Multiple Amino Research Articles

Reconstructed chitosan with alkylamine for enhanced gene delivery by promoting endosomal escape

Poor buffering capacity of chitosan (CS) results in insufficient intracellular gene release which poses the major barrier in gene delivery. Herein, we reconstructed pristine CS with propylamine (PA), (diethylamino) propylamine (DEAPA), and N, N-dimethyl- dipropylenetriamine (DMAMAPA) to obtain a series of alkylamine-chitosan (AA-CS). The introduction of multiple amino groups with rational ratios functionally enhance the buffering capacity of AA-CS, among which DMAPAPA-CS showed buffering capacity of 1.58 times that of chitosan. The reconstructed AA-CS functionally enhance the ability of gene binding and endosomal escape. It was observed that the DMAPAPA-CS/pDNA complexes exhibit a notable gene delivery efficiency, which promotes the functionalization of loaded pDNA. Importantly, the in vivo delivery assay reveals that the deep penetration issue can be resolved using DMAPAPA-CS gene delivery vector. Finally, the DMAPAPA-CS is applied to deliver the therapeutic p53 gene in A549 bearing mice, showing efficient therapeutic potential for cancer.

Differentiation of Deprotonated Acyl-, N-, and O-Glucuronide Drug Metabolites by Using Tandem Mass Spectrometry Based on Gas-Phase Ion-Molecule Reactions Followed by Collision-Activated Dissociation.

Glucuronidation, a common phase II biotransformation reaction, is one of the major in vitro and in vivo metabolism pathways of xenobiotics. In this process, glucuronic acid is conjugated to a drug or a drug metabolite via a carboxylic acid, a hydroxy, or an amino group to form acyl-, O-, and/or N-glucuronide metabolites, respectively. This process is traditionally thought to be a detoxification pathway. However, some acyl-glucuronides react with biomolecules in vivo, which may result in immune-mediated idiosyncratic drug toxicity (IDT). In order to avoid this, one may attempt in early drug discovery to modify the lead compounds in such a manner that they then have a lower probability of forming reactive acyl-glucuronide metabolites. Because most drugs or drug candidates bear multiple functionalities, e.g., hydroxy, amino, and carboxylic acid groups, glucuronidation can occur at any of those. However, differentiation of isomeric acyl-, N-, and O-glucuronide derivatives of drugs is challenging. In this study, gas-phase ion-molecule reactions between deprotonated glucuronide metabolites and BF3 followed by collision-activated dissociation (CAD) in a linear quadrupole ion trap mass spectrometer were demonstrated to enable the differentiation of acyl-, N-, and O-glucuronides. Only deprotonated N-glucuronides and deprotonated, migrated acyl-glucuronides form the two diagnostic product ions: a BF3 adduct that has lost two HF molecules, [M - H + BF3 - 2HF]-, and an adduct formed with two BF3 molecules that has lost three HF molecules, [M - H + 2BF3 - 3HF]-. These product ions were not observed for deprotonated O-glucuronides and unmigrated, deprotonated acyl-glucuronides. Upon CAD of the [M - H + 2BF3 - 3HF]- product ion, a diagnostic fragment ion is formed via the loss of 2-fluoro-1,3,2-dioxaborale (MW of 88 Da) only in the case of deprotonated, migrated acyl-glucuronides. Therefore, this method can be used to unambiguously differentiate acyl-, N-, and O-glucuronides. Further, coupling this methodology with HPLC enables the differentiation of unmigrated 1-β-acyl-glucuronides from the isomeric acyl-glucuronides formed upon acyl migration. Quantum chemical calculations at the M06-2X/6-311++G(d,p) level of theory were employed to probe the mechanisms of the reactions of interest.

Removal of biogenic amines from hydroalcoholic solutions by functionalized silica

The structure and the cation-exchange functional groups of hybrid silica materials were evaluated for the effective detoxification of hydroalcoholic solutions containing eight toxic biogenic amines (BA) usually found in fermented beverages. Results show the effectiveness of the removal is related to the number of amino functions in the extracted molecule, retention by the solid being more effective in the case of multiple amino groups, since retention is stabilized through interaction with the material surface at several points. BA with one amino function (isoamylamine, tyramine, β-phenylethylamine), in general, showed a weak retention by the solids. For BA with more than two amine groups (spermine, spermidine), the removal rate was close to 100% for all studied materials. For histamine, cadaverine and putrescine, the removal percentages were higher with a lamellar structured sulfonic acid functionalized material and with bifunctional materials (SBA-15 type and macroporous) containing sulfonic/phosphonic acid groups obtained by co-condensation sol-gel route.

Identification of charged amino acids required for nuclear localization of human L1 ORF1 protein

BackgroundLong Interspersed Element 1 (LINE-1) is a retrotransposon that is present in 500,000 copies in the human genome. Along with Alu and SVA elements, these three retrotransposons account for more than a third of the human genome sequence. These mobile elements are able to copy themselves within the genome via an RNA intermediate, a process that can promote genome instability. LINE-1 encodes two proteins, ORF1p and ORF2p. Association of ORF1p, ORF2p and a full-length L1 mRNA in a ribonucleoprotein (RNP) particle, L1 RNP, is required for L1 retrotransposition. Previous studies have suggested that fusion of a tag to L1 proteins can interfere with L1 retrotransposition.ResultsUsing antibodies detecting untagged human ORF1p, western blot analysis and manipulation of ORF1 sequence and length, we have identified a set of charged amino acids in the C-terminal region of ORF1p that are important in determining its subcellular localization. Mutation of 7 non-identical lysine residues is sufficient to make the resulting ORF1p to be predominantly cytoplasmic, demonstrating intrinsic redundancy of this requirement. These residues are also necessary for ORF1p to retain its association with KPNA2 nuclear pore protein. We demonstrate that this interaction is significantly reduced by RNase treatment. Using co-IP, we have also determined that human ORF1p associates with all members of the KPNA subfamily.ConclusionsThe prediction of NLS sequences suggested that specific sequences within ORF1p could be responsible for its subcellular localization by interacting with nuclear binding proteins. We have found that multiple charged amino acids in the C-terminus of ORF1p are involved in ORF1 subcellular localization and interaction with KPNA2 nuclear pore protein. Our data demonstrate that different amino acids can be mutated to have the same phenotypic effect on ORF1p subcellular localization, demonstrating that the net number of charged residues or protein structure, rather than their specific location, is important for the ORF1p nuclear localization. We also identified that human ORF1p interacts with all members of the KPNA family of proteins and that multiple KPNA family genes are expressed in human cell lines.

Atmospheric CO2 captured by biogenic polyamines is transferred as a possible substrate to Rubisco for the carboxylation reaction

Biogenic polyamines are involved in a wide range of plant cellular processes, including cell division, morphogenesis and stress responses. However, the exact roles of biogenic polyamines are not well understood. We recently reported that biogenic polyamines that have multiple amino groups can react with CO2 and accelerate calcium carbonate formation in seawater. The ability of biogenic polyamines to capture atmospheric CO2 prompted us to examine their roles in photosynthesis. Here, we demonstrated that atmospheric CO2 captured by biogenic polyamines is a candidate substrate for the carboxylation reaction of ribulose 1,5-bisphosphate carboxylase/oxygenase (Rubisco), which is an enzyme involved in the first major step of carbon fixation during photosynthesis, and that biogenic polyamines can accelerate the carboxylation reaction of this enzyme because of their specific affinity for CO2. Moreover, the results of our nuclear magnetic resonance (NMR) analysis showed that putrescine, which is the most common biogenic polyamine, reacts with atmospheric CO2 and promotes the formation of carbamate derivatives and bicarbonate in aqueous environments. A sufficient amount of CO2 is well known to be produced by carbonic anhydrase from bicarbonate in vivo. The present study indicates that CO2 would be also produced by the equilibrium reaction from carbonate produced by biogenic polyamines and would be used as a substrate of Rubisco, too. Our results may suggest a new photosynthetic research strategy that involves CO2-concentrating mechanisms and also possibly constitutes a potential tool for reducing atmospheric CO2 levels and, consequently, global warming.

Plasmonic enhancement in lateral flow sensors for improved sensing of E. coli O157:H7

We propose a plasmonic enhanced lateral flow sensor (pLFS) concept with an enhanced colorimetric signal by utilizing liposome encapsulating reagent to trigger the aggregation of gold nanoparticles (GNPs). Our signal enhancement strategy incorporates the simplicity of lateral flow immunoassays (LFIA) utilizing plasmonic enhancement. The conceptualized hybrid pLFS for onsite rapid detection of pathogens in low numbers in a user friendly format requiring simple steps is the first step in the translation of plasmonic enhancement sensing to a practical regime. The pLFS was carried out with a biotinylated liposome label ruptured to release branched polyethylenimine (BPEI) to trigger the aggregation of GNPs for colorimetric signal generation. BPEI has multiple amino groups and more positive charges in PBS buffer, therefore few of the BPEI groups could induce the aggregation of GNPs, resulting in an enhanced colorimetric signal to detect E. coli O157:H7. Compared with the reported conventional LFIA, the proposed pLFS demonstrated more than 1000-fold improvement in sensitivity. The pLFS could detect as low as 100 CFU/ml of E. coli O157:H7 in buffer and 600 CFU/ml E. coli O157:H7 in liquid food systems.

Development of a quadruple qRT-PCR assay for simultaneous identification of highly and low pathogenic H7N9 avian influenza viruses and characterization against oseltamivir resistance

BackgroundDuring the fifth wave of human H7N9 infections, a novel highly pathogenic (HP) H7N9 variant emerged with an insertion of multiple basic amino acids in the HA cleavage site. Moreover, a neuraminidase inhibitor (NAI) resistance (R292K in NA) mutation was found in H7N9 isolates from humans, poultry and the environment. In this study, we set out to develop and validate a multiplex quantitative reverse transcript polymerase chain reaction (qRT-PCR) to simultaneously detect the presence of H7N9 and further identify the HP and NAI-resistance mutations.MethodsA quadruple qRT-PCR to simultaneously detect the presence of H7N9 and further identify the HP and NAI-resistance mutations was designed based on the analyses of the HA and NA genes of H7N9. This assay was further tested for specificity and sensitivity, and validated using clinical samples.ResultsThe assay was highly specific and able to detect low pathogenic (LP)- or HP-H7N9 with/without the NAI-resistance mutation. The detection limit of the assay was determined to be 50 genome-equivalent copies and 2.8 × 10− 3 50% tissue culture infectious doses (TCID50) of live H7N9 per reaction. Clinical validation was confirmed by commercial kits and Sanger sequencing with ten clinical samples.ConclusionsWe developed and validated a rapid, single-reaction, one-step, quadruple real-time qRT-PCR to simultaneously detect the presence of H7N9 and further identify the HP- and NAI-resistance strains with excellent performance in specificity and sensitivity. This assay could be used to monitor the evolution of H7N9 viruses in the laboratory, field and the clinic for early-warning and the prevention of H7N9 infections.

Polyamines and their possible mechanisms involved in plant physiological processes and elicitation of secondary metabolites

Polyamines are amine-containing, low molecular weight, and ubiquitous polycationic molecules present in almost all cells and free-living microbes, which are formed by aliphatic hydrocarbons replaced with multiple amino groups. They have been considered as a new kind of plant biostimulant, which play vital roles in diverse plant growth and developmental processes, and environmental stress responses. However, little is known regarding the effects of polyamines specifically on the elicitation of bioactive compounds in medicinal plant production. Therefore, in this review, we attempt to cover these gaps of information. Supply of polyamines, whether by exogenous application or through genetic engineering, could positively affect medicinal plant growth, productivity, and stress tolerance; however, these effects depend on type and dose of polyamine application and plant species. Furthermore, polyamines play as precursor for the several groups of alkaloids (pyrrolizidine, tropane, and quinolizidine alkaloids) and phenolamides, so these bioactive compounds could significantly increase the concentration of the above-mentioned natural products.

Linear self-assembly formation between gold nanoparticles and aminoglycoside antibiotics.

Ribostamycin is a broad-spectrum aminoglycoside antibiotic with a molecular weight of 454.5 g/mol. Under neutral pH conditions, ribostamycin is highly positive charged because it carries multiple amino groups in its structure. Negatively charged citrate ligand capped-gold nanoparticles (AuNPs) have been studied extensively for their interactions with a wide range of biomolecules including proteins, carbohydrates, and small drug compounds. These studies are aimed at developing new therapeutics and diagnostics by exploiting the unique properties of gold nanoparticles. Under this general aim, we studied the interaction between ribostamycin and AuNPs. Using a suite of analytical techniques including dynamic light scattering (DLS), UV-vis absorption spectroscopy, and dark field optical microscope imaging (DFM), we analyzed the mixture products of AuNPs with various sizes and ribostamycin under different concentrations. Our study revealed for the first time that ribostamycin has a tendency to self-assemble into linear oligomers at increased concentrations (above 250-500 μM). Such self-assembled oligomers then interact with negatively charged AuNPs to produce rod-like AuNP assemblies. Similar findings were observed from another structurally related aminoglycoside antibiotic, amikacin. It is technically challenging to detect and characterize oligomer formation of small molecules. It is especially challenging when the interactions that are holding the oligomers are not very strong. Through their interaction with gold nanoparticles that have exceptionally strong light scattering properties, we were able to observe the self-assembling of ribostamycin and amikacin in solution using various spectroscopic and microscopic techniques. This concentration-dependent self-assembling behavior of ribostamycin and amikacin may have direct relevance to the antibiotic effect of ribostamycin, amikacin and other structurally similar antibiotics.

Effects of medical food leucine content in the management of methylmalonic and propionic acidemias.

The current review highlights the varied effects of medical foods high in leucine (Leu) and devoid of valine (Val) and isoleucine (Ile) in the management of methylmalonic acidemia (MMA) and propionic acidemia and cobalamin C (cblC) deficiency, aiming to advance dietary practices. Leu is a key metabolic regulator with a multitude of effects on different organ systems. Recent observational studies have demonstrated that these effects can have unintended consequences in patients with MMA as a result of liberal use of medical foods. The combination of protein restriction and medical food use in MMA and propionic acidemia results in an imbalanced branched-chain amino acid (BCAA) dietary content with a high Leu-to-Val and/or Ile ratio. This leads to decreased plasma levels of Val and Ile and predicts impaired brain uptake of multiple essential amino acids. Decreased transport of methionine (Met) across the blood-brain barrier due to high circulating Leu levels is of particular concern in cblC deficiency in which endogenous Met synthesis is impaired. Investigations into the optimal composition of medical foods for MMA and propionic acidemia, and potential scenarios in which Leu supplementation may be beneficial are needed. Until then, MMA/propionic acidemia medical foods should be used judiciously in the dietary management of these patients and avoided altogether in cblC deficiency.

Antimicrobial Activity of ε-Poly-l-lysine after Forming a Water-Insoluble Complex with an Anionic Surfactant.

ε-Poly-l-lysine (ε-PL) is one of the few homopoly(amino-acid)s occurring in nature. ε-PL, which possesses multiple amino groups, is highly soluble in water, where it forms the antimicrobial polycationic chain (PLn+). Although the high water-solubility is advantageous for the use of ε-PL as a food preservative, it has limited the applicability of ε-PL as a biopolymer plastic. Here, we report on the preparation and availability of a water-insoluble complex formed with PLn+ and an anionic surfactant, bis(2-ethylhexyl) sulfosuccinate (BEHS-, is also commercialized as AOT) anion. The PLn+/BEHS--complex, which is soluble in organic solvents, was successfully used as a coating material for a cellulose acetate membrane to create a water-resistant antimicrobial membrane. In addition, the thermoplastic PLn+/BEHS--complex was able to be uniformly mixed with polypropylene by heating, resulting in materials exhibiting antimicrobial activities.

Genetic characterization of emergent GII.17 norovirus variants from 2013 to 2015 in Nanjing, China.

During the 2014/15 winter season, a newly emergent GII.P17-GII.17 variant overwhelmed currently dominant GII.4 viruses, causing outbreaks of acute gastroenteritis in China and Japan. In Nanjing area, this novel GII.17 variant was first identified in a sporadic case of acute gastroenteritis in July 2013, 18 months ahead of reports from other parts of China. In this study, epidemiological features and genotyping of noroviruses from 2013 to 2015 were depicted. Twenty-eight local GII.17 sequences of capsid N-terminus originating from July 2013 to August 2015 were aligned, among which complete genome of seven strains obtained from two outbreaks and five sporadic cases was extensively characterized. The differences of local GII.17 variants led to at least two clusters, with strains from 2013/14 season and those from 2014/15 season grouped differently. Multiple nucleotide and amino acid variations between different clusters of GII.17 were elucidated, including residue substitutions and insertion occurring in or near antigenic and receptor-binding sites of viral protein 1. In addition, sequence hypervariability from residue 279 through 406 of viral protein 2 was identified. The modifications may reveal a distinctive adaptive process which could in part explain the rapid spread of emerging GII.17 variants. Continued monitoring on novel GII.17 is essential.

Behavioral History of Withdrawal Influences Regulation of Cocaine Seeking by Glutamate Re-Uptake.

Withdrawal from cocaine regulates expression of distinct glutamate re-uptake transporters in the nucleus accumbens (NAc). In this study, we examined the cumulative effect of glutamate re-uptake by multiple excitatory amino acid transporters (EAATs) on drug-seeking at two different stages of withdrawal from self-administered cocaine. Rats were trained on fixed ratio 1 (FR1), progressing to FR5 schedule of reinforcement. After one day of withdrawal, microinfusion of a broad non-transportable EAAT antagonist, DL-threo-beta-benzyloxyaspartate (DL-TBOA), into the NAc shell dose-dependently attenuated self-administration of cocaine. Sucrose self-administration was not affected by DL-TBOA, indicating an effect specific to reinforcing properties of cocaine. The attenuating effect on cocaine seeking was not due to suppression of locomotor response, as DL-TBOA was found to transiently increase spontaneous locomotor activity. Previous studies have established a role for EAAT2-mediated re-uptake on reinstatement of cocaine seeking following extended withdrawal and extinction training. We found that blockade of NAc shell EAATs did not affect cocaine-primed reinstatement of cocaine seeking. These results indicate that behavioral history of withdrawal influences the effect of re-uptake mediated glutamate clearance on cocaine seeking. Dynamic regulation of glutamate availability by re-uptake mechanisms may impact other glutamate signaling pathways to account for such differences.

Different Duck Species Infected Intramuscularly with Duck-Origin Genotype IX APMV-1 Show Discrepant Mortality and Indicate Another Fatal Genotype APMV-1 to Ducks

Isolations of genotype IX (gIX) avian paramyxovirus type 1 (APMV-1) from various bird species have been more common recently, with isolates showing variable pathogenicity in different species of poultry. Here we sequenced the genome of a Muscovy duck origin gIX virus strain XBT14 and characterized the virulence and pathogenicity of this isolate in chickens and ducks. The genome sequence of strain XBT14 is 15,192 nt in length, containing multiple basic amino acids at the fusion protein cleavage site. The XBT14 strain shared 91.6%-91.9% nucleotide identities with early-genotype viruses (such as genotype III and IV) and shared 85.3%-85.9% nucleotide homologies with later genotype viruses (such as genotype VII). Pathogenicity tests showed that strain XBT14 could cause death in different duck breeds with a mortality rate of 44.4% in Muscovy duck, 25.9% in Sheldrake, and 11.1% in Cherry Valley duck, respectively. Similar mortality discrepancies were also observed in different ducks when infected with chicken-origin gIX virus strain F48E8. These results indicate that XBT14-like velogenic gIX APMV-1 (such as XBT14, F48E8, and GD09-2) could cause fatal infection in duck, and genotype IX is another genotype velogenic to duck as well as genotype VII. Accompanied by genetic differences in the vaccine strains or dominant strains prevailing in poultry, the virulent XBT14-like gIX viruses might become potentially endemic strains in poultry in the future.

Preparation and Characterization of Cured Epoxy Resin with Hexachloro-Cyclo-Triphosphazene

ABSTRACTEpoxy resins can exhibit some excellent properties. The basic principle of curing epoxy resins with a curing agent containing multiple amino groups is the crosslinking reaction between active hydrogen atoms from the curing agent and the oxirane groups in the epoxy resin structure. This study deals with the synthesis of derivative of hexachloro-cyclo-triphosphazene (HCCTP) using curing of epoxy resins. The study of our interest is nucleophilic substitution of HCCTP using N-[3-(trimethoxysilyl)propyl]ethylene diamine. The prepared derivative offers two potential advantages over conventional curing systems, namely improving properties during burning.

Enantiomeric discrimination of α-hydroxy acids and N-Ts-α-amino acids by 1H NMR spectroscopy

A new kind of chiral compounds with multiple amino, amido and phenolic hydroxy groups has been synthesized from d-phenylalanine and d-phenylglycine, respectively. The enantiomeric discriminations of α-hydroxy acids and N-Ts-α-amino acids have been finished in the presence of the above chiral compounds as chiral solvating agents by 1H NMR spectroscopy. The results show that the chiral compounds are highly effective and practical chiral solvating agents towards α-hydroxy acids and N-Ts-α-amino acids.

Synthesis of curing agent for epoxy resin based on halogenophosphazene

ABSTRACTEpoxy resins are, due to their excellent properties (such as chemical resistance, dimensional stability, and heat resistence), widely used in practice. The basic principle of curing epoxy resins with a hardener containing multiple amino groups is the crosslinking reaction between active hydrogen atoms in the hardener and the oxirane groups in the epoxy resin. This study deals with the synthesis and characterization of hexachloro‐cyclo‐triphosphazene derivative and its subsequent use for curing epoxy resins. The new hardener was prepared from hexachloro‐cyclo‐triphosphazene by nucleophilic substitution with isophorone diamine and its curing capability was compared with original isophorone diamine. The prepared derivative hexaisophorone diamino‐cyclo‐triphosphazene (HICTP) provided advantages over conventional curing system, as it improved mechanical properties as well as the flame resistance. Testing of the cured epoxy resin during burning was carried out using dual cone calorimeter, which enables more extensive monitoring of parameters in comparison with testing using oxygen index that has been used in many publications. The epoxy resin cured with the prepared phosphorus containing HICTP exhibits lower values for total heat release, amount of smoke released and oxygen consumed, which may cause a slower flame spread. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 42917.

Covalent immobilization of molecularly imprinted polymer nanoparticles on a gold surface using carbodiimide coupling for chemical sensing

One challenging task in building (bio)chemical sensors is the efficient and stable immobilization of receptor on a suitable transducer. Herein, we report a method for covalent immobilization of molecularly imprinted core–shell nanoparticles for construction of robust chemical sensors. The imprinted nanoparticles with a core–shell structure have selective molecular binding sites in the core and multiple amino groups in the shell. The model Au transducer surface is first functionalized with a self-assembled monolayer of 11-mercaptoundecanoic acid. The 11-mercaptoundecanoic acid is activated by treatment with carbodiimide/N-hydroxysuccinimide and then reacted with the core–shell nanoparticles to form amide bonds. We have characterized the process by studying the treated surfaces after each preparation step using atomic force microscopy, scanning electron microscopy, fluorescence microscopy, contact angle measurements and X-ray photoelectron spectroscopy. The microscopy results show the successful immobilization of the imprinted nanoparticles on the surface. The photoelectron spectroscopy results further confirm the success of each functionalization step. Further, the amino groups on the MIP surface were activated by electrostatically adsorbing negatively charged Au colloids. The functionalized surface was shown to be active for surface enhanced Raman scattering detection of propranolol. The particle immobilization and surface enhanced Raman scattering approach described here has a general applicability for constructing chemical sensors in different formats.

Highly efficient carbon dioxide capture by a novel amine solvent containing multiple amino groups

AbstractBACKGROUNDAqueous solutions of amine are considered to be effective absorbents for CO2 capture. Special attention is increasingly being given to developing efficient solvents with both high absorption rate and absorption loading for CO2 capture.RESULTSA novel amine 2‐[(3‐aminopropyl)methylamino]ethanol (HMPDA) containing a primary amino group and a tertiary amino group was screened to improve the CO2 absorption performance. The equilibrium loading of CO2 in aqueous HMPDA solution was found to be 1.65 mol CO2 mol−1 HMPDA at 313 K and 1 MPa, which is larger than those of conventional amines like monoethanolamine (MEA, 0.75 mol CO2 mol−1 MEA) and N‐methyldiethanolamine (MDEA, 1.05 mol CO2 mol−1 MDEA) at 313 K and 1 MPa. Moreover, the HMPDA solution demonstrated a faster absorption rate of CO2 than those of MEA and MDEA solutions. The viscosity of HMPDA solution increases by around 66% after CO2 absorption, which is smaller than the 88% increase of MEA solution.CONCLUSIONSEfficient results for CO2 absorption using HMPDA were obtained through assessing the absorption rate, absorption loading of CO2 and related physical properties. This novel amine shows both fast absorption rate and high absorption loading due to the multiple‐site reaction elaborated by the zwitterion and single‐step termolecular mechanism. © 2015 Society of Chemical Industry

Covalent immobilization of molecularly imprinted polymer nanoparticles using an epoxy silane

Molecularly imprinted polymers (MIPs) can be used as antibody mimics to develop robust chemical sensors. One challenging problem in using MIPs for sensor development is the lack of reliable conjugation chemistry that allows MIPs to be fixed on transducer surface. In this work, we study the use of epoxy silane to immobilize MIP nanoparticles on model transducer surfaces without impairing the function of the immobilized nanoparticles. The MIP nanoparticles with a core–shell structure have selective molecular binding sites in the core and multiple amino groups in the shell. The model transducer surface is functionalized with a self-assembled monolayer of epoxy silane, which reacts with the core–shell MIP particles to enable straightforward immobilization. The whole process is characterized by studying the treated surfaces after each preparation step using atomic force microscopy, scanning electron microscopy, fluorescence microscopy, contact angle measurements and X-ray photoelectron spectroscopy. The microscopy results show that the MIP particles are immobilized uniformly on surface. The photoelectron spectroscopy results further confirm the action of each functionalization step. The molecular selectivity of the MIP-functionalized surface is verified by radioligand binding analysis. The particle immobilization approach described here has a general applicability for constructing selective chemical sensors in different formats.