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Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives
Institute for Research in Biomedicine (IRB Barcelona), Baldiri Reixac 10, E-08028 Barcelona, Spain
Institute for Advanced Chemistry of Catalonia (IQAC), CSIC, CIBER-BBN Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Jordi Girona 18, E-08034 Barcelona, Spain
Department of Agro-Food Molecular Sciences (DISMA), University of Milan, Via Celoria 2, 20133 Milan, Italy
* Author to whom correspondence should be addressed.
Received: 8 May 2012; in revised form: 24 May 2012 / Accepted: 4 June 2012 / Published: 8 June 2012
Abstract: Several acridine derivatives were synthesized and their anti-proliferative activity was determined. The most active molecules were derivatives of 5-methylacridine-4-carboxylic acid. The DNA binding properties of the synthesized acridines were analyzed by competitive dialysis and compared with the anti-proliferative activities. While inactive acridine derivatives showed high selectivity for G-quadruplex structures, the most active 5-methylacridine-4-carboxamide derivatives had high affinity for DNA but showed poor specificity. An NMR titration study was performed with the most active 5-methylacridine-4-carboxamide, confirming the high affinity of this compound for both duplex and quadruplex DNAs.
Keywords: acridine; DNA-binding drugs; solid-phase synthesis; G-quadruplex; NMR
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MDPI and ACS Style
Ferreira, R.; Aviñó, A.; Mazzini, S.; Eritja, R. Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives. Molecules 2012, 17, 7067-7082.
Ferreira R, Aviñó A, Mazzini S, Eritja R. Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives. Molecules. 2012; 17(6):7067-7082.
Ferreira, Rubén; Aviñó, Anna; Mazzini, Stefania; Eritja, Ramon. 2012. "Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives." Molecules 17, no. 6: 7067-7082.