Synthesis and Characterization of Novel Photoswitchable Tool Compounds to Enlighten β-Adrenoceptor Signalling

 -adrenergic receptors ( -AR), a family of class A G Protein-Coupled Receptors, include three subtypes:  1-AR,  2-AR, and  3-AR. They are considered key targets in treating diseases such as heart failure and asthma with betablockers such as propranolol and agonists that are commonly structurall...

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Detalles Bibliográficos
Autor: Božić, Sasha
Tipo de recurso: tesis doctoral
Fecha de publicación:2025
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:dnet:digitalcsic_::c0e7effca2d4af0bd9d7043a4f6c6514
Acceso en línea:http://hdl.handle.net/10261/428415
Access Level:acceso abierto
Palabra clave:Synthesis of drugs
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Descripción
Sumario: -adrenergic receptors ( -AR), a family of class A G Protein-Coupled Receptors, include three subtypes:  1-AR,  2-AR, and  3-AR. They are considered key targets in treating diseases such as heart failure and asthma with betablockers such as propranolol and agonists that are commonly structurally based on endogenous ligands adrenaline and noradrenaline. To be able to study the complex nature of  -AR signalling, developing new tool compounds with singular properties is considered appealing. For example, photopharmacology approaches allow for the spatial-temporal control of receptor activity. An established way to gain this spatial-temporal control is by the incorporation of a photoswitchable chemical moiety, (e.g. azobenzene), in the structure of ligands. Ideally, these photoswitchable ligands photo-isomerize between two isomers with different binding/functional properties toward the target receptor. In this work, three series of photoswitchable ligands for  -ARs have been developed. In particular, the designed compounds include the common azobenzene moiety on either the ethanolamine N-tail of a conventional agnoists (series 1) or on the aromatic ring (series 2 and 3). The compounds of series 2 and 3 bear different N-tails in order to further elucidate the structure-activity relationship of photoagonists for  -ARs and to potentially induce  1/ 2-AR selectivity. In total, one, six and six compounds of series 1, 2 and 3 respectively have been entirely synthesized and characterized and were shown to exhibit photoswitchable characteristics.