4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents

Detalhes bibliográficos
Autor(a) principal: Kamal, Ahmed
Data de Publicação: 2013
Outros Autores: Suresh, Paidakula, Ramaiah, M. Janaki, Reddy, T. Srinivasa, Kapavarapu, Ravi Kumar, Rao, Bolla Narasimha, Imthiajali, Syed, Reddy, T. Lakshminarayan, Pushpavalli, S. N. C. V. L., Shankaraiah, Nagula, Pal-Bhadra, Manika
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/27241
https://doi.org/10.1016/j.bmc.2013.06.033
Resumo: A series of 4β-[4′-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a–l) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11l showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and IIα enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure–activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11l were presented.
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spelling 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agentsEtoposidePodophyllotoxinCell cycleCytotoxicityTopoisomerase-IIα enzymeTopoisomerase-I enzymeA series of 4β-[4′-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a–l) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11l showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and IIα enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure–activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11l were presented.Elsevier2013-09-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/27241http://hdl.handle.net/10316/27241https://doi.org/10.1016/j.bmc.2013.06.033engKAMAL, Ahmed [et. al] - 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents. "Bioorganic & Medicinal Chemistry". ISSN 0968-0896. Vol. 21 Nº. 17 (2013) p. 5198-52080968-0896http://www.sciencedirect.com/science/article/pii/S0968089613005646Kamal, AhmedSuresh, PaidakulaRamaiah, M. JanakiReddy, T. SrinivasaKapavarapu, Ravi KumarRao, Bolla NarasimhaImthiajali, SyedReddy, T. LakshminarayanPushpavalli, S. N. C. V. L.Shankaraiah, NagulaPal-Bhadra, Manikainfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2019-06-02T10:19:13Zoai:estudogeral.uc.pt:10316/27241Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:53:35.729254Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
title 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
spellingShingle 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
Kamal, Ahmed
Etoposide
Podophyllotoxin
Cell cycle
Cytotoxicity
Topoisomerase-IIα enzyme
Topoisomerase-I enzyme
title_short 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
title_full 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
title_fullStr 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
title_full_unstemmed 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
title_sort 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
author Kamal, Ahmed
author_facet Kamal, Ahmed
Suresh, Paidakula
Ramaiah, M. Janaki
Reddy, T. Srinivasa
Kapavarapu, Ravi Kumar
Rao, Bolla Narasimha
Imthiajali, Syed
Reddy, T. Lakshminarayan
Pushpavalli, S. N. C. V. L.
Shankaraiah, Nagula
Pal-Bhadra, Manika
author_role author
author2 Suresh, Paidakula
Ramaiah, M. Janaki
Reddy, T. Srinivasa
Kapavarapu, Ravi Kumar
Rao, Bolla Narasimha
Imthiajali, Syed
Reddy, T. Lakshminarayan
Pushpavalli, S. N. C. V. L.
Shankaraiah, Nagula
Pal-Bhadra, Manika
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Kamal, Ahmed
Suresh, Paidakula
Ramaiah, M. Janaki
Reddy, T. Srinivasa
Kapavarapu, Ravi Kumar
Rao, Bolla Narasimha
Imthiajali, Syed
Reddy, T. Lakshminarayan
Pushpavalli, S. N. C. V. L.
Shankaraiah, Nagula
Pal-Bhadra, Manika
dc.subject.por.fl_str_mv Etoposide
Podophyllotoxin
Cell cycle
Cytotoxicity
Topoisomerase-IIα enzyme
Topoisomerase-I enzyme
topic Etoposide
Podophyllotoxin
Cell cycle
Cytotoxicity
Topoisomerase-IIα enzyme
Topoisomerase-I enzyme
description A series of 4β-[4′-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a–l) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11l showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and IIα enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure–activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11l were presented.
publishDate 2013
dc.date.none.fl_str_mv 2013-09-01
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 http://hdl.handle.net/10316/27241
http://hdl.handle.net/10316/27241
https://doi.org/10.1016/j.bmc.2013.06.033
url http://hdl.handle.net/10316/27241
https://doi.org/10.1016/j.bmc.2013.06.033
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv KAMAL, Ahmed [et. al] - 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents. "Bioorganic & Medicinal Chemistry". ISSN 0968-0896. Vol. 21 Nº. 17 (2013) p. 5198-5208
0968-0896
http://www.sciencedirect.com/science/article/pii/S0968089613005646
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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