Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers

• Published in: Molecules (Basel, Switzerland) Vol. 23; no. 2; p. 266
• Main Authors: Huang, Yu, Wu, Chun-Xia, Song, Yu, Huang, Min, Tian, Da-Nian, Yang, Xin-Bin, Fan, Yan-Ru
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 29.01.2018; MDPI
• Subjects: Binding; bis-naphthalimide derivatives; Cytotoxicity; Deoxyribonucleic acid; DNA; DNA binding; DNA biosynthesis; Ethylenediamine; Lysine; Titration; Viscosity; DNA binding; cytotoxicity; bis-naphthalimide derivatives
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23020266

A series of bis-naphthalimide derivatives with different diamine linkers were designed and synthesized. All of the synthesized bis-naphthalimide derivatives were characterized by NMR and HRMS spectra. The binding ability between the compounds and CT DNA was evaluated by using UV-Vis titration experiments. The bis-naphthalimide compound with an ethylenediamine linker showed the largest binding constant with CT DNA. Hence, it was used as the model compound to study the DNA binding selectivity by UV-Vis titration aiming at different DNA duplexes. As a result, this compound showed binding preference to AT-rich duplexes. The DNA binding modes of the compounds were also measured by viscosity titration. The cytotoxicity of the compounds was evaluated by MTT assay. Compounds with 1,6-diaminohexane or 1,4-phenylenedimethanamine linkers showed higher cytotoxicity compared with other bis-naphthalimide derivatives.