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; Pedro V. Baptista; Alexandra R. Fernandes; Sónia Barroso; Ana Luísa Carvalho; Carlos A. M. Afonso; Luisa M. Ferreira; Paula S. Branco

doi:10.1002/ejoc.201701500

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, Pedro V. Baptista, Alexandra R. Fernandes, Sónia Barroso, Ana Luísa Carvalho, Carlos A. M. Afonso, Luisa M. Ferreira, Paula S. Branco

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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) × 10⁵ m^–1], which is 10 × higher than that described for doxorubicin [K_b = 3.2 (±0.23) × 10⁴ 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) × 10³ m^–1 calculated by the Stern–Volmer equation.

Original language	English
Pages (from-to)	545-549
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	4
DOIs	https://doi.org/10.1002/ejoc.201701500 https://doi.org/10.1002/ejoc.201701500
Publication status	Published - 31 Jan 2018

Keywords

Anthracenecarboxaldehyde
Anthrone
Decarbonylation
DNA intercalation
Imidazolium salt

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Peixoto, D., Figueiredo, M., Malta, G., Roma-Rodrigues, C., Baptista, P. V., Fernandes, A. R., Barroso, S., Carvalho, A. L., Afonso, C. A. M., Ferreira, L. M., & Branco, P. S. (2018). Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone. European Journal of Organic Chemistry, 2018(4), 545-549. https://doi.org/10.1002/ejoc.201701500, https://doi.org/10.1002/ejoc.201701500

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. ; Branco, Paula S. / Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 4. pp. 545-549.

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

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.",

keywords = "Anthracenecarboxaldehyde, Anthrone, Decarbonylation, DNA intercalation, Imidazolium salt",

author = "Daniela Peixoto and Margarida Figueiredo and Gabriela Malta and Catarina Roma-Rodrigues and Baptista, {Pedro V.} and Fernandes, {Alexandra R.} and S{\'o}nia Barroso and Carvalho, {Ana Lu{\'i}sa} and Afonso, {Carlos A. M.} and Ferreira, {Luisa M.} and Branco, {Paula S.}",

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Peixoto, D, Figueiredo, M, Malta, G , Roma-Rodrigues, C , Baptista, PV , Fernandes, AR , Barroso, S , Carvalho, AL, Afonso, CAM, Ferreira, LM & Branco, PS 2018, 'Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone', European Journal of Organic Chemistry, vol. 2018, no. 4, pp. 545-549. https://doi.org/10.1002/ejoc.201701500, https://doi.org/10.1002/ejoc.201701500

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.; Branco, Paula S.

In: European Journal of Organic Chemistry, Vol. 2018, No. 4, 31.01.2018, p. 545-549.

Research output: Contribution to journal › Article

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AU - Roma-Rodrigues, Catarina

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AU - Fernandes, Alexandra R.

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AU - Carvalho, Ana Luísa

AU - Afonso, Carlos A. M.

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AU - Branco, Paula S.

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AB - 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.

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KW - Anthrone

KW - Decarbonylation

KW - DNA intercalation

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