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Novel acenaphthopyrazine derivatives as antitumor agents against MCF-7 cells: molecular synthesis, optical properties, and DNA-binding studies

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Abstract

A series of novel acenaphthopyrazine derivatives was synthesized from acenaphthylene-1,2-dione via three steps, including bromination, cyclization, and SNArH reaction. These new compounds exhibited potential antiproliferative activity against MCF-7 cells in vitro, and 3-[2-(dimethylamino)ethylamino]acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile exhibited the highest activity (IC 50 = 4.60 μM). DNA-binding experiments suggested that these derivatives bind to DNA through intercalation with intrinsic binding constants K all above 105 M−1. Optical property studies indicated that these compounds have long emission wavelength (λ em > 560 nm), high quantum yields in toluene (Φf = 0.59 for 3-(morpholin-4-yl)acenaphtho[1,2-b]pyrazine-8,9-dicarbonitrile), and large Stokes shift (ΔS > 130 nm).

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Acknowledgments

We are grateful to the Natural Science Foundation of China (90713030; 20876025) and the National Basic Research Program of China (2009CB724706).

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, PO Box 89, Zhongshan Road 158, Dalian, 116012, China

    Junling Xing, Jingnan Cui, Shuang Wang, Jin Gao & Zhichao Zhang

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  1. Junling Xing
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  2. Jingnan Cui
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  3. Shuang Wang
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Correspondence to Jingnan Cui.

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Xing, J., Cui, J., Wang, S. et al. Novel acenaphthopyrazine derivatives as antitumor agents against MCF-7 cells: molecular synthesis, optical properties, and DNA-binding studies. Monatsh Chem 143, 243–250 (2012). https://doi.org/10.1007/s00706-011-0653-9

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  • DOI: https://doi.org/10.1007/s00706-011-0653-9

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