For research use only. Not for therapeutic Use.
Ametantrone (AM)(Cat.No:I001993) is a synthetic 9,10-anthracenedione bearing two (hydroxyethylamino)ethylamino residues at positions 1 and 4; along with other anthraquinones and anthracyclines, it shares a polycyclic intercalating moiety and charged side chains that stabilize DNA binding. Ametantrone is the second anthracene derivative to enter clinical trials.
| Catalog Number | I001993 |
| CAS Number | 64862-96-0 |
| Synonyms | CI881; NSC196473; NSC 287513; NSC-196473; NSC 287513; ametantrone diacetate.;1,4-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione |
| Molecular Formula | C22H28N4O4 |
| Purity | ≥95% |
| Target | DNA/RNA Synthesis |
| Solubility | Soluble in DMSO, not in water |
| Storage | 0 - 4°Cfor short term (days to weeks), or -20 °C for long term (months). |
| IUPAC Name | 1,4-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione |
| InChI | InChI=1S/C22H28N4O4/c27-13-11-23-7-9-25-17-5-6-18(26-10-8-24-12-14-28)20-19(17)21(29)15-3-1-2-4-16(15)22(20)30/h1-6,23-28H,7-14H2 |
| InChIKey | FFGSXKJJVBXWCY-UHFFFAOYSA-N |
| SMILES | C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)NCCNCCO)NCCNCCO |
| Reference | </br>1:Synthesis and tau RNA binding evaluation of ametantrone-containing ligands. Artigas G, Marchán V.J Org Chem. 2015 Feb 20;80(4):2155-64. doi: 10.1021/jo502661j. Epub 2015 Jan 29. PMID: 25602935 </br>2:Ametantrone-based compounds as potential regulators of Tau pre-mRNA alternative splicing. Artigas G, López-Senín P, González C, Escaja N, Marchán V.Org Biomol Chem. 2015 Jan 14;13(2):452-64. doi: 10.1039/c4ob01925c. Epub 2014 Nov 5. PMID: 25372055 </br>3:Novel ametantrone-amsacrine related hybrids as topoisomerase IIβ poisons and cytotoxic agents. Zagotto G, Gianoncelli A, Sissi C, Marzano C, Gandin V, Pasquale R, Capranico G, Ribaudo G, Palumbo M.Arch Pharm (Weinheim). 2014 Oct;347(10):728-37. doi: 10.1002/ardp.201400111. Epub 2014 Jul 17. PMID: 25042690 </br>4:Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone. Gianoncelli A, Basili S, Scalabrin M, Sosic A, Moro S, Zagotto G, Palumbo M, Gresh N, Gatto B.ChemMedChem. 2010 Jul 5;5(7):1080-91. doi: 10.1002/cmdc.201000106. PMID: 20458714 </br>5:Molecular basis of the low activity of antitumor anthracenediones, mitoxantrone and ametantrone, in oxygen radical generation catalyzed by NADH dehydrogenase. Enzymatic and molecular modelling studies. Tarasiuk J, Mazerski J, Tkaczyk-Gobis K, Borowski E.Eur J Med Chem. 2005 Apr;40(4):321-8. Epub 2004 Dec 15. PMID: 15804531 </br>6:Mitoxantrone and ametantrone induce interstrand cross-links in DNA of tumour cells. Skladanowski A, Konopa J.Br J Cancer. 2000 Apr;82(7):1300-4. PMID: 10755405 Free PMC Article</br>7:Binding of a macrocyclic bisacridine and ametantrone to CGTACG involves similar unusual intercalation platforms. Yang XL, Robinson H, Gao YG, Wang AH.Biochemistry. 2000 Sep 12;39(36):10950-7. PMID: 10998231 </br>8:Ultrastructural nucleolar alterations induced by an ametantrone–poly r(A-U) complex. Jamison JM, Gilloteaux J, Thiry M, Authelet M, Goessens G, Summers JL.Tissue Cell. 1998 Aug;30(4):475-84. PMID: 9787478 </br>9:[The study of the interaction of antineoplastic drugs mitoxantrone and ametantrone with DNA using the analysis of changes in circular dichroism spectra]. Babaian IuS, Sngrian AE, Kazarian RS, Avetisian MG, Sogomonian LR, Garibian DV.Biofizika. 1998 May-Jun;43(3):422-6. Russian. PMID: 9702332 </br>10:The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: molecular dynamics simulations. Mazerski J, Martelli S, Borowski E.Acta Biochim Pol. 1998;45(1):1-11. PMID: 9701490 Free Article |
