PMID- 35777271
OWN - NLM
STAT- MEDLINE
DCOM- 20220713
LR  - 20220730
IS  - 1464-3391 (Electronic)
IS  - 0968-0896 (Linking)
VI  - 69
DP  - 2022 Sep 1
TI  - SPION nanoparticles for delivery of dopaminergic isoquinoline and benzazepine 
      derivatives.
PG  - 116910
LID - S0968-0896(22)00303-0 [pii]
LID - 10.1016/j.bmc.2022.116910 [doi]
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 SiO(2) shell 
      (SPION@SiO(2)) and functionalized with carboxyl groups (SPION@SiO(2)-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@SiO(2)-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(1)H HRMAS-NMR) are used to 
      confirm the presence of THB and THIQ molecules onto the surface of the 
      nanoparticles. The hybrid SPION@SiO(2)-THIQ and THB systems show significant 
      activity toward the D(2) receptor, reaching Ki values of about 20 nM, thus having 
      potential application in the treatment of central nervous system (CNS) diseases.
CI  - Copyright (c) 2022 Elsevier Ltd. All rights reserved.
FAU - Lucena-Serrano, Cristina
AU  - Lucena-Serrano C
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain.
FAU - Lucena-Serrano, Ana
AU  - Lucena-Serrano A
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain.
FAU - Diaz, Amelia
AU  - Diaz A
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain. Electronic address: amelia@uma.es.
FAU - Valpuesta, Maria
AU  - Valpuesta M
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain.
FAU - Villaverde, Gonzalo
AU  - Villaverde G
AD  - Dep. Chemistry in Pharmaceutical Science, Universidad Complutense de Madrid, 
      Plaza Ramon y Cajal s/n, 28040 Madrid, Spain.
FAU - Manuel Lopez-Romero, J
AU  - Manuel Lopez-Romero J
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain. Electronic address: jmromero@uma.es.
FAU - Sarabia, Francisco
AU  - Sarabia F
AD  - Dpto. Quimica Organica, Universidad de Malaga, Campus de Teatinos s/n, 29071 
      Malaga, Spain.
FAU - Laurenti, Marco
AU  - Laurenti M
AD  - Dep. Chemistry in Pharmaceutical Science, Universidad Complutense de Madrid, 
      Plaza Ramon y Cajal s/n, 28040 Madrid, Spain; Instituto de Ciencia de Materiales 
      de Madrid, c/Sor Juana Ines de la Cruz, Canto- blanco, 28049 Madrid, Spain; 
      Instituto Ramon y Cajal de Investigacion Sanitaria, Hospital Universitario Ramon 
      y Cajal, 28034 Madrid, Spain.
FAU - Rubio-Retama, Jorge
AU  - Rubio-Retama J
AD  - Dep. Chemistry in Pharmaceutical Science, Universidad Complutense de Madrid, 
      Plaza Ramon y Cajal s/n, 28040 Madrid, Spain.
FAU - Contreras-Caceres, Rafael
AU  - Contreras-Caceres R
AD  - Dep. Chemistry in Pharmaceutical Science, Universidad Complutense de Madrid, 
      Plaza Ramon y Cajal s/n, 28040 Madrid, Spain. Electronic address: 
      rafcontr@ucm.es.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20220627
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (Benzazepines)
RN  - 0 (Ferric Compounds)
RN  - 0 (Isoquinolines)
RN  - 7631-86-9 (Silicon Dioxide)
SB  - IM
MH  - Benzazepines/pharmacology
MH  - *Ferric Compounds
MH  - Isoquinolines/pharmacology
MH  - Magnetic Iron Oxide Nanoparticles
MH  - *Nanoparticles/chemistry
MH  - Silicon Dioxide/chemistry
OTO - NOTNLM
OT  - Benzazepine
OT  - Dopamine receptors
OT  - Dopaminergic activity
OT  - Isoquinoline
OT  - SPIONs
OT  - SiO(2) shell
OT  - Surface functionalization
EDAT- 2022/07/02 06:00
MHDA- 2022/07/14 06:00
CRDT- 2022/07/01 18:27
PHST- 2022/01/31 00:00 [received]
PHST- 2022/06/23 00:00 [revised]
PHST- 2022/06/23 00:00 [accepted]
PHST- 2022/07/02 06:00 [pubmed]
PHST- 2022/07/14 06:00 [medline]
PHST- 2022/07/01 18:27 [entrez]
AID - S0968-0896(22)00303-0 [pii]
AID - 10.1016/j.bmc.2022.116910 [doi]
PST - ppublish
SO  - Bioorg Med Chem. 2022 Sep 1;69:116910. doi: 10.1016/j.bmc.2022.116910. Epub 2022 
      Jun 27.