Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica
Ano de defesa: | 2021 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Goiás
|
Programa de Pós-Graduação: |
Programa de Pós-graduação em Química (IQ)
|
Departamento: |
Instituto de Química - IQ (RG)
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.bc.ufg.br/tede/handle/tede/11929 |
Resumo: | The search for bioactive chemical substances, both natural and synthetic, starts from the same assumption: the reduction of the side effects caused by the drugs and increasing the effectiveness of the drug to its biological target. Same that several researches have been conducted for the synthesis of chalcones, neolignans and their analogues, there is not, so far, in the main databases used in this research, studies that have used these two classes of molecules coupled in the form of a hybrid on different therapeutic targets. The first stage of work consisted of synthesizing the reaction precursors, including 2-bromo-1-phenylethanone and 22 chalcones (2-hydroxychalcones, 3-hydroxychalcones and 4-hydroxychalcones) in which yields ranging from 15 to 100% were obtained. In possession of the different chalconas, the study of the reaction conditions that gave rise to the new analogue hybrids of 8,4'-oxyneolignans. Of the tested chalcones, those that showed promising results were the 3-hydroxychalcones and the 4-hydroxychalcones, obtaining 14 new hybrid molecules in yields ranging from 18 to 83%. The hybrid molecules synthesized had their properties biological agents evaluated for cytotoxic effects and the concentration that caused 50% of cell growth inhibition (IC50) in tumor cell lines of human glioblastoma (SNB-19), colon (HCT-116), prostate (PC-3) and leukemia acute promyelocytic (HL-60). The results of the cytotoxicity assay showed that 12 compounds (among the 14 tested) showed a percentage of inhibition of promising cell growth (≥75% cell inhibition). Compounds 67-80 were selected and the IC50 assay was evaluated revealing a moderate inhibition profile for compounds that present the chalcone moiety with groups that decrease the electronic density of the ring (deactivators), with compound 73 having the lowest IC50, for this methodology. Structural modifications of analogous compounds do not led to significant increases in cytotoxic activity when compared to the drug reference doxorubicin. |
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Oliveira, Guilherme Roberto dehttp://lattes.cnpq.br/8239498431579015Alonso, Christian Gonçalveshttp://lattes.cnpq.br/7285754665946583Oliveira, Guilherme Roberto deNoda Pérez, CaridadGomes, Marcelo do NascimentoAndrade, Fabiano Molinos deLemes, Geralda de Fámahttp://lattes.cnpq.br/1113241281083058Fernandes, Fernanda de Sousa2022-03-09T14:27:01Z2022-03-09T14:27:01Z2021-12-15FERNANDES, F. S. Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica. 2021. 275 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2021.http://repositorio.bc.ufg.br/tede/handle/tede/11929The search for bioactive chemical substances, both natural and synthetic, starts from the same assumption: the reduction of the side effects caused by the drugs and increasing the effectiveness of the drug to its biological target. Same that several researches have been conducted for the synthesis of chalcones, neolignans and their analogues, there is not, so far, in the main databases used in this research, studies that have used these two classes of molecules coupled in the form of a hybrid on different therapeutic targets. The first stage of work consisted of synthesizing the reaction precursors, including 2-bromo-1-phenylethanone and 22 chalcones (2-hydroxychalcones, 3-hydroxychalcones and 4-hydroxychalcones) in which yields ranging from 15 to 100% were obtained. In possession of the different chalconas, the study of the reaction conditions that gave rise to the new analogue hybrids of 8,4'-oxyneolignans. Of the tested chalcones, those that showed promising results were the 3-hydroxychalcones and the 4-hydroxychalcones, obtaining 14 new hybrid molecules in yields ranging from 18 to 83%. The hybrid molecules synthesized had their properties biological agents evaluated for cytotoxic effects and the concentration that caused 50% of cell growth inhibition (IC50) in tumor cell lines of human glioblastoma (SNB-19), colon (HCT-116), prostate (PC-3) and leukemia acute promyelocytic (HL-60). The results of the cytotoxicity assay showed that 12 compounds (among the 14 tested) showed a percentage of inhibition of promising cell growth (≥75% cell inhibition). Compounds 67-80 were selected and the IC50 assay was evaluated revealing a moderate inhibition profile for compounds that present the chalcone moiety with groups that decrease the electronic density of the ring (deactivators), with compound 73 having the lowest IC50, for this methodology. Structural modifications of analogous compounds do not led to significant increases in cytotoxic activity when compared to the drug reference doxorubicin.A busca por substâncias químicas bioativas, tanto naturais quanto sintéticas parte de um mesmo pressuposto: a diminuição dos efeitos colaterais causados pelos medicamentos e o aumento da efetividade do fármaco ao seu alvo biológico. Mesmo que várias pesquisas tenham sido conduzidas para síntese de chalconas, neolignanas e seus análogos, não há, até o momento, nas principais bases de dados utilizadas nesta pesquisa, estudos que tenham empregado estas duas classes de moléculas acopladas na forma de um híbrido sobre diferentes alvos terapêuticos. A primeira etapa do trabalho consistiu em sintetizar os precursores reacionais,dentre eles a 2-bromo-1-feniletanona e 22 chalconas (2-hidroxichalconas 3-hidroxichalconas e 4-hidroxichalconas) no qual foram obtidos rendimentos que variam de 15 a 100%. De posse das diferentes chalconas, iniciou-se o estudo das condições reacionais que deram origem aos novos híbridos análogos de 8,4‘-oxineolignanas. Das chalconas testadas, aquelas que apresentaram resultados promissores foram as 3-hidroxichalconas e as 4- hidroxichalconas, com a obtenção de14 moléculas híbridas inéditas em rendimentos que variam de 18 a 83%. As moléculas híbridas sintetizadas tiveram suas propriedades biológicas avaliadas quanto aos efeitos citotóxicos e a concentração que causou 50% da inibição do crescimento celular (IC50)em linhagens de células tumorais de glioblastoma humano (SNB-19), cólon (HCT-116), próstata (PC-3) e leucemia promielocítica aguda (HL-60). Os resultados do ensaio de citotoxidade mostraram que 12 compostos (dentre os 14 testados) apresentaram percentual de inibição de crescimento celular promissor (≥75%da inibição das células). Os compostos 67-80 foram selecionados e o ensaio IC50 foi avaliado revelando perfil de inibição moderado para os compostos que apresentam a porção chalcona com grupos que diminuem a densidade eletrônica do anel (desativadores), sendo o composto 73 com menor valor de IC50, para esta metodologia. As modificações estruturas dos compostos análogos não levaram a incrementos relevantes de atividade citotóxica, quando comparados à droga de referência doxorrubicina.Submitted by Marlene Santos (marlene.bc.ufg@gmail.com) on 2022-02-24T20:30:16Z No. of bitstreams: 2 Tese- Fernanda de Sousa Fernandes - 2021.pdf: 5637926 bytes, checksum: 82bbe91be5329fa95cac976cf1773314 (MD5) license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5)Rejected by Luciana Ferreira (lucgeral@gmail.com), reason: Marlene, certifique se os artigos que o discente inseriu na íntegra são de acesso livre. on 2022-03-03T13:10:17Z (GMT)Submitted by Marlene Santos (marlene.bc.ufg@gmail.com) on 2022-03-09T13:16:42Z No. of bitstreams: 2 license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5) Tese- Fernanda de Sousa Fernandes - 2021.pdf: 5637926 bytes, checksum: 82bbe91be5329fa95cac976cf1773314 (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2022-03-09T14:27:01Z (GMT) No. of bitstreams: 2 license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5) Tese- Fernanda de Sousa Fernandes - 2021.pdf: 5637926 bytes, checksum: 82bbe91be5329fa95cac976cf1773314 (MD5)Made available in DSpace on 2022-03-09T14:27:01Z (GMT). No. of bitstreams: 2 license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5) Tese- Fernanda de Sousa Fernandes - 2021.pdf: 5637926 bytes, checksum: 82bbe91be5329fa95cac976cf1773314 (MD5) Previous issue date: 2021-12-15Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado de GoiásporUniversidade Federal de GoiásPrograma de Pós-graduação em Química (IQ)UFGBrasilInstituto de Química - IQ (RG)Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessHidroxichalconasNeolignanas8,4‘-oxineolignanasCitoxicidadeHíbrido molecularHydroxychalconesNeolignans8,4'-oxineolignansCytotoxicityMolecular hybridCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAHibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásicaMolecular hybridization of chalcones and neolignans analogues with potential antineoplastic activityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis8350050050050050029109513reponame:Biblioteca Digital de Teses e Dissertações da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.bc.ufg.br/tede/bitstreams/799080c0-fdfb-4120-9e85-c2147a53cb45/download8a4605be74aa9ea9d79846c1fba20a33MD54CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.bc.ufg.br/tede/bitstreams/d1d610a9-1f0f-471d-b77a-78a48ed93e7b/download4460e5956bc1d1639be9ae6146a50347MD55ORIGINALTese - Fernanda de Sousa Fernandes - 2021.pdfTese - Fernanda de Sousa Fernandes - 2021.pdfapplication/pdf5637926http://repositorio.bc.ufg.br/tede/bitstreams/4b1f14e2-59d5-4e25-9832-cabfeba69d50/download82bbe91be5329fa95cac976cf1773314MD53tede/119292022-03-09 11:27:48.416http://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 Internationalopen.accessoai:repositorio.bc.ufg.br:tede/11929http://repositorio.bc.ufg.br/tedeBiblioteca Digital de Teses e Dissertaçõeshttp://repositorio.bc.ufg.br/PUBhttps://repositorio.bc.ufg.br/tede_oai/requesttesesdissertacoes.bc@ufg.br ||tesesdissertacoes.bc@ufg.bropendoar:32082022-03-09T14:27:48Biblioteca Digital de Teses e Dissertações da UFG - Universidade Federal de Goiás (UFG)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 |
dc.title.pt_BR.fl_str_mv |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
dc.title.alternative.eng.fl_str_mv |
Molecular hybridization of chalcones and neolignans analogues with potential antineoplastic activity |
title |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
spellingShingle |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica Fernandes, Fernanda de Sousa Hidroxichalconas Neolignanas 8,4‘-oxineolignanas Citoxicidade Híbrido molecular Hydroxychalcones Neolignans 8,4'-oxineolignans Cytotoxicity Molecular hybrid CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
title_short |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
title_full |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
title_fullStr |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
title_full_unstemmed |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
title_sort |
Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica |
author |
Fernandes, Fernanda de Sousa |
author_facet |
Fernandes, Fernanda de Sousa |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Oliveira, Guilherme Roberto de |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8239498431579015 |
dc.contributor.advisor-co1.fl_str_mv |
Alonso, Christian Gonçalves |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/7285754665946583 |
dc.contributor.referee1.fl_str_mv |
Oliveira, Guilherme Roberto de |
dc.contributor.referee2.fl_str_mv |
Noda Pérez, Caridad |
dc.contributor.referee3.fl_str_mv |
Gomes, Marcelo do Nascimento |
dc.contributor.referee4.fl_str_mv |
Andrade, Fabiano Molinos de |
dc.contributor.referee5.fl_str_mv |
Lemes, Geralda de Fáma |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1113241281083058 |
dc.contributor.author.fl_str_mv |
Fernandes, Fernanda de Sousa |
contributor_str_mv |
Oliveira, Guilherme Roberto de Alonso, Christian Gonçalves Oliveira, Guilherme Roberto de Noda Pérez, Caridad Gomes, Marcelo do Nascimento Andrade, Fabiano Molinos de Lemes, Geralda de Fáma |
dc.subject.por.fl_str_mv |
Hidroxichalconas Neolignanas 8,4‘-oxineolignanas Citoxicidade Híbrido molecular |
topic |
Hidroxichalconas Neolignanas 8,4‘-oxineolignanas Citoxicidade Híbrido molecular Hydroxychalcones Neolignans 8,4'-oxineolignans Cytotoxicity Molecular hybrid CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Hydroxychalcones Neolignans 8,4'-oxineolignans Cytotoxicity Molecular hybrid |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
description |
The search for bioactive chemical substances, both natural and synthetic, starts from the same assumption: the reduction of the side effects caused by the drugs and increasing the effectiveness of the drug to its biological target. Same that several researches have been conducted for the synthesis of chalcones, neolignans and their analogues, there is not, so far, in the main databases used in this research, studies that have used these two classes of molecules coupled in the form of a hybrid on different therapeutic targets. The first stage of work consisted of synthesizing the reaction precursors, including 2-bromo-1-phenylethanone and 22 chalcones (2-hydroxychalcones, 3-hydroxychalcones and 4-hydroxychalcones) in which yields ranging from 15 to 100% were obtained. In possession of the different chalconas, the study of the reaction conditions that gave rise to the new analogue hybrids of 8,4'-oxyneolignans. Of the tested chalcones, those that showed promising results were the 3-hydroxychalcones and the 4-hydroxychalcones, obtaining 14 new hybrid molecules in yields ranging from 18 to 83%. The hybrid molecules synthesized had their properties biological agents evaluated for cytotoxic effects and the concentration that caused 50% of cell growth inhibition (IC50) in tumor cell lines of human glioblastoma (SNB-19), colon (HCT-116), prostate (PC-3) and leukemia acute promyelocytic (HL-60). The results of the cytotoxicity assay showed that 12 compounds (among the 14 tested) showed a percentage of inhibition of promising cell growth (≥75% cell inhibition). Compounds 67-80 were selected and the IC50 assay was evaluated revealing a moderate inhibition profile for compounds that present the chalcone moiety with groups that decrease the electronic density of the ring (deactivators), with compound 73 having the lowest IC50, for this methodology. Structural modifications of analogous compounds do not led to significant increases in cytotoxic activity when compared to the drug reference doxorubicin. |
publishDate |
2021 |
dc.date.issued.fl_str_mv |
2021-12-15 |
dc.date.accessioned.fl_str_mv |
2022-03-09T14:27:01Z |
dc.date.available.fl_str_mv |
2022-03-09T14:27:01Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
FERNANDES, F. S. Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica. 2021. 275 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2021. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/11929 |
identifier_str_mv |
FERNANDES, F. S. Hibridação molecular de chalconas e análogos de neolignanas com potencial atividade antineoplásica. 2021. 275 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2021. |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/11929 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.program.fl_str_mv |
83 |
dc.relation.confidence.fl_str_mv |
500 500 500 500 500 |
dc.relation.department.fl_str_mv |
29 |
dc.relation.cnpq.fl_str_mv |
1095 |
dc.relation.sponsorship.fl_str_mv |
1 3 |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.publisher.program.fl_str_mv |
Programa de Pós-graduação em Química (IQ) |
dc.publisher.initials.fl_str_mv |
UFG |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Instituto de Química - IQ (RG) |
publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.source.none.fl_str_mv |
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Biblioteca Digital de Teses e Dissertações da UFG - Universidade Federal de Goiás (UFG) |
repository.mail.fl_str_mv |
tesesdissertacoes.bc@ufg.br ||tesesdissertacoes.bc@ufg.br |
_version_ |
1797047633108271104 |