Synthesis, characterization, computational study and covalentimmobilization of H۲saldien ligand on dendrimer functionalized magneticnanoparticles fordrugdeliveryapplication

Novel pH-sensitive, biocompatible and biodegradable magneto-dendrimers with imine andhydroxyfunctional groups based on polyamido-amine were synthesized for drug-delivery systemthat can enhance the therapeutic effects of drugs[۱]. In this study, MnFe۲O۴ magneticnanoparticles (MNPs) with a diameter of ۳۵ nm were prepared by using the hydrothermal route.MNPs were coated by tetraethoxysilane (TEOS) to obtain core/shell of MnFe۲O۴/SiO۲. Core–shell nanoparticles were modified by (۳‐aminopropyl) triethoxysilane (APTES) to fabricateamine‐functionalized magnetic nanoparticles (zero generation(G۰)). The half generation (G۰.۵)of the magneto-dendrimer with methyl estergroups were produced by Michael addition reactionusing the required amount of methylacrylate (MA). The first generation (G۱) of nanocarrier wassynthesized by the amidation reaction using the necessary amounts of N,N'-bis(salicylidene)diethylenetriamine (H۲saldien)(obtain from the reaction betweensalicylaldehyde(۲ equiv.)and diethylenetriamine(۱ equiv.)). The characterization of synthesized ligand andnanoparticles were performed by Fourier Transform Infrared spectroscopy (FT-IR),Nuclearmagnetic resonance spectroscopy (NMR),X-Ray Diffraction (XRD), Field Emission ScanningElectron Microscopy (FESEM), Energy Dispersive X-Ray Analysis (EDX), Elemental MappingDirectily from FESEM (MAP), Thermogravimetric Analysis (TGA) and Vibrating-SampleMagnetometer (VSM). Magnetic dendrimer wasusedas novel drugnanocarrier.Ibuprofen waschosen as model drug, which directly conjugated to imine, hydroxyandaromatic groups ofterminated dendrimer by hydrogen bond and π-π stacking interaction. Drug content and drugentrapment efficiency were determined for drug-loaded nanocarrier by UV-Vis spectroscopy andin vitro drug release studies were done in simulated gastric fluid (pH=۱.۲), colonic media(pH=۵.۵), blood environment (pH=۷.۴) and others (pH=۸.۵) at ۳۷ ºC. Such unique propertiesenable maintenance of the bioactivity of the drugs. Therefore, the findings in this study showedmagneto-dendrimer is a promising oral drug delivery nanocarrier. This improvement couldenhance the potential of magnetic targeting therapy in clinical applications of cancer treatments.Also, full optimization of the geometries of drug-loaded nanocarrier, natural bond orbital (NBO)analysis, vibrational frequencies, the HOMO–LUMO energy gap and Molecular electrostaticpotential (MEP), were calculated by using density functional theory (DFT) by Gaussiansoftware. Finally, a comparison has been made between computational and experimental results.The theoretical spectral properties show good agreement with the experimental ones.

کلیدواژه ها:

Magnetic nanoparticle ، Magneto-dendrimer ، Nanocarrier ، Drug delivery ، DFT study