Electrochemical investigation of the toxicity of a new nitrocompound and its interaction with β-cyclodextrin and polyamidoamine third-generation

Nitroaromatic compounds are widely used in the pharmaceutical industry for their known biological properties. Electrochemical techniques have proved to be an important tool for the study of the species of radicals from different nitro compounds. One feature of the nitro compound studied here, 2-[(4-nitrophenyl) amino]-4,5,6,7-tetrahydro-4H-benzo [β] thiophene-3-carbonitrile, (6CN10) is its low solubility in water, which explains its combination with substances such as cyclodextrins and PAMAM. Electrochemical experiments were performed in buffered (phosphate pH 7.0 and acetate pH 4.5) and aprotic medium (DMF/TBAP). These studies were performed in the presence and absence of oxygen, in the presence of β-cyclodextrin and with a ds and ssDNA. The results in protic/co-solvent medium demonstrate that 6CN10 exhibits the characteristics of a nitroaromatic. Without the co-solvent, 6CN10 does not present any response. However, with well-marked additions of β-cyclodextrin, peak reduction of the substance was observed. In aprotic medium, the compound exhibits reactivity with O2 at an apparent constant of 0.45 s−1 and its mechanism of action may be associated the ability to generate oxidative stress. 6CN10 interact with DNA. By spectroscopy and electrochemistry experiments, 6CN10 was found to form inclusion complexes with β-cyclodextrin and PAMAM and apparent formation constants were obtained.

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