Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment
Autor(a) principal: | |
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Data de Publicação: | 2024 |
Outros Autores: | , , , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Bioscience journal (Online) |
Texto Completo: | https://seer.ufu.br/index.php/biosciencejournal/article/view/69502 |
Resumo: | Chagas disease is a public health problem affecting approximately seven million people worldwide. Thus, there is a need to discover drugs for the adequate treatment of this disease because currently available drugs have serious side effects. Therefore, this study aimed to evaluate the in vitro trypanocidal activity of (-)-6,6'-dinitrohinokinin, obtained from the partial synthesis of (-)-hinokinin, on the trypomastigotes and amastigotes forms. For the trypomastigote assay, blood was collected from mice infected with Trypanosoma cruzi through cardiac puncture at the parasitemic peak. The results show that (-)-6,6'-dinitrohinokinin was effective against the trypomastigote forms, presenting an IC50 of 19.83 µM and lysis percentage values of 78.4% and 69.4% at concentrations of 200 and 100 µM, respectively. Molecular docking calculations indicate that (-)-6,6'-dinitrohinokinin favorably interacts with the amino acids present in the active site of the protein trypanothione reductase, a typical target for anti-trypanosomal drug development. According to the results, the (-)-6,6'-dinitrohinokinin showed more significant trypanocidal activity with IC50 of 1.83 µM than benzonidazole positive control with IC50 of 53.2 µM, showing to be a prototype molecule promising for the development of a new antiparasitic drug. |
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Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessmentMolecular dockingNatural productsTrypanocideTrypanosoma cruzi.Health SciencesChagas disease is a public health problem affecting approximately seven million people worldwide. Thus, there is a need to discover drugs for the adequate treatment of this disease because currently available drugs have serious side effects. Therefore, this study aimed to evaluate the in vitro trypanocidal activity of (-)-6,6'-dinitrohinokinin, obtained from the partial synthesis of (-)-hinokinin, on the trypomastigotes and amastigotes forms. For the trypomastigote assay, blood was collected from mice infected with Trypanosoma cruzi through cardiac puncture at the parasitemic peak. The results show that (-)-6,6'-dinitrohinokinin was effective against the trypomastigote forms, presenting an IC50 of 19.83 µM and lysis percentage values of 78.4% and 69.4% at concentrations of 200 and 100 µM, respectively. Molecular docking calculations indicate that (-)-6,6'-dinitrohinokinin favorably interacts with the amino acids present in the active site of the protein trypanothione reductase, a typical target for anti-trypanosomal drug development. According to the results, the (-)-6,6'-dinitrohinokinin showed more significant trypanocidal activity with IC50 of 1.83 µM than benzonidazole positive control with IC50 of 53.2 µM, showing to be a prototype molecule promising for the development of a new antiparasitic drug.Universidade Federal de Uberlândia2024-03-15info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://seer.ufu.br/index.php/biosciencejournal/article/view/6950210.14393/BJ-v40n0a2024-69502Bioscience Journal ; Vol. 40 (2024): Continuous Publication; e40016Bioscience Journal ; v. 40 (2024): Continuous Publication; e400161981-3163reponame:Bioscience journal (Online)instname:Universidade Federal de Uberlândia (UFU)instacron:UFUenghttps://seer.ufu.br/index.php/biosciencejournal/article/view/69502/38421Brazil; Contemporary Copyright (c) 2024 Suziene Caroline Silva Cardoso, Wilson R. Cunha, Pedro S. dos S. R. Cavallari, Samarah Gomes de Almeida, Ana Helena Januário, Patrícia Mendonça Pauletti, Fernanda Amorim Santos, Rosângela da Silva Laurentiz, Giulia Stavrakas Miranda, João Victor Andrade, Renato Pereira Orenha, Renato Luis Tame Parreira, Márcio Luís Andrade e Silva, Mario F. C. Santos, Viviane Esperandimhttps://creativecommons.org/licenses/by/4.0info:eu-repo/semantics/openAccessCardoso, Suziene Caroline SilvaCunha, Wilson R.Cavallari, Pedro S. dos S. R.Almeida, Samarah Gomes deJanuário, Ana HelenaPauletti, Patrícia MendonçaSantos, Fernanda AmorimLaurentiz, Rosângela da SilvaMiranda, Giulia StavrakasAndrade, João VictorOrenha, Renato PereiraParreira, Renato Luis TameSilva, Márcio Luís Andrade eSantos, Mario F. C.Esperandim, Viviane2024-04-03T20:47:42Zoai:ojs.www.seer.ufu.br:article/69502Revistahttps://seer.ufu.br/index.php/biosciencejournalPUBhttps://seer.ufu.br/index.php/biosciencejournal/oaibiosciencej@ufu.br||1981-31631516-3725opendoar:2024-04-03T20:47:42Bioscience journal (Online) - Universidade Federal de Uberlândia (UFU)false |
dc.title.none.fl_str_mv |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
title |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
spellingShingle |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment Cardoso, Suziene Caroline Silva Molecular docking Natural products Trypanocide Trypanosoma cruzi. Health Sciences |
title_short |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
title_full |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
title_fullStr |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
title_full_unstemmed |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
title_sort |
Synthesis of (-) - 6,6'-dinitrohinokinin from hinokinin natural product and in silico and in vitro trypanocidal activity assessment |
author |
Cardoso, Suziene Caroline Silva |
author_facet |
Cardoso, Suziene Caroline Silva Cunha, Wilson R. Cavallari, Pedro S. dos S. R. Almeida, Samarah Gomes de Januário, Ana Helena Pauletti, Patrícia Mendonça Santos, Fernanda Amorim Laurentiz, Rosângela da Silva Miranda, Giulia Stavrakas Andrade, João Victor Orenha, Renato Pereira Parreira, Renato Luis Tame Silva, Márcio Luís Andrade e Santos, Mario F. C. Esperandim, Viviane |
author_role |
author |
author2 |
Cunha, Wilson R. Cavallari, Pedro S. dos S. R. Almeida, Samarah Gomes de Januário, Ana Helena Pauletti, Patrícia Mendonça Santos, Fernanda Amorim Laurentiz, Rosângela da Silva Miranda, Giulia Stavrakas Andrade, João Victor Orenha, Renato Pereira Parreira, Renato Luis Tame Silva, Márcio Luís Andrade e Santos, Mario F. C. Esperandim, Viviane |
author2_role |
author author author author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Cardoso, Suziene Caroline Silva Cunha, Wilson R. Cavallari, Pedro S. dos S. R. Almeida, Samarah Gomes de Januário, Ana Helena Pauletti, Patrícia Mendonça Santos, Fernanda Amorim Laurentiz, Rosângela da Silva Miranda, Giulia Stavrakas Andrade, João Victor Orenha, Renato Pereira Parreira, Renato Luis Tame Silva, Márcio Luís Andrade e Santos, Mario F. C. Esperandim, Viviane |
dc.subject.por.fl_str_mv |
Molecular docking Natural products Trypanocide Trypanosoma cruzi. Health Sciences |
topic |
Molecular docking Natural products Trypanocide Trypanosoma cruzi. Health Sciences |
description |
Chagas disease is a public health problem affecting approximately seven million people worldwide. Thus, there is a need to discover drugs for the adequate treatment of this disease because currently available drugs have serious side effects. Therefore, this study aimed to evaluate the in vitro trypanocidal activity of (-)-6,6'-dinitrohinokinin, obtained from the partial synthesis of (-)-hinokinin, on the trypomastigotes and amastigotes forms. For the trypomastigote assay, blood was collected from mice infected with Trypanosoma cruzi through cardiac puncture at the parasitemic peak. The results show that (-)-6,6'-dinitrohinokinin was effective against the trypomastigote forms, presenting an IC50 of 19.83 µM and lysis percentage values of 78.4% and 69.4% at concentrations of 200 and 100 µM, respectively. Molecular docking calculations indicate that (-)-6,6'-dinitrohinokinin favorably interacts with the amino acids present in the active site of the protein trypanothione reductase, a typical target for anti-trypanosomal drug development. According to the results, the (-)-6,6'-dinitrohinokinin showed more significant trypanocidal activity with IC50 of 1.83 µM than benzonidazole positive control with IC50 of 53.2 µM, showing to be a prototype molecule promising for the development of a new antiparasitic drug. |
publishDate |
2024 |
dc.date.none.fl_str_mv |
2024-03-15 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://seer.ufu.br/index.php/biosciencejournal/article/view/69502 10.14393/BJ-v40n0a2024-69502 |
url |
https://seer.ufu.br/index.php/biosciencejournal/article/view/69502 |
identifier_str_mv |
10.14393/BJ-v40n0a2024-69502 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
https://seer.ufu.br/index.php/biosciencejournal/article/view/69502/38421 |
dc.rights.driver.fl_str_mv |
https://creativecommons.org/licenses/by/4.0 info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by/4.0 |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.coverage.none.fl_str_mv |
Brazil; Contemporary |
dc.publisher.none.fl_str_mv |
Universidade Federal de Uberlândia |
publisher.none.fl_str_mv |
Universidade Federal de Uberlândia |
dc.source.none.fl_str_mv |
Bioscience Journal ; Vol. 40 (2024): Continuous Publication; e40016 Bioscience Journal ; v. 40 (2024): Continuous Publication; e40016 1981-3163 reponame:Bioscience journal (Online) instname:Universidade Federal de Uberlândia (UFU) instacron:UFU |
instname_str |
Universidade Federal de Uberlândia (UFU) |
instacron_str |
UFU |
institution |
UFU |
reponame_str |
Bioscience journal (Online) |
collection |
Bioscience journal (Online) |
repository.name.fl_str_mv |
Bioscience journal (Online) - Universidade Federal de Uberlândia (UFU) |
repository.mail.fl_str_mv |
biosciencej@ufu.br|| |
_version_ |
1797069065850716160 |