Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity
Twenty-five piperidines were studied as potential radical scavengers and antitumor agents. Quantitative interaction of compounds with ctDNA using spectroscopic techniques was also evaluated. Our results demonstrate that the evaluated piperidines possesses different abilities to scavenge the radical...
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doaj-debfd9ebdf3749f2a4c98b00d61eb23b2020-11-24T23:00:04ZengElsevierJournal of Advanced Research2090-12322090-12242018-01-019C516110.1016/j.jare.2017.10.010Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activitySuvankar Das0Cristiane J. da Silva1Marina de M. Silva2Maria Dayanne de A. Dantas3Ângelo de Fátima4Ana Lúcia T. Góis Ruiz5Cleiton M. da Silva6João Ernesto de Carvalho7Josué C.C. Santos8Isis M. Figueiredo9Edeildo F. da Silva-Júnior10Thiago M. de Aquino11João X. de Araújo-Júnior12Goutam Brahmachari13Luzia Valentina Modolo14Department of Chemistry, Visva-Bharati (a Central University), Santiniketan 731 235, West Bengal, IndiaDepartment of Botany, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilChemical, Biological and Agricultural Pluridisciplinary Research Center, Universidade Estadual de Campinas, Paulínia, SP, BrazilDepartment of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilChemical, Biological and Agricultural Pluridisciplinary Research Center, Universidade Estadual de Campinas, Paulínia, SP, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilInstitute of Chemistry and Biotechnology, Universidade Federal de Alagoas, Maceió, AL, BrazilDepartment of Chemistry, Visva-Bharati (a Central University), Santiniketan 731 235, West Bengal, IndiaDepartment of Botany, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilTwenty-five piperidines were studied as potential radical scavengers and antitumor agents. Quantitative interaction of compounds with ctDNA using spectroscopic techniques was also evaluated. Our results demonstrate that the evaluated piperidines possesses different abilities to scavenge the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the anion radical superoxide (·O2−). The piperidine 19 was the most potent radical DPPH scavenger, while the most effective to ·O2− scavenger was piperidine 10. In general, U251, MCF7, NCI/ADR-RES, NCI-H460 and HT29 cells were least sensitive to the tested compounds and all compounds were considerably more toxic to the studied cancer cell lines than to the normal cell line HaCaT. The binding mode of the compounds and ctDNA was preferably via intercalation. In addition, these results were confirmed based on theoretical studies. Finally, a linear and exponential correlation between interaction constant (Kb) and GI50 for several human cancer cell was observed.http://www.sciencedirect.com/science/article/pii/S2090123217301145Piperidine derivativesFree radical scavengingAnticancer activityDNA interaction |
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DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Suvankar Das Cristiane J. da Silva Marina de M. Silva Maria Dayanne de A. Dantas Ângelo de Fátima Ana Lúcia T. Góis Ruiz Cleiton M. da Silva João Ernesto de Carvalho Josué C.C. Santos Isis M. Figueiredo Edeildo F. da Silva-Júnior Thiago M. de Aquino João X. de Araújo-Júnior Goutam Brahmachari Luzia Valentina Modolo |
spellingShingle |
Suvankar Das Cristiane J. da Silva Marina de M. Silva Maria Dayanne de A. Dantas Ângelo de Fátima Ana Lúcia T. Góis Ruiz Cleiton M. da Silva João Ernesto de Carvalho Josué C.C. Santos Isis M. Figueiredo Edeildo F. da Silva-Júnior Thiago M. de Aquino João X. de Araújo-Júnior Goutam Brahmachari Luzia Valentina Modolo Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity Journal of Advanced Research Piperidine derivatives Free radical scavenging Anticancer activity DNA interaction |
author_facet |
Suvankar Das Cristiane J. da Silva Marina de M. Silva Maria Dayanne de A. Dantas Ângelo de Fátima Ana Lúcia T. Góis Ruiz Cleiton M. da Silva João Ernesto de Carvalho Josué C.C. Santos Isis M. Figueiredo Edeildo F. da Silva-Júnior Thiago M. de Aquino João X. de Araújo-Júnior Goutam Brahmachari Luzia Valentina Modolo |
author_sort |
Suvankar Das |
title |
Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity |
title_short |
Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity |
title_full |
Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity |
title_fullStr |
Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity |
title_full_unstemmed |
Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity |
title_sort |
highly functionalized piperidines: free radical scavenging, anticancer activity, dna interaction and correlation with biological activity |
publisher |
Elsevier |
series |
Journal of Advanced Research |
issn |
2090-1232 2090-1224 |
publishDate |
2018-01-01 |
description |
Twenty-five piperidines were studied as potential radical scavengers and antitumor agents. Quantitative interaction of compounds with ctDNA using spectroscopic techniques was also evaluated. Our results demonstrate that the evaluated piperidines possesses different abilities to scavenge the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the anion radical superoxide (·O2−). The piperidine 19 was the most potent radical DPPH scavenger, while the most effective to ·O2− scavenger was piperidine 10. In general, U251, MCF7, NCI/ADR-RES, NCI-H460 and HT29 cells were least sensitive to the tested compounds and all compounds were considerably more toxic to the studied cancer cell lines than to the normal cell line HaCaT. The binding mode of the compounds and ctDNA was preferably via intercalation. In addition, these results were confirmed based on theoretical studies. Finally, a linear and exponential correlation between interaction constant (Kb) and GI50 for several human cancer cell was observed. |
topic |
Piperidine derivatives Free radical scavenging Anticancer activity DNA interaction |
url |
http://www.sciencedirect.com/science/article/pii/S2090123217301145 |
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