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Molecules 2012, 17(6), 7067-7082; doi:10.3390/molecules17067067
Article

Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives

1,2
, 1,2
, 3
 and 1,2,*
Received: 8 May 2012; in revised form: 24 May 2012 / Accepted: 4 June 2012 / Published: 8 June 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
Download PDF [395 KB, uploaded 18 June 2014]
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 acridine; DNA-binding drugs; solid-phase synthesis; G-quadruplex; NMR
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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.

Chicago/Turabian Style

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.


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