Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares

ilustraciones, gráficas, tablas

Autores:: Porras Argüello, Julián David

Tipo de recurso:

Fecha de publicación:: 2022

Institución:: Universidad Nacional de Colombia

Repositorio:: Universidad Nacional de Colombia

Idioma:: spa

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dc.title.spa.fl_str_mv	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
dc.title.translated.eng.fl_str_mv	Design of copolymers based on PEG-PCL for encapsulation of apolar drugs
title	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
spellingShingle	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares 540 - Química y ciencias afines::542 - Técnicas, procedimientos, aparatos, equipos, materiales Polymers Polímeros Acids, fatty Capsules (Pharmacy) Ácidos grasos Cápsulas (Farmacia) Química clic Curcumina Cannabidiol Micelas Ácidos grasos Click chemistry Curcumin Cannabidiol Micelles Fatty acids
title_short	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
title_full	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
title_fullStr	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
title_full_unstemmed	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
title_sort	Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares
dc.creator.fl_str_mv	Porras Argüello, Julián David
dc.contributor.advisor.spa.fl_str_mv	Pérez Pérez, León Darío
dc.contributor.author.spa.fl_str_mv	Porras Argüello, Julián David
dc.contributor.researchgroup.spa.fl_str_mv	Grupo de Investigación en Macromoléculas
dc.subject.ddc.spa.fl_str_mv	540 - Química y ciencias afines::542 - Técnicas, procedimientos, aparatos, equipos, materiales
topic	540 - Química y ciencias afines::542 - Técnicas, procedimientos, aparatos, equipos, materiales Polymers Polímeros Acids, fatty Capsules (Pharmacy) Ácidos grasos Cápsulas (Farmacia) Química clic Curcumina Cannabidiol Micelas Ácidos grasos Click chemistry Curcumin Cannabidiol Micelles Fatty acids
dc.subject.decs.eng.fl_str_mv	Polymers
dc.subject.decs.spa.fl_str_mv	Polímeros
dc.subject.lemb.eng.fl_str_mv	Acids, fatty Capsules (Pharmacy)
dc.subject.lemb.spa.fl_str_mv	Ácidos grasos Cápsulas (Farmacia)
dc.subject.proposal.spa.fl_str_mv	Química clic Curcumina Cannabidiol Micelas Ácidos grasos
dc.subject.proposal.eng.fl_str_mv	Click chemistry Curcumin Cannabidiol Micelles Fatty acids
description	ilustraciones, gráficas, tablas
publishDate	2022
dc.date.accessioned.none.fl_str_mv	2022-08-26T15:50:14Z
dc.date.available.none.fl_str_mv	2022-08-26T15:50:14Z
dc.date.issued.none.fl_str_mv	2022
dc.type.spa.fl_str_mv	Trabajo de grado - Maestría
dc.type.driver.spa.fl_str_mv	info:eu-repo/semantics/masterThesis
dc.type.version.spa.fl_str_mv	info:eu-repo/semantics/acceptedVersion
dc.type.content.spa.fl_str_mv	Text
dc.type.redcol.spa.fl_str_mv	http://purl.org/redcol/resource_type/TM
status_str	acceptedVersion
dc.identifier.uri.none.fl_str_mv	https://repositorio.unal.edu.co/handle/unal/82137
dc.identifier.instname.spa.fl_str_mv	Universidad Nacional de Colombia
dc.identifier.reponame.spa.fl_str_mv	Repositorio Institucional Universidad Nacional de Colombia
dc.identifier.repourl.spa.fl_str_mv	https://repositorio.unal.edu.co/
url	https://repositorio.unal.edu.co/handle/unal/82137 https://repositorio.unal.edu.co/
identifier_str_mv	Universidad Nacional de Colombia Repositorio Institucional Universidad Nacional de Colombia
dc.language.iso.spa.fl_str_mv	spa
language	spa
dc.relation.indexed.spa.fl_str_mv	Bireme
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repository.mail.fl_str_mv	repositorio_nal@unal.edu.co
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spelling	Atribución-NoComercial-SinDerivadas 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Pérez Pérez, León Daríoa85c642b1834ea9bb160b576c9ba2f87Porras Argüello, Julián David21c629fde991b5db8f015ccc46a116bdGrupo de Investigación en Macromoléculas2022-08-26T15:50:14Z2022-08-26T15:50:14Z2022https://repositorio.unal.edu.co/handle/unal/82137Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones, gráficas, tablasEn la actualidad existen múltiples moléculas con interés farmacológico de carácter lipofílico que presentan baja solubilidad en agua y baja biodisponibilidad, por ejemplo, la curcumina con propiedades antioxidantes y los cannabinoides como el cannabidiol (CBD) y Δ-9-tetrahidrocannabinol (THC) que interactúan con el sistema endocannabinoide. Se han desarrollado diferentes vehículos de transporte para abordar los anteriores problemas, que han mostrado la capacidad de aumentar la biodisponibilidad de los fármacos, sin embargo, presentan desventajas asociadas principalmente a su baja capacidad de carga de fármaco y toxicidad. Por esta razón se plantea el desarrollo de un vehículo polimérico funcionalizado con ácidos grasos en esta investigación. Para la obtención de este polímero, en primer lugar, se llevó a cabo la síntesis de copolímeros de polietilenglicol (PEG), con ϵ-caprolactona (ϵ-CL) y 5-metil-5-propargiloxicarbonil-1,3-dioxan-2-ona (MCP), mediante polimerización por apertura de anillo (ROP, por sus siglas en ingles). Seguido de ello, se probaron diferentes metodologías de reacción por química clic que incluyen el uso de una azida de acilo o una 3-azidopropilamida basada en ácido linoleico como sustratos, solventes como DMF o anisol y varias temperaturas. La tendencia general de estas reacciones fue evaluada usando resonancia magnética nuclear de protón (RMN-1H), en donde las condiciones que aumentan la solubilidad del polímero se correlacionaron con un aumento de la conversión de los grupos funcionales. Los polímeros obtenidos fueron caracterizados mediante el uso de cromatografía por permeación en gel (GPC), RMN-1H y espectroscopia infrarroja (FT-IR). La encapsulación de los fármacos se llevó a cabo usando nanoprecipitación. Se evaluó el efecto de los polímeros modificados, solventes usados, velocidad de agitación y evaporación por vacío sobre la encapsulación de curcumina (CUR), la cual fue cuantificada por cromatografía líquida de alta resolución (HPLC). Estos experimentos permitieron concluir que hay un efecto cinético asociado a la velocidad en la cual se forman los núcleos de las micelas y el fármaco, en donde el uso de evaporación por vacío fue el método que permitió obtener mayores valores de encapsulación (aproximadamente 40% en peso curcumina/ peso micela cargada). Por otra parte, los valores de encapsulación de CBD fueron mucho más altos que los de curcumina (aproximadamente 60% en peso CBD/peso micela cargada), lo que se asoció a la partición del principio activo desde el medio continuo hacia el núcleo micelar, aun cuando los coloides ya están formados. Debido a las altas cargas de fármaco, se estudió la estabilidad coloidal de las micelas cargadas con CBD y la degradación del fármaco encapsulado. Se observó que los polímeros con 5 ácidos grasos en su estructura alcanzaron micelas más estables que los que tenían 2 ácidos y se observaron sistemas estables con PEG-PCL. La degradación del CBD en el interior del núcleo micelar fue significativa luego de varios meses de almacenamiento en las micelas con mayor carga de fármaco. Por último, se llevó a cabo la encapsulación y la liberación de extractos enriquecidos en CBD y THC. Las encapsulaciones de los extractos fueron menos eficientes que las encontradas con el CBD puro, lo cual fue asociado a efectos antagónicos de los componentes del extracto. Los valores obtenidos para las cinéticas de liberación ajustaron principalmente al modelo de Higuchi, lo que sugiere una liberación mediada por difusión. Además, se realizaron ensayos in-vivo usando las formulaciones obtenidas que mostraron un efecto analgésico sostenido en el tiempo. (Texto tomado de la fuente).Currently, there are multiple lipophilic drugs with pharmacological interest which present low water solubility and poor bioavailability, for instance, curcumin with antioxidant properties and cannabinoids such as cannabidiol (CBD) and Δ-9-tetrahydrocannabinol (THC) that interact with the endocannabinoid system. Different vehicles have been developed to tackle those problems which increase the bioavailability of drugs; however, they have drawbacks associated with their low drug loading capacity and toxicity. For this reason, a modified polymeric vehicle with fatty acids is proposed in this research. To obtain this polymer, firstly, the synthesis of polyethylene glycol (PEG) copolymers with ϵ-caprolactone (ϵ-CL), and 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MCP) was conducted by ring-opening polymerization (ROP). Then, different click chemistry reaction methodologies were tested including an acyl-azide or a 3-azidopropylamide based on linoleic acid as substrates, DMF or anisole as solvents, and various temperatures. General tendency of these reactions was evaluated using proton nuclear magnetic resonance (1H-NMR), where conditions that increase solubility of the polymer were correlated with an increment in the conversion of the functional groups. Obtained polymers were characterized by gel permeation chromatography (GPC), 1H-NMR and infrared spectroscopy (FT-IR). Drug encapsulation was conducted by nanoprecipitation. Effect of modified polymers, solvents, speed of stirring and rotaevaporation were evaluated on curcumin encapsulation, which was quantified by high performance liquid chromatography (HPLC). These experiments allowed to conclude that there is a possible kinetic effect associated to the speed at which the nuclei of the micelles and the drug are formed, where the highest drug loading capacity was obtained with rotaevaporation (approximately 40 % weight curcumin/ weight of charged micelle). On the other hand, encapsulation values of CBD were higher than those of curcumin (approximately 60 % weight CBD/ weight of charged micelle), which was associated with partition of the compound from the continuous phase into the micellar nucleus, even when colloids were already formed. Considering their high drug loading capacity, colloidal stability of micelles loaded with CBD and degradation of the encapsulated drug were studied. It was observed that polymers with 5 fatty acids in their structure were more stable micelles than those with 2 acids, although stable systems with PEG-PCL were obtained. Degradation of CBD was significant after several months of storing for micelles with highest drug loading capacity. Finally, the encapsulation and release profiles of extracts CBD and THC rich were conducted. Encapsulation of the extracts was lower than those found with pure CBD, which was associated with antagonistic effects of the components of the extract. Release´s profiles adjusted mainly to the Higuchi model, which suggests a release mediated by diffusion. Also, In-vivo essays were done with extracts encapsulated using modified polymers that presented an analgesic sustained effect during days.Incluye anexosMaestríaMagíster en Ciencias - QuímicaSíntesis de polímeros116 páginasapplication/pdfspaUniversidad Nacional de ColombiaBogotá - Ciencias - Maestría en Ciencias - QuímicaDepartamento de QuímicaFacultad de CienciasBogotá, ColombiaUniversidad Nacional de Colombia - Sede Bogotá540 - Química y ciencias afines::542 - Técnicas, procedimientos, aparatos, equipos, materialesPolymersPolímerosAcids, fattyCapsules (Pharmacy)Ácidos grasosCápsulas (Farmacia)Química clicCurcuminaCannabidiolMicelasÁcidos grasosClick chemistryCurcuminCannabidiolMicellesFatty acidsDiseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolaresDesign of copolymers based on PEG-PCL for encapsulation of apolar drugsTrabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionTexthttp://purl.org/redcol/resource_type/TMBiremeN. 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Diseño de copolímeros basados en PEG-PCL para encapsulación de fármacos apolares

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