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Synthesis of naphthalimide derivatives with potential anticancer activity, their comparative ds- and G-quadruplex-DNA binding studies and related biological activities

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Abstract

Two new cytotoxic 1,8-naphthalimide derivatives have been synthesized and characterized. Their biological activities as cytotoxicity and antimicrobial activities and inhibitory activities against DNA-polymerase were evaluated. The interactions of compounds with double-stranded- and quadruple-DNA have been studied by UV–Vis, fluorescent intercalator displacement, competition dialysis, circular dichroism and the findings were compared with the parent naphthalimide and the other compounds. The results show that both compounds (1 and 2) and the parent compound NI have strong cytotoxic activities against Beas-2B, MCF-7, HepG2 and MDA-MB-231 cancer cell lines, antimicrobial activities against Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212 and inhibitory activities towards Taq-polymerase and transcriptase. These novel cationic compounds 1 and 2 can stabilize G-quadruplexes DNA according to thermal denaturation experiments, they change the 3D structure of the DNA (see details in CD experiments) and they exhibit different binding affinities for q-DNA and ds-DNA revealed by spectrophotometric titrations and competitive dialysis studies.

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Acknowledgements

We are grateful for the support of Bulent Ecevit University with Grant # 2014-72118496-04.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Zonguldak Bulent Ecevit University, 67100, Zonguldak, Turkey

    Ufuk Yildiz & Burak Coban

  2. Department of Biology, Faculty of Science, Ankara University, 06100, Tandoğan, Ankara, Turkey

    Irfan Kandemir

  3. Department of Microbiology, Faculty of Medicine, Bulent Ecevit University, 67600, Kozlu, Zonguldak, Turkey

    Füsun Cömert

  4. Department of Chemistry, Faculty of Science, Erciyes University, 38030, Melikgazi, Kayseri, Turkey

    Senem Akkoç

  5. Faculty of Pharmacy, Süleyman Demirel University, 32260, Isparta, Turkey

    Senem Akkoç

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  1. Ufuk Yildiz
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Correspondence to Burak Coban.

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Yildiz, U., Kandemir, I., Cömert, F. et al. Synthesis of naphthalimide derivatives with potential anticancer activity, their comparative ds- and G-quadruplex-DNA binding studies and related biological activities. Mol Biol Rep 47, 1563–1572 (2020). https://doi.org/10.1007/s11033-019-05239-y

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  • DOI: https://doi.org/10.1007/s11033-019-05239-y

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