Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero‐Arylidene‐9(10H)‐Anthrone

Citation:
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero‐Arylidene‐9(10H)‐Anthrone, Daniela, Peixoto, Margarida Figueiredo, Gabriela Malta, Catarina Roma‐Rodrigues, V. Baptista Pedro, R. Fernandes Alexandra, Sónia Barroso, Luísa Carvalho Ana, M. Afonso Carlos A., M. Ferreira Luisa, and S. Branco Paula , European Journal of Organic ChemistryEuropean Journal of Organic Chemistry, 2018, Volume 2018, Issue 4, p.545 - 549, (2018)

Abstract:

A new and never before reported hetero?arylidene?9(10H)?anthrone structure (4) was unexpectedly isolated on reaction of 1,2?dimethyl?3?ethylimidazolium iodide (2) and 9?anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X?ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT?DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0?(±0.20)???105 m?1], which is 10?? higher than that described for doxorubicin [Kb = 3.2?(±0.23)???104 m?1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed?CT?DNA system with a quenching constant (KSV) of 3.3?(±0.3)???103 m?1 calculated by the Stern?Volmer equation.

Notes:

doi: 10.1002/ejoc.201701500

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