Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | https://doi.org/10.1002/ejoc.201701500 |
Resumo: | POCI-01-0145- 710-FEDER-007265 POCI-01-0145-FEDER-007728 |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-AnthroneAnthracenecarboxaldehydeAnthroneDecarbonylationDNA intercalationImidazolium saltPhysical and Theoretical ChemistryOrganic ChemistrySDG 3 - Good Health and Well-beingPOCI-01-0145- 710-FEDER-007265 POCI-01-0145-FEDER-007728A new and never before reported hetero-arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0 (±0.20) × 105 m–1], which is 10 × higher than that described for doxorubicin [Kb = 3.2 (±0.23) × 104 m–1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT-DNA system with a quenching constant (KSV) of 3.3 (±0.3) × 103 m–1 calculated by the Stern–Volmer equation.LAQV@REQUIMTEDQ - Departamento de QuímicaUCIBIO - Applied Molecular Biosciences UnitDCV - Departamento de Ciências da VidaRUNPeixoto, DanielaFigueiredo, MargaridaMalta, GabrielaRoma-Rodrigues, CatarinaBaptista, Pedro V.Fernandes, Alexandra R.Barroso, SóniaCarvalho, Ana LuísaAfonso, Carlos A. M.Ferreira, Luisa M.Branco, Paula S.2019-04-01T22:02:19Z2018-01-312018-01-31T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article5application/pdfhttps://doi.org/10.1002/ejoc.201701500eng1434-193XPURE: 3678031http://www.scopus.com/inward/record.url?scp=85041287294&partnerID=8YFLogxKhttps://doi.org/10.1002/ejoc.201701500info: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:RCAAP2024-03-11T04:31:00Zoai:run.unl.pt:10362/65254Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:34:17.215691Repositório 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 |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| title |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| spellingShingle |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone Peixoto, Daniela Anthracenecarboxaldehyde Anthrone Decarbonylation DNA intercalation Imidazolium salt Physical and Theoretical Chemistry Organic Chemistry SDG 3 - Good Health and Well-being |
| title_short |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| title_full |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| title_fullStr |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| title_full_unstemmed |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| title_sort |
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone |
| author |
Peixoto, Daniela |
| author_facet |
Peixoto, Daniela Figueiredo, Margarida Malta, Gabriela Roma-Rodrigues, Catarina Baptista, Pedro V. Fernandes, Alexandra R. Barroso, Sónia Carvalho, Ana Luísa Afonso, Carlos A. M. Ferreira, Luisa M. Branco, Paula S. |
| author_role |
author |
| author2 |
Figueiredo, Margarida Malta, Gabriela Roma-Rodrigues, Catarina Baptista, Pedro V. Fernandes, Alexandra R. Barroso, Sónia Carvalho, Ana Luísa Afonso, Carlos A. M. Ferreira, Luisa M. Branco, Paula S. |
| author2_role |
author author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
LAQV@REQUIMTE DQ - Departamento de Química UCIBIO - Applied Molecular Biosciences Unit DCV - Departamento de Ciências da Vida RUN |
| dc.contributor.author.fl_str_mv |
Peixoto, Daniela Figueiredo, Margarida Malta, Gabriela Roma-Rodrigues, Catarina Baptista, Pedro V. Fernandes, Alexandra R. Barroso, Sónia Carvalho, Ana Luísa Afonso, Carlos A. M. Ferreira, Luisa M. Branco, Paula S. |
| dc.subject.por.fl_str_mv |
Anthracenecarboxaldehyde Anthrone Decarbonylation DNA intercalation Imidazolium salt Physical and Theoretical Chemistry Organic Chemistry SDG 3 - Good Health and Well-being |
| topic |
Anthracenecarboxaldehyde Anthrone Decarbonylation DNA intercalation Imidazolium salt Physical and Theoretical Chemistry Organic Chemistry SDG 3 - Good Health and Well-being |
| description |
POCI-01-0145- 710-FEDER-007265 POCI-01-0145-FEDER-007728 |
| publishDate |
2018 |
| dc.date.none.fl_str_mv |
2018-01-31 2018-01-31T00:00:00Z 2019-04-01T22:02:19Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.uri.fl_str_mv |
https://doi.org/10.1002/ejoc.201701500 |
| url |
https://doi.org/10.1002/ejoc.201701500 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
1434-193X PURE: 3678031 http://www.scopus.com/inward/record.url?scp=85041287294&partnerID=8YFLogxK https://doi.org/10.1002/ejoc.201701500 |
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info:eu-repo/semantics/openAccess |
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openAccess |
| dc.format.none.fl_str_mv |
5 application/pdf |
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reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
| reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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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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1799137964377243648 |