For research use only. Not for therapeutic Use.
Merbarone(CAT: I007959), also known as NSC-109555, is a synthetic compound with antineoplastic properties. It acts as a topoisomerase II inhibitor, specifically targeting the enzyme DNA topoisomerase II, which is involved in DNA replication and repair. By inhibiting this enzyme, merbarone interferes with the DNA replication process and induces DNA damage, leading to cell death in rapidly dividing cancer cells. It has been studied for its potential use in the treatment of various types of cancer, including leukemia and solid tumors.
| Catalog Number | I007959 |
| CAS Number | 97534-21-9 |
| Synonyms | Merbarone; NSC-336628; RLBN-1001; NSC336628; RLBN1001.;5-(N-Phenylcarboxamido)-2-thiobarbituric acid |
| Molecular Formula | C11H9N3O3S |
| Purity | ≥95% |
| Target | Topoisomerase |
| Solubility | Soluble in DMSO |
| Storage | 0 - 4 °C for short term, or -20 °C for long term |
| IUPAC Name | 4,6-dioxo-N-phenyl-2-sulfanylidene-1,3-diazinane-5-carboxamide |
| InChI | InChI=1S/C11H9N3O3S/c15-8(12-6-4-2-1-3-5-6)7-9(16)13-11(18)14-10(7)17/h1-5,7H,(H,12,15)(H2,13,14,16,17,18) |
| InChIKey | JARCFMKMOFFIGZ-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C=C1)NC(=O)C2C(=O)NC(=S)NC2=O |
| Reference | </br>1:Further SAR studies on bicyclic basic merbarone analogues as potent antiproliferative agents. Spallarossa A, Rotolo C, Sissi C, Marson G, Greco ML, Ranise A, La Colla P, Busonera B, Loddo R.Bioorg Med Chem. 2013 Nov 1;21(21):6328-36. doi: 10.1016/j.bmc.2013.08.056. Epub 2013 Sep 6. PMID: 24063907 </br>2:The DNA topoisomerase II catalytic inhibitor merbarone is genotoxic and induces endoreduplication. Pastor N, Domínguez I, Orta ML, Campanella C, Mateos S, Cortés F.Mutat Res. 2012 Oct-Nov;738-739:45-51. doi: 10.1016/j.mrfmmm.2012.07.005. Epub 2012 Aug 15. PMID: 22921906 </br>3:Dominant lethal mutations of topoisomerase II inhibitors etoposide and merbarone in male mice: a mechanistic study. Attia SM.Arch Toxicol. 2012 May;86(5):725-31. doi: 10.1007/s00204-011-0799-6. Epub 2011 Dec 30. PMID: 22207148 </br>4:Differential cell cycle-specificity for chromosomal damage induced by merbarone and etoposide in V79 cells. Wang L, Roy SK, Eastmond DA.Mutat Res. 2007 Mar 1;616(1-2):70-82. Epub 2006 Dec 15. PMID: 17174356 </br>5:Merbarone induces activation of caspase-activated DNase and excision of chromosomal DNA loops from the nuclear matrix. Otake Y, Mims A, Fernandes DJ.Mol Pharmacol. 2006 Apr;69(4):1477-85. Epub 2006 Jan 24. PMID: 16434617 Free Article</br>6:Synthesis and antiproliferative activity of basic thioanalogues of merbarone. Ranise A, Spallarossa A, Schenone S, Bruno O, Bondavalli F, Pani A, Marongiu ME, Mascia V, La Colla P, Loddo R.Bioorg Med Chem. 2003 Jun 12;11(12):2575-89. PMID: 12757725 </br>7:Evidence from studies with intact mammalian cells that merbarone and bis(dioxopiperazine)s are topoisomerase II poisons. Snyder RD.Drug Chem Toxicol. 2003 Feb;26(1):15-22. PMID: 12643037 </br>8:Etoposide and merbarone are clastogenic and aneugenic in the mouse bone marrow micronucleus test complemented by fluorescence in situ hybridization with the mouse minor satellite DNA probe. Attia SM, Kliesch U, Schriever-Schwemmer G, Badary OA, Hamada FM, Adler ID.Environ Mol Mutagen. 2003;41(2):99-103. PMID: 12605378 </br>9:Catalytic inhibitors of topoisomerase II are DNA-damaging agents: induction of chromosomal damage by merbarone and ICRF-187. Wang L, Eastmond DA.Environ Mol Mutagen. 2002;39(4):348-56. PMID: 12112387 </br>10:Merbarone, a catalytic inhibitor of DNA topoisomerase II, induces apoptosis in CEM cells through activation of ICE/CED-3-like protease. Khélifa T, Beck WT.Mol Pharmacol. 1999 Mar;55(3):548-56. PMID: 10051540 Free Article |
