Diethylamino Ethyl Methacrylate Research Articles

In Situ Incorporation of Praziquantel in Polymer Microparticles through Suspension Polymerization for Treatment of Schistosomiasis

AbstractSchistosomiasis is one of the major public health problems worldwide. Even though this is a common illness among preschool children in poor countries, treatment is carried out mainly through the administration of praziquantel tablets, which has some disadvantages, such as the strong bitter taste. As an alternative to overcome this problem, the development of new encapsulated praziquantel formulations is demanded. For this reason, suspension polymerizations are carried out for the in situ encapsulation of praziquantel into polymer microparticles, using methyl methacrylate (MMA) and cationic compounds (diethylaminoethyl methacrylate, DEAEMA, and dimethylaminoethyl methacrylate, DMAEMA) as comonomers. This technique allows for the preparation of polymer microparticles with high encapsulation efficiencies (>90%) with characteristic sizes ranging from 0.5 to 1500 µm. Drug release profiles show that praziquantel is released from poly(methyl methacrylate) microparticles slowly due to the existence of strong diffusional resistance. On the other hand, the addition of cationic comonomers renders polymer particles sensitive to pH variations, allowing for faster release of praziquantel in acidic environments, as found in the stomach.

Uptake and function of membrane-destabilizing cationic nanogels for intracellular drug delivery.

The design of intracellular drug delivery vehicles demands an in‐depth understanding of their internalization and function upon entering the cell to tailor the physicochemical characteristics of these platforms and achieve efficacious treatments. Polymeric cationic systems have been broadly accepted to be membrane disruptive thus being beneficial for drug delivery inside the cell. However, if excessive destabilization takes place, it can lead to adverse effects. One of the strategies used to modulate the cationic charge is the incorporation of hydrophobic moieties, thus increasing the hydrophobic content. We have demonstrated the successful synthesis of nanogels based on diethylaminoethyl methacrylate and poly(ethylene glycol) methyl ether methacrylate. Addition of the hydrophobic monomers tert‐butyl methacrylate or 2‐(tert‐butylamino)ethyl methacrylate shows improved polymer hydrophobicity and modulation of the critical swelling pH. Here, we evaluate the cytocompatibility, uptake, and function of these membrane‐destabilizing cationic methacrylated nanogels using in vitro models. The obtained results suggest that the incorporation of hydrophobic monomers decreases the cytotoxicity of the nanogels to epithelial colorectal adenocarcinoma cells. Furthermore, analysis of the internalization pathways of these vehicles using inhibitors and imaging flow cytometry showed a significant decrease in uptake when macropinocytosis/phagocytosis inhibitors were present. The membrane‐disruptive abilities of the cationic polymeric nanogels were confirmed using three different models. They demonstrated to cause hemolysis in sheep erythrocytes, lactate dehydrogenase leakage from a model cell line, and disrupt giant unilamellar vesicles. These findings provide new insights of the potential of polymeric nanoformulations for intracellular delivery.

Improvement of fatigue strength and fracture toughness of bone cement by incorporation of aromatic structures to formulations

It has been postulated that the incorporation of cyclic or aromatic groups to the chemical structure of monomers/polymers could improve the mechanical performance of the polymeric materials prepared from them. In this work, N-methacryloyloxyethyl-m-toluidine (MEET) monomer, a compound whose chemical structure is similar to diethylamino ethyl methacrylate (DEAEM) but having an aromatic ring, was synthesized. Acrylic bone cements were prepared using either MEET or DEAEM as co-monomer and a systematic study of the potential influence of adding aromatic structures on the fatigue properties and fracture toughness of such bone cements was performed. Results indicated that the formulations prepared with the aromatic co-monomer (MEET) exhibited a higher fatigue resistance than those containing the aliphatic counterpart (DEAEM), at all co-monomer concentrations. These results confirm the hypothesis that the inclusion of aromatic structures in the bone cement formulations increases the fatigue life of these materials. It was also found that presence of aromatic structures in bone cement formulations improve the fracture toughness of cements.

Synthesis of Well-Defined Pyrrolidone-Based Homopolymers and Stimulus-Responsive Diblock Copolymers via RAFT Aqueous Solution Polymerization of 2-(N-Acryloyloxy)ethylpyrrolidone.

Poly(N-vinylpyrrolidone) (PNVP) is a well-known, highly polar, nonionic water-soluble polymer. However, N-vinylpyrrolidone (NVP) usually exhibits strongly non-ideal behavior when copolymerized with methacrylic or styrenic monomers. Moreover, NVP is not particularly well-controlled under living radical polymerization conditions. For these reasons, alternative pyrrolidone-based monomers have been investigated. For example, the reversible addition–fragmentation chain transfer (RAFT) polymerization of 2-(N-methacryloyloxy)ethylpyrrolidone (NMEP) has been recently investigated using various polymerization formulations. However, PNMEP homopolymers are significantly less hydrophilic than PNVP and exhibit inverse temperature solubility in aqueous solution. In the present work, we studied the RAFT aqueous solution polymerization of 2-(N-acryloyloxy)ethylpyrrolidone (NAEP) using either AIBN at 70 °C or a low-temperature redox initiator at 30 °C. PNAEP homopolymers are obtained in high yield (>99%) with good control (Mw/Mn < 1.20) for target degrees of polymerization (DP) of up to 400 using the latter initiator, which produced relatively fast rates of polymerization. However, targeting DPs above 400 led to lower NAEP conversions and broader molecular weight distributions. 2-Hydroxyethyl acrylate (HEA) and oligo(ethylene glycol) methyl ether acrylate (OEGA) were chain-extended using a PNAEPx macro-CTA via RAFT aqueous solution polymerization, yielding double-hydrophilic acrylic diblock copolymers with high conversions (>99%) and good control (Mw/Mn < 1.31). In addition, a PNAEP95 macro-CTA was chain-extended via RAFT aqueous solution polymerization of N-isopropylacrylamide (NIPAM) at 22 °C. Dynamic light scattering (DLS) analysis indicated that heating above the lower critical solution temperature of PNIPAM led to so-called “anomalous micellization” at 35 °C and the formation of near-monodisperse spherical micelles at 40 °C. Finally, 2-(diethylamino)ethyl methacrylate (DEA) was polymerized using an N-morpholine-functionalized trithiocarbonate-based RAFT chain transfer agent and subsequently chain-extended using NAEP to form a novel pH-responsive diblock copolymer. Above the pKa of PDEA (∼7.3), DLS and 1H NMR studies indicated the formation of well-defined PDEA-core spherical micelles.

Novel block glycopolymers prepared as delivery nanocarriers for controlled release of bortezomib

To explore block glycopolymers as novel polymeric delivery nanocarriers for anticancer drug bortezomib (BTZ), three types of block glycopolymers, poly(ethylene glycol)-block-poly(gluconamido ethyl methacrylate) (PEG113-b-PGAMA20), poly(ethylene glycol)-block-poly(styrene)-block-poly(gluconamido ethyl methacrylate) (PEG113-b-PS50-b-PGAMA20), and poly(ethylene glycol)-block-poly(2-(diethyl amino) ethyl methacrylate)-block-poly(gluconamido ethyl methacrylate) (PEG113-b-PDEA50-b-PGAMA20), were synthesized via atom transfer radical polymerization (ATRP) using a PEG-based ATRP macroinitiator. Three glycopolymers possess the capacity to load BTZ via pH-induced dynamic covalent bonding and/or hydrophobic interaction with their specific self-assembly behaviors, and PEG113-b-PS50-b-PGAMA20 carrier maintains the sustain release behavior of BTZ due to the stable micellar structure; PEG113-b-PDEA50-b-PGAMA20 carrier realizes the abrupt release at pH 5.5 by collapse of micellar structure, while PEG113-b-PGAMA20 carrier exhibits the fastest release at studied solution pHs. This study would provide a light to develop novel block glycopolymer carrier for the delivery of anticancer drug bearing boronic acid groups.Graphical abstractᅟᅟ

Gas-responsive cationic microgels for forward osmosis desalination

Polymers as draw materials for forward osmosis (FO) desalination have attracted increasing attention in recent years, where the water adsorption and dewatering abilities of draw materials are crucial to overall desalination performance. Here, we developed gas-responsive microgels as new draw materials for FO desalination in which water adsorption and dewatering are driven by sweeping CO2 and N2. Cationic microgels of 2-(diethylamino) ethyl methacrylate (DEAEMA) and 2-(dimethylamino) ethyl methacrylate microgels (DMAEMA) were synthesised. The gas-responsivity of these microgels on water-flux and water recovery was systematically examined in a laboratory FO desalination system. CO2 is able to protonate DEAEMA microgels to enhance water adsorption. The DEAEMA microgels with 1 wt% polyethylene glycol diacrylate crosslinker show the highest water flux of 56 LMH. At the isoelectric points, the adsorbed water can be released by purging N2 gas at room temperature due to the hydrophobic characteristics of deprotonated DEAEMA microgels. Water recovery by 50% can be achieved for these microgels. Comparing with more hydrophilic DMAEMA microgels, the gas-responsive DEAEMA microgels perform higher swelling ratio, water-flux and recovery capability. Our results reveal that these gas-responsive microgels can be used as promising draw materials for future FO process with high water permeability and low-operation cost.

Micellization of a di‐block copolymer in ethylene glycol and its utilization for suspension of carbonaceous nanostructures

ABSTRACTSuspensions of carbonaceous nanoparticles (NPs) in ethylene glycol (EG) can be used as colloidal inks for additive manufacturing and nano‐fluids for heat‐transfer applications. While micellar solutions of surfactants are often used for suspension of the NPs in water, micellization of surfactants in EG is suppressed as compared to aqueous solutions and a well‐defined critical micellization concentration (CMC) is often not observed. Unlike the surfactants, a di‐block copolymer comprising a poly(ethylene glycol) monomethylether methacrylate (PEGMA) segment, 2‐(diethylaminoethyl) methacrylate (DEAEMA) and butyl methacrylate (BMA), poly(O950)‐b‐(DEAEMA‐co‐BMA) was found to assemble into spherical micelles in EG. Surface tension measurements show a well‐defined CMC that depends on the volume fraction of EG. Cryogenic transmission electron microscopy and dynamic light scattering show the presence of spherical micelles with a diameter that reduces with the volume fraction of EG. The micellar solutions were further used for suspending carbonaceous NPs of different geometry and characteristic dimensions: C60 fullerenes, multi‐walled carbon nanotubes, and nanodiamonds. The flow behavior of the suspensions exhibits a relatively low viscosity and mostly Newtonian behavior due to strong interaction between the NPs and the micelles. These suspensions may be used as colloidal inks for two‐dimensional and three‐dimensional printing. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46518.

Copolymers of 4-Acryloylmorpholine with 2-Dimethyl- and 2-Diethylaminoethyl Methacrylate and Silver-Containing Nanocomposites Based on Them

Copolymers of 4-acryloylmorpholine with 2-dimethyl- and 2-diethylaminoethyl methacrylates of variable composition and molecular mass were prepared by free-radical copolymerization. The reactivity ratios of the comonomers were determined for the first time. The copolymers synthesized are capable to reduce Ag+ ions without using additional agents to form stable nanodispersions of zerovalent silver with spherical nanoparticles of 8–10 nm size.

Zwitterion-functionalized polymer microspheres as a sorbent for solid phase extraction of trace levels of V(V), Cr(III), As(III), Sn(IV), Sb(III) and Hg(II) prior to their determination by ICP-MS.

This paper describes the preparation of zwitterion-functionalized polymer microspheres (ZPMs) and their application to simultaneous enrichment of V(V), Cr(III), As(III), Sn(IV), Sb(III) and Hg(II) from environmental water samples. The ZPMs were prepared by emulsion copolymerization of ethyl methacrylate, 2-diethylaminoethyl methacrylate and triethylene glycol dimethyl acrylate followed by modification with 1,3-propanesultone. The components were analyzed by elemental analyses as well as Fourier transform infrared spectroscopy, and the structures were characterized by scanning electron microscopy and transmission electron microscopy. The ZPMs were packed into a mini-column for on-line solid-phase extraction (SPE) of the above metal ions. Following extraction with 40mM NH4NO3 and 0.5M HNO3 solution, the ions were quantified by ICP-MS. Under the optimized conditions, the enrichment factors (from a 40 mL sample) are up to 60 for the ions V(V), As(III), Sb(III) and Hg(II), and 55 for Cr(III) and Sn(IV). The detection limits are 1.2, 3.4, 1.0, 3.7, 2.1 and 1.6ngL-1 for V(V), Cr(III), As(III), Sn(IV), Sb(III) and Hg(II), respectively, and the relative standard deviations (RSDs) are below 5.2%. The feasibility and accuracy of the method were validated by successfully analyzing six certified reference materials as well as lake, well and river waters. Graphical abstract Zwitterion-functionalized polymer microspheres (ZPMs) were prepared and packed into a mini-column for on-line solid-phase extraction (SPE) via pump 1. Then V(V), Cr(III), As(III), Sn(IV), Sb(III) and Hg(II) ions in environmental waters were eluted and submittedto ICP-MS via pump 2.

CO2 switchable hollow nanospheres

HypothesisHollow nanospheres, characterized by a cavity inside a solid shell, have potential applications due to their unique structure, but the unchangeable morphology and permeability of the shell restrain their further practical utilization. While several smart hollow nanospheres that can respond to pH, ion strength, and temperature have been developed, they are inclined to suffer from problems associated with high energy consumption or the difficult removal of residual stimulants. Thus, it is desirable to develop a novel and free-of-residual trigger stimulating mode. ExperimentsIn this work, CO2 is used to fabricate smart hollow nanospheres composed of crosslinked poly(diethylamino-ethyl methacrylate) (PDEAEMA) network from polystyrene (PS)/PDEAEMA core-shell nanospheres by a template-removal technique. The morphology evolution of the resultant nanospheres during the fabrication process was characterized by X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR), thermogravimetry analysis (TGA) and dynamic light scattering (DLS) and was visualized by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). FindingsHollow nanospheres can be generated by experiencing a morphology change from a core nanosphere, core-shell, yolk-shell to a final hollow structure. The increase in shell-stiffness can restrain the collapse of hollow spheres. It is demonstrated that CO2 is easy to introduce and remove (via N2 input) without stimulation residues in this system. In addition, mild CO2/N2 purging can only reversibly change the swelling/collapse of hollow particles; violent CO2/N2 bubbling can reversibly regulate both the size and aggregation/re-dispersion state of the hollow nanospheres, which can be intuitively observed by atomic force microscopy (AFM).

CO2-Triggered Recoverable Metal Catalyst Nanoreactors using Unimolecular Core–Shell Star Copolymers as Carriers

Metallic nanocatalysts are highly active in a variety of organic transformations, but their durable and facile reuse without comprising activity remains a great challenge. Herein, we describe the use of a CO2-triggered unimolecular core–shell star copolymer as carrier for immobilizing gold (Au) and silver (Ag) nanocatalysts for preserving high activity, while achieving facile recoverability. The core–shell star polymers comprising an inert hyperbranched polyethylene (HBPE) core and multiple CO2-responsive arms with tertiary amine groups were synthesized by palladium-catalyzed chain walking polymerization of ethylene and 2-(2-bromoisobutyryloxy)ethyl acrylate, followed by atom-transfer radical polymerization of dimethylaminoethyl methacrylate (DMAEMA) and diethylaminoethyl methacrylate (DEAEMA) using HBPE as a macroinitiator. The star copolymers were synergistically engineered via chain topology, composition, and functionality control. They form well-dispersed unimolecular micelles in aqueous solution with...

CO2-Switchable Membranes Prepared by Immobilization of CO2-Breathing Microgels.

Herein, we report the development of a novel CO2-responsive membrane system through immobilization of CO2-responsive microgels into commercially available microfiltration membranes using a method of dynamic adsorption. The microgels, prepared from soap-free emulsion polymerization of CO2-responsive monomer 2-(diethylamino)ethyl methacrylate (DEA), can be reversibly expanded and shrunken upon CO2/N2 alternation. When incorporated into the membranes, this switching behavior was preserved and further led to transformation between microfiltration and ultrafiltration membranes, as indicated from the dramatic changes on water flux and BSA rejection results. This CO2-regulated performance switching of membranes was caused by the changes of water transportation channel, as revealed from the dynamic water contact angle tests and SEM observation. This work represents a simple yet versatile strategy for making CO2-responsive membranes.

PH-Responsive Porous Nanocapsules for Controlled Release.

In this work pH-responsive porous nanocapsules have been successfully prepared from a ternary graft copolymer, poly(glycidyl methacrylate)-g-[poly(2-cinnamoyloxyethyl methacrylate)-r-poly(ethylene glycol) methyl ether-r-poly(2-diethylaminoethyl methacrylate)] or PGMA-g-(PCEMA-r-MPEG-r-PDEAEMA). The graft copolymers were fabricated by grafting three types of polymer chains onto the backbone polymer by using click chemistry. These ternary copolymers underwent self-assembly to form vesicles in a DMF/water solvent mixture. While the MPEG chains served as the corona and stabilized the vesicles, the vesicle wall was composed of a dominant PCEMA continuous phase that was interspersed by PDEAEMA domains. After photo-cross-linking, the PDEAEMA domains were embedded in the structurally locked PCEMA wall. By decreasing the pH of the external solution, we were able to trigger the release of encapsulated pyrene due to the capsule wall becoming porous as a result of the PDEAEMA chains bearing positively charged amine groups stretching into the water. While these pH-responsive porous nanocapsules exhibited potential applications in drug delivery, detection and catalysis, the strategy reported in this contribution also represented a new paradigm for the design and preparation of other novel stimuli-responsive porous nanocapsules.

Controlled release profile of 5-fluorouracil loaded P(AAM-co-NVP-co-DEAEMA) microgel prepared via free radical precipitation polymerization

A new microgel was prepared by free radical precipitation polymerization of acrylamide (AAM), 1-vinyl-2-pyrrolidone (NVP) and 2-(diethylamino)ethyl methacrylate (DEAEMA) to be used for the controlled drug release. The zeta-potential and particle size of P(AAM-co-NVP-co-DEAEMA) microgel were measured by dynamic light scattering (DLS) measurements and found to be around − 36.4 ± 6.29 mV and 592 nm, respectively. P(AAM-co-NVP-co-DEAEMA) microgel was loaded with 5-Fluorouracil (5-Fu) as a model drug. In vitro drug release profiles demonstrated that 5-Fu release from P(AAM-co-NVP-co-DEAEMA) microgel at pH 7.4 was much faster than at pH 5.5 and pH 2.1. In addition, release kinetic studies showed that P(AAM-co-NVP-co-DEAEMA) microgel fit into Higuchi model release. The cytotoxicity study indicated that P(AAM-co-NVP-co-DEAEMA) microgel did not exhibit apparent cytotoxicity against L929 cell line. When all of the results were evaluated, it can be seen that P(AAM-co-NVP-co-DEAEMA) microgel can be effectively used as a polymeric drug carrier for the potential drug delivery systems in medical applications.

CO₂-Responsive Graft Modified Chitosan for Heavy Metal (Nickel) Recovery.

Chitosan was chemically functionalized with poly(diethylaminoethyl methacrylate) (PDEAEMA) using a grafting to approach to produce a CO2-responsive material for adsorbing metals from wastewater streams. A need for improved economical and greener approaches to recover heavy metals from wastewater streams exists due to increasing resource scarcity. Chitosan is currently used as an adsorbent for heavy metals but suffers from some properties that can be disadvantageous to its effectiveness; it is difficult to effectively disperse in water (which limits available surface area) and to regenerate. We set out to improve its effectiveness by grafting CO2-responsive tertiary amine containing polymers onto the chitosan backbone, with the goals of preparing and assessing a new type of adsorbent based on a novel concept; using carbon dioxide switchable polymers to enhance the performance of chitosan. PDEAEMA chains prepared by nitroxide-mediated polymerization were grafted onto chitosan functionalized with glycidyl methacrylate. In carbonated water, the grafted chitosan displayed improved dispersibility and exhibited a Ni(II) adsorption capacity higher than several other chemically functionalized chitosan variants reported in the literature with the regenerated material having a higher capacity than all physical and chemical derivatives reported in the literature. The results of this study validate the continued development of this material for applications in heavy metal removal and recovery from wastewater streams.

Concentration dependent response to pH modification and salt addition of polymeric dispersions of C60 fullerenes

Diblockopolymers containing the pH-responsive monomer 2-(diethylaminoethyl) methacrylate (DEAEMA) were synthesized via RAFT polymerization. cryo-TEM imaging revealed the formation of micelles that were used for dispersion of C60 fullerenes in native pH, and their responsiveness to pH modification and salt addition was monitored at different concentrations. Concentration-dependent responsiveness was observed: Just above the CMC in native pH, pH reduction results in precipitation (release) of pre-dispersed C60. At high polymer concentrations the C60 dispersions are non-responsive. Dispersions of Carbon Black, a colloidal particle of much larger diameter, characterized as a reference system, showed a different nanomorphology and were not responsive to pH modifications, due to a different dispersion mechanism. We concluded that good size matching between the dispersed particles is necessary for the formation of micelle-entrapped dispersions, and that the responsivity of the C60 dispersion to pH reduction is limited to a concentration range between the CMC in native conditions and the CMC in acidic conditions.

Monitoring of the Critical Length of Cracklike Defects in the Bone-Cement Plate with Regard for their Different Geometry

We study the structural elements of materials made of bone-cement coupons with various impurities: diethylaminoethyl acrylate, dimethylaminoethyl methacrylate, and diethylaminoethyl methacrylate. With regard for values of the stress intensity factor, we present the characteristics of fracture factors for different times of soaking in simulated body fluid (0; 3; and 6 months) and also for different amounts of impurities in the analyzed material (2–10 wt.%). The data on the stress intensity factors used in the constructed models for different structural elements enable us to analyze possible risks of fracture of these elements in the case where they contain cracklike defects. Moreover, we obtain the values of the critical length of each considered cracklike defect and compute the number of loading cycles in this object that can be useful for the engineering recommendations concerning the tested material and specific structural elements made of this material.

Synthesis and morphological insight of new biocompatible smart hydrogels

We present a first report for developing stimulus responsive hydrogels via free radical aqueous polymerization technique using Acrylic acid (AAc), methacrylic acid (MAAc) and diethylaminoethyl methacrylate (DEAEMA). The morphological aspects of poly(AAc-co-DEAEMA) (pAcD) and poly(MAAc-co-DEAEMA) (pMcD) were investigated to delineate the relevant mechanism of hydrogel formation for better understanding of their mechanical behaviour. The formulated hydrogels were found to have a structural framework comprising inter-connected nanogels and continuous outer skin with macroporous interiors. An abrupt increase in the peak intensities specific to the polymer and a simultaneous decrease in the water related peaks in the attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectra exhibited the phenomenon of phase separation, whereas peaks of proton nuclear magnetic resonance (1HNMR) revealed hydrogen bonding and electrolytic complexation between the monomers. Biocompatibility is the hallmark for any drug carrier and was evaluated by both in vitro and in vivo testing. Administration of the prepared hydrogels to rat models did not cause any significant affect on the vital organs.

Synthesis of Biotinylated pH-Sensitive Glycopolymer with Different Architectures

Two pH-sensitive Glycopolymers with the same components but with different construction tailored biotin functionalities were developed for controlled release of bortezomib (BTZ).The initiator brominate biotin and glyco-monomer were synthesized precedently to produce the block-and random-biotinylated poly (2-Gluconamidoethyl methacrylate)-poly (2-Diethylaminoethyl methacrylate) (block/random Biotin-PGAMA-PDEA) via atom transfer radical polymerization (ATRP). The construction and composition of compounds and polymers were characterized by 1H NMR Spectroscopy. The block copolymer self-assembled into micelle according to the pH-response ability of the copolymer while the random one did not under certain conditions.

Study the role of poly(diethyl aminoethyl methacrylate) as a modified and grafted shell for TiO2 and ZnO nanoparticles, application in flutamide delivery

Diethyl aminoethyl methacrylate (DEAEMA) was polymerized and cross-linked simultaneously with direct atom transfer radical polymerization (ATRP) of the modified TiO2 and ZnO nanoparticles (CH3CHBrCO@ZnO and CH3CHBrCO@TiO2). In the other view, the surface of the TiO2 and ZnO nanoparticles were modified and grafted with poly(DEAEMA). During the ATRP of DEAEMA with CH3CHBrCO@ZnO and CH3CHBrCO@TiO2 nanoparticles, different ratios of flutamide, as an anti-cancer drug and the case for the simulation, were added to the polymerization matrix. Meanwhile, the polymer nanocomposites (PNCs) were obtained as a delivering system. Then, the different PNCs were characterized by transmission electron microscopy, Fourier transform infrared spectroscopy, thermogravimetry, and electrochemical investigations. In this regards, electrochemical investigations reveled the fact that the developed delivering systems have the drug release rates of 31.0 over 1560min and 22.8 in 1200min for the flutamide-loaded PDEAEMA-CH3CHBrCO@TiO2 and flutamide-loaded PDEAEMA-CH3CHBrCO@ZnO, respectively. Also, according to the TEM images, the synthesized delivering systems based on CH3CHBrCO@TiO2 shows the bowl-like arrangements, which likely support the obtained electrochemical and high performance liquid chromatography results. Finally, our study shows that the view of the modifying and grafting of TiO2 and ZnO nanoparticles by poly(DEAEMA) confirmed the great success for the introduced simulated drug delivery system than the view of the TiO2 and ZnO, as modifiers for poly(DEAEMA).