Abstract
The in situ DNA-damaging capacity of berenil (1) has been investigated usingan electrochemical approach employing double stranded (ds) DNA-modified glassy carbonelectrode biosensors. Electrochemical voltammetric sensing of damage caused by 1 todsDNA was monitored by the appearance of peaks diagnostic of the oxidation of guanineand adenine. When 1 was incorporated directly onto the biosensor surface, DNA damagecould be observed at concentrations of additive as low as 10 μM. In contrast, when thedsDNA-modified biosensor was exposed to 1, in acetate buffer solution, the method wasmuch less sensitive and DNA damage could be detected only in the presence of 100 μMberenil. When mixed solutions of 1 and single stranded (ss) DNA, polyguanylic acid orpolyadenylic acid were submitted to voltammetric study, the oxidation signals of therespective bases decreased in a concentration-dependent manner and the major variation ofthe adenine current peak indicated preferential binding of 1 to adenine. The electrochemical results were in close agreement with those deriving from a differentialscanning calorimetric study of the DNA-berenil complex.
Highlights
Many compounds bind and interact with DNA causing changes in structure and/or base sequence
In cyclic voltammetry (CV) performed on a glassy carbon (GC) electrode, the oxidation of 1 was represented in the anodic sweep by a well-defined, diffusion-controlled and irreversible peak Ia located at an EpIa of +0.942 V (Figure 2)
The electrochemical voltammetric sensing of oxidative damage to double stranded DNA (dsDNA) caused by berenil was achieved by monitoring the appearance of a peak diagnostic of guanine (G) oxidation
Summary
Many compounds bind and interact with DNA causing changes in structure and/or base sequence. Intercalation and groove-binding are the two most common modes by which small molecules bind directly and selectively to DNA [1]. Groove-binding, which is predominantly entropically driven, involves covalent or non-covalent (electrostatic) interactions that do not perturb the duplex structure to any great extent [5]. Groove-binders are typically crescent-shaped, and fit snugly into the minor groove with little distortion of the DNA structure. It has been suggested, that some DNA-binding drugs, especially those classified as minor groove-binders, may exhibit mixed binding modes [6,7,8,9], and that the anticancer efficacy of such drugs may be linked to this ability [10,11]
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