Exploring the copper(II) coordination to 2′-hydroxy-4-benzyloxychalcone analogues and their potential pharmacological applications

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Autor(es): dc.contributorUniversidade Estadual de Campinas (UNICAMP)-
Autor(es): dc.contributorUniversidade Federal de Uberlândia (UFU)-
Autor(es): dc.contributorUniversity of Leeds-
Autor(es): dc.contributorUniversidade Federal de Goiás (UFG)-
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatordos Santos Oliveira, Laiane-
Autor(es): dc.creatorde Souza Guarda, Pedro Henrique-
Autor(es): dc.creatorRosa, Letícia Bazilio-
Autor(es): dc.creatorRodrigues, Gustavo Clauss-
Autor(es): dc.creatorAffonso, Daniele Daiane-
Autor(es): dc.creatorde Carvalho, João Ernesto-
Autor(es): dc.creatorSantos, Igor Andrade-
Autor(es): dc.creatorHarris, Mark-
Autor(es): dc.creatorNakahata, Douglas Hideki-
Autor(es): dc.creatorSabino, José Ricardo-
Autor(es): dc.creatorMiguel, Danilo Ciccone-
Autor(es): dc.creatorRuiz, Ana Lucia Tasca Gois-
Autor(es): dc.creatorJardim, Ana Carolina Gomes-
Autor(es): dc.creatorAbbehausen, Camilla-
Data de aceite: dc.date.accessioned2025-08-21T22:43:21Z-
Data de disponibilização: dc.date.available2025-08-21T22:43:21Z-
Data de envio: dc.date.issued2025-04-29-
Data de envio: dc.date.issued2024-01-23-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.ica.2023.121806-
Fonte completa do material: dc.identifierhttps://hdl.handle.net/11449/299774-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/299774-
Descrição: dc.descriptionChalcones are chemical precursors of flavonoids and exhibit a variety of biological properties, including anti-cancer, anti-inflammatory, and anti-malarial activities. According to the literature, different transition metal complexes of chalcones exhibit antitumor and antibacterial properties. Herein we report the synthesis, characterization, and the in vitro evaluation of antileishmanial, antiproliferative, and antiviral activities of novel copper(II)-2′-hydroxy-4-benzyloxychalcone complexes. Two of the complexes (1 and 2) had the formula [Cu(L)2], and the other two (3 and 4) were characterized as [Cu(L)(phen)Cl], where L is the deprotonated form of the 2′-hydroxy-4-benzyloxychalcones (HL1, is a fluorine substituted analog of HL2) and phen is 1,10- phenanthroline. Structures resolved by single-crystal X-ray diffraction showed that complexes 3 and 4 had a distorted square pyramid geometry, with chloride at the apical position. The stability of the complexes in dimethyl sulfoxide showed a significant variation. A wide range of ligand exchange kinetics was observed in the solution, influenced by chalcone fluorination and the presence of phenanthroline. Potential pharmacological applications were evaluated using in vitro assays for anti-proliferative, leishmanicidal, and antiviral activities. Complexes 1 and 3 showed cytostatic effects against the human breast tumor cell line (MCF-7, GI50 = 4.6 and 1.0 µM, respectively) that could be attributed to the free ligand HL1 (MCF-7, GI50 = 1.16 µM). Moreover, complex 1 showed higher selectivity to MCF-7 cells in comparison to murine immortalized 3T3 cells (GI50 > 100 µM). Complex 2 was inactive and toxic while complex 4 showed an unspecific cytostatic effect. Despite a weak leishmanicidal activity, at 25 µM, complex 3 inhibited (85,1 %) the SARS-CoV-2 replication at 2 µM. As complex 4 also showed good antiviral activity against SARS-CoV-2 (84,7 %), the antiviral activity seems to be related to copper(II)-phenanthroline fragment. This work demonstrates how simple changes in the structure of the ligand affect ligand exchange reactions and, consequently biological activity. It also expands the biological applications of Cu(II) chalcone complexes.-
Descrição: dc.descriptionInstitute of Chemistry University of Campinas-
Descrição: dc.descriptionInstitute of Biology University of Campinas-
Descrição: dc.descriptionFaculty of Pharmaceutical Sciences University of Campinas-
Descrição: dc.descriptionInstitute of Biomedical Sciences Federal University of Uberlândia-
Descrição: dc.descriptionSchool of Molecular and Cellular Biology Faculty of Biological Sciences University of Leeds-
Descrição: dc.descriptionInstitute of Chemistry Federal University of Goiás-
Descrição: dc.descriptionInstitute of Physics Federal University of Goiás-
Descrição: dc.descriptionInstitute of Biosciences Humanities and Exact Sciences São Paulo State University-
Descrição: dc.descriptionInstitute of Biosciences Humanities and Exact Sciences São Paulo State University-
Idioma: dc.languageen-
Relação: dc.relationInorganica Chimica Acta-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectAnti-SARS-CoV-2-
Palavras-chave: dc.subjectAntitumor-
Palavras-chave: dc.subjectChalcone-
Palavras-chave: dc.subjectCopper-
Palavras-chave: dc.subjectMetal complexes-
Título: dc.titleExploring the copper(II) coordination to 2′-hydroxy-4-benzyloxychalcone analogues and their potential pharmacological applications-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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