Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , , , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/31395 |
Resumo: | Instituto de Química e Biotecnologia (UFAL), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), FAPEAL (Process number 60030 000863/2016), FAPESB, FAPESQ and FACEPE. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001. |
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Silva, Marina de MagalhãesMacedo, Taís SoaresTeixeira, Helena Mariana PitangueiraMoreira, Diogo Rodrigo de MagalhaesSoares, Milena Botelho PereiraPereira, Ana Ligia da CostaSerafim, Vanessa de LimaMendonça Júnior, Francisco Jaime BezerraLima, Maria do Carmo Alves deMoura, Ricardo Olímpio deSilva Júnior, Edeildo Ferreira daAraújo Júnior, João Xavier deDantas, Maria Dayanne de AraujoNascimento, Eduarda de Omena OliveiraMaciel, Thamilla Maria SilvaAquino, Thiago Mendonça deFigueiredo, Isis MartinsSantos, Josué Carinhanha Caldas2019-02-04T13:08:06Z2019-02-04T13:08:06Z2018SILVA, M. M. et al. Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action. Journal of Photochemistry and Photobiology B: Biology, v. 189, p. 165-175, 2018.1011-1344https://www.arca.fiocruz.br/handle/icict/3139510.1016/j.jphotobiol.2018.10.016Instituto de Química e Biotecnologia (UFAL), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), FAPEAL (Process number 60030 000863/2016), FAPESB, FAPESQ and FACEPE. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil.Universidade Estadual da Paraíba. Laboratório de Síntese e Vetorização de Moléculas. Departamento de Ciências Biológicas. João Pessoa, PB, Brasil.Universidade Estadual da Paraíba. Laboratório de Síntese e Vetorização de Moléculas. Departamento de Ciências Biológicas. João Pessoa, PB, Brasil.Universidade Estadual da Paraíba. Laboratório de Síntese e Vetorização de Moléculas. Departamento de Ciências Biológicas. João Pessoa, PB, Brasil.Universidade Federal de Pernambuco. Laboratório de Planejamento e Síntese de Fármacos. Departamento de Antibióticos. Recife, PE, Brasil.Universidade Estadual da Paraíba. Laboratório de Síntese e Vetorização de Moléculas. Departamento de Ciências Biológicas. João Pessoa, PB, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil / Universidade Federal de Alagoas. Laboratório de Química Medicinal, Escola de Enfermagem e Farmácia. Macéio, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil / Universidade Federal de Alagoas. Laboratório de Química Medicinal, Escola de Enfermagem e Farmácia. Macéio, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Acridines are considered an important class of compounds due to their wide variety of biological activities. In this work, we synthesized four acridine derivatives (1-4) and evaluated their biological activity against the Plasmodium falciparum W2 line, as well as studied the interaction with ctDNA and HSA using spectroscopic techniques and molecular docking. The acridine derivative 2 (IC50 = 0.90 ± 0.08 μM) was more effective against P. falciparum than primaquine (IC50 = 1.70 ± 0.10 μM) and similar to amsacrine (IC50 = 0.80 ± 0.10 μM). In the fluorescence and UV-vis assays, it was verified that the acridine derivatives interact with ctDNA and HSA leading to a non-fluorescent supramolecular complex formation. The non-covalent binding constants ranged from 2.09 to 7.76 × 103 M-1, indicating moderate interaction with ctDNA. Through experiments with KI, fluorescence contact energy transfer and competition assays were possible to characterize the main non-covalent binding mode of the acridines evaluated with ctDNA as intercalation. The binding constants obtained showed a high linear correlation with the IC50 values against the antimalarial activity, suggesting that DNA may be the main biological target of these molecules. Finally, HSA interaction studies were performed and all evaluated compounds bind to the site II of the protein. The less active compounds (1 and 3) presented the highest affinity to HSA, indicating that the interaction with carrier protein can affect the (bio)availability of these compounds to the biological target.engElsevierAcridinasAtividade antimaláricaDNA de timo de bezerro e interação HSACorrelação atividade-interaçãoAcridinesAntimalarial activityCalf thymus DNA and HSA interactionActivity-interaction correlationCorrelation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of actioninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/31395/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALSILVA, M.M. Correlation between DNA-HSA...2018.pdfSILVA, M.M. 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| dc.title.pt_BR.fl_str_mv |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| title |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| spellingShingle |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action Silva, Marina de Magalhães Acridinas Atividade antimalárica DNA de timo de bezerro e interação HSA Correlação atividade-interação Acridines Antimalarial activity Calf thymus DNA and HSA interaction Activity-interaction correlation |
| title_short |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| title_full |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| title_fullStr |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| title_full_unstemmed |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| title_sort |
Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action |
| author |
Silva, Marina de Magalhães |
| author_facet |
Silva, Marina de Magalhães Macedo, Taís Soares Teixeira, Helena Mariana Pitangueira Moreira, Diogo Rodrigo de Magalhaes Soares, Milena Botelho Pereira Pereira, Ana Ligia da Costa Serafim, Vanessa de Lima Mendonça Júnior, Francisco Jaime Bezerra Lima, Maria do Carmo Alves de Moura, Ricardo Olímpio de Silva Júnior, Edeildo Ferreira da Araújo Júnior, João Xavier de Dantas, Maria Dayanne de Araujo Nascimento, Eduarda de Omena Oliveira Maciel, Thamilla Maria Silva Aquino, Thiago Mendonça de Figueiredo, Isis Martins Santos, Josué Carinhanha Caldas |
| author_role |
author |
| author2 |
Macedo, Taís Soares Teixeira, Helena Mariana Pitangueira Moreira, Diogo Rodrigo de Magalhaes Soares, Milena Botelho Pereira Pereira, Ana Ligia da Costa Serafim, Vanessa de Lima Mendonça Júnior, Francisco Jaime Bezerra Lima, Maria do Carmo Alves de Moura, Ricardo Olímpio de Silva Júnior, Edeildo Ferreira da Araújo Júnior, João Xavier de Dantas, Maria Dayanne de Araujo Nascimento, Eduarda de Omena Oliveira Maciel, Thamilla Maria Silva Aquino, Thiago Mendonça de Figueiredo, Isis Martins Santos, Josué Carinhanha Caldas |
| author2_role |
author author author author author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Silva, Marina de Magalhães Macedo, Taís Soares Teixeira, Helena Mariana Pitangueira Moreira, Diogo Rodrigo de Magalhaes Soares, Milena Botelho Pereira Pereira, Ana Ligia da Costa Serafim, Vanessa de Lima Mendonça Júnior, Francisco Jaime Bezerra Lima, Maria do Carmo Alves de Moura, Ricardo Olímpio de Silva Júnior, Edeildo Ferreira da Araújo Júnior, João Xavier de Dantas, Maria Dayanne de Araujo Nascimento, Eduarda de Omena Oliveira Maciel, Thamilla Maria Silva Aquino, Thiago Mendonça de Figueiredo, Isis Martins Santos, Josué Carinhanha Caldas |
| dc.subject.other.pt_BR.fl_str_mv |
Acridinas Atividade antimalárica DNA de timo de bezerro e interação HSA Correlação atividade-interação |
| topic |
Acridinas Atividade antimalárica DNA de timo de bezerro e interação HSA Correlação atividade-interação Acridines Antimalarial activity Calf thymus DNA and HSA interaction Activity-interaction correlation |
| dc.subject.en.pt_BR.fl_str_mv |
Acridines Antimalarial activity Calf thymus DNA and HSA interaction Activity-interaction correlation |
| description |
Instituto de Química e Biotecnologia (UFAL), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), FAPEAL (Process number 60030 000863/2016), FAPESB, FAPESQ and FACEPE. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001. |
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2018 |
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2018 |
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2019-02-04T13:08:06Z |
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2019-02-04T13:08:06Z |
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info:eu-repo/semantics/publishedVersion |
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| dc.identifier.citation.fl_str_mv |
SILVA, M. M. et al. Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action. Journal of Photochemistry and Photobiology B: Biology, v. 189, p. 165-175, 2018. |
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https://www.arca.fiocruz.br/handle/icict/31395 |
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1011-1344 |
| dc.identifier.doi.none.fl_str_mv |
10.1016/j.jphotobiol.2018.10.016 |
| identifier_str_mv |
SILVA, M. M. et al. Correlation between DNA/HSA-interactions and antimalarial activity of acridine derivatives: Proposing a possible mechanism of action. Journal of Photochemistry and Photobiology B: Biology, v. 189, p. 165-175, 2018. 1011-1344 10.1016/j.jphotobiol.2018.10.016 |
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https://www.arca.fiocruz.br/handle/icict/31395 |
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Elsevier |
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Elsevier |
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