Organically surface engineered mesoporous silica nanoparticles control the release of quercetin by pH stimuli

Abstract

Controlling the premature release of hydrophobic drugs like quercetin over physiological conditions remains a challenge motivating the development of smart and responsive drug carriers in recent years. This present work reported a surface modification of mesoporous silica nanoparticles (MSN) by a functional compound having both amines (as a positively charged group) and carboxylic (negatively charged group), namely 4-((2-aminoethyl)amino)-4-oxobut-2-enoic acid (AmEA) prepared via simple mechanochemistry approach. The impact of MSN surface modification on physical, textural, and morphological features was evaluated by TGA, N2 adsorption–desorption, PSA-zeta, SEM, and TEM. The BET surface area of AmEA-modified MSN (MSN-AmEA) was found to be 858.41 m2 g−1 with a pore size of 2.69 nm which could accommodate a high concentration of quercetin 118% higher than MSN. In addition, the colloidal stability of MSN-AmEA was greatly improved as indicated by high zeta potential especially at pH 4 compared to MSN. In contrast to MSN, MSN-AmEA has better in controlling quercetin release triggered by pH, thanks to the presence of the functional groups that have a pose-sensitive interaction hence it may fully control the quercetin release, as elaborated by the DFT study. Therefore, the controlled release of quercetin over MSN-AmEA verified its capability of acting as a smart drug delivery system.

Controlled Quercetin Release by Fluorescent Mesoporous Nanocarriers for Effective Anti-Adipogenesis

“…As a result, there is an increase of release rate due to the reduced electrostatic attraction between the drug and the A-F complex. 49 In addition, amine groups in the PDA layer become protonated in acidic conditions, and the oxidation of PDA reduces density and delocalization of π electrons, thereby weakening the π-π stacking interaction. This contributes to a further increased release rate of the drug under acidic pH conditions.…”

Effect of Amine, Carboxyl, or Thiol Functionalization of Mesoporous Silica Particles on Their Efficiency as a Quercetin Delivery System in Simulated Gastrointestinal Conditions

“…PS also influences biodistribution: particles with a diameter greater than 200 nm activate the complement system and are quickly removed from the bloodstream, accumulating in the liver and spleen [43]. On the contrary, negatively charged particles have unfavorable interactions with membrane lipid and plasma proteins [15]. There was no significant difference (p < 0.05) in diameter between LC-MSP and HC-MSP or their ζ potential when they were loaded with Q, suggesting that carboxyl groups do not interact with Q.…”

“…This allows the release of drugs in a specific area of interest, avoiding their premature release at off-target sites [14]. Moreover, MSP modifications could be made by adding organic moieties that can act as the gatekeeper in controlling the release of molecules via light, pH, ultrasound, thermal, redox, and other stimuli [15]. MSPs may also be used as matrices to enhance poorly water-soluble drugs' solubility and dissolution rate [16].…”

Effect of Nitric Acid on the Synthesis and Biological Activity of Silica–Quercetin Hybrid Materials via the Sol-Gel Route

“…Moreover, the use of HNO 3 to accelerate the synthesis process was evident in the sharp peak at 1384 cm −1 , attributable to the NO 3 − group. The encapsulation of quercetin within the inorganic silicon matrix is highlighted in the SiQ5-HNO 3 spectrum by the presence of a peak at 1165 cm −1 , attributed to the stretching of the ketone group C-CO-C and the appearance of the peak at 1757 cm −1 , due to the carbonyl group's vibration of the flavonoid in a hydroxybenzofuranone structure [38,39], validated by NMR analysis conducted in our previous work [25]. The increase in the broadness of -OH stretching vibration at 3457 cm −1 is indicative of the formation of H-bonds between the hydroxyl group of the silanol group from the silica matrix and the -OH groups of entrapped quercetin.…”