A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by...

Autores: Martínez, Maricel Anahí; Mariani, María Laura Lucía; García, Celina; Ceñal, Juan Pedro José; Penissi, Alicia Beatriz
Año de publicación: 2023
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: The goal of the present work was to develop novel β-substituted-α-halomethyl acrylates from a methodology in an aqueous phase and to evaluate their bioactivity as potential inhibitors of mast cell activation. Eleven β-substituted-α-halomethyl acrylates were synthesized through a modified Horner-Wadsworth-Emmons reaction. Compound 48/80 and the calcium ionophore A23187 stimulated the release of β-hexosaminidase from mast cells. The effect induced by compound 48/80 was inhibited by compound 5 (320 µM) and compound 9 (160 and 320 µM) without causing cytotoxic effects. The effect induced by A23187 was inhibited by compound 5 (40, 80, 160, and 320 µM) without affecting cell viability. The inhibitory effects exhibited by compounds 5 and 9 were more potent than those of the reference compound sodium cromoglycate at the same concentrations. The biochemical results were consistent with the morphological findings obtained by light and transmission electron microscopy. This study reports, for the first time, that the new synthetic compounds methyl (Z)- 2-bromo-3-(furan-3-yl)acrylate (compound 5) and methyl (E)- 2-bromo-3-(3-bromophenyl)acrylate (compound 9) strongly inhibit mast cell degranulation, without affecting cell viability. The implications of these results are relevant as a basis for developing new anti-inflammatory and mast cell stabilizing drugs.
Fil: Martínez, Maricel Anahí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Mariani, María Laura Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina
Fil: García, Celina. Universidad de La Laguna; España
Fil: Ceñal, Juan Pedro José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Penissi, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina
Materia: MAST CELLS
DEGRANULATION
AQUEOUS MEDIUM
ACRILATES
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/250476

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repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuliMartínez, Maricel AnahíMariani, María Laura LucíaGarcía, CelinaCeñal, Juan Pedro JoséPenissi, Alicia BeatrizMAST CELLSDEGRANULATIONAQUEOUS MEDIUMACRILATEShttps://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3The goal of the present work was to develop novel β-substituted-α-halomethyl acrylates from a methodology in an aqueous phase and to evaluate their bioactivity as potential inhibitors of mast cell activation. Eleven β-substituted-α-halomethyl acrylates were synthesized through a modified Horner-Wadsworth-Emmons reaction. Compound 48/80 and the calcium ionophore A23187 stimulated the release of β-hexosaminidase from mast cells. The effect induced by compound 48/80 was inhibited by compound 5 (320 µM) and compound 9 (160 and 320 µM) without causing cytotoxic effects. The effect induced by A23187 was inhibited by compound 5 (40, 80, 160, and 320 µM) without affecting cell viability. The inhibitory effects exhibited by compounds 5 and 9 were more potent than those of the reference compound sodium cromoglycate at the same concentrations. The biochemical results were consistent with the morphological findings obtained by light and transmission electron microscopy. This study reports, for the first time, that the new synthetic compounds methyl (Z)- 2-bromo-3-(furan-3-yl)acrylate (compound 5) and methyl (E)- 2-bromo-3-(3-bromophenyl)acrylate (compound 9) strongly inhibit mast cell degranulation, without affecting cell viability. The implications of these results are relevant as a basis for developing new anti-inflammatory and mast cell stabilizing drugs.Fil: Martínez, Maricel Anahí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Mariani, María Laura Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; ArgentinaFil: García, Celina. Universidad de La Laguna; EspañaFil: Ceñal, Juan Pedro José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Penissi, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; ArgentinaElsevier2023-12-21info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/250476Martínez, Maricel Anahí; Mariani, María Laura Lucía; García, Celina; Ceñal, Juan Pedro José; Penissi, Alicia Beatriz; A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli; Elsevier; Biomedicine and Pharmacotherapy; 170; 21-12-2023; 1-130753-33221950-6007CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0753332223018073info:eu-repo/semantics/altIdentifier/doi/DOI: 10.1016/J.BIOPHA.2023.116009info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:50Zoai:ri.conicet.gov.ar:11336/250476instacron: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:34982025-09-03 09:47:51.08CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
title	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
spellingShingle	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli Martínez, Maricel Anahí MAST CELLS DEGRANULATION AQUEOUS MEDIUM ACRILATES
title_short	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
title_full	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
title_fullStr	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
title_full_unstemmed	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
title_sort	A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli
dc.creator.none.fl_str_mv	Martínez, Maricel Anahí Mariani, María Laura Lucía García, Celina Ceñal, Juan Pedro José Penissi, Alicia Beatriz
author	Martínez, Maricel Anahí
author_facet	Martínez, Maricel Anahí Mariani, María Laura Lucía García, Celina Ceñal, Juan Pedro José Penissi, Alicia Beatriz
author_role	author
author2	Mariani, María Laura Lucía García, Celina Ceñal, Juan Pedro José Penissi, Alicia Beatriz
author2_role	author author author author
dc.subject.none.fl_str_mv	MAST CELLS DEGRANULATION AQUEOUS MEDIUM ACRILATES
topic	MAST CELLS DEGRANULATION AQUEOUS MEDIUM ACRILATES
purl_subject.fl_str_mv	https://purl.org/becyt/ford/3.1 https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv	The goal of the present work was to develop novel β-substituted-α-halomethyl acrylates from a methodology in an aqueous phase and to evaluate their bioactivity as potential inhibitors of mast cell activation. Eleven β-substituted-α-halomethyl acrylates were synthesized through a modified Horner-Wadsworth-Emmons reaction. Compound 48/80 and the calcium ionophore A23187 stimulated the release of β-hexosaminidase from mast cells. The effect induced by compound 48/80 was inhibited by compound 5 (320 µM) and compound 9 (160 and 320 µM) without causing cytotoxic effects. The effect induced by A23187 was inhibited by compound 5 (40, 80, 160, and 320 µM) without affecting cell viability. The inhibitory effects exhibited by compounds 5 and 9 were more potent than those of the reference compound sodium cromoglycate at the same concentrations. The biochemical results were consistent with the morphological findings obtained by light and transmission electron microscopy. This study reports, for the first time, that the new synthetic compounds methyl (Z)- 2-bromo-3-(furan-3-yl)acrylate (compound 5) and methyl (E)- 2-bromo-3-(3-bromophenyl)acrylate (compound 9) strongly inhibit mast cell degranulation, without affecting cell viability. The implications of these results are relevant as a basis for developing new anti-inflammatory and mast cell stabilizing drugs. Fil: Martínez, Maricel Anahí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Mariani, María Laura Lucía. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina Fil: García, Celina. Universidad de La Laguna; España Fil: Ceñal, Juan Pedro José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina Fil: Penissi, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos. Universidad Nacional de Cuyo. Facultad de Ciencias Médicas. Instituto de Histología y Embriología de Mendoza Dr. Mario H. Burgos; Argentina
description	The goal of the present work was to develop novel β-substituted-α-halomethyl acrylates from a methodology in an aqueous phase and to evaluate their bioactivity as potential inhibitors of mast cell activation. Eleven β-substituted-α-halomethyl acrylates were synthesized through a modified Horner-Wadsworth-Emmons reaction. Compound 48/80 and the calcium ionophore A23187 stimulated the release of β-hexosaminidase from mast cells. The effect induced by compound 48/80 was inhibited by compound 5 (320 µM) and compound 9 (160 and 320 µM) without causing cytotoxic effects. The effect induced by A23187 was inhibited by compound 5 (40, 80, 160, and 320 µM) without affecting cell viability. The inhibitory effects exhibited by compounds 5 and 9 were more potent than those of the reference compound sodium cromoglycate at the same concentrations. The biochemical results were consistent with the morphological findings obtained by light and transmission electron microscopy. This study reports, for the first time, that the new synthetic compounds methyl (Z)- 2-bromo-3-(furan-3-yl)acrylate (compound 5) and methyl (E)- 2-bromo-3-(3-bromophenyl)acrylate (compound 9) strongly inhibit mast cell degranulation, without affecting cell viability. The implications of these results are relevant as a basis for developing new anti-inflammatory and mast cell stabilizing drugs.
publishDate	2023
dc.date.none.fl_str_mv	2023-12-21
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/11336/250476 Martínez, Maricel Anahí; Mariani, María Laura Lucía; García, Celina; Ceñal, Juan Pedro José; Penissi, Alicia Beatriz; A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli; Elsevier; Biomedicine and Pharmacotherapy; 170; 21-12-2023; 1-13 0753-3322 1950-6007 CONICET Digital CONICET
url	http://hdl.handle.net/11336/250476
identifier_str_mv	Martínez, Maricel Anahí; Mariani, María Laura Lucía; García, Celina; Ceñal, Juan Pedro José; Penissi, Alicia Beatriz; A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by pro-inflammatory stimuli; Elsevier; Biomedicine and Pharmacotherapy; 170; 21-12-2023; 1-13 0753-3322 1950-6007 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://linkinghub.elsevier.com/retrieve/pii/S0753332223018073 info:eu-repo/semantics/altIdentifier/doi/DOI: 10.1016/J.BIOPHA.2023.116009
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv	openAccess
rights_invalid_str_mv	https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv	application/pdf application/pdf
dc.publisher.none.fl_str_mv	Elsevier
publisher.none.fl_str_mv	Elsevier
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	13.13397

A one-pot and eco-friendly synthesis of novel β-substituted-α-halomethyl acrylates and the bioactivity of these compounds in an in vitro model of mast cell degranulation induced by...

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