Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells

Rodríguez López, María Isabel; Mercader Ros, María Teresa; Pérez Garrido, Alfonso; Pérez Sánchez, Horacio; Pellicer, José Antonio; Lucas Abellán, Carmen; Montoro García, Silvia; Yáñez Gascón, María José; Gil Izquierdo, Ángel; Núñez Delicado, Estrella; Gabaldón, José Antonio

Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells

The aim of this study was to obtain solid carvacrol-cyclodextrin (CD) complexes for use in the pharmaceutical industry. To this end, the complexation of carvacrol at different pH values was studied in detail, to determine the type of CD and the reaction environment that supported the highest amount...

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Autores:	Rodríguez López, María Isabel, Mercader Ros, María Teresa, Pérez Garrido, Alfonso, Pérez Sánchez, Horacio, Pellicer, José Antonio, Lucas Abellán, Carmen, Montoro García, Silvia, Yáñez Gascón, María José, Gil Izquierdo, Ángel, Núñez Delicado, Estrella, Gabaldón, José Antonio
Tipo de recurso:	artículo
Fecha de publicación:	2022
País:	España
Institución:	Universidad Católica San Antonio de Murcia (UCAM)
Repositorio:	RIUCAM. Repositorio Institucional de la Universidad Católica San Antonio de Murcia
OAI Identifier:	oai:repositorio.ucam.edu:10952/7925
Acceso en línea:	http://hdl.handle.net/10952/7925 https://doi.org/10.3390/ pharmaceutics14122638
Access Level:	acceso abierto
Palabra clave:	HP-β-cyclodextrins Chemical characterization Cell viability Solid complexes Carvacrol Microwave irradiation

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spelling	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma CellsRodríguez López, María IsabelMercader Ros, María TeresaPérez Garrido, AlfonsoPérez Sánchez, HoracioPellicer, José AntonioLucas Abellán, CarmenMontoro García, SilviaYáñez Gascón, María JoséGil Izquierdo, ÁngelNúñez Delicado, EstrellaGabaldón, José AntonioHP-β-cyclodextrinsChemical characterizationCell viabilitySolid complexesCarvacrolMicrowave irradiationThe aim of this study was to obtain solid carvacrol-cyclodextrin (CD) complexes for use in the pharmaceutical industry. To this end, the complexation of carvacrol at different pH values was studied in detail, to determine the type of CD and the reaction environment that supported the highest amount of encapsulated carvacrol. Evidence of the capability of hydroxypropyl-β-cyclodextrins (HP-β-CD) to form inclusion complexes with carvacrol (KC = 5042 ± 176 L mol−1) and more high complexation efficiency (2.824) was demonstrated for HP-β-CDs using two different energy sources, ultrasound (US) (KC = 8129 ± 194 L mol−1 24 h) and microwave irradiation (MWI) (KC = 6909 ± 161 L mol−1), followed by spraying the resulting solution in a spray dryer. To confirm complex formation, the complexes were characterized using various instrumental methods to corroborate the carvacrol incorporation into the hydrophobic cavity of HP-β-CD. The obtained carvacrol solid complexes were analyzed by 1H nuclear magnetic resonance (1H-NMR) and 2D nuclear magnetic resonance (ROSEY), differential scanning calorimetry (DSC), thermogravimetric analysis (TG) and Fourier transform infrared spectroscopy (FTIR) characterization. The structures of the resulting complexes were also characterized by molecular modeling. Furthermore, 1 mM HP-β-CD-carvacrol complex has been shown to reduce cell proliferation in HCT-116 colorectal cancer cells by 43%, much more than in a healthy lung fibroblast MRC-5 cell line (11%).FarmaciaMedicina2022info:eu-repo/semantics/articlehttp://hdl.handle.net/10952/7925https://doi.org/10.3390/ pharmaceutics14122638reponame:RIUCAM. Repositorio Institucional de la Universidad Católica San Antonio de Murciainstname:Universidad Católica San Antonio de Murcia (UCAM)Inglésinfo:eu-repo/semantics/openAccessoai:repositorio.ucam.edu:10952/79252026-06-07T18:35:21Z
dc.title.none.fl_str_mv	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
title	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
spellingShingle	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells Rodríguez López, María Isabel HP-β-cyclodextrins Chemical characterization Cell viability Solid complexes Carvacrol Microwave irradiation
title_short	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
title_full	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
title_fullStr	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
title_full_unstemmed	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
title_sort	Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells
dc.creator.none.fl_str_mv	Rodríguez López, María Isabel Mercader Ros, María Teresa Pérez Garrido, Alfonso Pérez Sánchez, Horacio Pellicer, José Antonio Lucas Abellán, Carmen Montoro García, Silvia Yáñez Gascón, María José Gil Izquierdo, Ángel Núñez Delicado, Estrella Gabaldón, José Antonio
author	Rodríguez López, María Isabel
author_facet	Rodríguez López, María Isabel Mercader Ros, María Teresa Pérez Garrido, Alfonso Pérez Sánchez, Horacio Pellicer, José Antonio Lucas Abellán, Carmen Montoro García, Silvia Yáñez Gascón, María José Gil Izquierdo, Ángel Núñez Delicado, Estrella Gabaldón, José Antonio
author_role	author
author2	Mercader Ros, María Teresa Pérez Garrido, Alfonso Pérez Sánchez, Horacio Pellicer, José Antonio Lucas Abellán, Carmen Montoro García, Silvia Yáñez Gascón, María José Gil Izquierdo, Ángel Núñez Delicado, Estrella Gabaldón, José Antonio
author2_role	author author author author author author author author author author
dc.subject.none.fl_str_mv	HP-β-cyclodextrins Chemical characterization Cell viability Solid complexes Carvacrol Microwave irradiation
topic	HP-β-cyclodextrins Chemical characterization Cell viability Solid complexes Carvacrol Microwave irradiation
description	The aim of this study was to obtain solid carvacrol-cyclodextrin (CD) complexes for use in the pharmaceutical industry. To this end, the complexation of carvacrol at different pH values was studied in detail, to determine the type of CD and the reaction environment that supported the highest amount of encapsulated carvacrol. Evidence of the capability of hydroxypropyl-β-cyclodextrins (HP-β-CD) to form inclusion complexes with carvacrol (KC = 5042 ± 176 L mol−1) and more high complexation efficiency (2.824) was demonstrated for HP-β-CDs using two different energy sources, ultrasound (US) (KC = 8129 ± 194 L mol−1 24 h) and microwave irradiation (MWI) (KC = 6909 ± 161 L mol−1), followed by spraying the resulting solution in a spray dryer. To confirm complex formation, the complexes were characterized using various instrumental methods to corroborate the carvacrol incorporation into the hydrophobic cavity of HP-β-CD. The obtained carvacrol solid complexes were analyzed by 1H nuclear magnetic resonance (1H-NMR) and 2D nuclear magnetic resonance (ROSEY), differential scanning calorimetry (DSC), thermogravimetric analysis (TG) and Fourier transform infrared spectroscopy (FTIR) characterization. The structures of the resulting complexes were also characterized by molecular modeling. Furthermore, 1 mM HP-β-CD-carvacrol complex has been shown to reduce cell proliferation in HCT-116 colorectal cancer cells by 43%, much more than in a healthy lung fibroblast MRC-5 cell line (11%).
publishDate	2022
dc.date.none.fl_str_mv	2022
dc.type.none.fl_str_mv	info:eu-repo/semantics/article
format	article
dc.identifier.none.fl_str_mv	http://hdl.handle.net/10952/7925 https://doi.org/10.3390/ pharmaceutics14122638
url	http://hdl.handle.net/10952/7925 https://doi.org/10.3390/ pharmaceutics14122638
dc.language.none.fl_str_mv	Inglés
language_invalid_str_mv	Inglés
dc.rights.none.fl_str_mv	info:eu-repo/semantics/openAccess
eu_rights_str_mv	openAccess
dc.source.none.fl_str_mv	reponame:RIUCAM. Repositorio Institucional de la Universidad Católica San Antonio de Murcia instname:Universidad Católica San Antonio de Murcia (UCAM)
instname_str	Universidad Católica San Antonio de Murcia (UCAM)
reponame_str	RIUCAM. Repositorio Institucional de la Universidad Católica San Antonio de Murcia
collection	RIUCAM. Repositorio Institucional de la Universidad Católica San Antonio de Murcia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score	15,812455

Carvacrol and HP-β-Cyclodextrin Complexes: Extensive Characterization and Potential Cytotoxic Effect in Human Colorectal Carcinoma Cells

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