Issue 9, 2013

Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

Abstract

The reaction of phenanthrene-9,10-dione with N-phenylbenzene-1,2-diamine in methanol in the presence of anhydrous CuCl2 and HCl affords a 9-phenyldibenzo[a,c]phenazin-9-ium cation, [1]+, as in [1][CuCl2], in good yields. The reaction of [1][CuCl2] in methanol with excess iodide salt affords [1][I]. The formations of [1][CuCl2] and [1][I] have been confirmed by elemental analyses, mass, IR, UV-vis and 1H NMR spectra including the single crystal X-ray structure determination of [1][CuCl2]. DNA binding studies by UV-vis spectra, fluorescence spectra, circular dichroism spectra, hydrodynamic, isothermal titration calorimetric (ITC), UV optical melting and gel electrophoresis experiments have substantiated that [1]+, like ethidium bromide, is a strong DNA intercalator.

Graphical abstract: Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2012
Accepted
20 Dec 2012
First published
20 Dec 2012

RSC Adv., 2013,3, 3054-3061

Synthesis, structure and DNA binding studies of 9-phenyldibenzo[a,c] phenazin-9-ium

S. Kundu, M. K. Biswas, A. Banerjee, K. Bhadra, G. S. Kumar, M. G. B. Drew, R. Bhadra and P. Ghosh, RSC Adv., 2013, 3, 3054 DOI: 10.1039/C2RA22317A

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