Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers
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 experi...
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| Format: | Article |
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MDPI AG
2018-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/2/266 |
| _version_ | 1818981387685855232 |
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| author | Yu Huang Chun-Xia Wu Yu Song Min Huang Da-Nian Tian Xin-Bin Yang Yan-Ru Fan |
| author_facet | Yu Huang Chun-Xia Wu Yu Song Min Huang Da-Nian Tian Xin-Bin Yang Yan-Ru Fan |
| author_sort | Yu Huang |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-20T17:30:31Z |
| format | Article |
| id | doaj.art-2e5babafa4e344cab4f1b02628850289 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-20T17:30:31Z |
| publishDate | 2018-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2e5babafa4e344cab4f1b026288502892022-12-21T19:31:25ZengMDPI AGMolecules1420-30492018-01-0123226610.3390/molecules23020266molecules23020266Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine LinkersYu Huang0Chun-Xia Wu1Yu Song2Min Huang3Da-Nian Tian4Xin-Bin Yang5Yan-Ru Fan6Key Laboratory of Hui Ethnic Medicine Modernization, Ministry of Education, Ningxia Engineering and Technology Research Centre of Hui Medicine Modernization, College of Pharmacy, Ningxia Medical University, Yinchuan 750004, ChinaKey Laboratory of Hui Ethnic Medicine Modernization, Ministry of Education, Ningxia Engineering and Technology Research Centre of Hui Medicine Modernization, College of Pharmacy, Ningxia Medical University, Yinchuan 750004, ChinaKey Laboratory of Hui Ethnic Medicine Modernization, Ministry of Education, Ningxia Engineering and Technology Research Centre of Hui Medicine Modernization, College of Pharmacy, Ningxia Medical University, Yinchuan 750004, ChinaCollege of Public Health, Ningxia Medical University, Yinchuan 750004, ChinaCollege of Public Health, Ningxia Medical University, Yinchuan 750004, ChinaRongchang Campus, Southwest University, Chongqing 402460, ChinaKey Laboratory of Hui Ethnic Medicine Modernization, Ministry of Education, Ningxia Engineering and Technology Research Centre of Hui Medicine Modernization, College of Pharmacy, Ningxia Medical University, Yinchuan 750004, ChinaA 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.http://www.mdpi.com/1420-3049/23/2/266bis-naphthalimide derivativesDNA bindingcytotoxicity |
| spellingShingle | Yu Huang Chun-Xia Wu Yu Song Min Huang Da-Nian Tian Xin-Bin Yang Yan-Ru Fan Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers Molecules bis-naphthalimide derivatives DNA binding cytotoxicity |
| title | Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers |
| title_full | Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers |
| title_fullStr | Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers |
| title_full_unstemmed | Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers |
| title_short | Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers |
| title_sort | synthesis dna binding and anticancer properties of bis naphthalimide derivatives with lysine modified polyamine linkers |
| topic | bis-naphthalimide derivatives DNA binding cytotoxicity |
| url | http://www.mdpi.com/1420-3049/23/2/266 |
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