Citation:

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

info:eu-repo/grantAgreement/FCT/5876/147218/PT# info:eu-repo/grantAgreement/FCT/5876/147258/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/125363/PT# POCI-01-0145- 710-FEDER-007265 POCI-01-0145-FEDER-007728