Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1

Anandamide or N-arachidonoyl-ethanolamide (AEA) is an endocannabinoid compound that is synthesised from phospholipids present in the membranes of different cells, in the brain and in the peripheral nervous system. It is involved in biological processes such as: memory, movement control, attenuation...

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Autores:: Rojas Bustamante, Lida Rosmary

Tipo de recurso:

Fecha de publicación:: 2023

Institución:: Universidad Pedagógica y Tecnológica de Colombia

Repositorio:: RiUPTC: Repositorio Institucional UPTC

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dc.title.spa.fl_str_mv	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
title	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
spellingShingle	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1 Maestría en Química -- Tesis y disertaciones académicas Propiedad química Gestión de los recursos hídricos Administración de la ciencia Metabolismo Bioquímica
title_short	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
title_full	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
title_fullStr	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
title_full_unstemmed	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
title_sort	Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1
dc.creator.fl_str_mv	Rojas Bustamante, Lida Rosmary
dc.contributor.advisor.spa.fl_str_mv	Cárdenas Chaparro, Agobardo
dc.contributor.author.none.fl_str_mv	Rojas Bustamante, Lida Rosmary
dc.subject.unesco.none.fl_str_mv	Maestría en Química -- Tesis y disertaciones académicas Propiedad química Gestión de los recursos hídricos Administración de la ciencia Metabolismo Bioquímica
topic	Maestría en Química -- Tesis y disertaciones académicas Propiedad química Gestión de los recursos hídricos Administración de la ciencia Metabolismo Bioquímica
description	Anandamide or N-arachidonoyl-ethanolamide (AEA) is an endocannabinoid compound that is synthesised from phospholipids present in the membranes of different cells, in the brain and in the peripheral nervous system. It is involved in biological processes such as: memory, movement control, attenuation of pain sensation, reproduction, among others. In addition, due to their lipophilic nature, they can cross the blood-brain barrier and generate psychoactive effects including euphoria, drowsiness, motor incoordination, alterations in temporal and spatial perception, disorientation and confusion. In order to counteract these effects, analogue structures were designed with lower theoretical partition coefficients of AEA and with a possible binding capacity to the endocannabinoid receptor type 1 (CB1). In this research, 30 anandamide analogues were designed, retaining ethanolamide as the neuromodulatory pharmacophore and using different bioisosteric groups as substituents. Subsequently, the Administration, Digestion, Metabolism, Excretion, Metabolism and Toxicity (ADMET) properties of these compounds were predicted and a molecular docking study was performed, determining the ligand-protein interactions and the affinity energy with the CB1 receptor. From these results, two AEA analogue structures were selected: (S)-3-(4 hydroxy-3-(1-hydroxyhexyl)phenyl)-N-(2-hydroxyethyl)propanamide (-104.45 kcal/mol) and (S)-3-(4-hydroxy-3-(1-hydroxyethyl)phenyl)-N-(2-hydroxyethyl)propanamide ( 98.60kcal/mol). The synthesis was from the 3-(4-hydroxyphenyl)propanoic acid compound obtained in the Chemical Systems laboratory of the UPTC. The preparation of the two Anandamide analogues was carried out using a four-step methodology: Friedel-Crafts orthoacylation, reduction, esterification and amidation. The products were purified and characterised by FTIR, 1H NMR and 13C NMR spectroscopy and mass spectrometry.
publishDate	2023
dc.date.issued.none.fl_str_mv	2023
dc.date.accessioned.none.fl_str_mv	2025-09-20T20:15:03Z
dc.date.available.none.fl_str_mv	2025-09-20T20:15:03Z
dc.type.none.fl_str_mv	Trabajo de grado - Maestría
dc.type.spa.fl_str_mv	Trabajo de grado - Maestría
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dc.identifier.bibliographicCitation.none.fl_str_mv	T. Behl et al., “Exploration of Multiverse Activities of Endocannabinoids in Biological Systems,” Int. J. Mol. Sci., vol. 23, no. 10, p. 5734, May 2022, doi: 10.3390/IJMS23105734. K. Klatt-Schreiner et al., “High Glucosylceramides and Low Anandamide Contribute to Sensory Loss and Pain in Parkinson’s Disease,” Mov. Disord., vol. 35, no. 10, pp. 1822–1833, 2020, doi: 10.1002/mds.28186. A. Dlugos, E. Childs, K. L. Stuhr, C. J. Hillard, and H. De Wit, “Acute stress increases circulating anandamide and other n-acylethanolamines in healthy humans,” Neuropsychopharmacology, vol. 37, no. 11, pp. 2416–2427, 2012, doi: 10.1038/npp.2012.100. M. McKenna and J. J. McDougall, “Cannabinoid control of neurogenic inflammation,” Br. J. Pharmacol., vol. 177, no. 19, pp. 4386–4399, 2020, doi: 10.1111/bph.15208 A. Sobiepanek, M. Milner-Krawczyk, P. Musolf, T. Starecki, and T. Kobiela, “Anandamide Modulated Changes in Metabolism, Glycosylation Profile and Migration of Metastatic Melanoma Cells,” Cancers (Basel)., vol. 14, no. 6, 2022, doi: 10.3390/cancers14061419 D. Melck et al., “Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation,” Endocrinology, vol. 141, no. 1, pp. 118–126, 2000, doi: 10.1210/endo.141.1.7239. J. Ravi, A. Sneh, K. Shilo, M. W. Nasser, and R. K. Ganju, “FAAH inhibition enhances anandamide mediated anti-tumorigenic effects in non-small cell lung cancer by downregulating the EGF/EGFR pathway,” Oncotarget, vol. 5, no. 9, pp. 2475–2486, 2014, doi: 10.18632/oncotarget.1723. B. S. Tanturovska, R. Manaila, D. Fabbro, and A. Huwiler, “Lipids as Targets for Renal Cell Carcinoma Therapy,” 2023. D. Z. Doyuran and Ö. Eronat, “The clinical and pathological significance of increased expression of the cannabinoid receptors CB-1R and CB-2R in patients with papillary thyroid carcinomas compared to benign thyroid lesions,” Int. J. Biol. Markers, 2023, doi: 10.1177/03936155231200285. D. Halatek, “Improving Prostamide Anti-Cancer Activity Through Derivatization and Micellar Delivery,” East Carolina University, 2023. B. Gagestein et al., “Chemical Proteomics Reveals Off-Targets of the Anandamide Reuptake Inhibitor WOBE437,” Cite This ACS Chem. Biol, vol. 2022, pp. 1174–1183, 2022, doi: 10.1021/acschembio.2c00122.
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dc.format.extent.none.fl_str_mv	110 páginas : ilustraciones, gráficas
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spelling	Cárdenas Chaparro, AgobardoRojas Bustamante, Lida Rosmary2025-09-20T20:15:03Z2025-09-20T20:15:03Z2023https://repositorio.uptc.edu.co/handle/001/18268T. Behl et al., “Exploration of Multiverse Activities of Endocannabinoids in Biological Systems,” Int. J. Mol. Sci., vol. 23, no. 10, p. 5734, May 2022, doi: 10.3390/IJMS23105734.K. Klatt-Schreiner et al., “High Glucosylceramides and Low Anandamide Contribute to Sensory Loss and Pain in Parkinson’s Disease,” Mov. Disord., vol. 35, no. 10, pp. 1822–1833, 2020, doi: 10.1002/mds.28186.A. Dlugos, E. Childs, K. L. Stuhr, C. J. Hillard, and H. De Wit, “Acute stress increases circulating anandamide and other n-acylethanolamines in healthy humans,” Neuropsychopharmacology, vol. 37, no. 11, pp. 2416–2427, 2012, doi: 10.1038/npp.2012.100.M. McKenna and J. J. McDougall, “Cannabinoid control of neurogenic inflammation,” Br. J. Pharmacol., vol. 177, no. 19, pp. 4386–4399, 2020, doi: 10.1111/bph.15208A. Sobiepanek, M. Milner-Krawczyk, P. Musolf, T. Starecki, and T. Kobiela, “Anandamide Modulated Changes in Metabolism, Glycosylation Profile and Migration of Metastatic Melanoma Cells,” Cancers (Basel)., vol. 14, no. 6, 2022, doi: 10.3390/cancers14061419D. Melck et al., “Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation,” Endocrinology, vol. 141, no. 1, pp. 118–126, 2000, doi: 10.1210/endo.141.1.7239.J. Ravi, A. Sneh, K. Shilo, M. W. Nasser, and R. K. Ganju, “FAAH inhibition enhances anandamide mediated anti-tumorigenic effects in non-small cell lung cancer by downregulating the EGF/EGFR pathway,” Oncotarget, vol. 5, no. 9, pp. 2475–2486, 2014, doi: 10.18632/oncotarget.1723.B. S. Tanturovska, R. Manaila, D. Fabbro, and A. Huwiler, “Lipids as Targets for Renal Cell Carcinoma Therapy,” 2023.D. Z. Doyuran and Ö. Eronat, “The clinical and pathological significance of increased expression of the cannabinoid receptors CB-1R and CB-2R in patients with papillary thyroid carcinomas compared to benign thyroid lesions,” Int. J. Biol. Markers, 2023, doi: 10.1177/03936155231200285.D. Halatek, “Improving Prostamide Anti-Cancer Activity Through Derivatization and Micellar Delivery,” East Carolina University, 2023.B. Gagestein et al., “Chemical Proteomics Reveals Off-Targets of the Anandamide Reuptake Inhibitor WOBE437,” Cite This ACS Chem. Biol, vol. 2022, pp. 1174–1183, 2022, doi: 10.1021/acschembio.2c00122.Anandamide or N-arachidonoyl-ethanolamide (AEA) is an endocannabinoid compound that is synthesised from phospholipids present in the membranes of different cells, in the brain and in the peripheral nervous system. It is involved in biological processes such as: memory, movement control, attenuation of pain sensation, reproduction, among others. In addition, due to their lipophilic nature, they can cross the blood-brain barrier and generate psychoactive effects including euphoria, drowsiness, motor incoordination, alterations in temporal and spatial perception, disorientation and confusion. In order to counteract these effects, analogue structures were designed with lower theoretical partition coefficients of AEA and with a possible binding capacity to the endocannabinoid receptor type 1 (CB1). In this research, 30 anandamide analogues were designed, retaining ethanolamide as the neuromodulatory pharmacophore and using different bioisosteric groups as substituents. Subsequently, the Administration, Digestion, Metabolism, Excretion, Metabolism and Toxicity (ADMET) properties of these compounds were predicted and a molecular docking study was performed, determining the ligand-protein interactions and the affinity energy with the CB1 receptor. From these results, two AEA analogue structures were selected: (S)-3-(4 hydroxy-3-(1-hydroxyhexyl)phenyl)-N-(2-hydroxyethyl)propanamide (-104.45 kcal/mol) and (S)-3-(4-hydroxy-3-(1-hydroxyethyl)phenyl)-N-(2-hydroxyethyl)propanamide ( 98.60kcal/mol). The synthesis was from the 3-(4-hydroxyphenyl)propanoic acid compound obtained in the Chemical Systems laboratory of the UPTC. The preparation of the two Anandamide analogues was carried out using a four-step methodology: Friedel-Crafts orthoacylation, reduction, esterification and amidation. The products were purified and characterised by FTIR, 1H NMR and 13C NMR spectroscopy and mass spectrometry.La anandamida o N-araquidonoil-etanolamida (AEA) es un compuesto endocanabinoide que es sintetizado a partir de fosfolípidos presentes en las membranas de diferentes células, en el cerebro y en el sistema nervioso periférico. Esta interviene en procesos biológicos tales como: la memoria, el control del movimiento, la atenuación de la sensación del dolor, la reproducción, entre otros. Adicionalmente, debido su carácter lipofílico, pueden atravesar la barrera hematoencefálica y generar efectos psicoactivos entre los que se incluyen euforia, somnolencia, descoordinación motora, alteraciones en la percepción temporal y espacial, desorientación y confusión. Con el fin de contrarrestar estos efectos, se diseñaron estructuras análogas con coeficientes de partición teóricos menores de la AEA y con una posible capacidad de acoplamiento al receptor endocannabinoides tipo 1 (CB1). En esta investigación se diseñaron 30 análogos de anandamida, conservando la etanolamida como farmacóforo neuromodulador y usando diferentes grupos bioisósteros como sustituyentes. Posteriormente, se predijo las propiedades de Administración, Digestión, Metabolismo, Excreción y Toxicidad (ADMET), a estos compuestos y se les realizó un estudio de acoplamiento molecular (Docking), determinando las interacciones ligando-proteína y la energía de afinidad con el receptor CB1. A partir de estos resultados, se seleccionaron dos estructuras análogas de AEA: (S)-3-(4-hidroxi-3-(1-hidroxihexil)fenil)-N-(2 hidroxietil)propanamida (-104.45 kcal/mol) y el (S)-3-(4-hidroxi-3-(1-hidroxietil)fenil)-N (2-hidroxietil)propanamida (-98.60kcal/mol). La síntesis fue a partir del ácido 3-(4 hidroxifenil) propanoico compuesto obtenido en el Laboratorio de Sistemas Químicos de la UPTC. La elaboración de los dos análogos de Anandamida transcurrió usando una metodología de cuatro etapas: ortoacilación de Friedel-Crafts, reducción, esterificación y amidación. Los productos se purificaron y se caracterizaron por espectroscopías FTIR, 1H RMN y 13C RMN y espectrometría de masas.MaestríaMagíster en Químicaapplication/pdf110 páginas : ilustraciones, gráficasapplication/pdfUniversidad Pedagógica y Tecnológica de ColombiaFacultad de CienciasFacultad de Ciencias. Escuela de Posgrados. 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Diseño, estudio teórico computacional y síntesis de dos análogos estructurales de anandamida, como posibles ligandos de receptores cannabinoides CB1

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