A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.tca.2020.178782 http://hdl.handle.net/11449/205298 |
Resumo: | This work reports the mechanochemical synthesis and characterization of a cocrystal formed by norfloxacin (NOR) and nicotinic acid (NCA). The thermal analysis provided the thermal stability and appropriated stoichiometry of NOR-NCA cocrystal. In addition, the crystalline structure and the coordination sites were obtained through Fourier-transform infrared spectroscopy (FTIR) and X-ray powder diffraction (XRPD). This allowed the determination of NOR-NCA interaction in the cocrystal state: the amine group of NOR interacts simultaneously with the aromatic nitrogen and the hydroxyl of the carboxyl group of NCA. Moreover, NOR-NCA crystallized in the monoclinic crystal system, space group Pa, and Z = 4, Z’ = 2. Finally, solubility assays showed an increase of NOR solubility of 2 times in pH 6.1 buffer solution. On the other hand, the cocrystal did not show a significant change in NOR solubility in pH 3.0 buffer solution, while presented a slight decrease in pH 8.5 buffer solution, which shows a pH-dependency. |
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A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assaysCocrystalCrystal structureNorfloxacinSolubilityThermal analysisX-ray powder diffractometryThis work reports the mechanochemical synthesis and characterization of a cocrystal formed by norfloxacin (NOR) and nicotinic acid (NCA). The thermal analysis provided the thermal stability and appropriated stoichiometry of NOR-NCA cocrystal. In addition, the crystalline structure and the coordination sites were obtained through Fourier-transform infrared spectroscopy (FTIR) and X-ray powder diffraction (XRPD). This allowed the determination of NOR-NCA interaction in the cocrystal state: the amine group of NOR interacts simultaneously with the aromatic nitrogen and the hydroxyl of the carboxyl group of NCA. Moreover, NOR-NCA crystallized in the monoclinic crystal system, space group Pa, and Z = 4, Z’ = 2. Finally, solubility assays showed an increase of NOR solubility of 2 times in pH 6.1 buffer solution. On the other hand, the cocrystal did not show a significant change in NOR solubility in pH 3.0 buffer solution, while presented a slight decrease in pH 8.5 buffer solution, which shows a pH-dependency.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)São Paulo State University (UNESP) Institute of ChemistrySão Paulo State University (UNESP) School of SciencesFederal University of ABC (UFABC) Center for Natural and Human SciencesFederal University of Goias (UFG) School of PharmacySão Paulo State University (UNESP) Institute of ChemistrySão Paulo State University (UNESP) School of SciencesCAPES: 001CNPq: 159936/2018-7FAPESP: 2013/09022-7FAPESP: 2017/14936-9FAPESP: 2018/12463-9FAPESP: 2018/24378-6CNPq: 305601/2019-9CNPq: 421469/2016-1CAPES: 88887.468152/2019Universidade Estadual Paulista (Unesp)Universidade Federal do ABC (UFABC)School of PharmacyFerreira, Patricia Osorio [UNESP]de Almeida, Amanda Cosmo [UNESP]dos Santos, Éverton Carvalho [UNESP]Droppa, RooseveltFerreira, Fabio FurlanKogawa, Ana CarolinaCaires, Flávio Junior [UNESP]2021-06-25T10:13:03Z2021-06-25T10:13:03Z2020-12-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.tca.2020.178782Thermochimica Acta, v. 694.0040-6031http://hdl.handle.net/11449/20529810.1016/j.tca.2020.1787822-s2.0-85092484362Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengThermochimica Actainfo:eu-repo/semantics/openAccess2021-10-23T12:31:20Zoai:repositorio.unesp.br:11449/205298Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462021-10-23T12:31:20Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
title |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
spellingShingle |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays Ferreira, Patricia Osorio [UNESP] Cocrystal Crystal structure Norfloxacin Solubility Thermal analysis X-ray powder diffractometry |
title_short |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
title_full |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
title_fullStr |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
title_full_unstemmed |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
title_sort |
A norfloxacin-nicotinic acid cocrystal: Mechanochemical synthesis, thermal and structural characterization and solubility assays |
author |
Ferreira, Patricia Osorio [UNESP] |
author_facet |
Ferreira, Patricia Osorio [UNESP] de Almeida, Amanda Cosmo [UNESP] dos Santos, Éverton Carvalho [UNESP] Droppa, Roosevelt Ferreira, Fabio Furlan Kogawa, Ana Carolina Caires, Flávio Junior [UNESP] |
author_role |
author |
author2 |
de Almeida, Amanda Cosmo [UNESP] dos Santos, Éverton Carvalho [UNESP] Droppa, Roosevelt Ferreira, Fabio Furlan Kogawa, Ana Carolina Caires, Flávio Junior [UNESP] |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade Federal do ABC (UFABC) School of Pharmacy |
dc.contributor.author.fl_str_mv |
Ferreira, Patricia Osorio [UNESP] de Almeida, Amanda Cosmo [UNESP] dos Santos, Éverton Carvalho [UNESP] Droppa, Roosevelt Ferreira, Fabio Furlan Kogawa, Ana Carolina Caires, Flávio Junior [UNESP] |
dc.subject.por.fl_str_mv |
Cocrystal Crystal structure Norfloxacin Solubility Thermal analysis X-ray powder diffractometry |
topic |
Cocrystal Crystal structure Norfloxacin Solubility Thermal analysis X-ray powder diffractometry |
description |
This work reports the mechanochemical synthesis and characterization of a cocrystal formed by norfloxacin (NOR) and nicotinic acid (NCA). The thermal analysis provided the thermal stability and appropriated stoichiometry of NOR-NCA cocrystal. In addition, the crystalline structure and the coordination sites were obtained through Fourier-transform infrared spectroscopy (FTIR) and X-ray powder diffraction (XRPD). This allowed the determination of NOR-NCA interaction in the cocrystal state: the amine group of NOR interacts simultaneously with the aromatic nitrogen and the hydroxyl of the carboxyl group of NCA. Moreover, NOR-NCA crystallized in the monoclinic crystal system, space group Pa, and Z = 4, Z’ = 2. Finally, solubility assays showed an increase of NOR solubility of 2 times in pH 6.1 buffer solution. On the other hand, the cocrystal did not show a significant change in NOR solubility in pH 3.0 buffer solution, while presented a slight decrease in pH 8.5 buffer solution, which shows a pH-dependency. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-01 2021-06-25T10:13:03Z 2021-06-25T10:13:03Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.tca.2020.178782 Thermochimica Acta, v. 694. 0040-6031 http://hdl.handle.net/11449/205298 10.1016/j.tca.2020.178782 2-s2.0-85092484362 |
url |
http://dx.doi.org/10.1016/j.tca.2020.178782 http://hdl.handle.net/11449/205298 |
identifier_str_mv |
Thermochimica Acta, v. 694. 0040-6031 10.1016/j.tca.2020.178782 2-s2.0-85092484362 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Thermochimica Acta |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1799965677643104256 |