Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole

Autores
Gutiérrez, Eduardo Luciano; Godoy, Agustín Alejandro; Narda, Griselda Edith; Ellena, Javier
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two novel bicomponent solid forms of mebendazole (MBZ) were developed as a means to modulate its psychochemical and pharmaceutical properties. Supramolecular synthesis of MBZ A or C with perchloric or methyl sulfuric acids yields two salts of 1 : 1 stoichiometry, which were analyzed through single crystal X-ray diffraction. MBZ perchlorate crystallizes in the P21/n space group, while MBZ methyl sulfate crystallizes in the P1 space group. The API and its counterions are interconnected in both crystal packings by an R22(8) supramolecular motif. The 3-dimensional crystal structure is also stabilized by other strong intermolecular hydrogen bonds as well as non-classical interactions. FT-IR spectra are consistent with the inclusion of the anions in the crystal structure. MBZ perchlorate is stable up to 210 °C when it undergoes endothermic loss of the ester moiety. MBZ methyl sulfate is stable up to 160 °C when endothermic elimination of the methylcarbamate moiety occurs. The solubility behavior of MBZ perchlorate, studied by UV-visible spectroscopy, suggests an improvement by a factor of seven with respect to MBZ A, in the apparent solubility of MBZ in 0.1 mol L-1 HCl. Further experiments are required to evaluate both the stability of the solids and the maximum solubility of the API.
Fil: Gutiérrez, Eduardo Luciano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Godoy, Agustín Alejandro. 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: Narda, Griselda Edith. 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: Ellena, Javier. Universidade de Sao Paulo; Brasil
Materia
Crystal engineering
X-ray diffraction
Solid-state stability
Thermal analysis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/138175
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/138175
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazoleGutiérrez, Eduardo LucianoGodoy, Agustín AlejandroNarda, Griselda EdithEllena, JavierCrystal engineeringX-ray diffractionSolid-state stabilityThermal analysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two novel bicomponent solid forms of mebendazole (MBZ) were developed as a means to modulate its psychochemical and pharmaceutical properties. Supramolecular synthesis of MBZ A or C with perchloric or methyl sulfuric acids yields two salts of 1 : 1 stoichiometry, which were analyzed through single crystal X-ray diffraction. MBZ perchlorate crystallizes in the P21/n space group, while MBZ methyl sulfate crystallizes in the P1 space group. The API and its counterions are interconnected in both crystal packings by an R22(8) supramolecular motif. The 3-dimensional crystal structure is also stabilized by other strong intermolecular hydrogen bonds as well as non-classical interactions. FT-IR spectra are consistent with the inclusion of the anions in the crystal structure. MBZ perchlorate is stable up to 210 °C when it undergoes endothermic loss of the ester moiety. MBZ methyl sulfate is stable up to 160 °C when endothermic elimination of the methylcarbamate moiety occurs. The solubility behavior of MBZ perchlorate, studied by UV-visible spectroscopy, suggests an improvement by a factor of seven with respect to MBZ A, in the apparent solubility of MBZ in 0.1 mol L-1 HCl. Further experiments are required to evaluate both the stability of the solids and the maximum solubility of the API.Fil: Gutiérrez, Eduardo Luciano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; ArgentinaFil: Godoy, Agustín Alejandro. 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: Narda, Griselda Edith. 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: Ellena, Javier. Universidade de Sao Paulo; BrasilRoyal Society of Chemistry2020-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/138175Gutiérrez, Eduardo Luciano; Godoy, Agustín Alejandro; Narda, Griselda Edith; Ellena, Javier; Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole; Royal Society of Chemistry; CrystEngComm; 22; 39; 10-2020; 6559-65681466-8033CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/d0ce00924einfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/ce/d0ce00924e/unauthinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:21:49Zoai:ri.conicet.gov.ar:11336/138175instacron: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:34982025-10-15 15:21:49.285CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
title Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
spellingShingle Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
Gutiérrez, Eduardo Luciano
Crystal engineering
X-ray diffraction
Solid-state stability
Thermal analysis
title_short Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
title_full Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
title_fullStr Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
title_full_unstemmed Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
title_sort Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole
dc.creator.none.fl_str_mv Gutiérrez, Eduardo Luciano
Godoy, Agustín Alejandro
Narda, Griselda Edith
Ellena, Javier
author Gutiérrez, Eduardo Luciano
author_facet Gutiérrez, Eduardo Luciano
Godoy, Agustín Alejandro
Narda, Griselda Edith
Ellena, Javier
author_role author
author2 Godoy, Agustín Alejandro
Narda, Griselda Edith
Ellena, Javier
author2_role author
author
author
dc.subject.none.fl_str_mv Crystal engineering
X-ray diffraction
Solid-state stability
Thermal analysis
topic Crystal engineering
X-ray diffraction
Solid-state stability
Thermal analysis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two novel bicomponent solid forms of mebendazole (MBZ) were developed as a means to modulate its psychochemical and pharmaceutical properties. Supramolecular synthesis of MBZ A or C with perchloric or methyl sulfuric acids yields two salts of 1 : 1 stoichiometry, which were analyzed through single crystal X-ray diffraction. MBZ perchlorate crystallizes in the P21/n space group, while MBZ methyl sulfate crystallizes in the P1 space group. The API and its counterions are interconnected in both crystal packings by an R22(8) supramolecular motif. The 3-dimensional crystal structure is also stabilized by other strong intermolecular hydrogen bonds as well as non-classical interactions. FT-IR spectra are consistent with the inclusion of the anions in the crystal structure. MBZ perchlorate is stable up to 210 °C when it undergoes endothermic loss of the ester moiety. MBZ methyl sulfate is stable up to 160 °C when endothermic elimination of the methylcarbamate moiety occurs. The solubility behavior of MBZ perchlorate, studied by UV-visible spectroscopy, suggests an improvement by a factor of seven with respect to MBZ A, in the apparent solubility of MBZ in 0.1 mol L-1 HCl. Further experiments are required to evaluate both the stability of the solids and the maximum solubility of the API.
Fil: Gutiérrez, Eduardo Luciano. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Química de San Luis. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Química de San Luis; Argentina
Fil: Godoy, Agustín Alejandro. 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: Narda, Griselda Edith. 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: Ellena, Javier. Universidade de Sao Paulo; Brasil
description Two novel bicomponent solid forms of mebendazole (MBZ) were developed as a means to modulate its psychochemical and pharmaceutical properties. Supramolecular synthesis of MBZ A or C with perchloric or methyl sulfuric acids yields two salts of 1 : 1 stoichiometry, which were analyzed through single crystal X-ray diffraction. MBZ perchlorate crystallizes in the P21/n space group, while MBZ methyl sulfate crystallizes in the P1 space group. The API and its counterions are interconnected in both crystal packings by an R22(8) supramolecular motif. The 3-dimensional crystal structure is also stabilized by other strong intermolecular hydrogen bonds as well as non-classical interactions. FT-IR spectra are consistent with the inclusion of the anions in the crystal structure. MBZ perchlorate is stable up to 210 °C when it undergoes endothermic loss of the ester moiety. MBZ methyl sulfate is stable up to 160 °C when endothermic elimination of the methylcarbamate moiety occurs. The solubility behavior of MBZ perchlorate, studied by UV-visible spectroscopy, suggests an improvement by a factor of seven with respect to MBZ A, in the apparent solubility of MBZ in 0.1 mol L-1 HCl. Further experiments are required to evaluate both the stability of the solids and the maximum solubility of the API.
publishDate 2020
dc.date.none.fl_str_mv 2020-10
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/11336/138175
Gutiérrez, Eduardo Luciano; Godoy, Agustín Alejandro; Narda, Griselda Edith; Ellena, Javier; Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole; Royal Society of Chemistry; CrystEngComm; 22; 39; 10-2020; 6559-6568
1466-8033
CONICET Digital
CONICET
url http://hdl.handle.net/11336/138175
identifier_str_mv Gutiérrez, Eduardo Luciano; Godoy, Agustín Alejandro; Narda, Griselda Edith; Ellena, Javier; Rational design, supramolecular synthesis and solid state characterization of two bicomponent solid forms of mebendazole; Royal Society of Chemistry; CrystEngComm; 22; 39; 10-2020; 6559-6568
1466-8033
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/d0ce00924e
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/ce/d0ce00924e/unauth
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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