Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vag...

Autores: González González, Alonzo; Sánchez Sánchez, Oscar; Yépez Mulia, Lilián; Delgado Maldonado, Timoteo; Vázquez Jiménez, Lenci K.; López Velázquez, Gabriel; de la Mora de la Mora, José Ignacio; Pacheco Gutierrez, Sebastian; Chino Ríos, Laura; Arias, Diego Gustavo; Moreno Rodríguez, Adriana; Paz González, Alma; Ortíz Pérez, Eyra; Rivera, Gildardo
Año de publicación: 2024
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: In this study, n-butyl and iso-butyl quinoxaline-7-carboxylate-1,4-di-N-oxide derivatives were evaluated in vitro against Giardia lamblia (G. lamblia), Trichomonas vaginalis (T. vaginalis), and Entamoeba histolytica (E. histolytica). The potential mechanism of action determination was approached by in silico analysis on G. lamblia and T. vaginalis triosephosphate isomerase (GlTIM and TvTIM, respectively), and on E. histolytica thioredoxin reductase (EhTrxR). Enzyme inactivation assays were performed on recombinant GlTIM and EhTrxR. Compound T-167 showed the best giardicidal activity (IC50 = 25.53 nM) and the highest inactivation efficiency against GlTIM without significantly perturbing its human homolog. Compounds T-142 and T-143 showed the best amoebicidal (IC50 = 9.20 nM) and trichomonacidal (IC50 = 45.20 nM) activity, respectively. Additionally, T-143 had a high activity as giardicial (IC50 = 29.13 nM) and amoebicidal (IC50 = 15.14 nM), proposing it as a broad-spectrum antiparasitic agent. Compounds T-145, and T-161 were the best EhTrxR inhibitors with IC50 of 16 µM, and 18 µM, respectively.
Fil: González González, Alonzo. Instituto Politécnico Nacional; México
Fil: Sánchez Sánchez, Oscar. Instituto Politécnico Nacional; México
Fil: Yépez Mulia, Lilián. Instituto Mexicano del Seguro Social; México
Fil: Delgado Maldonado, Timoteo. Instituto Politécnico Nacional; México
Fil: Vázquez Jiménez, Lenci K.. Instituto Politécnico Nacional; México
Fil: López Velázquez, Gabriel. Instituto Nacional de Pediatría; México
Fil: de la Mora de la Mora, José Ignacio. Instituto Nacional de Pediatría; México
Fil: Pacheco Gutierrez, Sebastian. Instituto Nacional de Pediatría; México
Fil: Chino Ríos, Laura. Instituto Nacional de Pediatría; México
Fil: Arias, Diego Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Agrobiotecnología del Litoral. Universidad Nacional del Litoral. Instituto de Agrobiotecnología del Litoral; Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Fil: Moreno Rodríguez, Adriana. Universidad Autonoma de Benito Juarez de Oaxaca (univ. A. B. Juarez de Oaxaca); México
Fil: Paz González, Alma. Instituto Politécnico Nacional; México
Fil: Ortíz Pérez, Eyra. Instituto Politécnico Nacional; México
Fil: Rivera, Gildardo. Instituto Politécnico Nacional; México
Materia: Quinoxaline-1,4-di-N-oxide
Antiprotozoal activity
Giardia lamblia
Trichomonas vaginalis
Entamoeba histolytica
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/266119

Acceder

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network_acronym_str	CONICETDig
repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approachGonzález González, AlonzoSánchez Sánchez, OscarYépez Mulia, LiliánDelgado Maldonado, TimoteoVázquez Jiménez, Lenci K.López Velázquez, Gabrielde la Mora de la Mora, José IgnacioPacheco Gutierrez, SebastianChino Ríos, LauraArias, Diego GustavoMoreno Rodríguez, AdrianaPaz González, AlmaOrtíz Pérez, EyraRivera, GildardoQuinoxaline-1,4-di-N-oxideAntiprotozoal activityGiardia lambliaTrichomonas vaginalisEntamoeba histolyticahttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1In this study, n-butyl and iso-butyl quinoxaline-7-carboxylate-1,4-di-N-oxide derivatives were evaluated in vitro against Giardia lamblia (G. lamblia), Trichomonas vaginalis (T. vaginalis), and Entamoeba histolytica (E. histolytica). The potential mechanism of action determination was approached by in silico analysis on G. lamblia and T. vaginalis triosephosphate isomerase (GlTIM and TvTIM, respectively), and on E. histolytica thioredoxin reductase (EhTrxR). Enzyme inactivation assays were performed on recombinant GlTIM and EhTrxR. Compound T-167 showed the best giardicidal activity (IC50 = 25.53 nM) and the highest inactivation efficiency against GlTIM without significantly perturbing its human homolog. Compounds T-142 and T-143 showed the best amoebicidal (IC50 = 9.20 nM) and trichomonacidal (IC50 = 45.20 nM) activity, respectively. Additionally, T-143 had a high activity as giardicial (IC50 = 29.13 nM) and amoebicidal (IC50 = 15.14 nM), proposing it as a broad-spectrum antiparasitic agent. Compounds T-145, and T-161 were the best EhTrxR inhibitors with IC50 of 16 µM, and 18 µM, respectively.Fil: González González, Alonzo. Instituto Politécnico Nacional; MéxicoFil: Sánchez Sánchez, Oscar. Instituto Politécnico Nacional; MéxicoFil: Yépez Mulia, Lilián. Instituto Mexicano del Seguro Social; MéxicoFil: Delgado Maldonado, Timoteo. Instituto Politécnico Nacional; MéxicoFil: Vázquez Jiménez, Lenci K.. Instituto Politécnico Nacional; MéxicoFil: López Velázquez, Gabriel. Instituto Nacional de Pediatría; MéxicoFil: de la Mora de la Mora, José Ignacio. Instituto Nacional de Pediatría; MéxicoFil: Pacheco Gutierrez, Sebastian. Instituto Nacional de Pediatría; MéxicoFil: Chino Ríos, Laura. Instituto Nacional de Pediatría; MéxicoFil: Arias, Diego Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Agrobiotecnología del Litoral. Universidad Nacional del Litoral. Instituto de Agrobiotecnología del Litoral; Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; ArgentinaFil: Moreno Rodríguez, Adriana. Universidad Autonoma de Benito Juarez de Oaxaca (univ. A. B. Juarez de Oaxaca); MéxicoFil: Paz González, Alma. Instituto Politécnico Nacional; MéxicoFil: Ortíz Pérez, Eyra. Instituto Politécnico Nacional; MéxicoFil: Rivera, Gildardo. Instituto Politécnico Nacional; MéxicoTaylor & Francis Ltd2024-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/266119González González, Alonzo; Sánchez Sánchez, Oscar; Yépez Mulia, Lilián; Delgado Maldonado, Timoteo; Vázquez Jiménez, Lenci K.; et al.; Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 39; 1; 10-2024; 1-151475-6366CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.1080/14756366.2024.2413018info:eu-repo/semantics/altIdentifier/doi/10.1080/14756366.2024.2413018info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:07Zoai:ri.conicet.gov.ar:11336/266119instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:00:08.26CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
title	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
spellingShingle	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach González González, Alonzo Quinoxaline-1,4-di-N-oxide Antiprotozoal activity Giardia lamblia Trichomonas vaginalis Entamoeba histolytica
title_short	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
title_full	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
title_fullStr	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
title_full_unstemmed	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
title_sort	Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach
dc.creator.none.fl_str_mv	González González, Alonzo Sánchez Sánchez, Oscar Yépez Mulia, Lilián Delgado Maldonado, Timoteo Vázquez Jiménez, Lenci K. López Velázquez, Gabriel de la Mora de la Mora, José Ignacio Pacheco Gutierrez, Sebastian Chino Ríos, Laura Arias, Diego Gustavo Moreno Rodríguez, Adriana Paz González, Alma Ortíz Pérez, Eyra Rivera, Gildardo
author	González González, Alonzo
author_facet	González González, Alonzo Sánchez Sánchez, Oscar Yépez Mulia, Lilián Delgado Maldonado, Timoteo Vázquez Jiménez, Lenci K. López Velázquez, Gabriel de la Mora de la Mora, José Ignacio Pacheco Gutierrez, Sebastian Chino Ríos, Laura Arias, Diego Gustavo Moreno Rodríguez, Adriana Paz González, Alma Ortíz Pérez, Eyra Rivera, Gildardo
author_role	author
author2	Sánchez Sánchez, Oscar Yépez Mulia, Lilián Delgado Maldonado, Timoteo Vázquez Jiménez, Lenci K. López Velázquez, Gabriel de la Mora de la Mora, José Ignacio Pacheco Gutierrez, Sebastian Chino Ríos, Laura Arias, Diego Gustavo Moreno Rodríguez, Adriana Paz González, Alma Ortíz Pérez, Eyra Rivera, Gildardo
author2_role	author author author author author author author author author author author author author
dc.subject.none.fl_str_mv	Quinoxaline-1,4-di-N-oxide Antiprotozoal activity Giardia lamblia Trichomonas vaginalis Entamoeba histolytica
topic	Quinoxaline-1,4-di-N-oxide Antiprotozoal activity Giardia lamblia Trichomonas vaginalis Entamoeba histolytica
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.6 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	In this study, n-butyl and iso-butyl quinoxaline-7-carboxylate-1,4-di-N-oxide derivatives were evaluated in vitro against Giardia lamblia (G. lamblia), Trichomonas vaginalis (T. vaginalis), and Entamoeba histolytica (E. histolytica). The potential mechanism of action determination was approached by in silico analysis on G. lamblia and T. vaginalis triosephosphate isomerase (GlTIM and TvTIM, respectively), and on E. histolytica thioredoxin reductase (EhTrxR). Enzyme inactivation assays were performed on recombinant GlTIM and EhTrxR. Compound T-167 showed the best giardicidal activity (IC50 = 25.53 nM) and the highest inactivation efficiency against GlTIM without significantly perturbing its human homolog. Compounds T-142 and T-143 showed the best amoebicidal (IC50 = 9.20 nM) and trichomonacidal (IC50 = 45.20 nM) activity, respectively. Additionally, T-143 had a high activity as giardicial (IC50 = 29.13 nM) and amoebicidal (IC50 = 15.14 nM), proposing it as a broad-spectrum antiparasitic agent. Compounds T-145, and T-161 were the best EhTrxR inhibitors with IC50 of 16 µM, and 18 µM, respectively. Fil: González González, Alonzo. Instituto Politécnico Nacional; México Fil: Sánchez Sánchez, Oscar. Instituto Politécnico Nacional; México Fil: Yépez Mulia, Lilián. Instituto Mexicano del Seguro Social; México Fil: Delgado Maldonado, Timoteo. Instituto Politécnico Nacional; México Fil: Vázquez Jiménez, Lenci K.. Instituto Politécnico Nacional; México Fil: López Velázquez, Gabriel. Instituto Nacional de Pediatría; México Fil: de la Mora de la Mora, José Ignacio. Instituto Nacional de Pediatría; México Fil: Pacheco Gutierrez, Sebastian. Instituto Nacional de Pediatría; México Fil: Chino Ríos, Laura. Instituto Nacional de Pediatría; México Fil: Arias, Diego Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Agrobiotecnología del Litoral. Universidad Nacional del Litoral. Instituto de Agrobiotecnología del Litoral; Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina Fil: Moreno Rodríguez, Adriana. Universidad Autonoma de Benito Juarez de Oaxaca (univ. A. B. Juarez de Oaxaca); México Fil: Paz González, Alma. Instituto Politécnico Nacional; México Fil: Ortíz Pérez, Eyra. Instituto Politécnico Nacional; México Fil: Rivera, Gildardo. Instituto Politécnico Nacional; México
description	In this study, n-butyl and iso-butyl quinoxaline-7-carboxylate-1,4-di-N-oxide derivatives were evaluated in vitro against Giardia lamblia (G. lamblia), Trichomonas vaginalis (T. vaginalis), and Entamoeba histolytica (E. histolytica). The potential mechanism of action determination was approached by in silico analysis on G. lamblia and T. vaginalis triosephosphate isomerase (GlTIM and TvTIM, respectively), and on E. histolytica thioredoxin reductase (EhTrxR). Enzyme inactivation assays were performed on recombinant GlTIM and EhTrxR. Compound T-167 showed the best giardicidal activity (IC50 = 25.53 nM) and the highest inactivation efficiency against GlTIM without significantly perturbing its human homolog. Compounds T-142 and T-143 showed the best amoebicidal (IC50 = 9.20 nM) and trichomonacidal (IC50 = 45.20 nM) activity, respectively. Additionally, T-143 had a high activity as giardicial (IC50 = 29.13 nM) and amoebicidal (IC50 = 15.14 nM), proposing it as a broad-spectrum antiparasitic agent. Compounds T-145, and T-161 were the best EhTrxR inhibitors with IC50 of 16 µM, and 18 µM, respectively.
publishDate	2024
dc.date.none.fl_str_mv	2024-10
dc.type.none.fl_str_mv	info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo
format	article
status_str	publishedVersion
dc.identifier.none.fl_str_mv	http://hdl.handle.net/11336/266119 González González, Alonzo; Sánchez Sánchez, Oscar; Yépez Mulia, Lilián; Delgado Maldonado, Timoteo; Vázquez Jiménez, Lenci K.; et al.; Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 39; 1; 10-2024; 1-15 1475-6366 CONICET Digital CONICET
url	http://hdl.handle.net/11336/266119
identifier_str_mv	González González, Alonzo; Sánchez Sánchez, Oscar; Yépez Mulia, Lilián; Delgado Maldonado, Timoteo; Vázquez Jiménez, Lenci K.; et al.; Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vaginalis, and Entamoeba histolytica: An in vitro and in silico approach; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 39; 1; 10-2024; 1-15 1475-6366 CONICET Digital CONICET
dc.language.none.fl_str_mv	eng
language	eng
dc.relation.none.fl_str_mv	info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.1080/14756366.2024.2413018 info:eu-repo/semantics/altIdentifier/doi/10.1080/14756366.2024.2413018
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv	openAccess
rights_invalid_str_mv	https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv	application/pdf application/pdf
dc.publisher.none.fl_str_mv	Taylor & Francis Ltd
publisher.none.fl_str_mv	Taylor & Francis Ltd
dc.source.none.fl_str_mv	reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str	CONICET Digital (CONICET)
collection	CONICET Digital (CONICET)
instname_str	Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv	CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv	dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score	13.070432

Expanding the antiprotozoal activity and the mechanism of action of n-butyl and iso-butyl ester of quinoxaline-1,4-di- N -oxide derivatives against Giardia lamblia, Trichomonas vag...

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