023 Oct 11. PMID: 37818839. 7: Berthy C, Gagnoux-Palacios L, Madrange M, Bodemer C, Cagnard N, Hadj-Rabia S, Petit I, Aberdam D. PRIMA-1MET/APR-246 Can Partially Rescue In Vitro Cell Adhesion of Patient-Derived Junctional Epidermolysis Bullosa Epidermal Cells. J Invest Dermatol. 2024 Mar;144(3):717-719. doi: 10.1016/j.jid.2023.08.021. Epub 2023 Sep 16. PMID: 37722653. 8: Kotob SN, Kelts JL. PRIMA-1MET Does Not Restore Vitamin D Sensitivity to MDA-MB-231 and MDA-MB-468 Triple-Negative Breast Cancer Cells. ACS Omega. 2023 Aug 8;8(33):30500-30507. doi: 10.1021/acsomega.3c03719. PMID: 37636961; PMCID: PMC10448659. 9: Mohammed I, Alhammer AH, Arif IS. The p53 reactivator PRIMA-1MET synergises with 5-fluorouracil to induce apoptosis in pancreatic cancer cells. Invest New Drugs. 2023 Aug;41(4):587-595. doi: 10.1007/s10637-023-01380-5. Epub 2023 Jul 4. PMID: 37402008. 10: Meher RK, Mir SA, Anisetti SS. In silico and in vitro investigation of dual targeting Prima-1MET as precision therapeutic against lungs cancer. J Biomol Struct Dyn. 2024 May;42(8):4169-4184. doi: 10.1080/07391102.2023.2219323. Epub 2023 Jun 5. PMID: 37272907. 11: Paz MM, Ferretti GDS, Martins-Dinis MMC, Ferreira BIS, Faier-Pereira A, Barnoud T, Moreira OC, Silva JL, Cordeiro Y, Rangel LP. PRIMA-1 inhibits Y220C p53 amyloid aggregation and synergizes with cisplatin in hepatocellular carcinoma. Front Mol Biosci. 2023 Apr 10;10:1165132. doi: 10.3389/fmolb.2023.1165132. PMID: 37101558; PMCID: PMC10123287. 12: Magalhaes YT, Boell VK, Cardella GD, Forti FL. Downregulation of the Rho GTPase pathway abrogates resistance to ionizing radiation in wild-type p53 glioblastoma by suppressing DNA repair mechanisms. Cell Death Dis. 2023 Apr 21;14(4):283. doi: 10.1038/s41419-023-05812-1. PMID: 37085490; PMCID: PMC10121706. 13: Adib M, Taghadosi M, Tahmasebi MN, Sharafat Vaziri A, Jamshidi A, Mahmoudi M, Farhadi E. Anti-inflammatory effects of PRIMA-1MET (mutant p53 reactivator) induced by inhibition of nuclear factor-κB on rheumatoid arthritis fibroblast-like synoviocytes. Inflammopharmacology. 2023 Feb;31(1):385-394. doi: 10.1007/s10787-022-01094-9. Epub 2022 Nov 9. PMID: 36350424. 14: Fujihara KM, Zhang BZ, Jackson TD, Ogunkola MO, Nijagal B, Milne JV, Sallman DA, Ang CS, Nikolic I, Kearney CJ, Hogg SJ, Cabalag CS, Sutton VR, Watt S, Fujihara AT, Trapani JA, Simpson KJ, Stojanovski D, Leimkühler S, Haupt S, Phillips WA, Clemons NJ. Eprenetapopt triggers ferroptosis, inhibits NFS1 cysteine desulfurase, and synergizes with serine and glycine dietary restriction. Sci Adv. 2022 Sep 16;8(37):eabm9427. doi: 10.1126/sciadv.abm9427. Epub 2022 Sep 14. PMID: 36103522; PMCID: PMC9473576. 15: Brahme A. Quantifying Cellular Repair, Misrepair and Apoptosis Induced by Boron Ions, Gamma Rays and PRIMA-1 Using the RHR Formulation. Radiat Res. 2022 Sep 1;198(3):271-296. doi: 10.1667/RADE-22-00011.1. PMID: 35834822. 16: Endo M, Nishioka T, Numazaki K, Hasegawa H, Takahashi T, Sugawara S, Tada H. Reactivation of p53 by RITA Induces Apoptosis in Human Oral Squamous Cell Carcinoma Cells. Anticancer Res. 2022 Jun;42(6):2931-2937. doi: 10.21873/anticanres.15775. PMID: 35641264. 17: Oturkar CC, Gandhi N, Rao P, Eng KH, Miller A, Singh PK, Zsiros E, Odunsi KO, Das GM. Estrogen Receptor-Beta2 (ERβ2)-Mutant p53-FOXM1 Axis: A Novel Driver of Proliferation, Chemoresistance, and Disease Progression in High Grade Serous Ovarian Cancer (HGSOC). Cancers (Basel). 2022 Feb 22;14(5):1120. doi: 10.3390/cancers14051120. PMID: 35267428; PMCID: PMC8909529. 18: Amirtharaj F, Venkatesh GH, Wojtas B, Nawafleh HH, Mahmood AS, Nizami ZN, Khan MS, Thiery J, Chouaib S. p53 reactivating small molecule PRIMA‑1MET/APR‑246 regulates genomic instability in MDA‑MB‑231 cells. Oncol Rep. 2022 Apr;47(4):85. doi: 10.3892/or.2022.8296. Epub 2022 Mar 2. PMID: 35234267. 19: de Bakker T, Journe F, Descamps G, Saussez S, Dragan T, Ghanem G, Krayem M, Van Gestel D. Restoring p53 Function in Head and Neck Squamous Cell Carcinoma to Improve Treatments. Front Oncol. 2022 Jan 6;11:799993. doi: 10.3389/fonc.2021.799993. PMID: 35071005; PMCID: PMC8770810. 20: Umans RA, Martin J, Harrigan ME, Patel DC, Chaunsali L, Roshandel A, Iyer K, Powell MD, Oestreich K, Sontheimer H. Transcriptional Regulation of Amino Acid Transport in Glioblastoma Multiforme. Cancers (Basel). 2021 Dec 7;13(24):6169. doi: 10.3390/cancers13246169. PMID: 34944790; PMCID: PMC8699180.