Publication Type |
Journal Article |
Title |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
Authors |
Daniela Peixoto Margarida Figueiredo Gabriela Malta Catarina Roma-Rodrigues Pedro V. Baptista A.R. Fernandes Sonia Barroso A. L. Carvalho Carlos A. M. Afonso Luisa M. Ferreira Paula S. Branco |
Groups |
|
Journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
Year |
2018 |
Month |
January |
Volume |
|
Number |
4 |
Pages |
545-549 |
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 [K-b = 2.0(+/- 0.20)x10(5) m(-1)], which is 10x higher than that described for doxorubicin [K-b = 3.2(+/- 0.23)x10(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)x10(3) m(-1) calculated by the Stern-Volmer equation. |
DOI |
http://dx.doi.org/10.1002/ejoc.201701500 |
ISBN |
|
Publisher |
|
Book Title |
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ISSN |
1434-193X |
EISSN |
1099-0690 |
Conference Name |
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Bibtex ID |
ISI:000423772600015 |
Observations |
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