Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis

Detalhes bibliográficos
Ano de defesa: 2022
Autor(a) principal: Sarturi, Joelma Menegazzi lattes
Orientador(a): Rodrigues, Oscar Endrigo Dorneles lattes
Banca de defesa: Dalcol, Ionara Irion, Vargas, Josimar, Villetti, Marcos Antonio, Miranda, Milene Dias
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
1,10-fenantrolina-4,5-imidazo-benzocalcogenazois
Condensação de Debus-Radziszewski
SARS-CoV-2
Protease MPRO
Fotofísica
Palavras-chave em Inglês:
1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles
Condensation of Debus-Radziszewski
Protease M
Photophysical
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/26705
Resumo: In this work, a new serie of 1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g obtained through the Debus-Radziszeski condensation was synthesized. Benzoxazoles and benzothiazoles were previously synthesized and derivatives 1,10- phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g were obtained with yields ranging from 43 to 85%. The photophysical properties of compounds 5a-h/ 6a-g were evaluated against UV-Vis absorption, fluorescence emission and quantum yield fluorescence. Regarding the absorption spectrum of the derivatives, they had their spectra reported in the ultravioleta region and the fluorescence emission the compounds was observed in the purple to blue region. The quantum yield fluorescence (Φf) ranged from 0,10 – 0,71. The analyses of the biological activity about derivatives were carried out in silico, through molecular anchorage and in live, against the protease MPRO of the SARS-CoV-2 virus, which causes the disease COVID 19. The results of molecular anchorage demonstrate high affinity of the derivatives with the active place of the protease M. Additionally, the activity of these compounds as inhibitors of SARS-CoV2 was evaluated in vitro, and the compunds showed a very significant viral inhibition rate, with EC50 of 0,17 – 0,19 µM.
id UFSM-20_8840173c72dc92675f2d3ac739b22907
oai_identifier_str oai:repositorio.ufsm.br:1/26705
network_acronym_str UFSM-20
network_name_str Manancial - Repositório Digital da UFSM
repository_id_str
spelling 2022-10-31T13:16:28Z2022-10-31T13:16:28Z2022-08-29http://repositorio.ufsm.br/handle/1/26705In this work, a new serie of 1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g obtained through the Debus-Radziszeski condensation was synthesized. Benzoxazoles and benzothiazoles were previously synthesized and derivatives 1,10- phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g were obtained with yields ranging from 43 to 85%. The photophysical properties of compounds 5a-h/ 6a-g were evaluated against UV-Vis absorption, fluorescence emission and quantum yield fluorescence. Regarding the absorption spectrum of the derivatives, they had their spectra reported in the ultravioleta region and the fluorescence emission the compounds was observed in the purple to blue region. The quantum yield fluorescence (Φf) ranged from 0,10 – 0,71. The analyses of the biological activity about derivatives were carried out in silico, through molecular anchorage and in live, against the protease MPRO of the SARS-CoV-2 virus, which causes the disease COVID 19. The results of molecular anchorage demonstrate high affinity of the derivatives with the active place of the protease M. Additionally, the activity of these compounds as inhibitors of SARS-CoV2 was evaluated in vitro, and the compunds showed a very significant viral inhibition rate, with EC50 of 0,17 – 0,19 µM.No presente trabalho sintetizou-se uma nova série de 1,10-fenantrolina-4,5-imidazobenzocalcogenazois 5a-h/6a-h obtidos através de reação de condensação de DebusRadziszewski. Os benzoxazóis e benzotiazóis foram previamente sintetizados e os derivados 1,10-fenantrolina-4,5-imidazo-benzocalcogenazois 5a-h/6a-g foram obtidos com rendimentos que variaram de 43-85%. As propriedades fotofísicas dos compostos 5a-h e 6a-g foram avaliadas frente a absorção UV-Vis, emissão de fluorescência e rendimento quântico de fluorescência. Em relação ao espectro de absorção dos derivados, estes tiveram seus espectros relatados na região do ultravioleta e a emissão de fluorescência dos compostos foi observada na região do roxo a azul. Já o rendimento quântico de fluorescência (Φf) variou de 0,03-0,75. As análises de atividade biológica dos derivados foram realizadas in silico, através de ancoragem molecular e frente a protease MPRO do vírus SARS-CoV-2, causador da doença COVID 19. Os resultados da ancoragem molecular demonstram alta afinidade dos derivados 5a-h/6a-g com o sítio ativo da protease M. Adicionalmente, a atividade destes derivados como inibidores da SARS-CoV-2 foi avaliada in vitro, sendo que os compostos apresentaram uma taxa de inibição viral bastante significativa, com EC50 de 0,17 – 0,19 µM.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccess1,10-fenantrolina-4,5-imidazo-benzocalcogenazoisCondensação de Debus-RadziszewskiSARS-CoV-2Protease MPROFotofísica1,10-phenanthroline-4,5-imidazo-benzochalcogenazolesCondensation of Debus-RadziszewskiProtease MPhotophysicalCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóisSynthesis and anti-SARS-CoV-2 and photophysical evaluation of the 1,10-phenantroline-4,5-imidazo-benzochalcogenazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Dornelles, LucianoDalcol, Ionara IrionVargas, JosimarVilletti, Marcos AntonioMiranda, Milene Diashttp://lattes.cnpq.br/6713133698480485Sarturi, Joelma Menegazzi10060000000060060060060060060060060009fef019-ac43-4d8b-83d3-3565e4686d7ba7a413b3-8902-4373-a64e-eaf6264f6c3388ff8616-1678-47c5-b3c5-9a8e5085844f2cbacb00-be94-498b-9c77-1d47963baf690c8a098e-1b1c-4f5a-a71a-29ff4c12466b8437eadf-3a57-4c40-ac38-2583cb529b98aac1db45-29a2-4bf4-81ad-360824f2d57dreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2022_SARTURI_JOELMA.pdfTES_PPGQUÍMICA_2022_SARTURI_JOELMA.pdfTese de doutoradoapplication/pdf7337501http://repositorio.ufsm.br/bitstream/1/26705/1/TES_PPGQU%c3%8dMICA_2022_SARTURI_JOELMA.pdf8ef82f105c5a8f0368e316d7f655c420MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/26705/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/26705/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/267052022-10-31 10:16:28.35oai:repositorio.ufsm.br:1/26705TElDRU7Dh0EgREUgRElTVFJJQlVJw4fDg08gTsODTy1FWENMVVNJVkEKCkNvbSBhIGFwcmVzZW50YcOnw6NvIGRlc3RhIGxpY2Vuw6dhLCB2b2PDqiAobyBhdXRvciAoZXMpIG91IG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgZGUgYXV0b3IpIGNvbmNlZGUgw6AgVW5pdmVyc2lkYWRlCkZlZGVyYWwgZGUgU2FudGEgTWFyaWEgKFVGU00pIG8gZGlyZWl0byBuw6NvLWV4Y2x1c2l2byBkZSByZXByb2R1emlyLCAgdHJhZHV6aXIgKGNvbmZvcm1lIGRlZmluaWRvIGFiYWl4byksIGUvb3UKZGlzdHJpYnVpciBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gKGluY2x1aW5kbyBvIHJlc3VtbykgcG9yIHRvZG8gbyBtdW5kbyBubyBmb3JtYXRvIGltcHJlc3NvIGUgZWxldHLDtG5pY28gZQplbSBxdWFscXVlciBtZWlvLCBpbmNsdWluZG8gb3MgZm9ybWF0b3Mgw6F1ZGlvIG91IHbDrWRlby4KClZvY8OqIGNvbmNvcmRhIHF1ZSBhIFVGU00gcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250ZcO6ZG8sIHRyYW5zcG9yIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbwpwYXJhIHF1YWxxdWVyIG1laW8gb3UgZm9ybWF0byBwYXJhIGZpbnMgZGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIHRhbWLDqW0gY29uY29yZGEgcXVlIGEgVUZTTSBwb2RlIG1hbnRlciBtYWlzIGRlIHVtYSBjw7NwaWEgYSBzdWEgdGVzZSBvdQpkaXNzZXJ0YcOnw6NvIHBhcmEgZmlucyBkZSBzZWd1cmFuw6dhLCBiYWNrLXVwIGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIGRlY2xhcmEgcXVlIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyDDqSBvcmlnaW5hbCBlIHF1ZSB2b2PDqiB0ZW0gbyBwb2RlciBkZSBjb25jZWRlciBvcyBkaXJlaXRvcyBjb250aWRvcwpuZXN0YSBsaWNlbsOnYS4gVm9jw6ogdGFtYsOpbSBkZWNsYXJhIHF1ZSBvIGRlcMOzc2l0byBkYSBzdWEgdGVzZSBvdSBkaXNzZXJ0YcOnw6NvIG7Do28sIHF1ZSBzZWphIGRlIHNldQpjb25oZWNpbWVudG8sIGluZnJpbmdlIGRpcmVpdG9zIGF1dG9yYWlzIGRlIG5pbmd1w6ltLgoKQ2FzbyBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gY29udGVuaGEgbWF0ZXJpYWwgcXVlIHZvY8OqIG7Do28gcG9zc3VpIGEgdGl0dWxhcmlkYWRlIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgdm9jw6oKZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc8OjbyBpcnJlc3RyaXRhIGRvIGRldGVudG9yIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBwYXJhIGNvbmNlZGVyIMOgIFVGU00Kb3MgZGlyZWl0b3MgYXByZXNlbnRhZG9zIG5lc3RhIGxpY2Vuw6dhLCBlIHF1ZSBlc3NlIG1hdGVyaWFsIGRlIHByb3ByaWVkYWRlIGRlIHRlcmNlaXJvcyBlc3TDoSBjbGFyYW1lbnRlCmlkZW50aWZpY2FkbyBlIHJlY29uaGVjaWRvIG5vIHRleHRvIG91IG5vIGNvbnRlw7pkbyBkYSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gb3JhIGRlcG9zaXRhZGEuCgpDQVNPIEEgVEVTRSBPVSBESVNTRVJUQcOHw4NPIE9SQSBERVBPU0lUQURBIFRFTkhBIFNJRE8gUkVTVUxUQURPIERFIFVNIFBBVFJPQ8ONTklPIE9VCkFQT0lPIERFIFVNQSBBR8OKTkNJQSBERSBGT01FTlRPIE9VIE9VVFJPIE9SR0FOSVNNTyBRVUUgTsODTyBTRUpBIEEgVUZTTQosIFZPQ8OKIERFQ0xBUkEgUVVFIFJFU1BFSVRPVSBUT0RPUyBFIFFVQUlTUVVFUiBESVJFSVRPUyBERSBSRVZJU8ODTyBDT01PClRBTULDiU0gQVMgREVNQUlTIE9CUklHQcOHw5VFUyBFWElHSURBUyBQT1IgQ09OVFJBVE8gT1UgQUNPUkRPLgoKQSBVRlNNIHNlIGNvbXByb21ldGUgYSBpZGVudGlmaWNhciBjbGFyYW1lbnRlIG8gc2V1IG5vbWUgKHMpIG91IG8ocykgbm9tZShzKSBkbyhzKQpkZXRlbnRvcihlcykgZG9zIGRpcmVpdG9zIGF1dG9yYWlzIGRhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbywgZSBuw6NvIGZhcsOhIHF1YWxxdWVyIGFsdGVyYcOnw6NvLCBhbMOpbSBkYXF1ZWxhcwpjb25jZWRpZGFzIHBvciBlc3RhIGxpY2Vuw6dhLgoKRepositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132022-10-31T13:16:28Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
dc.title.alternative.eng.fl_str_mv Synthesis and anti-SARS-CoV-2 and photophysical evaluation of the 1,10-phenantroline-4,5-imidazo-benzochalcogenazoles
title Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
spellingShingle Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
Sarturi, Joelma Menegazzi
1,10-fenantrolina-4,5-imidazo-benzocalcogenazois
Condensação de Debus-Radziszewski
SARS-CoV-2
Protease MPRO
Fotofísica
1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles
Condensation of Debus-Radziszewski
Protease M
Photophysical
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
title_full Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
title_fullStr Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
title_full_unstemmed Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
title_sort Síntese e avaliação anti-SARS-CoV-2 e fotofísica dos 1,10- fenantrolina-4,5-imidazo-benzocalcogenazóis
author Sarturi, Joelma Menegazzi
author_facet Sarturi, Joelma Menegazzi
author_role author
dc.contributor.advisor1.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/6536519955416085
dc.contributor.advisor-co1.fl_str_mv Dornelles, Luciano
dc.contributor.referee1.fl_str_mv Dalcol, Ionara Irion
dc.contributor.referee2.fl_str_mv Vargas, Josimar
dc.contributor.referee3.fl_str_mv Villetti, Marcos Antonio
dc.contributor.referee4.fl_str_mv Miranda, Milene Dias
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/6713133698480485
dc.contributor.author.fl_str_mv Sarturi, Joelma Menegazzi
contributor_str_mv Rodrigues, Oscar Endrigo Dorneles
Dornelles, Luciano
Dalcol, Ionara Irion
Vargas, Josimar
Villetti, Marcos Antonio
Miranda, Milene Dias
dc.subject.por.fl_str_mv 1,10-fenantrolina-4,5-imidazo-benzocalcogenazois
Condensação de Debus-Radziszewski
SARS-CoV-2
Protease MPRO
Fotofísica
topic 1,10-fenantrolina-4,5-imidazo-benzocalcogenazois
Condensação de Debus-Radziszewski
SARS-CoV-2
Protease MPRO
Fotofísica
1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles
Condensation of Debus-Radziszewski
Protease M
Photophysical
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv 1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles
Condensation of Debus-Radziszewski
Protease M
Photophysical
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In this work, a new serie of 1,10-phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g obtained through the Debus-Radziszeski condensation was synthesized. Benzoxazoles and benzothiazoles were previously synthesized and derivatives 1,10- phenanthroline-4,5-imidazo-benzochalcogenazoles 5a-h/ 6a-g were obtained with yields ranging from 43 to 85%. The photophysical properties of compounds 5a-h/ 6a-g were evaluated against UV-Vis absorption, fluorescence emission and quantum yield fluorescence. Regarding the absorption spectrum of the derivatives, they had their spectra reported in the ultravioleta region and the fluorescence emission the compounds was observed in the purple to blue region. The quantum yield fluorescence (Φf) ranged from 0,10 – 0,71. The analyses of the biological activity about derivatives were carried out in silico, through molecular anchorage and in live, against the protease MPRO of the SARS-CoV-2 virus, which causes the disease COVID 19. The results of molecular anchorage demonstrate high affinity of the derivatives with the active place of the protease M. Additionally, the activity of these compounds as inhibitors of SARS-CoV2 was evaluated in vitro, and the compunds showed a very significant viral inhibition rate, with EC50 of 0,17 – 0,19 µM.
publishDate 2022
dc.date.accessioned.fl_str_mv 2022-10-31T13:16:28Z
dc.date.available.fl_str_mv 2022-10-31T13:16:28Z
dc.date.issued.fl_str_mv 2022-08-29
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.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/26705
url http://repositorio.ufsm.br/handle/1/26705
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
600
600
600
600
600
600
600
dc.relation.authority.fl_str_mv 09fef019-ac43-4d8b-83d3-3565e4686d7b
a7a413b3-8902-4373-a64e-eaf6264f6c33
88ff8616-1678-47c5-b3c5-9a8e5085844f
2cbacb00-be94-498b-9c77-1d47963baf69
0c8a098e-1b1c-4f5a-a71a-29ff4c12466b
8437eadf-3a57-4c40-ac38-2583cb529b98
aac1db45-29a2-4bf4-81ad-360824f2d57d
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 Santa Maria
Centro de Ciências Naturais e Exatas
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química
dc.publisher.initials.fl_str_mv UFSM
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.source.none.fl_str_mv reponame:Manancial - Repositório Digital da UFSM
instname:Universidade Federal de Santa Maria (UFSM)
instacron:UFSM
instname_str Universidade Federal de Santa Maria (UFSM)
instacron_str UFSM
institution UFSM
reponame_str Manancial - Repositório Digital da UFSM
collection Manancial - Repositório Digital da UFSM
bitstream.url.fl_str_mv http://repositorio.ufsm.br/bitstream/1/26705/1/TES_PPGQU%c3%8dMICA_2022_SARTURI_JOELMA.pdf
http://repositorio.ufsm.br/bitstream/1/26705/2/license_rdf
http://repositorio.ufsm.br/bitstream/1/26705/3/license.txt
bitstream.checksum.fl_str_mv 8ef82f105c5a8f0368e316d7f655c420
4460e5956bc1d1639be9ae6146a50347
2f0571ecee68693bd5cd3f17c1e075df
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)
repository.mail.fl_str_mv
_version_ 1794524452153720832

Registros relacionados