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DNA binding, anti-tumour activity and reactivity toward cell thiols of acridin-9-ylalkenoic derivatives

Content Provider	Springer Nature Link
Copyright Year	2015
Abstract	In this paper, we describe the synthesis, biochemical properties and biological activity of a series of new 9-substituted acridine derivatives with a reactive alkene moiety: 9-[(E)-2-phenylethenyl] acridine (1) and methyl (2E)-3-(acridin-9-yl)-prop-2-enoate (2). The interaction of derivatives 1 and 2 with calf thymus DNA was investigated using UV-Vis, fluorescence and circular dichroism spectroscopy. The binding constants K were estimated as being in the range of 1.9 to 7.1 × 10$^{5}$ M$^{−1}$, and the percentage of hypochromism was found to be 40–57% (from spectral titration). UV-Vis, fluorescence, and CD measurements indicate that the compounds were effective DNA-intercalating agents. Electrophoretic separation proved that ligands 1 and 2 relaxed topoisomerase I at a concentration of 5 μM. Ester 2 was shown to have a stronger cytostatic effect on leukemia cell line L1210 than alkene 1. The incubation of ligands 1 and 2 with the ovarian carcinoma cell line A2780 confirmed their extensive cytotoxic effects, an effect which was particularly pronounced in the case of ligand 2. Cytotoxicity tests against A2780 cells demonstrate that a conjugate of compound 2 with L-cysteine (3) is less cytotoxic than compound 2, especially at concentrations greater than 10 μM. Graphical Abstract Synthesis and biological activity of a series of novel acridine derivatives (1-3) are described. The interaction of these compounds with DNA indicates that the compounds are effective DNA-intercalating agents. Electrophoretic separation proved that the ligands relaxed topoisomerase I. The incubation of the derivatives with A2780 and L1210 cell lines confirmed their cytotoxic effects.
Starting Page	931
Ending Page	940
Page Count	10
File Format	PDF
ISSN	09743626
Journal	Journal of Chemical Sciences
Volume Number	127
Issue Number	5
e-ISSN	09737103
Language	English
Publisher	Springer India
Publisher Date	2015-07-14
Publisher Institution	Indian Academy of Sciences
Publisher Place	New Delhi
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	DNA binding anti-tumour activity acridin-9-ylalkenoic derivatives, glutathione Chemistry/Food Science
Content Type	Text
Resource Type	Article
Subject	Chemistry

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