New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity

Detalhes bibliográficos
Autor(a) principal: Argirova, Maria A.
Data de Publicação: 2021
Outros Autores: Georgieva, Miglena K., Hristova-Avakumova, Nadya G., Vuchev, Dimitar I., Popova-Daskalova, Galya V., Anichina, Kameliya K., Yancheva, Denitsa Y.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/135188
Resumo: Contract KII-06-H39/4
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spelling New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activityChemistry(all)Chemical Engineering(all)Contract KII-06-H39/4Parasitic infections, caused mainly by the speciesTrichinella spiralis(T. spiralis), are widespread around the world and lead to morbidity and mortality in the population. Meanwhile, some studies have showed that these parasites induce oxidative stress in the infected host. With the aim of developing a class of compounds combining anthelmintic with antioxidant properties, a series of new benzimidazolyl-2-hydrazones5a-l, bearing hydroxyl- and methoxy-groups, were synthesized. The anthelmintic activity on encapsulatedT. spiraliswas studiedin vitrothus indicating that all hydrazones were more active than the clinically used anthelmintic drugs albendazole and ivermectin.5band5dkilled the total parasitic larvae (100% effectiveness) after 24 hours incubation period at 37 °C in both concentrations (50 and 100 μg ml−1). The antioxidant activity of the target compounds was elucidatedin vitroagainst stable free radicals DPPH and ABTS as well as iron induced oxidative damage in model systems containing biologically relevant molecules lecithin and deoxyribose. The two 2,3- and 3,4-dihydroxy hydrazones5band5dwere the most effective radical scavengers in all studied systems. DFT calculations were applied to calculate the reaction enthalpies in polar and nonpolar medium and estimate the preferred mechanism of antioxidant activity. The relative radical scavenging ability of compounds5a-lshowed a good correlation to the experimentally observed trends. It was found that the studied compounds are capable to react with various free radicals - ˙OCH3, ˙OOH and ˙OOCH3, through several possible reaction pathways - HAT in nonpolar medium, SPLET in polar medium and RAF in both media.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNArgirova, Maria A.Georgieva, Miglena K.Hristova-Avakumova, Nadya G.Vuchev, Dimitar I.Popova-Daskalova, Galya V.Anichina, Kameliya K.Yancheva, Denitsa Y.2022-03-24T23:39:19Z2021-12-142021-12-14T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article21application/pdfhttp://hdl.handle.net/10362/135188eng2046-2069PURE: 42591743https://doi.org/10.1039/d1ra07419ainfo: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:RCAAP2024-03-11T05:13:38Zoai:run.unl.pt:10362/135188Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:48:20.753943Repositório 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 New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
title New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
spellingShingle New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
Argirova, Maria A.
Chemistry(all)
Chemical Engineering(all)
title_short New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
title_full New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
title_fullStr New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
title_full_unstemmed New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
title_sort New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
author Argirova, Maria A.
author_facet Argirova, Maria A.
Georgieva, Miglena K.
Hristova-Avakumova, Nadya G.
Vuchev, Dimitar I.
Popova-Daskalova, Galya V.
Anichina, Kameliya K.
Yancheva, Denitsa Y.
author_role author
author2 Georgieva, Miglena K.
Hristova-Avakumova, Nadya G.
Vuchev, Dimitar I.
Popova-Daskalova, Galya V.
Anichina, Kameliya K.
Yancheva, Denitsa Y.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Argirova, Maria A.
Georgieva, Miglena K.
Hristova-Avakumova, Nadya G.
Vuchev, Dimitar I.
Popova-Daskalova, Galya V.
Anichina, Kameliya K.
Yancheva, Denitsa Y.
dc.subject.por.fl_str_mv Chemistry(all)
Chemical Engineering(all)
topic Chemistry(all)
Chemical Engineering(all)
description Contract KII-06-H39/4
publishDate 2021
dc.date.none.fl_str_mv 2021-12-14
2021-12-14T00:00:00Z
2022-03-24T23:39:19Z
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/10362/135188
url http://hdl.handle.net/10362/135188
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2046-2069
PURE: 42591743
https://doi.org/10.1039/d1ra07419a
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 21
application/pdf
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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