Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study
Three 2-arylpiperidinyl-1,4-naphthoquinone derivatives were synthesized and evaluated in vitro to determine their cytotoxicity on cancer and normal cell lines. In order to establish their possible action mechanism, the electrochemical behaviour of these quinones was examined using cyclic voltammetry...
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doaj-e105db318c7f4ac2a62a8a2aff7d4c4f2020-11-25T01:43:54ZengElsevierArabian Journal of Chemistry1878-53522020-01-0113122332244Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational studyChristian Espinosa-Bustos0Camila Canales1Galo Ramírez2Pablo Jaque3Cristian O. Salas4Departmento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, Chile; Corresponding authors at: Departmento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, Chile.Departmento de Química Inorgánica, Facultad de Química, Pontificia Universidad Católica de ChileDepartmento de Química Inorgánica, Facultad de Química, Pontificia Universidad Católica de ChileDepartamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. República 275, Santiago, Chile; Nucleus Millennium of Chemical Processes and Catalysis, Faculty of Chemistry, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, ChileDepartmento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, Chile; Nucleus Millennium of Chemical Processes and Catalysis, Faculty of Chemistry, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, Chile; Corresponding authors at: Departmento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Avenida Vicuña Mackenna, 4860, Santiago, 702843, Chile.Three 2-arylpiperidinyl-1,4-naphthoquinone derivatives were synthesized and evaluated in vitro to determine their cytotoxicity on cancer and normal cell lines. In order to establish their possible action mechanism, the electrochemical behaviour of these quinones was examined using cyclic voltammetry (CV) as technique by using a three-electrode setup: a glassy carbon, Ag/AgCl (in 3 M KCl), and platinum wire as working, reference, and counter electrodes, respectively. Kinetic studies were done to determine the control of the reduction reaction and the number of transferred electrons in the process. Furthermore, the addition of dsDNA to the quinone solutions allowed for the observation of an interaction between each quinone and dsDNA as the current-peaks became lower in presence of dsDNA. Otherwise, motivated to support the aforementioned results, electronic structure calculations at the TPSS-D3/6-31+G(d,p) level of theory were carried out in order to find the most favourable noncovalently bonded complexes between quinones and DNA. Noncovalent complexes formed between DNA and 2-arylpiperidinyl-1,4-naphthoquinones and stabilized by π-stacking interactions along with the well-known hydrogen-bonded complexes were found, with the former being more stable than the latter. These results suggest that the intercalation of these quinone derivatives in DNA is the most likely action mechanism. Keywords: Naphthoquinone derivatives, Cytotoxicity, DNA interaction, Electrochemistry, Computational studyhttp://www.sciencedirect.com/science/article/pii/S1878535218300893 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Christian Espinosa-Bustos Camila Canales Galo Ramírez Pablo Jaque Cristian O. Salas |
spellingShingle |
Christian Espinosa-Bustos Camila Canales Galo Ramírez Pablo Jaque Cristian O. Salas Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study Arabian Journal of Chemistry |
author_facet |
Christian Espinosa-Bustos Camila Canales Galo Ramírez Pablo Jaque Cristian O. Salas |
author_sort |
Christian Espinosa-Bustos |
title |
Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study |
title_short |
Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study |
title_full |
Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study |
title_fullStr |
Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study |
title_full_unstemmed |
Unveiling interactions between DNA and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: A combined electrochemical and computational study |
title_sort |
unveiling interactions between dna and cytotoxic 2-arylpiperidinyl-1,4-naphthoquinone derivatives: a combined electrochemical and computational study |
publisher |
Elsevier |
series |
Arabian Journal of Chemistry |
issn |
1878-5352 |
publishDate |
2020-01-01 |
description |
Three 2-arylpiperidinyl-1,4-naphthoquinone derivatives were synthesized and evaluated in vitro to determine their cytotoxicity on cancer and normal cell lines. In order to establish their possible action mechanism, the electrochemical behaviour of these quinones was examined using cyclic voltammetry (CV) as technique by using a three-electrode setup: a glassy carbon, Ag/AgCl (in 3 M KCl), and platinum wire as working, reference, and counter electrodes, respectively. Kinetic studies were done to determine the control of the reduction reaction and the number of transferred electrons in the process. Furthermore, the addition of dsDNA to the quinone solutions allowed for the observation of an interaction between each quinone and dsDNA as the current-peaks became lower in presence of dsDNA. Otherwise, motivated to support the aforementioned results, electronic structure calculations at the TPSS-D3/6-31+G(d,p) level of theory were carried out in order to find the most favourable noncovalently bonded complexes between quinones and DNA. Noncovalent complexes formed between DNA and 2-arylpiperidinyl-1,4-naphthoquinones and stabilized by π-stacking interactions along with the well-known hydrogen-bonded complexes were found, with the former being more stable than the latter. These results suggest that the intercalation of these quinone derivatives in DNA is the most likely action mechanism. Keywords: Naphthoquinone derivatives, Cytotoxicity, DNA interaction, Electrochemistry, Computational study |
url |
http://www.sciencedirect.com/science/article/pii/S1878535218300893 |
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