Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/12885 https://doi.org/10.1016/j.bmc.2009.07.050 |
Resumo: | A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A number of compounds have shown IC50 values lower than 2 [mu]M against the cancer cell lines tested and the vast majority has shown a better cytotoxicity profile than betulinic acid, including the betulin derivatives. N-Acylimidazole derivatives 26 and 27 (IC50 0.8 and 1.7 [mu]M in HepG2 cells) and the C-3 carbamate derivative 16 (IC50 2.0 [mu]M in HepG2 cells) were the most promising compounds. Based on the observed cytotoxicity, structure-activity relationships have been established |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activityTriterpenoidsBetulinic acidImidazoleCytotoxicityA series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A number of compounds have shown IC50 values lower than 2 [mu]M against the cancer cell lines tested and the vast majority has shown a better cytotoxicity profile than betulinic acid, including the betulin derivatives. N-Acylimidazole derivatives 26 and 27 (IC50 0.8 and 1.7 [mu]M in HepG2 cells) and the C-3 carbamate derivative 16 (IC50 2.0 [mu]M in HepG2 cells) were the most promising compounds. Based on the observed cytotoxicity, structure-activity relationships have been establishedElsevier Ltd.2009-09-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/12885http://hdl.handle.net/10316/12885https://doi.org/10.1016/j.bmc.2009.07.050engBioorganic & Medicinal Chemistry. 17:17 (2009) 6241-62500968-0896Santos, Rita C.Salvador, Jorge A. R.Marín, SilviaCascante, Martainfo: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:RCAAP2022-05-25T04:37:30Zoai:estudogeral.uc.pt:10316/12885Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:47:27.749355Repositório 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 |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
title |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
spellingShingle |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity Santos, Rita C. Triterpenoids Betulinic acid Imidazole Cytotoxicity |
title_short |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
title_full |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
title_fullStr |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
title_full_unstemmed |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
title_sort |
Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity |
author |
Santos, Rita C. |
author_facet |
Santos, Rita C. Salvador, Jorge A. R. Marín, Silvia Cascante, Marta |
author_role |
author |
author2 |
Salvador, Jorge A. R. Marín, Silvia Cascante, Marta |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Santos, Rita C. Salvador, Jorge A. R. Marín, Silvia Cascante, Marta |
dc.subject.por.fl_str_mv |
Triterpenoids Betulinic acid Imidazole Cytotoxicity |
topic |
Triterpenoids Betulinic acid Imidazole Cytotoxicity |
description |
A series of new imidazole carboxylic esters (carbamates) and N-acylimidazole derivatives of betulin and betulinic acid (14-29) have been synthesized. The new compounds were screened for in vitro cytotoxicity activity against human cancer cell lines HepG2, Jurkat and HeLa. A number of compounds have shown IC50 values lower than 2 [mu]M against the cancer cell lines tested and the vast majority has shown a better cytotoxicity profile than betulinic acid, including the betulin derivatives. N-Acylimidazole derivatives 26 and 27 (IC50 0.8 and 1.7 [mu]M in HepG2 cells) and the C-3 carbamate derivative 16 (IC50 2.0 [mu]M in HepG2 cells) were the most promising compounds. Based on the observed cytotoxicity, structure-activity relationships have been established |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-09-01 |
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/10316/12885 http://hdl.handle.net/10316/12885 https://doi.org/10.1016/j.bmc.2009.07.050 |
url |
http://hdl.handle.net/10316/12885 https://doi.org/10.1016/j.bmc.2009.07.050 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Bioorganic & Medicinal Chemistry. 17:17 (2009) 6241-6250 0968-0896 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Elsevier Ltd. |
publisher.none.fl_str_mv |
Elsevier Ltd. |
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 |
repository.mail.fl_str_mv |
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1799133752106942464 |