Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells

Detalhes bibliográficos
Autor(a) principal: Piló, Elisa D. L.
Data de Publicação: 2016
Outros Autores: Ferreira, Isabella P., Recio-Despaigne, Angel A., Silva, Jeferson G. Da, Ramos, Jonas P., Marques, Lucas B., Prazeres, Pedro H. D. M., Takahashi, Jacqueline A., Souza-Fagundes, Elaine M., Rocha, Willian, Beraldo, Heloisa
Tipo de documento: Artigo
Idioma: eng
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: https://doi.org/10.1016/j.bmc.2016.05.007
http://www.locus.ufv.br/handle/123456789/18807
Resumo: Complexes [Bi(2AcPh)Cl2]·0.5H2O (1), [Bi(2AcpClPh)Cl2] (2), [Bi(2AcpNO2Ph)Cl2] (3), [Bi(2AcpOHPh)Cl2]·2H2O (4), [Bi(H2BzPh)Cl3]·2H2O (5), [Bi(H2BzpClPh)Cl3] (6), [Bi(2BzpNO2Ph)Cl2]·2H2O (7) and [Bi(H2BzpOHPh)Cl3]·2H2O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl- (H2AcpClPh), -para-nitro-phenyl (H2AcpNO2Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO2Ph, H2BzpOHPh). Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4). The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts. Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO2Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer.
id UFV_d057d6147bb1aa9313b1164b63150570
oai_identifier_str oai:locus.ufv.br:123456789/18807
network_acronym_str UFV
network_name_str LOCUS Repositório Institucional da UFV
repository_id_str 2145
spelling Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cellsAcetylpyridinephenyl hydrazonesBenzoylpyridinephenyl hydrazonesBismuth(III) complexesAntibacterial activityCytotoxic activityClonogenic survivalComplexes [Bi(2AcPh)Cl2]·0.5H2O (1), [Bi(2AcpClPh)Cl2] (2), [Bi(2AcpNO2Ph)Cl2] (3), [Bi(2AcpOHPh)Cl2]·2H2O (4), [Bi(H2BzPh)Cl3]·2H2O (5), [Bi(H2BzpClPh)Cl3] (6), [Bi(2BzpNO2Ph)Cl2]·2H2O (7) and [Bi(H2BzpOHPh)Cl3]·2H2O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl- (H2AcpClPh), -para-nitro-phenyl (H2AcpNO2Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO2Ph, H2BzpOHPh). Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4). The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts. Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO2Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer.Bioorganic & Medicinal Chemistry2018-04-19T10:44:08Z2018-04-19T10:44:08Z2016-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlepdfapplication/pdf14643391https://doi.org/10.1016/j.bmc.2016.05.007http://www.locus.ufv.br/handle/123456789/18807engv. 24, n. 13, p. 2988-2998, july 2016Elsevier Ltdinfo:eu-repo/semantics/openAccessPiló, Elisa D. L.Ferreira, Isabella P.Recio-Despaigne, Angel A.Silva, Jeferson G. DaRamos, Jonas P.Marques, Lucas B.Prazeres, Pedro H. D. M.Takahashi, Jacqueline A.Souza-Fagundes, Elaine M.Rocha, WillianBeraldo, Heloisareponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFV2024-07-12T08:48:18Zoai:locus.ufv.br:123456789/18807Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452024-07-12T08:48:18LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.none.fl_str_mv Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
title Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
spellingShingle Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
Piló, Elisa D. L.
Acetylpyridinephenyl hydrazones
Benzoylpyridinephenyl hydrazones
Bismuth(III) complexes
Antibacterial activity
Cytotoxic activity
Clonogenic survival
title_short Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
title_full Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
title_fullStr Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
title_full_unstemmed Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
title_sort Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
author Piló, Elisa D. L.
author_facet Piló, Elisa D. L.
Ferreira, Isabella P.
Recio-Despaigne, Angel A.
Silva, Jeferson G. Da
Ramos, Jonas P.
Marques, Lucas B.
Prazeres, Pedro H. D. M.
Takahashi, Jacqueline A.
Souza-Fagundes, Elaine M.
Rocha, Willian
Beraldo, Heloisa
author_role author
author2 Ferreira, Isabella P.
Recio-Despaigne, Angel A.
Silva, Jeferson G. Da
Ramos, Jonas P.
Marques, Lucas B.
Prazeres, Pedro H. D. M.
Takahashi, Jacqueline A.
Souza-Fagundes, Elaine M.
Rocha, Willian
Beraldo, Heloisa
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Piló, Elisa D. L.
Ferreira, Isabella P.
Recio-Despaigne, Angel A.
Silva, Jeferson G. Da
Ramos, Jonas P.
Marques, Lucas B.
Prazeres, Pedro H. D. M.
Takahashi, Jacqueline A.
Souza-Fagundes, Elaine M.
Rocha, Willian
Beraldo, Heloisa
dc.subject.por.fl_str_mv Acetylpyridinephenyl hydrazones
Benzoylpyridinephenyl hydrazones
Bismuth(III) complexes
Antibacterial activity
Cytotoxic activity
Clonogenic survival
topic Acetylpyridinephenyl hydrazones
Benzoylpyridinephenyl hydrazones
Bismuth(III) complexes
Antibacterial activity
Cytotoxic activity
Clonogenic survival
description Complexes [Bi(2AcPh)Cl2]·0.5H2O (1), [Bi(2AcpClPh)Cl2] (2), [Bi(2AcpNO2Ph)Cl2] (3), [Bi(2AcpOHPh)Cl2]·2H2O (4), [Bi(H2BzPh)Cl3]·2H2O (5), [Bi(H2BzpClPh)Cl3] (6), [Bi(2BzpNO2Ph)Cl2]·2H2O (7) and [Bi(H2BzpOHPh)Cl3]·2H2O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl- (H2AcpClPh), -para-nitro-phenyl (H2AcpNO2Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO2Ph, H2BzpOHPh). Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4). The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts. Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO2Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer.
publishDate 2016
dc.date.none.fl_str_mv 2016-07-01
2018-04-19T10:44:08Z
2018-04-19T10:44:08Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv 14643391
https://doi.org/10.1016/j.bmc.2016.05.007
http://www.locus.ufv.br/handle/123456789/18807
identifier_str_mv 14643391
url https://doi.org/10.1016/j.bmc.2016.05.007
http://www.locus.ufv.br/handle/123456789/18807
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv v. 24, n. 13, p. 2988-2998, july 2016
dc.rights.driver.fl_str_mv Elsevier Ltd
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Elsevier Ltd
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Bioorganic & Medicinal Chemistry
publisher.none.fl_str_mv Bioorganic & Medicinal Chemistry
dc.source.none.fl_str_mv reponame:LOCUS Repositório Institucional da UFV
instname:Universidade Federal de Viçosa (UFV)
instacron:UFV
instname_str Universidade Federal de Viçosa (UFV)
instacron_str UFV
institution UFV
reponame_str LOCUS Repositório Institucional da UFV
collection LOCUS Repositório Institucional da UFV
repository.name.fl_str_mv LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)
repository.mail.fl_str_mv fabiojreis@ufv.br
_version_ 1817560044871352320