Abstract
In this work, new nanohybrids based on superparamagnetic iron oxide nanoparticles (SPIONs) were elaborated and discussed for the first time as nanovectors of a derivative molecule of trans-resveratrol (RSV), a natural antioxidant molecule, which can be useful for brain disease treatment. The derivative molecule was chemically synthesized (4’-hydroxy-4-(3-aminopropoxy) trans-stilbene: HAPtS) and then grafted onto SPIONs surface using an organosilane coupling agent, which is 3-chloropropyltriethoxysilane (CPTES) and based on nucleophilic substitution reactions. The amount of HAPtS loaded onto SPIONs surface was estimated by thermogravimetric analysis (TGA) and X-ray photoelectron spectroscopy (XPS) analyses at 116 µmol·g−1 SPIONs. The synthesized HAPtS molecule, as well as the associated nanohybrids, were fully characterized by transmission electron microscopy (TEM), XPS, TGA, infrared (IR) and UV-visible spectroscopies, dynamic light scattering (DLS), and zeta potential measurements. The in vitro biological assessment of the synthesized nanohybrid’s efficiency was carried out on C6 glioma cells and showed that the nanovector SPIONs-CPTES-HAPtS do not affect the mitochondrial metabolism (MTT test), but damage the plasma membrane (FDA test), which could contribute to limiting the proliferation of cancerous cells (clonogenic test) at a HAPtS concentration of 50 µM. These nanoparticles have a potential cytotoxic effect that could be used to eliminate cancer cells.
Highlights
Trans-resveratrol, or 3,4’,5-trihydroxy-trans-stilbene (RSV) (Figure 1A), is a polyphenolic compound that belongs to the stilbene family
As oxidative damage has been considered the main cause of many neurodegenerative diseases, including Alzheimer’s disease (AD), Parkinson’s disease (PD), and stroke [10,11], RSV has extensively been studied as a therapeutic molecule for these kinds of diseases based on its antioxidant properties [12]
A total of 50 mg of as prepared superparamagnetic iron oxide nanoparticles (SPIONs) were dispersed in a mixture of EtOH and DI water, with a volume ratio 3:1. 600 μL of CPTES, which was added to the suspension and the pH was adjusted tNoan4owmaittehriaNlsa2O01H9, 9s,oxluFOtiRonPE(E0R.1RMEV).IETWhe suspension was kept under magnetic stirring at 360 rpm for52o4f 2h1 at 25 ◦C
Summary
Trans-resveratrol, or 3,4’,5-trihydroxy-trans-stilbene (RSV) (Figure 1A), is a polyphenolic compound that belongs to the stilbene family. SPIONs are considered as one of the most developed nanoparticles for various biomedical applications thanks to their small size, high magnetic moment, high surface to volume ratio, and biocompatibility [31] They have been used for magnetic resonance imaging (MRI) as a contrast agent [32,33], cell labeling, tissue repair, gene and drug delivery, hyperthermia [34], and nano-sensors [35]. We studied the surface modification of SPIONs with a derivative molecule of RSV, used as a therapeutic molecule, for further application in neurodegenerative diseases This molecule has the same stilbene core as RSV—4’-hydroxy-4-(3-aminopropoxy) trans-stilbene, hereafter referred to as HAPtS (Figure 1)—and it was exclusively synthesized for this purpose. CChhememiciaclalstsrtuructcuturereoof f(A(A)) ththee nnaattuurraall ttrraannss--rreessvveerraattrrooll mmoolleeccuulele ((RRSSVV)) aanndd ((BB)) tthhee ttrraannss--rreessvveerraattrrooll ddeerriivvaattiivvee mmoolleeccuullee:: 44’’--hhyyddrrooxxyy--44--((33--aammiinnoopprrooppooxxyy)) ttrraannss--ssttiillbbeennee ((HHAAPPttSS))
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