Zwitterionic Molecules Research Articles

The role of π-linkers and electron acceptors in tuning the nonlinear optical properties of BODIPY-based zwitterionic molecules.

Intramolecular charge transfer process can play a key role in developing strong nonlinear optical (NLO) response in a molecule for technological application. Herein, two series of boron dipyrromethene (BODIPY)-based push–pull systems have been designed with zwitterionic donor–acceptor groups, and their NLO properties have been evaluated using a density functional theory-based approach. Different π-conjugated linkers and electron acceptor groups were used to understand their roles in tuning the NLO properties. The molecules were analyzed through HOMO–LUMO gaps, frontier molecular orbitals, polarizabilities, hyperpolarizabilities, Δr indices, transition dipole moment densities, ionization potentials, electron affinities and reorganization energies for holes and electrons. These observations correlated well with the computed absorption spectra of the molecules. It is found that with the introduction of different π-linkers in the molecule, planarity is maintained and the HOMO–LUMO gap is systematically decreased, which leads to a large NLO response. It was noted that the electronic absorption wavelength maxima were found in the near-infrared region (934–1650 nm). The results show that compared to the pyridinium acceptor group, the imidazolium acceptor group in the BODIPY systems amplifies the NLO response to a larger extent. It is also observed that the BODIPY-based dye with an imidazolium acceptor and thienothiophene π-linker shows the highest first hyperpolarizability value of 3194 × 10−30 esu. Furthermore, the charge transfer occurs in the z-direction, as the z-component of the first hyperpolarizability is the dominant factor in this system. Here, the designed molecules show a characteristic reorganisation energy value, which is a deciding factor in the rate of hole/electron transport for favourable intermolecular coupling. As a whole, this theoretical work highlights that π-conjugated linkers and electron acceptor groups can be used judiciously to design new molecular systems for optoelectronic applications.

Quinonoid Zwitterion: An Amphiphilic Cathode Interlayer with Initial Thickness-Insensitive and Self-Organizing Properties for Inverted Polymer Solar Cells.

Orthogonal solvent processability is generally considered as one of the key requirements for an efficient interfacial material. Here, we showed that in inverted polymer solar cells (PSCs), solvent orthogonality is not required for an effective and reliable cathode interlayer. A quinonoid zwitterionic molecule with amphiphilic property [dissolved in both methanol and o-dichlorobenzene (o-DCB)] named ZW-Bu was first applied as the cathode interlayer in inverted PSCs. For three different photoactive systems, the devices with ZW-Bu cathode buffer layers (CBLs) exhibited better performance than those with commonly used ZnO CBLs. Most importantly, the device efficiency was fairly insensitive to the initial thickness of ZW-Bu. In addition, due to the high surface energy of the ZW-Bu film, it was successfully used as a self-organized CBL in poly(3-hexylthiophene) (P3HT):[6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) systems, yielding a desirable efficiency compared to the PSCs fabricated via the layer-by-layer deposition method.

Effect of Zwitterionic Molecules on Ionic Transport under Electric Fields: A Molecular Simulation Study

Zwitterionic molecules can associate with both cations and anions in electrolytes. This ability can be leveraged to manipulate ionic associations and transport if we understand the related mechanisms. We investigate the effect of zwitterionic molecules on ionic associations and transport in the electrolytes composed of 1:1 Li salts (anions: [TFSI]− and [BETI]−) and zwitterionic molecules containing imidazolium and sulfonate groups under 0–1.1 V/nm electric fields using molecular dynamics simulations. The ionic associations and transport in the electrolytes are analyzed using Li+-zwitterion and Li+-anion radial distribution functions, association number and lifetimes, and diffusion coefficients of Li+, anion, and zwitterionic molecules. The simulation results show a close correlation between the ionic association and transport. Small Li+ ions and large anions diffuse at the same level with the presence of zwitterionic molecules. The electric field must be stronger than a threshold to influence diffusion an...

Multicharge zwitterionic molecules: Hydration, kosmotropicity and anti-fouling potential

This manuscript presents a comparative study of the physico-chemical behaviour of sulfobetaine-type single and double zwitterions and zwitterionic salts, and structurally similar mono- and di-cationic tetraalkylammonium salts in aqueous solutions. The study includes experimental determination of the density and viscosity of highly diluted aqueous solutions with derivation of the Jones-Dole viscosity B-coefficient, partial molal volumes at infinite dilution, and hydration numbers. The study also examines the effects of addition of the salts on the surface tension of cationic and anionic surfactants, upper critical solution temperature of a non-ionic surfactant, solubility of amino acids, and stability of a protein. The experimental investigation was performed taking a broad bottom-up approach with the aim to elucidate the effect of molecular architecture and charge (two versus four) on the degree of surface hydration of a molecule, kosmotropicity, and interactions with charged and hydrophilic/hydrophobic surfaces - all-important characteristics which define ability of a functional group to resist protein attachment. The novel multicharged zwitterionic materials have exhibited superior qualities, thus paving the way to development of a new platform in design of hydrophilic and anti-fouling surfaces by employing the four-charge bearing molecular motifs.

Peripherally substituted soluble nickel phthalocyanines: Synthesis, characterization, aggregation behavior and antioxidant properties

Tetra-zwitterionic-substituted nickel(II) phthalocyanine derivatives were newly synthesized starting from nonionic 2(3),9(10),16(17),23(24)-tetrakis-[2-([Formula: see text]-((3-dimethylamino)propyl)carbamate)oxyethyl)phthalocyaninato nickel (II). The novel compounds have been characterized by a combination of UV-vis, FT-IR and mass spectroscopies and elemental analysis. The critical micelle concentrations of the prepared compounds were measured, and the antioxidant activities were analyzed with radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and with 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS). The zwitterionic molecules showed aggregated spectra in the UV-vis region, and they might be good surfactant candidates for the detergent industry with their appropriate critical micelle concentration (CMC) properties in water. The compounds exhibited ABTS radical scavenging activity and thus they have antioxidant activity.

A novel and simple route for bromide replacement in pyrazolyl-pyridazine ReI tricarbonyl complexes leads to a zwitterion stabilized by hydrogen bonding

The reaction of 3-pyrazolyl-pyridazine-6-carboxylic (LCOOH) and 3-3,5-dimethylpyrazolyl-pyridazine-6-carboxylic (Me2LCOOH) acids with bromotricarbonyl-tetrahydrofuran-rhenium(I) dimer in DMF solution followed by water addition, leads simple and cleanly to the rhenium(I) de-halided fac-aquo-tricarbonyl-complexes [(LCOO)(H2O)Re(CO)3] and [(Me2LCOO)(H2O)Re(CO)3] respectively, without the requirement of using a silver salt. It was possible to isolate each compound with the pyrazolyl-pyridazine carboxylate ligand showing the chelating N,O-mode ([(N,O-LCOO)(H2O)Re(CO)3] and [(N,O-Me2LCOO)(H2O)Re(CO)3]). For the [(Me2LCOO)(H2O)Re(CO)3] compound, it was also possible to isolate the ligand as a chelating diimine ([(N,N-Me2LCOO)(H2O)Re(CO)3]). This last coordination mode leads to a zwitterionic but neutral molecule, with a naked carboxylate as negative extreme and the metal with positive charge in the other side. The negative formal charge in the carboxylate is stabilized within the crystal structure of [(N,N-Me2LCOO)(H2O)Re(CO)3] through hydrogen bonds to water molecules from neighboring molecules dimers, with donor acceptor distances (D···A) of 2.566(10)Å and 2.645(6)Å. DFT optimization of the zwitterion in the gas phase suggests that its geometry would twist to allow the formation of an intramolecular hydrogen bond between carboxylate and the coordinated water molecule. This shows the key stabilizing effect of the hydrogen bond for the negative charge of the carboxylate into the zwitterion crystal structure.

Unraveling the Origin of the Apparent Charge of Zwitterionic Lipid Layers.

The structure of water molecules in contact with zwitterionic lipid molecules is of great biological relevance, because biological membranes are largely composed of such lipids. The interaction of the interfacial water molecules with the amphiphilic lipid molecules drives the formation of membranes and greatly influences various processes at the membrane surface, as the field that arises from the aligned interfacial water molecules masks the charges of the lipid headgroups from the approaching metabolites. To increase our understanding of the influence of water molecules on biological processes we study their structure at the interface using sum-frequency generation spectroscopy and molecular dynamics simulations. Interestingly, we find that water molecules at zwitterionic lipid molecules are mainly oriented by the field arising between the two oppositely charged molecular moieties within the lipid headgroups.

Dimethyl Sulfoxide-Free Cryopreservation of Chondrocytes Based on Zwitterionic Molecule and Polymers.

Cartilage tissue engineering highly relies on the ability to store and transport chondrocytes in order to be clinically successful. Cryopreservation is a most reliable technology for chondrocyte storage, but it suffers from the intrinsic toxicity of current state-of-the-art cryoprotectant, dimethyl sulfoxide (DMSO). In this work, we used the first fully zwitterionic compound-based approach for effective chondrocyte cryopreservation. A zwitterionic molecule combined with zwitterionic polymers could balance intra/extracellular osmotic stress and prevent ice formation, which were the keys of successful cryopreservation. Moreover, this zwitterionic combination showed noncytotoxicity due to its high biocompatibility, superior to cytotoxic DMSO. On the basis of these performances, chondrocytes could be well cryopreserved (∼90% post-thaw survival efficiency) for a long time without any addition of DMSO, and the recovered cells could maintain their normal functionalities. In view of the association between polymer molecular weight and cryopreservation efficacy, further mechanism of cryoprotection provided by zwitterionic molecule/polymer was proposed. This work opens a new window of opportunity for DMSO-free cryopreservation using biocompatible zwitterionic materials.

Antileishmanial and cytotoxic activities of ionic surfactants compared to those of miltefosine

Using the electron paramagnetic resonance (EPR) of spin-labeled stearic acid and a spin label chemically attached to the membrane proteins, the interaction of miltefosine (MIL) and the ionic surfactants sodium dodecyl sulfate (SDS, anionic), cetyltrimethylammonium chloride (CTAC, cationic) and N-hexadecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (HPS, zwitterionic) with the plasma membrane of Leishmania (L.) amazonensis promastigotes was studied. The spin-label EPR data indicated that the four compounds studied have the ability to increase the molecular dynamics of membrane proteins to a large extent. Compared to the other compounds, SDS produced the smallest increases in dynamics and demonstrated the lowest antileishmanial activity and cytotoxicity to J774.A1 macrophages. The activities of the other three compounds were not different from each other, but CTAC had a stronger activity against L. amazonensis promastigotes at higher cellular concentrations (> 1 × 109 cells/mL) and was the most effective against L. amazonensis-infected macrophages. However, CTAC was also the most cytotoxic to macrophages. By measuring the IC50/CC50 values for assays of different cell concentrations, we estimated the membrane-water partition coefficient (KM/W) as well as the concentrations in the membrane (cm50) and aqueous phase (cw50) of the compounds at their IC50/CC50. Compared to the other compounds, SDS showed the lowest value of KM/W and the highest value of cm50. In all experiments in this study, the data for the zwitterionic molecules HPS and MIL were not significantly different.

Finely Tuned Cores in Star‐Shaped Zwitterionic Molecules for Interface Engineering of High‐Performance Polymer Solar Cells

Developing stable and cheap organic cathode interlayers (OCIs; to replace metal cathode and expensive OCIs for enhancing the device stability and reducing the manufacturing cost) is an important topic for commercial applications of polymer solar cells (PSCs). Herein, four one‐step synthesized organic electron transport layers (G‐Series electron‐transport layers [ETLs]) with a novel star‐shaped molecular structure consisting of a series of different heteroatom atoms as cores and sulfobetaine ions as a terminal substituent are explored. The energy levels can be finely tuned by applying different heteroatom atoms as cores. With the conventional device structure with poly[[2,6′‐4,8‐di(5‐ethylhexylthienyl)benzo[1,2‐b;3,3‐b]dithiophene][3‐fluoro‐2[(2‐ethylhexyl) carbonyl]thieno[3,4‐b]thiophenediyl]] (PTB7‐Th) as a donor and [6,6]‐phenyl‐C71‐butyric‐acid‐methyl‐ester (PC70BM) as an acceptor, the G‐C2‐based devices exhibit a power conversion efficiency (PCE) of 8.90% with Al as the top electrode, much higher than that of the corresponding Ca/Al‐based device (7.43%). Furthermore, G‐Series‐based solar cells are also more stable than the reference device based on Ca. In addition, these easy‐to‐get ETLs can be widely suitable for other PSCs based on different active layer systems. This work not only shows a new strategy for fine‐tuning energy levels of nonconjugated zwitterionic molecules but also provides simple and stable ETLs for low‐cost and high‐performance PSCs.

Surfactant Charge Modulates Structure and Stability of Lipase-Embedded Monolayers at Marine-Relevant Aerosol Surfaces.

Lipases, as well as other enzymes, are present and active within the sea surface microlayer (SSML). Upon bubble bursting, lipases partition into sea spray aerosol (SSA) along with surface-active molecules such as lipids. Lipases are likely to be embedded in the lipid monolayer at the SSA surface and thus have the potential to influence SSA interfacial structure and chemistry. Elucidating the structure of the lipid monolayer at SSA interfaces and how this structure is altered upon interaction with a protein system like lipase is of interest, given the importance of how aerosols interact with sunlight, influence cloud formation, and provide surfaces for chemical reactions. Herein, we report an integrated experimental and computational study of Burkholderia cepacia lipase (BCL) embedded in a lipid monolayer and highlight the important role of electrostatic, rather than hydrophobic, interactions as a driver for monolayer stability. Specifically, we combine Langmuir film experiments and molecular dynamics (MD) simulations to examine the detailed interactions between the zwitterionic dipalmitoylphosphatidylcholine (DPPC) monolayer and BCL. Upon insertion of BCL from the underlying subphase into the lipid monolayer, it is shown that BCL permeates and largely disorders the monolayer while strongly interacting with zwitterionic DPPC molecules, as experimentally observed by Langmuir adsorption curves and infrared reflectance absorbance spectroscopy. Explicitly solvated, all-atom MD is then used to provide insights into inter- and intramolecular interactions that drive these observations, with specific attention to the formation of salt bridges or ionic-bonding interactions. We show that after insertion into the DPPC monolayer, lipase is maintained at high surface pressures and in large BCL concentrations by forming a salt-bridge-stabilized lipase-DPPC complex. In comparison, when embedded in an anionic monolayer at low surface pressures, BCL preferentially forms intramolecular salt bridges, reducing its total favorable interactions with the surfactant and partitioning out of the monolayer shortly after injection. Overall, this study shows that the structure and dynamics of lipase-embedded SSA surfaces vary based on surface charge and pressure and that these variations have the potential to differentially modulate the properties of marine aerosols.

Polyelectrolyte vs Polyampholyte Behavior of Composite Chitosan/Gelatin Films.

Composite films of proteins and polysaccharides have a broad range of biomedical and food packaging applications, in which they are frequently exposed to fluid environments with varying ionic strengths. In the present work, we report the behavior of biopolymer films derived from chitosan (Ch), gelatin (GEL), and Ch/GEL mixture in salt solutions with varying concentrations and ion charges. The swelling and dissolution of the Ch films reduced with increasing salt concentration due to the polyelectrolyte behavior of this biopolymer, while the GEL films displayed a polyampholyte behavior, in which film swelling and dissolution were enhanced in salt solutions. Composite Ch/GEL films followed the behavior of GEL. The release of small ionic and zwitter-ionic molecules from the films was enhanced in ionic solutions due to the screened attraction between these molecules and the polymer matrix. These results provide insight into the behavior of protein/polysaccharide films in varying ionic environments, thus enabling enhanced design of biomaterials for a broad range of applications.

Structural behavior of phenylalanine–tryptophan peptide nanotubes at anhydrous conditions: a theoretical investigation

We study the structural behavior of peptide nanotubes formed by zwitterionic molecules under water-unfilled condition. The study is conducted via density functional-based tight-binding molecular dynamics simulations. During the simulation, each molecule that forms the peptide subunit keeps the zwitterionic structure stable without the presence of an external factor even at considerable temperatures. With our results, we can thus speculate on the temperature range the system will work without undergoing the degradation process and thus be safely used in possible applications.

Two metal-carboxylate-azide coordination networks derived from 1,4-bis(3-carboxylatopyridinium-1-methylene)benzene: Synthesis, structure and properties

Betaine-type ligands are an attractive class of zwitterionic molecule, which have attracted considerable interest because they may not only keep the versatile coordination modes of carboxylate groups but also provide a new way to adjust the charge distribution of coordination polymers by cationic pyridinium groups. In this article, two coordination polymers composed of betaine-type ligand and azide anions, {[Co2(L)(N3)4]n·2H2O}n (1), [Zn(L)(N3)2]n (2) (H2L·2Cl = 1,4-bis(3-carboxylatopyridinium-1-methylene)benzene dichloride), have been synthesized. These compounds were characterized by IR spectroscopy, elemental analysis, thermogravimetric analysis and single-crystal X-ray diffraction. The X-ray diffraction crystal structure analysis reveals that the complex 1 is a twofold interpenetrating three-dimensional framework. The magnetic measure shows that complex 1 exhibits a ferromagnetic behavior at low temperature. Complex 2 displays a one-dimensional chain, which is further extended into a 3D framework through hydrogen bond and van der Waals interactions. The luminescence data of complex 2 shows the emission of a yellow luminescence. Remarkably, complexes 1 and 2 both exhibit a good photocatalytic activity for degradation of rhodamine B (RhB) under the simulated sunlight irradiation.

A computational avenue towards understanding and design of zwitterionic anti-biofouling materials

ABSTRACTThis review introduces a computational avenue towards understanding and design of zwitterionic anti-biofouling materials. Biofouling means nonspecific adsorption of proteins, cells, and bacteria on materials and devices. It can sabotage materials functions and bring detrimental effects on the biological systems. Various anti-biofouling materials have been developed and zwitterionic materials emerge as promising candidates recently. The design and understanding of zwitterionic anti-biofouling materials rely on the answers of three fundamental questions: (a) what molecular properties govern the anti-biofouling performance of materials, (b) what is the structure–property-anti-biofouling relationship for materials, and (c) how to identify anti-biofouling materials based on the revealed mechanisms? This paper discussed the efforts of answering the three questions using molecular simulations. We first discuss the simulations that revealed the importance of hydration in the anti-biofouling performance of materials and why this mechanism leads to the discovery of zwitterionic anti-biofouling materials, then the simulations that investigated structure-properties-performance relationships of zwitterionic anti-biofouling materials, and the development of computational approaches that can identify zwitterionic anti-biofouling molecules. Finally, we discuss the opportunities in understanding and design of anti-biofouling biomaterials using computer simulations.

Electron beam irradiation of polyvinylidene fluoride/polyvinylpyrrolidone ultrafiltration membrane in presence of zwitterions molecules evaluation of filtration performances

In this research, the commercial PVDF/PVP membrane was irradiated at 10 and 100 kGy with electron beam (EB) to improve its fouling resistance capacity. Membrane irradiation was conducted in the presence of zwitterionic molecules (L-Cysteine, Phosphocholine) and with 2-(Dimethylamino)ethyl methacrylate). The main goal was to investigate the impact of irradiation in presence of zwitterions on the modification route of PVP within the polymer blend and to relate it to filtration performances. Globally, EB irradiation enhanced the membrane’s filtration performance but this improvement cannot be sustained after several filtration cycles. Membranes irradiated with the lower absorbed dose (10 kGy) displayed higher permeate flux and lower cake resistance than membranes irradiated with the 100 kGy dose. The best sustainable anti-fouling capacity was observed for the membrane irradiated with 10 kGy in the presence of L-Cysteine. Membrane characterization showed that the membrane surface was modified by EB irradiation, with features such as smoother surface, modification of PVP and increased amount of crosslinking emphasizing the potential formation of PVP hydrogels. Despite obvious changes observed on membrane surface depending on the chosen compounds used for irradiation, membranes’ analyses failed to identify sulphur, phosphorous grafted moieties. From this study, it is confirmed that membranes EB irradiation in presence of zwitterionic molecules is a promising technique to modify the PVDF/PVP blended polymer.

Measurements of Lipid Vesicle Charge in Solutions of Zwitterions

Binding of water soluble molecules to biological membranes is an important step in cellular signaling. We investigate the physical nature of such interactions using model lipid membranes. In particular, neutral lipid vesicles can acquire electrostatic charge by binding free ions from solution. Interestingly, they can also acquire charge from zwitterionic molecules that have dipole character. Examples are amino acids, pH buffers such as MOPS and HEPES, as well as adenosine triphosphate (ATP) and its hydrolysis products. By using x-ray scattering we have determined that the presence of zwitterions affects the lattice spacing of multilamellar phosphatidylcholine vesicles in a manner that is consistent with the presence of electrostatic repulsion between neighboring membranes. The remaining question is how to quantify the surface electric charge and, equally interesting, how to determine the sign of the charge conferred by zwitterions on membranes. Here we report measurements by dynamic light scattering (DLS) and by diffusion of phosphatidylcholine lipid vesicles in constant electric fields for a class of zwitterionic solutes. We find that the measured electrostatic charging can qualitatively account for the swelling of multilamellar structures and is consistent with NMR measurements of molecular binding. However, the results also show that more theoretical work is needed for quantitative analysis of electrostatic and van der Waals forces in these systems and for explanation of zwitterion affinities to biological membranes.

Interaction Mechanisms of Zwitterions with Opposite Dipoles in Aqueous Solutions.

Zwitterionic groups have been widely used in antibiofouling surfaces to resist nonspecific adsorption of proteins and other biomolecules. The interactions among zwitterionic groups have attracted considerable attention in bioengineering, whereas the understanding of their nanomechanical mechanism still remains limited. In this work, the interaction mechanisms between two zwitterionic groups with opposite dipoles, i.e., phosphorylcholine (PC) and sulfobetaine (SB), have been investigated via direct force measurements using an atomic force microscope (AFM) and dynamic adsorption tests using the quartz crystal microbalance with dissipation monitoring technique (QCM-D) in aqueous solutions. The AFM force measurements show that the adhesive forces between contacted zwitterionic surfaces during separation in both symmetric and asymmetric configurations were close, mainly due to the enforced alignment of opposing dipole pairs via complementary orientations under confinement. The solution salinity and pH had almost negligible influence on the adhesion measured during surface separation. The QCM-D adsorption tests of PC-headed lipid on PC and SB surfaces showed some degree of adsorption of lipid molecules on the SB surface, whereas not on the PC surface. The different adsorption behaviors indicate that because the outermost negatively charged sulfonic group on the SB faced the aqueous solution, this configuration could facilitate it to form an attractive electrostatic interaction with the PC head of lipid molecules in the solution. This work shows that in addition to hydration and steric interactions, the zwitterionic dipole-induced interactions play an important role in the adhesion and antifouling behaviors of the zwitterionic molecules and surfaces. The improved fundamental understanding provides useful insights into the development of new functional materials and coatings with antifouling applications.

Specific and universal interactions in Benzo-[f]-Quinolinium Acetyl-Benzoyl Methylid (BQABM) solutions; excited state dipole moment of BQABM.

The zwitterionic molecule Benzo-[f]-Quinolinium Acetyl Benzoyl Methylid (BQABM) is studied in this paper from quantum mechanical and solvatochromic point of view. The nature and contribution of each type of intermolecular interaction to the spectral shifts in different solvents were estimated based on solvatochromic analyze of BQABM visible absorption band. The correlation coefficients for the dependence of the wavenumber in the maximum of BQABM visible band vs. the solvent parameters were computed by Linear Energy Relationships Simulation (LERS). The optimized geometry of BQABM and some physical and chemical parameters for isolated molecule in its ground electronic state were obtained with Spartan'14 programs. The results obtained in quantum mechanical analysis and also LERS correlation coefficients were used to determine the excited state dipole moment of BQABM by a Variational method in McRae and Kawschi hypothesis that the molecular polarizability does not change in the visible absorption process. An increase in the BQABM electric dipole moment by excitation resulted in our study.

Synthesis and characterization of Au nanoshells with a magnetic core and betaine derivatives

The article describes preparation, characterization and further modification of hybrid magnetic particles (Au nanoshells with a magnetic core (MPs@silica@Au)) by zwitterionic molecules bearing diazonium functional groups. Such hybrid magnetic particles modified by zwitterionic molecules exhibit the following features:•Responsiveness towards external magnetic field applicable for various enrichment strategies due to magnetic core;•Golden outer layer exhibiting free surface plasmons could be used for grafting of zwitterionic molecules via diazonium functionality;•Zwitterionic interface on such particles provides resistivity towards non-specific protein binding; and at the same time such interface was applied for immobilization of antibodies against prostate specific antigen (PSA) applied for selective enrichment of PSA from serum samples with subsequent electrochemical assays.The approach presented here using hybrid magnetic particles can be easily applied for immobilization of antibodies using a highly robust surface patterning protocols i.e. by formation of a self-assembled monolayer with delivery of functional groups on the outer surface of magnetic particles. Hybrid magnetic particles with immobilized antibodies are applied for highly efficient and quick separation of protein of interest i.e. PSA from complex sample. Finally, hybrid magnetic particles with “fished-out” protein molecules could be incubated with lectins to form a sandwich configuration for glycoprofiling of PSA.