Journal of Electroanalytical Chemistry, volume 880, pages 114939

Novel chiral voltammetric sensor for tryptophan enantiomers based on 3-neomenthylindene as recognition element

Publication typeJournal Article
Publication date2021-01-01
scimago Q1
wos Q2
SJR0.755
CiteScore7.8
Impact factor4.1
ISSN15726657, 18732569
General Chemical Engineering
Analytical Chemistry
Electrochemistry
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.
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
Sun Y., He J., Huang J., Sheng Y., Xu D., Bradley M., Zhang R.
2020-05-01 citations by CoLab: 14 Abstract  
Electrochemical chiral interface based on achiral polyethyleneimine (PEI) and chiral peptide (D-BGAc) was constructed using self-assembly technology and used for electrochemical recognition of tryptophan (Trp) enantiomers via differential pulse voltammetry (DPV). Under optimized experimental conditions, the oxidation peak current ratio of D-Trp to L-Trp (ID/IL) was observed to be 3.4 using PEI/D-BGAc/GCE (glass carbon electrode). More interestingly, the PEI/D-BGAc chiral interface exhibited chiral recognition of D- and L-Trp via contact angle measurements. In addition, there was a good linear relationship between the peak current and Trp enantiomer concentration in the range of 0.002–0.15 mM. Finally, the PEI/D-BGAc/GCE system can be used to quickly determine the ratio of isomers in Trp racemic solution, which is of great significance for the chiral recognition in racemic mixtures of chiral compounds. Meanwhile, the PEI/D-BGAc/GCE showed good stability and reproducibility.
Zilberg R.A., Maistrenko V.N., Zagitova L.R., Guskov V.Y., Dubrovsky D.I.
2020-03-01 citations by CoLab: 25 Abstract  
A chiral electrochemical sensor based on carbon black paste electrode (CBPE), consisting of graphitized carbon black powder Carboblack C modified by nanoclusters of 3,4,9,10-perylenetetracarboxylic acid (PTCA) for the selective recognition and determination of warfarin (WA) enantiomers is described in this work. The spontaneous appearance of two-dimensional space group during self-assembly by an external induction of PTCA nanoclusters provides their chirality. It was found that the CBPE modified by PTCA afforded specific interaction with WA enantiomers and acted as a chiral selector, which affected the current and peak potential change. CBPE modified by PTCA was characterized by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS) and scanning electron microscopy (SEM). The electrochemical and analytical characteristics of the sensor, and conditions of the voltammogram registration were studied by differential pulse voltammetry (DPV). The experimental results indicate a linear correlation between the peak current of warfarin enantiomers and their concentration in the range from 5 μM to 0.16 mM, leading to a detection limit of 3.09 μM and 4.02 μM for R- and S-WA, respectively. The potential ability of proposed electrode for WA enantiomer determinations has been evaluated by analyzing human urine and blood plasma with a recovery ranging from 97.1% to 102.9%. The present sensor can determine ratio of WA isomer's in enantiomeric mixture.
Zhang C., Woolfork A.G., Suh K., Ovbude S., Bi C., Elzoeiry M., Hage D.S.
2020-01-01 citations by CoLab: 40 Abstract  
Affinity capillary electrophoresis (ACE) is a separation technique that combines a biologically-related binding agent with the separating power and efficiency of capillary electrophoresis. This review will examine several classes of binding agents that have been used in ACE and applications that have been described for the resulting methods in clinical or pharmaceutical analysis. Binding agents that will be considered are antibodies, aptamers, lectins, serum proteins, carbohydrates, and enzymes. This review will also describe the various formats in which each type of binding agent has been used in CE, including both homogeneous and heterogeneous methods. Specific areas of applications that will be considered are CE-based immunoassays, glycoprotein/glycan separations, chiral separations, and biointeraction studies. The general principles and formats of ACE for each of these applications will be examined, along with the potential advantages or limitations of these methods.
Zil’berg R.A., Maistrenko V.N., Yarkaeva Y.A., Dubrovskii D.I.
Journal of Analytical Chemistry scimago Q3 wos Q4
2019-12-30 citations by CoLab: 16 Abstract  
We developed an enantioselective voltammetric sensor system based on glassy carbon electrodes modified by polyarylenephthalide composites with α-, β-, and γ-cyclodextrins for the selective recognition and determination of tryptophan (Trp) enantiomers. The electrochemical characteristics of the electrodes and surface morphology were studied by cyclic voltammetry, electrochemical impedance spectroscopy, and atomic force microscopy. The proposed sensor system with recording voltammograms by three electrodes and the chemometric processing of the data using principal component analysis and projections to latent structures discriminant analysis was used to recognize tryptophan enantiomers in food additives and to determine their manufacturer.
Wang S., Li L., Xiao Y., Wang Y.
2019-12-01 citations by CoLab: 48 Abstract  
Chirality is one of the basic attributes of nature. Generally, enantiomers exhibit different or even entirely opposite metabolic, toxicological and pharmacological properties in organisms. Hence, chiral recognition is of great importance especially in areas of bioanalysis, pharmaceutics, biomedicines, etc. Cyclodextrins (CDs) are cyclic oligosaccharides with plenty of chiral centers, playing a crucial role in enantiomers discrimination. Due to the unique truncated cone shape structure including a hydrophobic inner cavity and a hydrophilic exterior, CDs are able to recognize optical stereoisomers through host-guest interaction. By far, a board range of analytical techniques has been developed based on CD derivatives for chiral recognition, such as electrochemistry, luminescence, nuclear magnetic resonance (NMR), etc. However, there are still very few reviews focusing on advances in CDs-based enantiomers discrimination techniques. Therefore, we present this review to summarize the recent advances in CDs-based chiral recognition techniques. Both the design strategies and the recognizing mechanisms that transform discriminating process into detectable signals are discussed in details.
Kazan R.M., Seddik H.A., Marstani Z.M., Elsutohy M.M., Yasri N.G.
Microchemical Journal scimago Q1 wos Q1
2019-11-01 citations by CoLab: 26 Abstract  
A sensitive method for the simultaneous detection of eight amino acids (AAs), glycine, alanine, serine, glutamic acid, arginine, tyrosine, phenylalanine, and tryptophan, in different tea species has been developed and validated. This method was based on separation and detection of AAs using high performance liquid chromatography (HPLC), with a fluorescence detector that permits ultra-sensitive detection. Pre-column derivatization was performed to convert the non-fluorescent AAs into fluorescent species, using a specific reagent, o-phthaldialdehyde (OPA) and 3-mercaptopropionic (3MPA), in an optimized ratio of 3:1. A reversed-phase HPLC-column with two gradient phases, acetate buffer (pH 7.6) containing 3% tetrahydrofuran and a mixture of acetate buffer (pH 7.6): acetonitrile: methanol (1:2:2,v/v/v), were used for the separation and detection of AAs over the linear ranges of 0.5–50 nmol/L. Further, the method was validated according to the official guidelines and successfully applied to determine the AAs content in tea products (green, black, oolong, and white). Considerable variations were observed based on the tea quality and type. In summary, this study could be used for the on-line monitoring of the tea production process to determine the grade quality, adulterations and detect the AAs intake.
Yang X., Niu X., Mo Z., Guo R., Liu N., Zhao P., Liu Z.
Electrochimica Acta scimago Q1 wos Q1
2019-10-01 citations by CoLab: 64 Abstract  
A novel approach for the fabrication of chiral sensing platform via the Michael addition or Schiff base reaction between functionalized graphene with polydopamine (rGO-PDA) and L-lysine (L-Lys) was first put forward. GO can be modified and reduced simultaneously via using dopamine. By utilizing catechol functional group on PDA, L-Lys combined with rGO-PDA via the Michael addition or Schiff base reaction. Michael addition reaction occurred between electrophilic conjugate system (L-Lys) and nucleophilic negative carbon ion (rGO-PDA). We firstly synthesized the L-Lys copper (II) (L-Lys-Cu) complex to protect the chiral sites on L-Lys. The terminal amino group on L-Lys-Cu will interact with rGO-PDA by Michael addition or Schiff base reaction to synthesize rGO-PDA/L-Lys copper (II) composite. The copper ions in rGO-PDA/L-Lys copper (II) composite were removed to prepare rGO-PDA-L-Lys chiral composite, which was served as electroactive materials to discriminate tryptophan (Trp) enantiomers via electrochemical method. The results showed that the rGO-PDA-L-Lys showed better affinity for D-Trp than L-Trp owing to the formation of diastereomeric complexes between enantiomer (D-Trp) and selector (L-Lys). Besides, the proposed rGO-PDA-L-Lys showed great application potential in actual samples.
Brooks E.L., Mutengwa V.S., Abdalla A., Yeoman M.S., Patel B.A.
The Analyst scimago Q2 wos Q2
2019-09-16 citations by CoLab: 12 Abstract  
Our study develops a methodology for monitoring of analytes from the kynurenine and serotonin pathway following tryptophan metabolism.
Niu X., Yang X., Mo Z., Liu N., Guo R., Pan Z., Liu Z.
Microchimica Acta scimago Q1 wos Q1
2019-07-20 citations by CoLab: 48 Abstract  
A chiral sensor is described for the enantioselective recognition of L- and D-tryptophan (Trp). The sensor is based on the use of (a) Cu(II) ions coordinated with β-cyclodextrin (Cu-β-CD) that was self-assembled with carboxymethyl cellulose (CD-Cu-CMC) as a chiral selector, (b) of N-doped reduced graphene oxide (N-rGO) as substrate materials, and (c) of differential pulse voltammetry that was used for enantiorecognition. The 3D N-rGO was prepared by using reduced graphene oxide and pyrrole as the starting materials. Electrostatic interaction occurs between the carboxy groups of CMC and Cu(II) ions in Cu-β-CD. The FT-IR, SEM, XRD and XPS techniques showed that 3D N-rGO and the CD-Cu-CMC composite were successfully synthesized. The 3D N-rGO enabled the immobilization of the chiral selector (CD-Cu-CMC) and improves the active areas. A glassy carbon electrode was modified with N-rGO/CD-Cu-CMC and then showed a stronger electrochemical signal for L-Trp than for D-Trp, typically at a working potential of around 0.78 V (vs. SCE). UV-vis spectroscopy proved that CD-Cu-CMC has a higher affinity for D-Trp. The enantioselectivity for D-Trp over L-Trp is 4.72. The modified electrode had a limit of detection of 0.063 μM and 0.0035 μM for L-Trp and D-Trp, respectively, with a linear response range of 0.01 mM to 5 mM. The sensor was used to detect Trp (D- or L-Trp) in spiked real human urine and human serum protein samples.
Yang X., Niu X., Mo Z., Guo R., Liu N., Zhao P., Liu Z.
Microchimica Acta scimago Q1 wos Q1
2019-05-07 citations by CoLab: 55 Abstract  
A composite was prepared from graphene functionalized with 3,4,9,10-perylene tetracarboxylic acid and chitosan (rGO-PTCA-chitosan) by a chemical method. It involves non-covalent functionalization of rGO with PTCA followed by amidation reaction with chitosan. Scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy and electrochemical methods were used to characterize the composites. By combining the chiral features of chitosan and the excellent electrochemical behaviors of rGO-PTCA, a graphene-based material with enantioselectivity was constructed for electrochemical chiral recognition of tryptophan (Trp) enantiomers. A glassy carbon electrode (GCE) modified with rGO-PTCA-chitosan had a higher recognition capability for L-Trp than for D-Trp. Best operated at a working voltage near 0.78 V (vs. SCE), the enantioselectivity coefficient is 3.0. The sensor has a linear response in the 1 mM to 10 mM Trp concentration range and a 1.2 μM detection limit (at S/N = 3) for L-Trp, and of 3.0 μM to D-Trp. The sensor was successfully used to detect Trp enantiomers in real samples, and a recognition mechanism is presented.
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%.
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.
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%.
Zilberg R., Teres Y., Agliulin M., Vakulin I., Bulysheva E., Sycheva M., Maistrenko V.
Electroanalysis scimago Q2 wos Q3
2024-02-15 citations by CoLab: 4 Abstract  
AbstractA voltammetric sensor comprising a paste electrode made of graphitized thermal carbon black CarboblackC and nanosized zeolite MFI was developed for selective recognition and determination of tryptophan enantiomers. It was found that in determining tryptophan enantiomers, the dependence remains linear at concentrations from 5×10−5 to 1×10−3 M. The detection limits of tryptophan L‐ and D‐enantiomers were calculated to be 4.98×10−7 M and 3.20×10−7 M, while their lower limits of determinable concentrations–1.66×10−6 M and 1.07×10−6 M, respectively. The sensor is more sensitive to D‐tryptophan (ΔEp=20 mV, ipD/ipL=1.58). The developed sensor was shown to successfully determine tryptophan enantiomers in model solutions of pure enantiomers, in a mixture of enantiomers, in biological fluids, and in tablet forms of biologically active additives. It was shown that the suggested sensor made it possible to determine the ratio of L‐ and D‐enantiomers of tryptophan in a mixture with a high probability.
Bourigua S., Boussema F., Bouaazi D., Mzoughi Z., Barhoumi H., Majdoub H., Maaref A., Jaffrezic-Renault N.
2024-01-01 citations by CoLab: 3 Abstract  
Pectin from Arthrocnemum indicum leaves (PAI) extracted from plants, harvested in the Tunisian Sahel, was used for the first time as a sensitive matrix for the design of an electrochemical sensor of L-tryptophan via differential pulse voltammetry (DPV). A glassy carbon electrode (GCE) was modified by a PAI layer through simple adsorption, leading to a DPV signal of L-tryptophan that was increased by a factor of 15. The PAI-modified electrode exhibited a good analytical performance towards the detection of L-tryptophan with a wide linear range between 9.10-5 mM to 2.10-2 mM, a detection limit of 0.09 µM, and a sensitivity of 90.15 µA. mM-1. Compared to other reported electrochemical sensors, PAI/GCE presents a lower detection limit, even without the use of nanomaterials. In addition, the PAI/GCE showed good reproducibility and good selectivity towards the determination of L-tryptophan versus other amino acids, uric acid, and ascorbic acid, making it suitable for the determination of L-tryptophan in biological fluids.
Lakshmipriya M., Kolanghiyappan D., Palanisamy N., Banik S., Suresh Kumar P., Selva Ganesan S.
2023-12-01 citations by CoLab: 0 Abstract  
Readily available, axially chiral (S)-BINOL derivative was developed as a probe to electrochemically distinguish between the tryptophan enantiomers. These enantiodiscrimination studies were successfully conducted with only a few nanogram quantity of the chiral probe. The electrochemical investigations revealed a higher current response for d-tryptophan than l-tryptophan (ID-Trp /IL-Trp = 2.319). This preferential interaction for d-tryptophan towards the (S)-BINOL derivative was further elucidated by carrying out density functional theory calculations. The key advantages of the developed method are one-step access to the chiral probe, facile and convenient loading of the probe on the electrode, the requirement of only a minuscule quantity of probe for enantiodiscrimination, and preferential selectivity of probe towards d-tryptophan.
Kaur J., Rangra N.K., Chawla P.A.
Separation Science Plus scimago Q3 wos Q4
2023-08-15 citations by CoLab: 3 Abstract  
AbstractThe process of growth, development, and reproduction cannot take place in a live body without the presence of amino acids (AAs) since they are necessary for appropriate functioning. Detection of AAs in pharmaceutical and food samples is required to ensure quality, quantity, and efficacy. The AAs generally do not contain chromophores; hence their chromatographic analysis requires derivatization. The research papers published in the last few years were used to compile this manuscript. This manuscript covers various analytical, bioanalytical, and electrochemical approaches used in the identification of AAs. The analytical techniques like high‐performance liquid chromatography, ultra‐performance liquid chromatography, etc., and the hyphenated analytical techniques like liquid chromatography‐mass spectrometry, ultra‐performance liquid chromatography‐electrospray tandem mass spectrometry, and hydrophilic interaction ultra‐performance liquid chromatography are also discussed. This manuscript also briefly outlines the electrochemical analytical techniques including sensors and biosensors. This review article will be useful to the researcher working in the area of the development of analytical techniques for the detection of AAs.
Liana R.Z., Ilya A.A., Vadim V.Z., Svetlana I.G., Valery N.M.
2023-07-01 citations by CoLab: 5 Abstract  
Antibiotics are one of the most important bioactive and chemotherapeutic groups of compounds. However, as a result of their excessive consumption for human treatment, veterinary and food industries, it can lead to direct toxic effects, pathogen resistance and allergic hypersensitivity in humans. The situation calls for developing sensitive and selective techniques for antibiotics analysis to monitor their appropriate use, public health, and new drugs design. In this study the glassy carbon voltammetric sensors (GCE) based on layer-by-layer deposited graphene oxide (rGO) and functionalized fullerene (C60) were proposed for the levofloxacin (Lev: S-(–)-Ofloxacin) sensing. Since Lev is an optically active substance, it can be assumed that the sensitive layer of sensor with chiral selector will selectively interact with the antibiotic through various intermolecular interactions. Therefore, a number of selectors with different optical center configurations were obtained and studied, such as S/R-2-chloro-N-(1-phenylethyl)acetamide fullerene (S/R-C60AA), and S/R-N,N'-bis(1-phenylethyl)malonamide fullerene (S/R-C60MA). The structure of obtained selectors was confirmed by NMR and IR spectroscopy, polarimetric studies were carried out. The proposed sensors were characterized by cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) using standard redox probe. Morphological studies were carried out by scanning electron microscopy (SEM). Possible binding sites between Lev and selectors were revealed by computational studies. Some patterns of changes in the electrochemical behavior of Lev depending on the composition of the sensitive layer of the sensor were obtained by differential pulse voltammetry (DPV). Quantitative determination of Lev was carried out using sensor GCE/rGO/S-C60AA. Calibration plot was found to be linear in two ranges, such as 1.0·10−6–3.0·10−5 M and 3.0·10−5–5.0·10−4 M with sensitivity values of 82.14 and 58.71 μA/mM, respectively. The limits of detection and quantitation were calculated to be 3.7·10−8 M and 1.2·10−7 M, respectively (according to 3Sb/m and 10Sb/m). The developed sensor has a simple design, good analytical and operational characteristics compared to some previous reports in the literature. In addition, the sensor was successfully tested for Lev quantification in real samples of biological fluids and pharmaceutical formulations with a good recovery percentage ranged in 91.5–104.4 %.
Nasimi H., Skov Madsen J., Zedan A.H., Malmendal A., Jörn Sloth Osther P., AlZahra'a Alatraktchi F.
Microchemical Journal scimago Q1 wos Q1
2023-07-01 citations by CoLab: 13 Abstract  
Amino acids such as tyrosine and tryptophan have garnered interest in recent years due to their potential use as biomarkers for various diseases. While metabolomic methods have been utilized to detect these amino acids, they can be costly, time-consuming, and require lengthy sample analysis. Electrochemical sensors, on the other hand, offer a simple, cost-effective, and highly sensitive alternative that can be used on-site for detection. This review discusses the application of electrochemical sensing for tyrosine and tryptophan detection in biological fluids, with a focus on their potential as biomarkers. It also covers various types of carbon, nanoparticle, and polymer-based electrochemical electrodes used for tyrosine and tryptophan detection, including their characteristics and performance. Finally, this review provides an overview of the current state of electrochemical detection of tyrosine and tryptophan and outlines directions for future research in this field.
Imanzadeh H., Sefid-Sefidehkhan Y., Afshary H., Afruz A., Amiri M.
2023-06-01 citations by CoLab: 39 Abstract  
Amino acids are the building blocks of proteins and muscle tissue. They also play a significant role in physiological processes related to energy, recovery, mood, muscle and brain function, fat burning and stimulating growth hormone or insulin secretion. Accurate determination of amino acids in biological fluids is necessary because any changes in their normal ranges in the body warn diseases like kidney disease, liver disease, type 2 diabetes and cancer. To date, many methods such as liquid chromatography, fluorescence mass spectrometry, etc. have been used for the determination of amino acids. Compared with the above techniques, electrochemical systems using modified electrodes offer a rapid, accurate, cheap, real-time analytical path through simple operations with high selectivity and sensitivity. Nanomaterials have found many interests to create smart electrochemical sensors in different application fields e.g. biomedical, environmental, and food analysis because of their exceptional properties. This review summarizes recent advances in the development of nanomaterial-based electrochemical sensors in 2017-2022 for the detection of amino acids in various matrices such as serum, urine, blood and pharmaceuticals.
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.

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