SPION nanoparticles for delivery of dopaminergic isoquinoline and benzazepine derivatives

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dc.contributor.authorLucena-Serrano, Cristina
dc.contributor.authorLucena-Serrano, Ana
dc.contributor.authorDíaz, Amelia
dc.contributor.authorValpuesta, María
dc.contributor.authorVillaverde Cantizano, Gonzalo
dc.contributor.authorLópez-Romero, J. Manuel
dc.contributor.authorSarabia, Francisco
dc.contributor.authorLaurenti, Marco
dc.contributor.authorRubio Retama, Benito Jorge
dc.contributor.authorContreras Cáceres, Rafael
dc.date.accessioned2024-02-02T14:09:35Z
dc.date.available2024-02-02T14:09:35Z
dc.date.issued2022
dc.description.abstractSuperparamagnetic iron nanoparticles (SPIONs) have become one of the most useful colloidal systems in nanomedicine. We report here the preparation of new hybrid core@shell systems based on SPION nanoparticles coated with a SiO2 shell (SPION@SiO2) and functionalized with carboxyl groups SPION@SiO2-COOH). A series of new N-alkylamino- and N-alkylamido-terminated 1-phenyl- tetrahydroisoquinolines (THIQs) and 3 tetrahydrobenzazepines (THBs) derivatives presenting -SMe and -Cl groups, respectively, with potential dopaminergic activity, are synthesized and incorporated to the hybrid system. We include the synthetic details for THIQs and THBs derivatives preparation and investigate the influence of the terminal-functional group as well as the number of carbon atoms linked to THIQ and THB molecules during the coupling to the SPION@SiO2-COOH. Nuclear magnetic resonance (NMR) and electron ionization mass spectrometry (EI-MS) are used to characterize the synthesized THIQs and THBs. High-angle annular dark-field transmission electron microscopy (HAADFTEM), energy dispersive X-ray transmission electron microscopy (EDX-TEM), and proton high-resolution magic angle spinning NMR spectroscopy1 H HRMAS-NMR) are used to confirm the presence of THB and THIQ molecules onto the surface of the nanoparticles. The hybrid SPION@SiO2-THIQ and THB systems show significant activity toward the D2 receptor, reaching Ki values of about 20 nM, thus having potential application in the treatment of central nervous system (CNS) diseases.eng
dc.description.departmentDepto. de Química en Ciencias Farmacéuticas
dc.description.facultyFac. de Farmacia
dc.description.refereedTRUE
dc.description.sponsorshipComunidad de Madrid
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades (España)
dc.description.statuspub
dc.identifier.doi10.1016/j.bmc.2022.116910
dc.identifier.issn0968-0896
dc.identifier.officialurlhttps://doi.org/10.1016/j.bmc.2022.116910
dc.identifier.urihttps://hdl.handle.net/20.500.14352/98351
dc.journal.titleBioorganic & Medicinal Chemistry
dc.language.isoeng
dc.relation.projectIDinfo:eu-repo/grantAgreement/RTI2018- 094859-B-100
dc.relation.projectIDinfo:eu-repo/grantAgreement/2018-T1/IND-10736
dc.relation.projectIDinfo:eu-repo/grantAgreement/FQM397
dc.rights.accessRightsrestricted access
dc.subject.cdu615:54
dc.subject.cdu615.31
dc.subject.keywordSPIONs
dc.subject.keywordDopamine receptors
dc.subject.keywordDopaminergic activity
dc.subject.keywordSurface functionalization
dc.subject.keywordBenzazepine
dc.subject.keywordSiO2 shell Isoquinoline
dc.subject.ucmQuímica farmaceútica
dc.subject.unesco23 Química
dc.titleSPION nanoparticles for delivery of dopaminergic isoquinoline and benzazepine derivatives
dc.typejournal article
dc.type.hasVersionAM
dc.volume.number69
dspace.entity.typePublication
relation.isAuthorOfPublication13785694-551d-4e51-90ca-f777965d8413
relation.isAuthorOfPublication3f84ff29-c7f1-4213-82be-e2bff4127a45
relation.isAuthorOfPublicatione472b936-73b0-45a5-b92a-7b3be8543cc8
relation.isAuthorOfPublication62736d2d-0790-4279-b601-4b367ae735ad
relation.isAuthorOfPublication.latestForDiscovery13785694-551d-4e51-90ca-f777965d8413
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