Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies

Detalhes bibliográficos
Autor(a) principal: Shankaraiah,Nagula
Data de Publicação: 2019
Outros Autores: Kumar,Niggula P., Tokala,Ramya, Gayatri,Bulusu S., Talla,Venu, Santos,Leonardo S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300454
Resumo: Cancer is a complex disease which involves abnormalities of multiple cellular pathways. Current chemotherapeutic drugs are mainly designed to target the DNA and cell division. Therefore, in the present study, we have synthesized a new series of 1,2,3-triazolo-naphthalimide/phthalimide conjugates and evaluated their in vitro cytotoxicity against selected human cancer cells. Among the tested compounds, one of them displayed notable cytotoxic activity against A549 lung cancer cells with an IC50 (half maximal inhibitory concentration) value of 7.6 ± 0.78 µM. To determine the effect of this compound on cell viability, acridine orange/ethidium bromide (AO/EB) and 4',6-diamidino-2-phenylindole (DAPI) staining studies were performed. These apoptotic features were clearly indicating that the compound inhibited cell proliferation by apoptosis. Further, relative viscosity measurements and molecular docking studies with the most three active compounds indicated that these new compounds bind to DNA by intercalation.
id SBQ-2_2d1b5f2720268cdd4e4b2785ce872d84
oai_identifier_str oai:scielo:S0103-50532019000300454
network_acronym_str SBQ-2
network_name_str Journal of the Brazilian Chemical Society (Online)
repository_id_str
spelling Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studiesnaphthalimides1,2,3-triazolesDNA intercalationclick reactionCancer is a complex disease which involves abnormalities of multiple cellular pathways. Current chemotherapeutic drugs are mainly designed to target the DNA and cell division. Therefore, in the present study, we have synthesized a new series of 1,2,3-triazolo-naphthalimide/phthalimide conjugates and evaluated their in vitro cytotoxicity against selected human cancer cells. Among the tested compounds, one of them displayed notable cytotoxic activity against A549 lung cancer cells with an IC50 (half maximal inhibitory concentration) value of 7.6 ± 0.78 µM. To determine the effect of this compound on cell viability, acridine orange/ethidium bromide (AO/EB) and 4',6-diamidino-2-phenylindole (DAPI) staining studies were performed. These apoptotic features were clearly indicating that the compound inhibited cell proliferation by apoptosis. Further, relative viscosity measurements and molecular docking studies with the most three active compounds indicated that these new compounds bind to DNA by intercalation.Sociedade Brasileira de Química2019-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300454Journal of the Brazilian Chemical Society v.30 n.3 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180111info:eu-repo/semantics/openAccessShankaraiah,NagulaKumar,Niggula P.Tokala,RamyaGayatri,Bulusu S.Talla,VenuSantos,Leonardo S.eng2019-02-14T00:00:00Zoai:scielo:S0103-50532019000300454Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-02-14T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
title Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
spellingShingle Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
Shankaraiah,Nagula
naphthalimides
1,2,3-triazoles
DNA intercalation
click reaction
title_short Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
title_full Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
title_fullStr Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
title_full_unstemmed Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
title_sort Synthesis of New 1,2,3-Triazolo-naphthalimide/phthalimide Conjugates via ‘Click' Reaction: DNA Intercalation and Cytotoxic Studies
author Shankaraiah,Nagula
author_facet Shankaraiah,Nagula
Kumar,Niggula P.
Tokala,Ramya
Gayatri,Bulusu S.
Talla,Venu
Santos,Leonardo S.
author_role author
author2 Kumar,Niggula P.
Tokala,Ramya
Gayatri,Bulusu S.
Talla,Venu
Santos,Leonardo S.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Shankaraiah,Nagula
Kumar,Niggula P.
Tokala,Ramya
Gayatri,Bulusu S.
Talla,Venu
Santos,Leonardo S.
dc.subject.por.fl_str_mv naphthalimides
1,2,3-triazoles
DNA intercalation
click reaction
topic naphthalimides
1,2,3-triazoles
DNA intercalation
click reaction
description Cancer is a complex disease which involves abnormalities of multiple cellular pathways. Current chemotherapeutic drugs are mainly designed to target the DNA and cell division. Therefore, in the present study, we have synthesized a new series of 1,2,3-triazolo-naphthalimide/phthalimide conjugates and evaluated their in vitro cytotoxicity against selected human cancer cells. Among the tested compounds, one of them displayed notable cytotoxic activity against A549 lung cancer cells with an IC50 (half maximal inhibitory concentration) value of 7.6 ± 0.78 µM. To determine the effect of this compound on cell viability, acridine orange/ethidium bromide (AO/EB) and 4',6-diamidino-2-phenylindole (DAPI) staining studies were performed. These apoptotic features were clearly indicating that the compound inhibited cell proliferation by apoptosis. Further, relative viscosity measurements and molecular docking studies with the most three active compounds indicated that these new compounds bind to DNA by intercalation.
publishDate 2019
dc.date.none.fl_str_mv 2019-03-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300454
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300454
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20180111
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.30 n.3 2019
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
_version_ 1750318181637947392

Registros relacionados