Investigations on Photoinduced Interaction of 9-Aminoacridine with Certain Catechols and Rutin

Abstract

The fluorescence quenching of 9-aminoacridine by certain biologically important catechols and rutin was investigated using absorption, steady state and time resolved fluorescence measurements. The in vitro-antioxidant activities of the above compounds were studied using deoxyribose degradation assay and nitric oxide scavenging assay. The experimental results showed that the fluorescence of 9-aminoacridine was quenched by quencher molecules via forming ground state complex. The bimolecular quenching rate constant k(q), binding constant (K) and number of binding sites (n) were calculated at different temperatures from relevant fluorescence data. Static quenching mechanism was supported by lifetime measurement. The free energy change (ΔG(et)) for electron transfer process was calculated by Rehm-Weller equation. The binding distance of 4-nitrocatechol with 9-aminoacridine was obtained according to Forster's non-radiative energy transfer theory. Nature of binding forces and their interactions was probed based on thermodynamic parameters.

X-ray Structures of Target–Ligand Complexes Containing Compounds with Assay Interference Potential

“…For example, fluorescent dyes such as the 9-aminoacridine derivative shown in Figure a are potent DNA intercalating agents that can act as topoisomerase inhibitors and mutagenic agents . While the X-ray structure of its complex with DNA validates the contribution of the chromophoric acridine moiety to DNA intercalation, there is no doubt that photoinduction of 9-aminoacridines can cause false-positive signals in photometric and fluorometric assays …”

“…39 While the X-ray structure of its complex with DNA validates the contribution of the chromophoric acridine moiety to DNA intercalation, there is no doubt that photoinduction of 9-aminoacridines can cause false-positive signals in photometric and fluorometric assays. 40 Catechols represent another prime PAINS motif that is not only present in synthetic compounds but also widely distributed among natural products. 41 The tendency of catechols to chelate metals, their redox activity, and reactivity against nucleophiles in oxidized form cause frequent assay artifacts.…”

Effects of rutin on acrylamide-induced neurotoxicity

“…Rutin and catechol-compounds are electron donors, and antioxidant activities of rutin and catechol and its derivatives indicate that they are potential antioxidants [34,35]. It seems that the protective effect of rutin in this model may be at least, in part, due to suppression of ROS generation because rutin has exhibited antioxidant effect in different studies [36].…”

The Potential for Plant Derivatives against Acrylamide Neurotoxicity

“…There was also a significant reduction in lipid peroxidation in all animals treated with rutin. Rutin has been established to possess antioxidant activity in several studies (La Casa et al, 2000;Kamalakkannan and Prince, 2006;Anbazhagan et al, 2008;Manivannan et al, 2012;Becker et al, 2007), and scavenging of free radicals and prevention of lipid peroxidation have indeed been reported to be the main effects of rutin (Khan et al, 2009).…”