Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids

Autores
Insuasty, Daniel; Vidal, Oscar; Bernal, Anthony; Marquez, Edgar; Guzman, Juan; Insuasty, Braulio; Quiroga, Jairo; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Puerto, Gloria; Abonia, Rodrigo
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Eight quinoline-based hydroxyimidazolium hybrids 7a–h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c–d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 µg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 µg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 µg/mL and full inhibition at 50 µg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.
Fil: Insuasty, Daniel. Universidad del Norte; Colombia
Fil: Vidal, Oscar. Universidad del Norte; Colombia
Fil: Bernal, Anthony. Universidad del Norte; Colombia
Fil: Marquez, Edgar. Universidad del Norte; Colombia
Fil: Guzman, Juan. Justus Liebig Universitat Giessen; Alemania
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Puerto, Gloria. Instituto Nacional de Salud; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Materia
ANTIFUNGAL ACTIVITY
ANTIMICROBIAL ACTIVITY
CYTOTOXICITY
QUINOLINE-BASED HYDROXYIMIDAZOLIUM HYBRIDS
TUBERCULOSIS
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:11336/154137
Acceder
id CONICETDig_8faef77256983dcbdcadeb6e2473e5bc
oai_identifier_str oai:ri.conicet.gov.ar:11336/154137
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium HybridsInsuasty, DanielVidal, OscarBernal, AnthonyMarquez, EdgarGuzman, JuanInsuasty, BraulioQuiroga, JairoSvetaz, Laura AndreaZacchino, Susana Alicia StellaPuerto, GloriaAbonia, RodrigoANTIFUNGAL ACTIVITYANTIMICROBIAL ACTIVITYCYTOTOXICITYQUINOLINE-BASED HYDROXYIMIDAZOLIUM HYBRIDSTUBERCULOSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Eight quinoline-based hydroxyimidazolium hybrids 7a–h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c–d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 µg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 µg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 µg/mL and full inhibition at 50 µg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.Fil: Insuasty, Daniel. Universidad del Norte; ColombiaFil: Vidal, Oscar. Universidad del Norte; ColombiaFil: Bernal, Anthony. Universidad del Norte; ColombiaFil: Marquez, Edgar. Universidad del Norte; ColombiaFil: Guzman, Juan. Justus Liebig Universitat Giessen; AlemaniaFil: Insuasty, Braulio. Universidad del Valle; ColombiaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Puerto, Gloria. Instituto Nacional de Salud; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaMDPI2019-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/154137Insuasty, Daniel; Vidal, Oscar; Bernal, Anthony; Marquez, Edgar; Guzman, Juan; et al.; Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids; MDPI; Antibiotics; 8; 4; 11-2019; 1-112079-63822079-6382CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2079-6382/8/4/239info:eu-repo/semantics/altIdentifier/doi/10.3390/antibiotics8040239info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:13:36Zoai:ri.conicet.gov.ar:11336/154137instacron: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:34982025-09-10 13:13:36.611CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
title Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
spellingShingle Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
Insuasty, Daniel
ANTIFUNGAL ACTIVITY
ANTIMICROBIAL ACTIVITY
CYTOTOXICITY
QUINOLINE-BASED HYDROXYIMIDAZOLIUM HYBRIDS
TUBERCULOSIS
title_short Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
title_full Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
title_fullStr Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
title_full_unstemmed Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
title_sort Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids
dc.creator.none.fl_str_mv Insuasty, Daniel
Vidal, Oscar
Bernal, Anthony
Marquez, Edgar
Guzman, Juan
Insuasty, Braulio
Quiroga, Jairo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Puerto, Gloria
Abonia, Rodrigo
author Insuasty, Daniel
author_facet Insuasty, Daniel
Vidal, Oscar
Bernal, Anthony
Marquez, Edgar
Guzman, Juan
Insuasty, Braulio
Quiroga, Jairo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Puerto, Gloria
Abonia, Rodrigo
author_role author
author2 Vidal, Oscar
Bernal, Anthony
Marquez, Edgar
Guzman, Juan
Insuasty, Braulio
Quiroga, Jairo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Puerto, Gloria
Abonia, Rodrigo
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGAL ACTIVITY
ANTIMICROBIAL ACTIVITY
CYTOTOXICITY
QUINOLINE-BASED HYDROXYIMIDAZOLIUM HYBRIDS
TUBERCULOSIS
topic ANTIFUNGAL ACTIVITY
ANTIMICROBIAL ACTIVITY
CYTOTOXICITY
QUINOLINE-BASED HYDROXYIMIDAZOLIUM HYBRIDS
TUBERCULOSIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Eight quinoline-based hydroxyimidazolium hybrids 7a–h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c–d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 µg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 µg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 µg/mL and full inhibition at 50 µg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.
Fil: Insuasty, Daniel. Universidad del Norte; Colombia
Fil: Vidal, Oscar. Universidad del Norte; Colombia
Fil: Bernal, Anthony. Universidad del Norte; Colombia
Fil: Marquez, Edgar. Universidad del Norte; Colombia
Fil: Guzman, Juan. Justus Liebig Universitat Giessen; Alemania
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Puerto, Gloria. Instituto Nacional de Salud; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
description Eight quinoline-based hydroxyimidazolium hybrids 7a–h were prepared and evaluated in vitro against a panel of clinically important fungal and bacterial pathogens, including mycobacteria. Hybrid compounds 7c–d showed remarkable antifungal activity against Cryptococcus neoformans with a minimum inhibitory concentration (MIC) value of 15.6 µg/mL. Against other opportunistic fungi such as Candida spp. and Aspergillus spp., these hybrids showed MIC values of 62.5 µg/mL. Regarding their antibacterial activity, all the synthetic hybrids demonstrated little inhibition of Gram-negative bacteria (MIC ≥50 µg/mL), however, hybrid 7b displayed >50% inhibition against Klebsiella pneumoniae at 20 µg/mL and full inhibition at 50 µg/mL. Moreover, this hybrid was shown to be a potent anti-staphylococcal molecule, with a MIC value of 2 µg/mL (5 µM). In addition, hybrid 7h also demonstrated inhibition of Staphylococcus aureus at 20 µg/mL (47 µM). Hybrids 7a and 7b were the most potent against Mycobacterium tuberculosis H37Rv with MIC values of 20 and 10 µg/mL (46 and 24 µM), respectively. The 7b hybrid demonstrated high selectivity in killing S. aureus and M. tuberculosis H37Rv in comparison with mammalian cells (SI >20), and thus it can be considered a hit molecule for mechanism of action studies and the exploration of related chemical space.
publishDate 2019
dc.date.none.fl_str_mv 2019-11
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/11336/154137
Insuasty, Daniel; Vidal, Oscar; Bernal, Anthony; Marquez, Edgar; Guzman, Juan; et al.; Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids; MDPI; Antibiotics; 8; 4; 11-2019; 1-11
2079-6382
2079-6382
CONICET Digital
CONICET
url http://hdl.handle.net/11336/154137
identifier_str_mv Insuasty, Daniel; Vidal, Oscar; Bernal, Anthony; Marquez, Edgar; Guzman, Juan; et al.; Antimicrobial Activity of Quinoline-Based Hydroxyimidazolium Hybrids; MDPI; Antibiotics; 8; 4; 11-2019; 1-11
2079-6382
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.mdpi.com/2079-6382/8/4/239
info:eu-repo/semantics/altIdentifier/doi/10.3390/antibiotics8040239
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 MDPI
publisher.none.fl_str_mv MDPI
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 12.993085

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