RT Journal Article
T1 SPION Nanoparticles for Delivery of Dopaminergic Isoquinoline and Benzazepine Derivatives.
A1 Lucena-Serrano, Cristina
A1 Lucena-Serrano, Ana
A1 Díaz-Morilla, Amelia
A1 Valpuesta-Fernández, María
A1 Villaverde, Gonzalo
A1 López-Romero, Juan Manuel
A1 Sarabia-García, Francisco Ramón
A1 Laurenti, Marco
A1 Rubio Retama, Jorge
A1 Contreras-Cáceres, Rafael
K1 Nanopartículas
K1 Nanomedicina
K1 Dopamina - Receptores
K1 Isoquinolina
AB Superparamagnetic 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 (HAADF-TEM), energy dispersive X-ray transmission electron microscopy (EDX-TEM), and proton high-resolution magic angle spinning NMR spectroscopy (1H 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.
PB Elsevier
YR 2022
FD 2022-06-27
LK https://hdl.handle.net/10630/29361
UL https://hdl.handle.net/10630/29361
LA eng
NO Lucena-Serrano, C., Lucena-Serrano, A., Díaz, A., Valpuesta, M., Villaverde, G., Manuel López-Romero, J., Sarabia, F., Laurenti, M., Rubio-Retama, J., & Contreras-Cáceres, R. (2022). SPION nanoparticles for delivery of dopaminergic isoquinoline and benzazepine derivatives. Bioorganic & Medicinal Chemistry, 69, 116910.
NO The authors acknowledge Adolfo Martinez Orellana for his collaboration in the TEM characterization at the Universidad de Málaga. Furthermore, the authors acknowledge the ICTS-CNME of the Universidad Complutense de Madrid. Images from Servier Medical Art (and their PowerPoint image bank) have been employed to produce Fig. 1 in this article. This research was funded by: FQM397 Research Group (Junta de Andalucía); Comunidad de Madrid Atracción de Talento, grant number 2018-T1/IND-10736; and MICINN, grant number RTI2018-094859-B-100.
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 20 ene 2026