In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches

Autores
Prieto Cárdenas, Lina S.; Arias Soler, Karen A.; Nossa González, Diana Lisseth; Rozo Núñez, Wilson E.; Cárdenas-Chaparro, Agobardo; Duchowicz, Pablo Román; Gómez Castaño, Jovanny Arles
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Chagas and leishmaniasis are two neglected diseases considered as public health problems worldwide, for which there is no effective, low-cost, and low-toxicity treatment for the host. Naphthoquinones are ligands with redox properties involved in oxidative biological processes with a wide variety of activities, including antiparasitic. In this work, in silico methods of quantitative structure–activity relationship (QSAR), molecular docking, and calculation of ADME (absorption, distribution, metabolism, and excretion) properties were used to evaluate naphthoquinone derivatives with unknown antiprotozoal activity. QSAR models were developed for predicting antiparasitic activity against Trypanosoma cruzi, Leishmania amazonensis, and Leishmania infatum, as well as the QSAR model for toxicity activity. Most of the evaluated ligands presented high antiparasitic activity. According to the docking results, the family of triazole derivatives presented the best affinity with the different macromolecular targets. The ADME results showed that most of the evaluated compounds present adequate conditions to be administered orally. Naphthoquinone derivatives show good biological activity results, depending on the substituents attached to the quinone ring, and perhaps the potential to be converted into drugs or starting molecules.
Fil: Prieto Cárdenas, Lina S.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Arias Soler, Karen A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Nossa González, Diana Lisseth. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rozo Núñez, Wilson E.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Cárdenas-Chaparro, Agobardo. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Gómez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Materia
ADME
ANTIPROTOZOAL EVALUATION
CHAGAS
LEISHMANIASIS
MOLECULAR DOCKING
NAPHTHOQUINONES
QSAR
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/213525
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/213525
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME ApproachesPrieto Cárdenas, Lina S.Arias Soler, Karen A.Nossa González, Diana LissethRozo Núñez, Wilson E.Cárdenas-Chaparro, AgobardoDuchowicz, Pablo RománGómez Castaño, Jovanny ArlesADMEANTIPROTOZOAL EVALUATIONCHAGASLEISHMANIASISMOLECULAR DOCKINGNAPHTHOQUINONESQSARhttps://purl.org/becyt/ford/1.2https://purl.org/becyt/ford/1Chagas and leishmaniasis are two neglected diseases considered as public health problems worldwide, for which there is no effective, low-cost, and low-toxicity treatment for the host. Naphthoquinones are ligands with redox properties involved in oxidative biological processes with a wide variety of activities, including antiparasitic. In this work, in silico methods of quantitative structure–activity relationship (QSAR), molecular docking, and calculation of ADME (absorption, distribution, metabolism, and excretion) properties were used to evaluate naphthoquinone derivatives with unknown antiprotozoal activity. QSAR models were developed for predicting antiparasitic activity against Trypanosoma cruzi, Leishmania amazonensis, and Leishmania infatum, as well as the QSAR model for toxicity activity. Most of the evaluated ligands presented high antiparasitic activity. According to the docking results, the family of triazole derivatives presented the best affinity with the different macromolecular targets. The ADME results showed that most of the evaluated compounds present adequate conditions to be administered orally. Naphthoquinone derivatives show good biological activity results, depending on the substituents attached to the quinone ring, and perhaps the potential to be converted into drugs or starting molecules.Fil: Prieto Cárdenas, Lina S.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Arias Soler, Karen A.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Nossa González, Diana Lisseth. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Rozo Núñez, Wilson E.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Cárdenas-Chaparro, Agobardo. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Gómez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; ColombiaMultidisciplinary Digital Publishing Institute2022-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/213525Prieto Cárdenas, Lina S.; Arias Soler, Karen A.; Nossa González, Diana Lisseth; Rozo Núñez, Wilson E.; Cárdenas-Chaparro, Agobardo; et al.; In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches; Multidisciplinary Digital Publishing Institute; Pharmaceuticals; 15; 6; 6-2022; 1-341424-8247CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/ph15060687info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1424-8247/15/6/687info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:29Zoai:ri.conicet.gov.ar:11336/213525instacron: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 09:49:29.749CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
title In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
spellingShingle In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
Prieto Cárdenas, Lina S.
ADME
ANTIPROTOZOAL EVALUATION
CHAGAS
LEISHMANIASIS
MOLECULAR DOCKING
NAPHTHOQUINONES
QSAR
title_short In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
title_full In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
title_fullStr In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
title_full_unstemmed In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
title_sort In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches
dc.creator.none.fl_str_mv Prieto Cárdenas, Lina S.
Arias Soler, Karen A.
Nossa González, Diana Lisseth
Rozo Núñez, Wilson E.
Cárdenas-Chaparro, Agobardo
Duchowicz, Pablo Román
Gómez Castaño, Jovanny Arles
author Prieto Cárdenas, Lina S.
author_facet Prieto Cárdenas, Lina S.
Arias Soler, Karen A.
Nossa González, Diana Lisseth
Rozo Núñez, Wilson E.
Cárdenas-Chaparro, Agobardo
Duchowicz, Pablo Román
Gómez Castaño, Jovanny Arles
author_role author
author2 Arias Soler, Karen A.
Nossa González, Diana Lisseth
Rozo Núñez, Wilson E.
Cárdenas-Chaparro, Agobardo
Duchowicz, Pablo Román
Gómez Castaño, Jovanny Arles
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ADME
ANTIPROTOZOAL EVALUATION
CHAGAS
LEISHMANIASIS
MOLECULAR DOCKING
NAPHTHOQUINONES
QSAR
topic ADME
ANTIPROTOZOAL EVALUATION
CHAGAS
LEISHMANIASIS
MOLECULAR DOCKING
NAPHTHOQUINONES
QSAR
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.2
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Chagas and leishmaniasis are two neglected diseases considered as public health problems worldwide, for which there is no effective, low-cost, and low-toxicity treatment for the host. Naphthoquinones are ligands with redox properties involved in oxidative biological processes with a wide variety of activities, including antiparasitic. In this work, in silico methods of quantitative structure–activity relationship (QSAR), molecular docking, and calculation of ADME (absorption, distribution, metabolism, and excretion) properties were used to evaluate naphthoquinone derivatives with unknown antiprotozoal activity. QSAR models were developed for predicting antiparasitic activity against Trypanosoma cruzi, Leishmania amazonensis, and Leishmania infatum, as well as the QSAR model for toxicity activity. Most of the evaluated ligands presented high antiparasitic activity. According to the docking results, the family of triazole derivatives presented the best affinity with the different macromolecular targets. The ADME results showed that most of the evaluated compounds present adequate conditions to be administered orally. Naphthoquinone derivatives show good biological activity results, depending on the substituents attached to the quinone ring, and perhaps the potential to be converted into drugs or starting molecules.
Fil: Prieto Cárdenas, Lina S.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Arias Soler, Karen A.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Nossa González, Diana Lisseth. Universidad Pedagógica y Tecnológica de Colombia; Colombia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rozo Núñez, Wilson E.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Cárdenas-Chaparro, Agobardo. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Gómez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; Colombia
description Chagas and leishmaniasis are two neglected diseases considered as public health problems worldwide, for which there is no effective, low-cost, and low-toxicity treatment for the host. Naphthoquinones are ligands with redox properties involved in oxidative biological processes with a wide variety of activities, including antiparasitic. In this work, in silico methods of quantitative structure–activity relationship (QSAR), molecular docking, and calculation of ADME (absorption, distribution, metabolism, and excretion) properties were used to evaluate naphthoquinone derivatives with unknown antiprotozoal activity. QSAR models were developed for predicting antiparasitic activity against Trypanosoma cruzi, Leishmania amazonensis, and Leishmania infatum, as well as the QSAR model for toxicity activity. Most of the evaluated ligands presented high antiparasitic activity. According to the docking results, the family of triazole derivatives presented the best affinity with the different macromolecular targets. The ADME results showed that most of the evaluated compounds present adequate conditions to be administered orally. Naphthoquinone derivatives show good biological activity results, depending on the substituents attached to the quinone ring, and perhaps the potential to be converted into drugs or starting molecules.
publishDate 2022
dc.date.none.fl_str_mv 2022-06
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/11336/213525
Prieto Cárdenas, Lina S.; Arias Soler, Karen A.; Nossa González, Diana Lisseth; Rozo Núñez, Wilson E.; Cárdenas-Chaparro, Agobardo; et al.; In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches; Multidisciplinary Digital Publishing Institute; Pharmaceuticals; 15; 6; 6-2022; 1-34
1424-8247
CONICET Digital
CONICET
url http://hdl.handle.net/11336/213525
identifier_str_mv Prieto Cárdenas, Lina S.; Arias Soler, Karen A.; Nossa González, Diana Lisseth; Rozo Núñez, Wilson E.; Cárdenas-Chaparro, Agobardo; et al.; In Silico Antiprotozoal Evaluation of 1,4-Naphthoquinone Derivatives against Chagas and Leishmaniasis Diseases Using QSAR, Molecular Docking, and ADME Approaches; Multidisciplinary Digital Publishing Institute; Pharmaceuticals; 15; 6; 6-2022; 1-34
1424-8247
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/ph15060687
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1424-8247/15/6/687
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 Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
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

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