Abstract
In this work, we designed and synthesized two novel 2-nitroimidazole-naphthalimide-derived antitumor agents N-(2-(naphthalimide)ethyl)-2-(2-nitroimidazole)acetamide (D-2) and N-(2-(5-nitro-naphthalimide)ethyl)-2-(2-nitroimidazole)acetamide (D-5). The oxidative damage induced by the interaction between D-2 (D-5) and DNA was investigated by CV and DPV. The efficient electrochemical biosensors were prepared through modifying GCE with calf thymus DNA, poly dA and poly dG, respectively. The redox mechanism of D-2 (D-5) on GCE surface involved the reduction of 2-nitro group on imidazole ring and the oxidation of methylene linked naphthalimide skeleton and 2-nitroimidazole. The results of voltametric evaluation of interaction between antitumor agent and DNA/GCE revealed the oxidative damage of DNA caused by D-2 (D-5). In addition, UV–vis absorption and fluorescence spectra were investigated to further distinguish the interaction mode between D-2 (D-5) and DNA, implying the intercalation mode of D-2 (D-5) toward base pairs of DNA with a high affinity. At last, D-2 and D-5 were proved to have significantly better cell selectivity than mitonafide, the fact indicated that D-2 and D-5 had the potential for becoming lead antitumor agents and eliminating the side effects toward normal cells.
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