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Substituent Effects on Cytotoxic Activity, Spectroscopic Property, and DNA Binding Property of Naphthalimide Derivatives
Author(s) -
Wang KeRang,
Qian Feng,
Sun Qian,
Ma CuiLan,
Rong RuiXue,
Cao ZhiRan,
Wang XiaoMan,
Li XiaoLiu
Publication year - 2016
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12698
Subject(s) - substituent , chemistry , property (philosophy) , dna , cytotoxic t cell , stereochemistry , combinatorial chemistry , biochemistry , in vitro , philosophy , epistemology
A series of novel naphthalimide derivatives NI 1‐5 containing piperazine moieties ( N ‐(2‐hydroxyethyl)piperazine and 1‐piperazinepropanol) and piperidine moieties (4‐piperidinemethanol, 4‐hydroxypiperidine and 4‐piperidineethanol) have been synthesized and evaluated for their cytotoxic activity, spectroscopic property, and DNA binding behaviors. It was found that substituents at the 4‐position remarkably influence the various activities of this series of compound. Compounds NI 3‐5 modified with piperidines exhibited potent cytotoxic activities against Hela, SGC ‐7901, and A549 cells with the IC 50 values from 0.73 μ m to 6.80 μ m , which are better than NI 1‐2 functionalized with piperazines. Compounds NI 1‐2 showed higher binding capacity with Ct‐ DNA than compounds NI 3‐5 based on studies of UV –vis, fluorescence and CD spectra. Furthermore, compounds NI 3‐5 , as DNA intercalators, showed fluorescence enhancement upon binding with Ct‐ DNA . More interestingly, fluorescence imaging studies of compound NI 4 with A549 cells showed that the fluorescence predominantly appeared in the cytoplasm. These results provided a potential application of NI 3‐5 as anticancer therapeutic and cancer cell imaging agents.