Journal of Electroanalytical Chemistry, volume 903, pages 115839

Voltammetric sensor system based on Cu(II) and Zn(II) amino acid complexes for recognition and determination of atenolol enantiomers

Publication typeJournal Article
Publication date2021-12-01
scimago Q1
wos Q2
SJR0.755
CiteScore7.8
Impact factor4.1
ISSN15726657, 18732569
General Chemical Engineering
Analytical Chemistry
Electrochemistry
Abstract
• A chiral sensors based on GCE modified by composites with amino acid complexes of Cu(II) and Zn(II) was developed. • R- and S-Atn interact with the Cu(II) and Zn(II) amino acid complexes by the ligands exchange. • Differences in the maximum currents and the potentials of R-, S-Atn oxidation peaks were observed. • For reliable recognition of R- and S-Atn, the proposed sensors were combined to sensor system by chemometric methods. • The sensor system correctly recognize R- and S-Atn in enantiomeric mixture. For recognition and determination of atenolol (Atn) enantiomers the enantioselective voltammetric sensor system based on glassy carbon electrodes modified by composites of polyarylenephthalide and chiral amino acid complexes of Cu(II) and Zn(II) – glycine- l -alaninate and glycine- l -argininate Cu(II), bis - l -phenylalaninate Zn(II) is developed. The enantioselectivity of the sensors is explained by the presence of chiral amino acids in the complexes which can be exchanged with Atn enantiomers and form mixed-ligand complexes of different stability. The electrochemical and analytical characteristics of the sensors were studied. It was shown that the sensors are cross-sensitive to Atn enantiomers. A sensor system based on them with chemometric processing of analytical signals using the methods of principal components and projection to latent structures was used to recognize and determine S- and R-Atn in mixtures with different ratios of enantiomers. The content of S-Atn was established with a relative standard deviation of less than 9% and recoveries ranging from 95% to 102%. The use of a sensor system makes it possible to eliminate errors of the first kind and to minimize errors of the second kind, to increase the percentage of correctly recognized samples up to 99%.
Stoian I., Iacob B., Ramalho J.P., Marian I.O., Bodoki E., Oprean R.
Electrochimica Acta scimago Q1 wos Q1
2021-08-01 citations by CoLab: 5 Abstract  
A new simple and convenient strategy for boosting the enantioselectivity of cyclodextrins (CDs) as highly available homochiral macrocyclic hosts using the co-assembly of physisorbed propranolol (PRNL) enantiomers on gold nanoparticles (AuNPs) and different CDs was reported, exploiting the gainful effects of surface-confined supramolecular associations. All the experiments were conducted both in bulk enantiomer solution (unrestricted, homogenous system) and on the antipodes physisorbed at the gold-liquid interface (surface confined, heterogenous system), employing various electroanalytical techniques (differential pulse voltammetry, cyclic voltammetry and electrochemical impedance spectroscopy), isothermal titration calorimetry and computational modeling. In the unrestricted system, where the freedom of movement of PRNL molecules is not hampered, unassailable enantioselectivity may not be allocated to either of the tested CDs. However, by limiting the degrees of freedom of PRNL antipodes upon their adsorption to a non-chiral surface of electrochemically-generated AuNPs, a particular amplification of the conformational differences between the resulting supramolecular complexes with native CDs may arise. Molecular dynamics simulations of the supramolecular interactions on both homogenous and heterogenous system revealed important differences compared to the previously reported quantum chemical calculations performed in vacuo . Besides the advances of fundamental knowledge, this proof-of-concept data may offer an alternative strategy for the fast chiral probing of various analytes by interfacial supramolecular electrochemistry.
Pei H., Chen F., Niu X., Jia Q., Guo R., Liu N., Mo Z.
2021-08-01 citations by CoLab: 16 Abstract  
• The CS-SA porous chiral composite was synthesized by electrostatic self-assembly. • The chiral sensor was constructed for electrochemical recognition of Tyr isomers. • The mechanism of chiral recognition was studied using molecular simulation docking. Chitosan-sodium alginate (CS-SA) chiral composite sensing material was prepared by electrostatic self-assembly method. Scanning electron microscope images show that the morphologies of chitosan (CS) and sodium alginate (SA) have changed after self-assembly, which resulted in a new porous network structure. The structure and composition of the chiral composite sensing material were also identified by infrared spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy. The self-assembled CS-SA chiral composite sensing material was drip-coated on the glass carbon electrode to construct an electrochemical sensing interface. The tested square wave voltammetry curve in the l -tyrosine ( l -Tyr) and d -tyrosine ( d -Tyr) solution presented that CS-SA chiral composite sensing material can specifically bind to l -tyrosine, and the binding force is determined as hydrogen bonding by the method of molecular docking calculation. Although chitosan molecules have abundant chiral sites, glassy carbon electrodes modified with pure CS molecules cannot effectively recognize tyrosine isomers. After being combined with sodium alginate by electrostatic self-assembly, the efficiency of chiral recognition is significantly improved. This experiment opens up a new method for the combination of chitosan with other materials, and at the same time, expands its application on chiral recognition.
Berestova T.V., Gizatov R.R., Galimov M.N., Mustafin A.G.
Journal of Molecular Structure scimago Q2 wos Q2
2021-07-01 citations by CoLab: 7 Abstract  
• The differences between the ATR-FTIR spectra and X-Ray diffraction phenyl-containing bis-(N,O)copper(II) chelates [Cu( S -phe) 2 ] and [Cu( S -phe)( R -phe)]. • DFT simulation the conformers of the geometric isomers of phenyl-containing bis-(N,O)copper(II) chelates [Cu( S -phe) 2 ] and [Cu( S -phe)( R -phe)]. • The distortion of the square-planar framework of the chelate rings into a “bath” or “chair” structure is determined by the absolute configuration of the chiral center ( R or S ) of the ligands and depends on axial or equatorial orientation of ligand in space. It was found that the absolute configuration of the chiral center of the phenyl substituent ( R or S ) may be the cause of the change on the structure of planar-square in the bis-(N,O)copper(II) chelates. Also, we found that the planar-square phenyl-containing complexes [Cu( S -phe) 2 ] ( 1 ) and [Cu( S -phe)( R -phe)] ( 2 ( 2′ )) have significant differences in the mid-wavelength region of the IR spectrum and XRD. By the method of quantum chemical modeling (method M06/6-311+G(d)), the IR spectra of the complexes [Cu( S -phe) 2 ] and [Cu( S -phe)( R -phe)] were simulated and the most optimal conformers were installed. It was found that the differences in the IR spectra and XRD of chelate copper(II) complexes 1-2 ( 2′ ) are arisen due to the influence of the phenyl-containing ligand and are more visible than for complexes with aliphatic ligands. It was shown that the distortion of the square-planar framework of the chelate rings into a “bath” or “chair” structure is determined by the absolute configuration of the chiral center ( R or S ) of the ligands and also depends on axial or equatorial orientation of ligand in space.
Khan S.B., Lee S.
Molecules scimago Q1 wos Q2 Open Access
2021-06-30 citations by CoLab: 54 PDF Abstract  
In recent times, researchers have emphasized practical approaches for capturing coordinated and selective guest entrap. The physisorbed nanoporous supramolecular complexes have been widely used to restrain various guest species on compact supporting surfaces. The host–guest (HG) interactions in two-dimensional (2D) permeable porous linkages are growing expeditiously due to their future applications in biocatalysis, separation technology, or nanoscale patterning. The different crystal-like nanoporous network has been acquired to enclose and trap guest molecules of various dimensions and contours. The host centers have been lumped together via noncovalent interactions (such as hydrogen bonds, van der Waals (vdW) interactions, or coordinate bonds). In this review article, we enlighten and elucidate recent progress in HG chemistry, explored via scanning tunneling microscopy (STM). We summarize the synthesis, design, and characterization of typical HG structural design examined on various substrates, under ambient surroundings at the liquid-solid (LS) interface, or during ultrahigh vacuum (UHV). We emphasize isoreticular complexes, vibrant HG coordination, or hosts functional cavities responsive to the applied stimulus. Finally, we critically discuss the significant challenges in advancing this developing electrochemical field.
Luo H., Li H., Ge Q., Cong H., Tao Z., Liu M.
Microchemical Journal scimago Q1 wos Q1
2021-05-01 citations by CoLab: 20 Abstract  
• A voltammetric sensor was achieved by modification of rGO with a chiral multifarene[3,3]. • The electrochemical sensor was applied for discrimination of tyrosine enantiomers. • The constructed sensor exhibited good results in anti-interference ability, reproducibility, and stability. A novel chiral sensor was developed to produce the distinguishing response to the enantiomers of tyrosine (Tyr), with high sensitivity and selectivity. The electrochemical sensor was modified by the inorganic-organic nanohybrid material with the functionalization of reduced graphene oxide (rGO) to be the amplifier and a chiral hetero-multifarene[3,2,1] (CHMF[3,2,1]) as the chiral receptor. The as-prepared rGO-CHMF was characterized by transmission electron microscopy (TEM), atomic force microscope (AFM), infrared spectroscopy (IR), thermogravimetric analysis (TGA), Raman spectroscopy and electrochemical methods. It was observed that the composites exhibited different binding ability for Tyr enantiomers. The proposed sensor presented significant difference with peak potential separation value (ΔE p = 70 mV) and the ratio of peak current ( I L-Tyr / I D-Tyr = 1.58) for Tyr enantiomers by differential pulse voltammetry. In addition, the peak currents increased linearly with the concentration of Tyr enantiomers in the concentration range 0.1–10 μM with detection limits of 78 nM and 83 nM for l -Tyr and d -Tyr (S/N = 3), respectively. It also exhibited the ability to determine the percentage of one Tyr enantiomer in the racemic mixture. Moreover, the selectivity, reproducibility, and stability of the chiral sensor were investigated to give satisfactory results. The above discoveries offered an alternative technology for chiral recognition with electrochemical response to actualize a real-time and quantitative determination.
Sun Y., Zhang D., Sheng Y., Xu D., Zhang R., Bradley M.
Analytical Methods scimago Q2 wos Q1
2021-04-03 citations by CoLab: 14 Abstract  
The β-CD@PEI-Fc chiral interface was prepared based on the supramolecular host–guest interaction between ferrocene (Fc) grafted polyethyleneimine (PEI-Fc) and chiral β-cyclodextrin (β-CD).
Wei X., Li L., Lian H., Cao X., Liu B.
2021-04-01 citations by CoLab: 33 Abstract  
Due to the widespread application of chiral substances in current society, the electrochemical strategy to assemble chiral metal–organic frameworks (CMOFs) as sensors has shown great potential for sensitive enantiorecognition. In this paper, an efficient and highly selective electrochemical sensor was proposed based on multi-walled carbon nanotube (MWCNT) and CMOF, and successfully achieved sensitive chiral recognition of Tryptophan (Trp) enantiomers. Numerous MOFs in multiple synthesis conditions were investigated for a regular process to access the electrochemical chiral recognition. A variety of amino acids were introduced into the MOFs skeleton by a simple hydrothermal method for the enantio -specificity. Meanwhile the MWCNT smoothly integrated with the CMOF to form a functional electrosensing interface with the increase of conductivity. Based on the current ratio ( R cp ) of tryptophan enantiomers by different modified electrodes, a series of experimental conditions were optimized for the optimal chiral recognition performance of the CMOF/MWCNT-based sensor, finally reaching 2.9 times of ΔI L/D between enantiomers. In addition, D/ l -Trp showed a good linear relationship with the current in the range from 0.4 μM to 19 μM with the detection limit of 0.11 μM for l -Trp and 0.16 μM for d -Trp. The prepared composite-functionalized sensor owned the desired reproducibility and selectivity to identify Tryptophan enantiomers with robust chiral recognition. The research on the structure–activity relationship of chiral MOFs to Tryptophan enantiomers provides a new path to construct more electrochemical sensors for the application of enantiorecognition in pharmaceutical analysis.
Yu S., Wang Y., Chatterjee S., Liang F., Zhu F., Li H.
Chinese Chemical Letters scimago Q1 wos Q1
2021-01-01 citations by CoLab: 25 Abstract  
Chirality is a fascinating and essential feature of life and highly associated with many significant pharmaceutical, chemical, and biological processes. The construction of chiral recognition platform is a hot research topic and challenging assignment. Herein, we report an electrochemical method by differential pulse voltammetry (DPV) for the enantioselective recognition of chiral drug propranolol (R/S-PPL) through a nanochannel platform based on the N-acetyl- l -cysteine functionalized pillar[5]arenes derivative NALC-P5 and the porous polycarbonate membrane. The chiral discrimination depends on the difference in the supramolecular host-guest interaction between the chiral NALC-P5 and the R/S-PPL. The transmission rate of the R/S-PPL can be regulated in the nanochannel and we can achieve the selective transport of the chiral drugs. This simple electrochemical technique has potential applications as a general platform for the recognition of chiral molecules.
Zagitova L.R., Maistrenko V.N., Yarkaeva Y.A., Zagitov V.V., Zilberg R.A., Kovyazin P.V., Parfenova L.V.
2021-01-01 citations by CoLab: 30 Abstract  
To achieve satisfactory recognition and determination of tryptophan (TRP) enantiomers a chiral voltammetric sensor based on carbon black paste electrode (CBPE) containing Carboblack C powder and 3-neomenthylindene (NMI) chiral selector is developed in this work. A possible recognition mechanism as well as chiral selectivity have been explained using the molecular dynamics simulation. It was shown that 3-neomenthylindene attracts to TRP enantiomers via Van der Waals and π-π-stacking interactions. Compared with D-TRP, the sensor indicates favorable chiral recognition towards L-TRP with a selectivity coefficient of 1.34. The higher response signal of L-TRP than D-TRP is due to the energetically more favorable interaction of 3-neomenthylindene with L-TRP, which is confirmed by a change in the total energy of the system. CBPE modified by NMI was characterized by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), scanning electron microscopy (SEM), and Fourier transform infrared spectroscopy (FT-IR). The electrochemical and analytical characteristics of the sensor and conditions of the voltammogram registration were studied by differential pulse voltammetry (DPV). It was found that the oxidation of TRP enantiomers on CBPE/NMI is the diffusion-controlled process. The experimental results indicate a linear correlation between the peak currents of TRP enantiomers and their concentration in the range from 2.5 μM to 0.3 mM, leading to a detection limit of 1.71 μM and 2.23 μM for L- and D-TRP, respectively. The practical capabilities of the proposed sensor were demonstrated by analyzing human urine and blood plasma with satisfactory recoveries ranging from 95.2% to 99.0%. L-TRP was recognized in dietary supplements using projection to latent structures discriminant analysis. The present sensor also can detect the enantiomeric composition based on current signals with the different total concentrations of the mixture. The selectivity, stability, and reproducibility of the proposed sensor were studied as well.
Maistrenko V.N., Zil’berg R.A.
Journal of Analytical Chemistry scimago Q3 wos Q4
2020-12-19 citations by CoLab: 17 Abstract  
The review presents exhaustive information for the last 5 years on the trends and methods of research, development, and application of enantioselective voltammetric sensors on the basis of new chiral materials for the recognition of enantiomers of biologically active and medicinal compounds. Enantioselective sensors on the basis of chiral Cu, Au, Ag, Pt, and Pd nanoparticles and single crystals, mesoporous metals with molecular imprints, single-wall carbon nanotubes, smart polymers, metal–organic frameworks and supramolecular assemblies, and chiral ionic liquids are considered. Examples of the recognition and determination of enantiomers in various samples and analytical characteristics of the proposed sensors are given. Problems and prospects of using enantioselective voltammetric sensors for the chiral recognition of optically active compounds are discussed.
Ariga K., Shionoya M.
2020-12-15 citations by CoLab: 93 Abstract  
AbstractNanoarchitectonics is a concept envisioned to produce functional materials from nanoscale units through fusion of nanotechnology with other scientific disciplines. For component selection, coordination complexes with metallic elements have a wider variety of element selection because metallic elements cover ca. 80% of the periodic table of the elements. Application of nanoarchitectonics approaches to coordination chemistry leads to huge expansion of this concept to a much wider range of elements. Especially, coordination asymmetry strategy architects asymmetrical and/or chiral structures and/or electronic states through formation of metal coordination complexes, leading to functional material systems in certain anisotropy and selectivity. This review article presents expansion of the nanoarchitectonics concept to coordination asymmetry through collecting recent examples in the field of coordination asymmetry. Introduced examples are classified into several categories from various viewpoints: (i) basic molecular and material designs; (ii) specific features depending on interfacial media, space and contact with bio-functions; (iii) functions; (iv) supporting techniques such as analyses and theory.
Niu X., Yang X., Li H., Liu J., Liu Z., Wang K.
Microchimica Acta scimago Q1 wos Q1
2020-11-27 citations by CoLab: 75 Abstract  
Chirality is a universal phenomenon in nature and an essential attribute of life systems. Chiral recognition has very important research value in many fields. Amino acids and other chiral molecules are the basic components of human body. Understanding the configuration of chiral molecules is beneficial not only to the development of life science, but also to the development of chiral recognition. Compared with other traditional chiral recognition methods, electrochemical methods have the advantages of rapid detection, simple operation, low price, and high sensitivity, which has been widely concerned. In this review, we present an overview of chiral materials in a view of various chiral selectors, including amino acids and their derivatives, proteins, polysaccharides, chiral ligand exchange compounds, chiral cavity compounds (such as cyclodextrin, cucurbituril, calixarene, crown ether), and chiral ionic liquids, which were applied for the recognition of chiral molecules. Besides the chiral recognition mechanisms, some critical challenges and outlooks in the field of electrochemical chiral sensing interfaces are also discussed.
Ashwin B.C., Shanmugavelan P., Muthu Mareeswaran P.
2020-09-29 citations by CoLab: 13 Abstract  
The electrochemical behaviour of the host–guest complexes formed by cyclodextrin, calixarene and cucurbiturils host molecules with simple organic guest molecules and their applications using electrochemical studies are discussed in detail in this review. The change in the redox behaviour of the individual molecules upon complexation and the unique properties of the complexes formed are elaborated. The methodology and various electrochemical techniques used for the investigation of these host–guest are categorised with respect to the analytical methods. The electrochemical behaviour upon binding of host with guest and their applications are analysed in detail. The applications are ranging from simple molecular detection to sensing of toxicants, pollutants and biomolecules. The identification of cancer cells and discrimination of chiral molecules are the noteworthy application of these supramolecular electrochemical sensing systems. The aspects discussed in this review could help to extend the electrochemical applications of host–guest systems to utilize them in the highly important applications like cancer detection and pollutant detection.
Grecchi S., Arnaboldi S., Korb M., Cirilli R., Araneo S., Guglielmi V., Tomboni G., Magni M., Benincori T., Lang H., Mussini P.R.
ChemElectroChem scimago Q2 wos Q2 Open Access
2020-07-13 citations by CoLab: 16
Yarkaeva Y.A., Dubrovskii D.I., Zil’berg R.A., Maistrenko V.N.
2020-07-01 citations by CoLab: 10 Abstract  
Voltammetric sensors and a sensor system based on gold electrodes modified with polyarylenephthalides (chlorinated polyphthalidylidene fluorene and polyphthalidylidene diphenyl and brominated polyphthalidylidene diphenyl) for the identification of cysteine are developed. The surface morphology of the modified electrodes and electrochemical and analytical characteristics of the sensors are studied, the conditions for the electrochemical oxidation of cysteine and the production of an analytical signal are optimized. The proposed sensors and sensor system, with chemometric processing of response signals, allows recognizing manufacturers of cysteine-containing pharmaceutical preparations. The use of the voltammetric sensor system can significantly increase the percentage of correctly recognized samples in comparison with the registration of voltammograms on separate electrodes.
Yarkaeva Y.A., Nazyrov M.I., Dymova D.A., Maistrenko V.N.
2024-12-22 citations by CoLab: 0 Abstract  
For selective determination of the antibiotic clarithromycin, a voltammetric sensor based on a glass-carbon electrode modified with a composite of chitosan, Carboblack C graphitized carbon black and polyarylenephthalide containing diphenylene-thio- and diphenylene oxide fragments in the main chain of the polymer in the ratio of 1 : 2 with molecular imprints of clarithromycin obtained by phase inversion method was developed. The composition and morphology of the modifying coating were studied using IR spectroscopy and scanning electron microscopy. The electrochemical and analytical characteristics of the sensor were studied by electrochemical impedance spectroscopy, cyclic and differential-pulse voltammetry. Optimal conditions for analytical signal registration were selected. Using [Fe(CN) ]63−/4− as a probe, the linear range of determined concentrations was 1 × 10-7 -5 × 10-4 M with a detection limit of 5.3 × 10-8 M. It is shown that the use of a polymer with molecular imprints of clarithromycin increases the sensitivity of the sensor almost 10 times compared to the non-imprinted polymer. The proposed sensor was tested on samples of urine, blood plasma, as well as food products (meat, milk), the degree of extraction was 90-96, 80 and 92%, respectively, and the relative standard deviation did not exceed 10% in all cases.
Nazyrov M.I., Perfilova Y.A., Abdullin Y.R., Kovyazin P.V., Maistrenko V.N.
2024-12-22 citations by CoLab: 0 Abstract  
To recognize and determine the enantiomers of clopidogrel, a sensor system based on a glassy carbon electrode modified with Carbopack X mesoporous carbon black and cyclopentadiene derivatives – (1S)-2-cyclopenta-2,4-dien-1-yl-1,7,7-trimethylbicyclo[2.2.1]heptane; (1S, 2S, 4R)-2-cyclopenta-1,3-dien-1-yl-1-isopropyl-4-methylcyclohexane; 9-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]-9H-fluorene. Due to the unique properties of Carbopack X, such as large surface area and high conductivity, it was possible to obtain a mechanically stable and sensitive sensor layer that firmly retains chiral selector molecules on its surface. The morphological, electrochemical and analytical properties of the obtained sensors were studied by scanning electron microscopy, electrochemical impedance spectroscopy, cyclic and differential pulse voltammetry. The determination of clopidogrel enantiomers in biological fluids has been carried out; linear dependences of oxidation peak currents on their concentration in solution for all sensors are preserved in the concentration range from 1 × 10–6 to 5 × 10–4 M. The sensors are cross-sensitized, which allowed combining them into a sensor system with high enantioselectivity and sensitivity towards clopidogrel enantiomers. With the proposed sensor system, the probability of correctly recognizing samples increases compared to single sensors. In all cases, the content of R-clopidogrel in the mixture is correctly determined with a relative error not exceeding 9% and a degree of discovery ranging from 96 to 102%.
Zhang L., Xiao J., Xu X., Li K., Li D., Li J.
2024-07-16 citations by CoLab: 0
Zagitova Liana R., Gainanova Svetlana I., Perfilova Yuliya A., Nazyrov Marat I., Abramov Ilya A., Gubaidullin Rinat R.
Microchemical Journal scimago Q1 wos Q1
2024-07-01 citations by CoLab: 2 Abstract  
Enantioselective sensors are potentially in demand at all stages of the production, storage and use of drugs, including identifying impurities of undesirable isomers and improving stereoselective synthesis methods. A key aspect for enantioselective sensors design is the development of appropriate molecular architectures that make it possible to create recognition sites with different affinities for enantiomers. This experimental work proposes a new chiral sensor based on glassy carbon electrode (GCE) modified by graphene oxide (GO) covalent functionalized with pentacyclic triterpenoid betulonic acid (BetA) for voltammetric recognition and determination of propranolol (Prop) enantiomers. Characterization of the materials was carried out using FTIR spectroscopy, scanning electron microscopy and cyclic voltammetry. Differential pulse voltammetry was used for Prop enantiomers recognition and quantification. The potential difference reached 30 mV along with enanitoselectivity coefficient ipS/ipR equal to 1.30. The calculated binding energy for S-Prop/GO-BetA complex is higher by 4.801 kcal moll−1 compared to R-Prop/GO-BetA indicating a more favorable mutual arrangement of molecules. The linear determination range was established as 5.0 × 10-6 ∼ 1.0 × 10-4 mol·L-1 and 1.0 × 10-4 ∼ 4.0 × 10-4 mol·L-1 for both enantiomers. The detection limits were determined to be 3.9⋅10-7 mol·L-1 and 5.0⋅10-7 mol·L-1 for S-Prop and R-Prop, respectively. The standard spike-recovery tests were carried out in human biological fluids with recoveries 97.3 % − 106.9 % for both enantiomers. The proposed sensor was used to determine the ratio of Prop enantiomers in mixture by regression analysis with projection to latent structures (PLS). The purpose was to build a PLS-model based on a calibration set containing a known number of Prop enantiomers and recognize a test set prepared independently. All samples of test set are correctly identified and the RSD did not exceed 8.7 %. GCE modified by covalent functionalized GO with BetA showed better stability compared with noncovalent functionalization in terms of electrode degradation.
Zilberg R.A., Teres J.B., Bulysheva E.O., Vakulin I.V., Mukhametdinov G.R., Khromova O.V., Panova M.V., Medvedev M.G., Maleev V.I., Larionov V.A.
Electrochimica Acta scimago Q1 wos Q1
2024-07-01 citations by CoLab: 3 Abstract  
Enantioselective voltammetric sensors (EVSs) have significant interest in analytical and medicinal chemistry, as they allow for the express analysis and recognition of pharmacologically active components in drugs, as well as the establishment of the enantiopurity of compounds. The most common methods of modifying the electrode surface are through molecular imprinting techniques and the addition of a non-electroactive chiral modifier to the electrode composition. By varying the structure and properties of the chiral modifier, the sensor can be designed to have the highest enantioselectivity for a chosen chiral analyte. In this study, we describe the development of a new type of EVS based on a Carboblack C paste electrode modified with a chiral octahedral cobalt(III) complex for use as a selective enantioselector. It was found that the EVS, prepared from enantiopure Co(III) complexes, can selectively recognize L- and D-tryptophan (Trp) in phosphate buffer solution (PBS) with pH = 6.86. The peak current ratio (iD/iL) between the two enantiomers reached 1.36, demonstrating the effectiveness of the sensor. The experimental results indicate a linear correlation between the peak currents of Trp enantiomers and their concentration in the range from 1.00·10−6 to 5.00·10−4 М, leading to a detection limit of 2.42 µM and 3.30 µM for D- and L-Trp, respectively, when using chiral octahedral Co(III) complex with chloride counter-anion. Next, the EVSs developed demonstrated practical applicability in measuring the concentration of Trp in pharmaceutical samples and human urine and blood plasma. An important advantage of these sensors is the difference in the oxidation potentials between Trp enantiomers (ΔEp=35 mV), which makes it possible to determine Trp enantiomers in their mixtures. Quantum chemical calculations and experimental data show that the octahedral Co(III) complex binds to one of the Trp enantiomers with a stronger affinity, thus increasing its concentration at the electrode surface and promoting its oxidation. The easy preparation of the chiral Co(III) complex from inexpensive commercial materials, its high stability and insolubility in water make it a promising selector for the creation of efficient multifunctional EVSs for the analysis of various aqueous solutions.
Walkowiak Z., Gągor A., Soliman S.M., Jerzykiewicz M., Sarewicz M., Fitta M., Pełka R., Wojciechowska A.
Journal of Molecular Structure scimago Q2 wos Q2
2024-07-01 citations by CoLab: 2 Abstract  
A new heteroleptic [CuBr(l−Arg)(bpy)]Br·2H2O (1) (l−Arg=l−Arginine, bpy=2,2'−bipyridine) complex has been synthesized and its molecular and supramolecular structure aspects have been discussed based on the X-ray single crystal structure and Hirshfeld analyses. In addition, the properties of complex 1 have been elucidated using different spectroscopic tools (FT−IR / FIR, Raman, NIR−Vis−UV, Q− and X− bands EPR) and magnetic measurements. In this complex, the bromide anion occupies the apex of slightly distorted square pyramid (τ = 0.12). The [CuBr(l−Arg)(bpy)]+ complex units exhibit a ribbon−like organization, with Cu(II) metal centers located at the corners of triangles where the shortest Cu∙∙∙Cu distance is 5.579 Å. The aromatic moieties of bpy are aligned nearly parallel leading to π···π interactions. Both, non−bonded and coordinated, Br− ions act as a hydrogen−bond acceptors for guanidinium groups. Hirshfeld analysis indicated the importance of the Br∙∙∙H (17.9−18.4%), O∙∙∙H (14.9−15.2%), and H∙∙∙H (42.3−43.1%) interactions in the molecular packing of the studied complex. Atoms in molecules calculations indicated mainly the closed shell character for the Cu−N, Cu−O and Cu−Br coordination interactions. The G value calculated using the EPR Q−band spectra parameters g|| = 2.235 and g⊥= 2.05 is 4.7, what indicates negligible coupling and that local tetragonal axes are aligned parallel. A negative value of Weiss temperature θCW = -0.32 K indicates the presence of weak antiferromagnetic coupling between the neighboring Cu(II) ions mediated through hydrogen bonds and π-π stacking of aromatic moieties of bpy (the shortest distances between the neighboring Cu(II) ions amount to 5.58, 6.73 and 7.03 Å). The value of gav= 2.113 obtained from Q−band EPR spectra is consistent with that corresponding to the Curie constant (C = 0.4138 emu K mol−1), i.e. g = 2.101, and that obtained from the best fitting to the Brillouin function: g = 2.139.
Yarkaeva Y.A., Nazyrov M.I., Dymova D.A., Maistrenko V.N.
Journal of Analytical Chemistry scimago Q3 wos Q4
2024-06-21 citations by CoLab: 0 Abstract  
A voltammetric sensor based on a glassy carbon electrode modified with a chitosan, Carboblack C graphitized carbon black, and molecularly imprinted polyarylene phthalide composite is developed for the selective detection of antibiotic clarithromycin. The polyarylene phthalide used for modification contains diphenylenethio- and diphenylene oxide fragments in a 1 : 2 ratio in the main polymer chain. Clarithromycin-imprinted polyarylene phthalide was obtained using the phase inversion method. The composition and morphology of the modifying coating were investigated by IR spectrometry and scanning electron microscopy. The electrochemical and analytical characteristics of the sensor were investigated by electrochemical impedance spectroscopy, cyclic voltammetry, and differential pulse voltammetry. Optimal conditions for recording the analytical signal were selected. Using [Fe(CN)6]3−/4− as a probe, the linear range of the detected concentrations was found to be 1 × 10–7–5 × 10–4 M with a limit of detection of 5.3 × 10–8 M. Using a clarithromycin-imprinted polymer enhances the sensor sensitivity by nearly tenfold compared to the nonimprinted polymer. The proposed sensor was tested using urine, blood plasma, and various food samples (meat, milk), the recovery values were 90–96, 80, and 92%, respectively, with relative standard deviations not exceeding 10% in all cases.
Nazyrov M.I., Perfilova Y.A., Abdullin Y.R., Kovyazin P.V., Maistrenko V.N.
Journal of Analytical Chemistry scimago Q3 wos Q4
2024-06-21 citations by CoLab: 0 Abstract  
To recognize and determine clopidogrel enantiomers, a sensor system was developed based on a glassy carbon electrode modified with mesoporous Carbopack X carbon black and cyclopentadiene derivatives (1S)-2-cyclopent-2,4-dien-1-yl-1,7,7-trimethylbicyclo[2.2.1]heptane, (1S,2S,4R)-2-cyclopent-1-en-1-yl-1-isopropyl-4-methylcyclohexane, and 9-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]-9H-fluorene. Because of the unique properties of Carbopack X, such as a large surface area and high conductivity, a mechanically stable and a sensitive sensor layer was obtained, which firmly retains chiral selector molecules on its surface. The morphological, electrochemical, and analytical properties of the obtained sensors were studied using scanning electron microscopy, electrochemical impedance spectroscopy, and cyclic and differential pulse voltammetry. Сlopidogrel enantiomers were determined in biological fluids, and linear dependences of oxidation peak currents on their concentration in solution were maintained for all sensors in the concentration range from 1 × 10–6 to 5 × 10–4 M. The sensors exhibited cross-sensitive properties, enabling them to be combined into a sensor array with high enantioselectivity and sensitivity towards clopidogrel enantiomers. Using the proposed sensor array system increases the probability of correctly identifying samples compared to individual sensors. In all cases, the concentration of R-clopidogrel in a mixture was determined correctly with a relative standard deviation not exceeded 9% and recovery ranged from 96 to 102%.
Kowalczyk A., Duszczyk M., Sęk S., Lipiński P.F., Kaczorek D., Kawęcki R., Grudzinski I.P., Rode J.E., Dobrowolski J.C., Nowicka A.M.
Advanced Functional Materials scimago Q1 wos Q1
2024-01-16 citations by CoLab: 0 Abstract  
AbstractAtenolol β‐blocker drug (ATN) to treat hypertension and cardiovascular disorders such as angina pectoris is manufactured commercially in a racemic form, while only its (S)‐enantiomer shows selective β1‐blocking activity. Here, a new axially chiral thiolated naphthalene diimide derivatives (HS‐BIN‐NDI) for the rapid, simple, and sensitive detection of ATN enantiomers is presented. The Surface Plasmon Resonance (SPR) and Atomic Force Microscopy (AFM) experiments show that interactions between a chiral selector and a chiral analyte occur only when their configurations are opposite. The extensive computational simulations support this finding. The association coefficient determined by SPR is high (105‐106 M−1 s−1) and indicates that the interactions are electrostatic. The analytical utility of atropisomeric HS‐BIN‐NDIs is proven, and the voltammetric sensors designed to determine ATN enantiomers are constructed. The developed sensors are characterized by a wide analytical operating range from 5.0·10−3 to 1.0 µm, nanomolar detection limit, high selectivity, and a long lifetime. Several additives like urea, creatinine, glucose, human albumin, and hemoglobin do not affect ATN sensing.
Abd El-Aziz H., Zeid A.M.
2024-01-01 citations by CoLab: 7 Abstract  
Fixed-dose combinations for treatment of hypertension are observed in many dosages in the global market because of their high efficacy compared to single component dosage forms. One of these effective combinations is atenolol/amlodipine which is usually administered to patients with hypertension. Hence, development of facile, accurate, and sensitive methods for simultaneous estimation of atenolol and amlodipine is of great importance for quality control testing and pharmacokinetic studies. In our study, we developed two spectrofluorimetric methods to estimate both compounds in different pharmaceuticals. The first method is based on the estimation of atenolol and amlodipine by double-scan conventional spectrofluorimetry where the fluorescence intensities of atenolol and amlodipine were measured at 299 and 434 nm after excitation at 274 and 358 nm, respectively. The second method depends on synchronous spectrofluorimetric measurements at Δλ = 70 nm, where atenolol is assayed at 266 nm and amlodipine is assayed at 363 nm. Methods’ optimizations were carried out to select the optimum conditions that render high selectivity and sensitivity. Such optimizations included assessment of solvents, surfactants, buffer volumes and pHs. The conventional spectrofluorimetric method was rectilinear over concentration range of 30.0–300.0 ng mL-1 for atenolol and 0.25–7.00 µg mL-1 for amlodipine while the synchronous spectrofluorimetric method showed linearity over the ranges of 0.60–6.00 µg mL-1 for atenolol and 0.25–7.00 µg mL-1 for amlodipine with low detection limits (≤ 0.12 µg mL-1) for both compounds in the two methods. It is the first work that demonstrates estimation of atenolol and amlodipine in their combinations by conventional and synchronous spectrofluorimetry. Both methods were applied to estimate atenolol and amlodipine in different pharmaceuticals with high %recovery and low %RSD.
Bathinapatla A., Kanchi S., Chokkareddy R., Puthalapattu R.P., Kumar M.R.
Microchemical Journal scimago Q1 wos Q1
2023-09-01 citations by CoLab: 8 Abstract  
Stress, ingrained human behaviors, an inactive lifestyle, and poor dietary decisions are the primary causes of hypertension and the related coronary artery disease (CAD), which is also commonly referred to as angina pectoris. Effective high blood pressure (BP) treatment represents a substantial approach to reducing the burden of hypertension-related cardiovascular and renal diseases. A group of drugs known as β-blockers and calcium channel blockers (CCBs) are frequently used to treat diseases like hypertension (high blood pressure), cardiac arrhythmias and heart failure. For efficient therapeutic use and to reduce potential side effects, β-blocker concentration monitoring is essential. Chromatographic techniques are employed in a wide range to detect β-blockers and CCBs without interference, among other analytical methods that have been described. For the detection of β-blockers and CCBs, electrochemical sensors provide numerous benefits including sensitivity, selectivity, rapidity, and cost-effectiveness. These sensors can help with patient monitoring in clinical settings, ensuring that the prescription β-blocker dosage is within the therapeutic range. Since β-blockers are frequently consumed by people, the contamination can be occurred through discharge of wastewater. The presence and measurement of β-blockers in water samples enables researchers to evaluate potential risks to aquatic life and public health. In this regard, this review addresses recently developed electrochemical (voltammetric) methodologies and measurement protocols for the determination of both β-blockers and CCBs in pharmaceuticals, biological fluids, and environmental samples. Additionally, this review also provides an overview of the various advanced nanomaterials such as carbon nanotubes, graphene oxide, metal and metal oxide nanoparticles, polymeric structures, zeolite materials, ionic liquids, perovskite semiconductor-based materials, MXenes, Quantum dots, Nano MIPs and various dimensional materials applied to fabricate chemically modified electrodes/electrochemical sensors to determine the β-blockers and CCBs. Moreover supplied are tables listing the analyte, modified electrode, measurement method, measuring medium pH, linear detection range (LDR), limit of detection (LOD) and sensitivity as they are cited in the original research. Furthermore, important conclusions are made from the published reports in the last decade and some future perspectives are also suggested.
Aboshabana R., Zeid A.M., Ibrahim F.A.
2023-07-01 citations by CoLab: 7 Abstract  
In this work, a label-free, rapid, and sensitive synchronous spectrofluorometric method was implemented to assay atenolol (ATL) and ivabradine hydrochloride (IVB) in pharmaceutical and biological matrices. Simultaneous determination of ATL and IVB by conventional spectrofluorometry cannot be implemented because of the clear overlap of the emmision spectra of ATL and IVB.. To overcome this problem, synchronous fluorescence measurements at a constant wavelength difference (Δλ) combined with mathematical derivatization of the zero order spectra were perforemed. The results indicated a good resolution between emission spectra of the studied drugs when the first-order derivative of the synchronous fluorescence scans at Δλ= 40 nm was conducted using ethanol as the optimum solvent which is less hazardous than other organic solvents such as methanol and acetonitrile, keeping the method safe and green. The amplitudes of the first derivative synchronous fluorescent scans of ATL and IVB in ethanol were monitored at 286 and 270 nm to simultaneously estimate ATL and IVB, respectively. Method optimisation was conducted by assessing different solvents, buffer pHs, and surfactants. The optimum results were obtained when ethanol was utilized as a solvent without using any other additives. The developed method was linear over concentration ranges of 10.0–250.0 ng mL-1 for IVB and 100.0–800.0 ng mL-1 for ATL with detection limits of 3.07 and 26.49 ng mL-1 for IVB and ATL, respectively. The method was utilized to assay the studied drugs in their dosages and in human urine samples with acceptable % recoveries and RSD values. The greenness of the method was implemented by three approaches involving the recently reported metric (AGREE) which ensured the eco-freindship and safety of the method.
Yarkaeva Y.A., Dymova D.A., Nazyrov M.I., Zagitova L.R., Maistrenko V.N.
Chimica Techno Acta scimago Q4 Open Access
2023-04-28 citations by CoLab: 0 Abstract  
For the selective detection of the antibiotic lincomycin, we developed a voltammetric sensor based on a glassy carbon electrode modified with reduced graphene oxide and polyarylenephthalide containing diphenylenethio and diphenyleneoxide fragments in the main chain of the polymer in the 1:1 ratio with lincomycin molecular imprints obtained by phase inversion. Using FTIR spectroscopy, electrochemical impedance spectroscopy, cyclic and differential-pulse voltammetry, the electrochemical and analytical characteristics of the sensor were studied. The detection of lincomycin was carried out by differential pulse voltammetry. The linear concentration range was 2.5·10–7–5·10–4 M with a limit of detection of 6.8·10–8 M. It was shown that the presence of molecular imprints increases the sensitivity of the developed sensor in comparisons with a sensor with non-imprinted polymer by a factor of 3.05.
Daneshvar Tarigh G.
Journal of Separation Science scimago Q2 wos Q2
2023-04-12 citations by CoLab: 6

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