Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity

Stability, thermal characterization, and identification of possible polymorphism are relevant in the development of novel therapeutic drugs. In this context, thirty new nonsteroidal anti-inflammatory drug (NSAID) derivatives containing selenium (Se) as selenoesters or diacyl diselenides with demonst...

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Autores: Ramos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7, Almagro, E. (Eneko)|||/items/5bc2c449-2df2-4814-8656-e390d19483ce, Font, M. (María)|||/items/8d1cec88-6750-4756-a4a8-1199aa1e6559, Encío-Martínez, I.J. (Ignacio José)|||/items/468e76be-1795-41af-a6a3-f7c4472e416c, Plano-Amatriain, D. (Daniel)|||/items/238881e4-7d5e-4598-924d-4392e3b7e02e, Sanmartin-Grijalba, C. (Carmen)|||/items/d36bd105-ab64-427d-9745-5812cf5e7af7, Sirera-Bejarano, R. (Rafael)|||/items/dd5ea901-439c-4cbe-9798-b1ad5efb610d, Lizarraga, E. (Elena)|||/items/84976e6e-e72a-45c2-a275-612ce7e38f3f
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad de Navarra
Repositorio:Dadun. Depósito Académico Digital de la Universidad de Navarra
Idioma:español
OAI Identifier:oai:dadun.unav.edu:10171/68168
Acceso en línea:https://hdl.handle.net/10171/68168
Access Level:acceso abierto
Palabra clave:Materias Investigacion::Química
Selenium
NSAID
Polymorphism
TG/DSC analysis
X-ray diffraction
Cytotoxicity
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spelling Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activityRamos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7Almagro, E. (Eneko)|||/items/5bc2c449-2df2-4814-8656-e390d19483ceFont, M. (María)|||/items/8d1cec88-6750-4756-a4a8-1199aa1e6559Encío-Martínez, I.J. (Ignacio José)|||/items/468e76be-1795-41af-a6a3-f7c4472e416cPlano-Amatriain, D. (Daniel)|||/items/238881e4-7d5e-4598-924d-4392e3b7e02eSanmartin-Grijalba, C. (Carmen)|||/items/d36bd105-ab64-427d-9745-5812cf5e7af7Sirera-Bejarano, R. (Rafael)|||/items/dd5ea901-439c-4cbe-9798-b1ad5efb610dLizarraga, E. (Elena)|||/items/84976e6e-e72a-45c2-a275-612ce7e38f3fMaterias Investigacion::QuímicaSeleniumNSAIDPolymorphismTG/DSC analysisX-ray diffractionCytotoxicityStability, thermal characterization, and identification of possible polymorphism are relevant in the development of novel therapeutic drugs. In this context, thirty new nonsteroidal anti-inflammatory drug (NSAID) derivatives containing selenium (Se) as selenoesters or diacyl diselenides with demonstrated anticancer activity were thermally characterized in order to establish thermal stability criteria and detect possible polymorphic forms. Compounds were analyzed by a combination of thermogravimetry, differential scanning calorimetry, and X-ray diffraction techniques, and five different calorimetric behaviors were identified. Two compounds based on naproxen (I.3d and I.3e) and an indomethacin-containing derivative (II.2) presented two crystalline forms. The stability under acid, alkaline and oxidative conditions of selected polymorphs was also assessed using high-performance liquid chromatography. In addition, the cytotoxic activity of Se-NSAID crystal- line polymorphs was studied in several cancer cell lines in vitro. Remarkably, no significant differences were found among the polymorphic forms tested, thus proving that these compounds are thermally qualified for further drug development.SpringerDadun. Depósito Académico Digital Universidad de Navarra20232023-12-2220232023-01-0120232023-01-01journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10171/68168reponame:Dadun. Depósito Académico Digital de la Universidad de Navarrainstname:Universidad de NavarraEspañolspaopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:dadun.unav.edu:10171/681682026-06-21T12:47:57Z
dc.title.none.fl_str_mv Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
title Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
spellingShingle Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
Ramos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7
Materias Investigacion::Química
Selenium
NSAID
Polymorphism
TG/DSC analysis
X-ray diffraction
Cytotoxicity
title_short Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
title_full Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
title_fullStr Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
title_full_unstemmed Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
title_sort Thermal characterization, polymorphism, and stability evaluation of Se-NSAID derivatives with potent anticancer activity
dc.creator.none.fl_str_mv Ramos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7
Almagro, E. (Eneko)|||/items/5bc2c449-2df2-4814-8656-e390d19483ce
Font, M. (María)|||/items/8d1cec88-6750-4756-a4a8-1199aa1e6559
Encío-Martínez, I.J. (Ignacio José)|||/items/468e76be-1795-41af-a6a3-f7c4472e416c
Plano-Amatriain, D. (Daniel)|||/items/238881e4-7d5e-4598-924d-4392e3b7e02e
Sanmartin-Grijalba, C. (Carmen)|||/items/d36bd105-ab64-427d-9745-5812cf5e7af7
Sirera-Bejarano, R. (Rafael)|||/items/dd5ea901-439c-4cbe-9798-b1ad5efb610d
Lizarraga, E. (Elena)|||/items/84976e6e-e72a-45c2-a275-612ce7e38f3f
author Ramos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7
author_facet Ramos-Inza, S. (Sandra)|||/items/47071a2d-ec1f-4594-8d86-b8297a5888e7
Almagro, E. (Eneko)|||/items/5bc2c449-2df2-4814-8656-e390d19483ce
Font, M. (María)|||/items/8d1cec88-6750-4756-a4a8-1199aa1e6559
Encío-Martínez, I.J. (Ignacio José)|||/items/468e76be-1795-41af-a6a3-f7c4472e416c
Plano-Amatriain, D. (Daniel)|||/items/238881e4-7d5e-4598-924d-4392e3b7e02e
Sanmartin-Grijalba, C. (Carmen)|||/items/d36bd105-ab64-427d-9745-5812cf5e7af7
Sirera-Bejarano, R. (Rafael)|||/items/dd5ea901-439c-4cbe-9798-b1ad5efb610d
Lizarraga, E. (Elena)|||/items/84976e6e-e72a-45c2-a275-612ce7e38f3f
author_role author
author2 Almagro, E. (Eneko)|||/items/5bc2c449-2df2-4814-8656-e390d19483ce
Font, M. (María)|||/items/8d1cec88-6750-4756-a4a8-1199aa1e6559
Encío-Martínez, I.J. (Ignacio José)|||/items/468e76be-1795-41af-a6a3-f7c4472e416c
Plano-Amatriain, D. (Daniel)|||/items/238881e4-7d5e-4598-924d-4392e3b7e02e
Sanmartin-Grijalba, C. (Carmen)|||/items/d36bd105-ab64-427d-9745-5812cf5e7af7
Sirera-Bejarano, R. (Rafael)|||/items/dd5ea901-439c-4cbe-9798-b1ad5efb610d
Lizarraga, E. (Elena)|||/items/84976e6e-e72a-45c2-a275-612ce7e38f3f
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Dadun. Depósito Académico Digital Universidad de Navarra
dc.subject.none.fl_str_mv Materias Investigacion::Química
Selenium
NSAID
Polymorphism
TG/DSC analysis
X-ray diffraction
Cytotoxicity
topic Materias Investigacion::Química
Selenium
NSAID
Polymorphism
TG/DSC analysis
X-ray diffraction
Cytotoxicity
description Stability, thermal characterization, and identification of possible polymorphism are relevant in the development of novel therapeutic drugs. In this context, thirty new nonsteroidal anti-inflammatory drug (NSAID) derivatives containing selenium (Se) as selenoesters or diacyl diselenides with demonstrated anticancer activity were thermally characterized in order to establish thermal stability criteria and detect possible polymorphic forms. Compounds were analyzed by a combination of thermogravimetry, differential scanning calorimetry, and X-ray diffraction techniques, and five different calorimetric behaviors were identified. Two compounds based on naproxen (I.3d and I.3e) and an indomethacin-containing derivative (II.2) presented two crystalline forms. The stability under acid, alkaline and oxidative conditions of selected polymorphs was also assessed using high-performance liquid chromatography. In addition, the cytotoxic activity of Se-NSAID crystal- line polymorphs was studied in several cancer cell lines in vitro. Remarkably, no significant differences were found among the polymorphic forms tested, thus proving that these compounds are thermally qualified for further drug development.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-12-22
2023
2023-01-01
2023
2023-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10171/68168
url https://hdl.handle.net/10171/68168
dc.language.none.fl_str_mv Español
spa
language_invalid_str_mv Español
language spa
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
dc.source.none.fl_str_mv reponame:Dadun. Depósito Académico Digital de la Universidad de Navarra
instname:Universidad de Navarra
instname_str Universidad de Navarra
reponame_str Dadun. Depósito Académico Digital de la Universidad de Navarra
collection Dadun. Depósito Académico Digital de la Universidad de Navarra
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