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Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero‐Arylidene‐9(10 H )‐Anthrone
Author(s) -
Peixoto Daniela,
Figueiredo Margarida,
Malta Gabriela,
RomaRodrigues Catarina,
Baptista Pedro V.,
Fernandes Alexandra R.,
Barroso Sónia,
Carvalho Ana Luísa,
Afonso Carlos A. M.,
Ferreira Luisa M.,
Branco Paula S.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701500
Subject(s) - chemistry , cytotoxicity , dna , intercalation (chemistry) , anthrone , iodide , quenching (fluorescence) , binding constant , stereochemistry , fluorescence , in vitro , cell culture , doxorubicin , biochemistry , binding site , organic chemistry , medicine , physics , surgery , chemotherapy , quantum mechanics , biology , genetics
A new and never before reported hetero‐arylidene‐9(10 H )‐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 [ K b = 2.0 (±0.20) × 10 5 m –1 ], which is 10 × higher than that described for doxorubicin [ K b = 3.2 (±0.23) × 10 4 m –1 ]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT‐DNA system with a quenching constant ( K SV ) of 3.3 (±0.3) × 10 3 m –1 calculated by the Stern–Volmer equation.