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Molecules 2012, 17(6), 7067-7082;

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 / Revised: 24 May 2012 / Accepted: 4 June 2012 / Published: 8 June 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
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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. View Full-Text
Keywords: acridine; DNA-binding drugs; solid-phase synthesis; G-quadruplex; NMR acridine; DNA-binding drugs; solid-phase synthesis; G-quadruplex; NMR

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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