Coordination Chemistry Reviews, volume 471, pages 214732

Fast and sensitive recognition of enantiomers by electrochemical chiral analysis: Recent advances and future perspectives

Jie Zou 1
Guoqing Zhao 1
Guo-Ling Zhao 2
Jin-Gang Yu 1
Publication typeJournal Article
Publication date2022-11-01
scimago Q1
wos Q1
SJR4.145
CiteScore34.3
Impact factor20.3
ISSN00108545, 18733840
Materials Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
• The basic principle of rational design of electrochemical chiral sensor for sensing is summarized. • Preparation of doped electrodes and their recognition performance for chiral enantiomers are summarized. • Construction of modified electrodes and their recognition performances are discussed. • The challenges and scientific prospects of new generation of modifiers in electrochemical chiral sensing are proposed. Chiral recognition, especially rendering specificity in biomolecular recognition, is a basic property of many biomolecules. Being closely related to the chirality of biomolecules, it has been regarded as one of the most important areas in biological and medical sciences due to the different effects in biological systems. Based on the possible interactions between chiral selectors and the enantiomers, various methods including chromatographic techniques such as gas or liquid chromatography, electromigration techniques such as capillary electrophoresis and so on were developed for the chiral separation and recognition of different optical isomers. Recently, chemical sensors and biosensors have been gradually designed and developed for the analysis of chiral compounds. Based on the difference in electrical response to different isomers, chiral identifications can be successfully implemented. Major successes in enantiomer recognition based on electrochemical analysis are reviewed. The research data available for highly enantio -selective recognition are categorized into several subgroups according to specific topics and critically discussed for the period since 1994, and the latest techniques for electrochemical chiral recognition of enantiomers were also reviewed. Simultaneously, a brief conclusive summary and future perspectives are presented, and the challenges and scientific prospects of the newest generation of electrode modifiers in electrochemical sensing are also proposed.
Wu D., Tan L., Ma C., Pan F., Cai W., Li J., Kong Y.
Analytical Chemistry scimago Q1 wos Q1
2022-04-07 citations by CoLab: 26 Abstract  
At present, chiral electroanalysis of nonelectroactive chiral compounds still remains a challenge because they cannot provide an electrochemical signal by themselves. Here, a strategy based on a competitive self-assembly interaction of a ferrocene (Fc) unit and the testing isomers entering into the cavity of β-cyclodextrin (β-CD) was carried out for chiral electroanalysis. First of all, the Fc derivative was directly bridged to silica microspheres, followed by inclusion into the cavity of β-CD. As expected, once it was modified onto the surface of a carbon working electrode as an electrochemical sensor, SiO2@Fc-CD-WE, its differential pulse voltammetry signal would markedly decrease compared with the uncovered Fc. Next, when l- and d-isomers of amino acids that included histidine, threonine, phenylalanine, and glutamic acid were examined using SiO2@Fc-CD-WE, it showed an enantioselective entry of amino acids into the cavity of β-cyclodextrin instead of Fc, resulting in the release of Fc with signal enhancement. For histidine, glutamic acid, and threonine, l-isomers showed a higher peak current response compared with d-isomers. The peak current ratios between l- and d-isomers were 2.88, 1.21, and 1.40, respectively. At the same time, the opposite phenomenon occurred for phenylalanine with a peak current ratio of 3.19 between d- and l-isomers. In summary, we are assured that the recognition strategy based on the supramolecular interaction can enlarge the detection range of chiral compounds by electrochemical analysis.
Hou H., Tang S., Liu Y., Wang W., Liang A., Sun L., Luo A.
2022-01-01 citations by CoLab: 7 Abstract  
A faithful and facile strategy to significantly improve the electrochemical chiral recognition ability of chitosan is proposed via drop-coating molybdenum disulfide-ionic liquid (MoS 2 -IL) nanocomposite. • MoS 2 -IL was first used to improve the enantiorecognition ability of CS. • There is a good linear relationship between the DPV peak potential and ee. • The proposed sensor exhibited satisfactory reproducibility and stability. • The proposed sensor exhibited enantiorecognition ability for other enantiomers. A faithful strategy to significantly improve the enantiorecognition ability of chitosan (CS) is proposed via drop-coating molybdenum disulfide (MoS 2 )-ionic liquid (IL) nanocomposite. The present work describes a novel, simple, and effective chiral interface based on MoS 2 -IL/CS nanocomposite which was elaborately integrated to combine the electrical signal amplification and space complexity of MoS 2 -IL and vast enantiorecognition sites of CS for the electrochemical enantiorecognition of tryptophan (Trp) enantiomers. Differential pulse voltammetry (DPV) was adopted to evaluate the potential differences (ΔE P ) between the oxidation peaks of l -Trp and d -Trp. MoS 2 -IL/CS nanocomposite showed higher chiral recognition ability result from spatial asymmetry of MoS 2 -IL/CS. Herein, several parameters, such as drop-coated volume and concentration of MoS 2 -IL, electrodeposited viscosity, time and temperature of CS, detection temperature and pH were optimized in order to obtain a large ΔE P signal between l -Trp and d -Trp, and the ΔE P value can reach 53.3 mV under optimal conditions. Furthermore, different percentages of Trp mixtures and DPV peaks potential were detected with a good linear relationship even in the real sample, which indicated that MoS 2 -IL/CS chiral interface could effectively quantify the enantiomer excess (ee) of Trp enantiomers in Trp mixtures.
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.
Wu D., Ma C., Pan F., Tao Y., Kong Y.
Analytical Chemistry scimago Q1 wos Q1
2021-07-13 citations by CoLab: 15 Abstract  
In the past, various chiral isomers accompanied by electroactive units have been distinguished using electrochemical techniques, which can produce electrochemical signals by themselves. However, it is still difficult to use an electrochemical technique to detect nonelectroactive samples. To address this bottleneck, an electroactive chiral polymer (S,S)-p-CVB-Fc that contains one redox-active ferrocene unit was designed and synthesized in this study. The electroactive polymer can give electrochemical signals as an alternative to the tested chiral samples, regardless of whether the isomers have electroactive units. Then, it was fixed on the surface of a glassy carbon electrode as an electrochemical chiral sensor. When nonelectroactive amino acids including proline, threonine, and alanine were examined by the sensor, clear discrimination in the response of peak current could be observed toward l- and d-isomers at pH 6.5. The peak current ratios (IL/ID) for proline and alanine were 1.47 and 1.48, respectively. In contrast, for threonine, the d-isomer exhibited a higher peak current than the l -isomer with a ratio of 2.59. In summary, the results ensure that the current work can enlarge the testing scope of chiral samples in the field of chiral electroanalysis using an electroactive sensor.
Liu N., Liu J., Niu X., Wang J., Guo R., Mo Z.
Microchimica Acta scimago Q1 wos Q1
2021-04-11 citations by CoLab: 23 Abstract  
A facile chiral composite (3D-NGMWCNT@(S,S)-CIL) was prepared by integrating three-dimensional N-doped graphene oxide multi-walled carbon nanotubes (3D-NGMWCNT) and chiral ionic liquid ((S,S)-CIL) via electrodeposition. SEM, XRD, XPS, and electrochemical methods were used to characterize this composite and it revealed that the integrated 3D-NGMWCNT@(S,S)-CIL composite showed excellent electrochemical performance. Therefore, a 3D-NGMWCNT@(S,S)-CIL/GCE electrochemical sensor was constructed for enantioselective recognition of Trp enantiomers. The coefficient (IL/ID) of the 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor was 2.26 by differential pulse voltammograms (DPV), revealing that the synthesized 3D-NGMWCNT@(S,S)-CIL had a higher affinity for L-Trp than D-Trp. Moreover, UV-V is spectroscopy and a water contact angle test also proved this result. The 3D-NGMWCNT@(S,S)-CIL/GCE sensor had a detection limit of 0.024 μM and 0.055 μM, and sensitivity of 62.35 μA·mM−1·cm−2 and 30.40 μA·mM−1·cm−2 for L-Trp and D-Trp, respectively, with a linear response range of 0.01 to 5 mM. In addition, the 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor showed excellent stability, and good reproducibility and was applied to detect L-Trp or D-Trp in real samples. The novel 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor provides an efficient and convenient strategy for chiral enantioselective recognition.
Grecchi S., Ferdeghini C., Longhi M., Mezzetta A., Guazzelli L., Khawthong S., Arduini F., Chiappe C., Iuliano A., Mussini P.R.
ChemElectroChem scimago Q2 wos Q2 Open Access
2021-04-01 citations by CoLab: 11 Abstract  
Chiral ionic liquids (CILs), or ionic liquids (ILs) with chiral additives, are very attractive chiral media for enantioselective electroanalysis, on account of their high chiral structural order at the electrochemical interphase. A family of molecular salts with CIL properties is now introduced, based on the chiral steroid building block of deoxycholic acid implemented either in the anion or cation. Testing them as chiral additives in a commercial achiral IL, they enable voltammetric discrimination of the enantiomers of a model chiral probe on disposable screen-printed electrodes in terms of peak potential differences, which is the most desirable transduction mode of the enantiorecognition event. The probe enantiomer sequence is the same for all selectors, consistent with their sharing the same chiral building block configuration. This proof-of-concept widens the application fields of bile acid derivatives as chiral selectors, while also enriching the still very few CIL families so far explored for applications in chiral electroanalysis.
Sun Z., Hou J., Li L., Tang Z.
Coordination Chemistry Reviews scimago Q1 wos Q1
2020-12-01 citations by CoLab: 46 Abstract  
Chirality is well known as a ubiquitous feature for the sustainability of life in nature. For instance, chiral substances with pure enantiomeric forms are essential for the generation and evolution of life. Therefore, the chiral separation of enantiomers is of great significance in both life science and pharmaceutical industry. The two most widely adopted chiral separation strategies are chromatographic separation and membrane-assisted separation, the latter one of which is promising for large-scale production due to its potential advantages. In this review, we summarized the innovative materials with intrinsic micropores developed in recent years and their application for chiral resolution either as stationary phases in chromatography or as separation membranes, including metal organic frameworks (MOFs), covalent organic frameworks (COFs), modified graphene or graphene-oxides (GO), porous organic cages (POCs) and others.
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.
Zou J., Lan X., Zhao G., Huang Z., Liu Y., Yu J.
Microchimica Acta scimago Q1 wos Q1
2020-11-03 citations by CoLab: 21 Abstract  
A novel chiral sensing platform, 6-O-α-maltosyl-β-cyclodextrin (Mal-βCD)-based film, is proposed for selective electrochemical recognition of tyrosine (Tyr) enantiomers. Black phosphorus nanosheets (BP NSs) and Mal-βCD modified glassy carbon electrode (Mal-βCD/BP NSs/GCE) were prepared by a layer-to-layer drop-casting method, and the platform was easy to fabricate and facile to operate. It is proposed that the amino and hydroxyl groups of the Tyr enantiomers and the chiral hydroxyl groups of Mal-βCD selectively form intermolecular hydrogen bonds to dominate effective chiral recognition. Two linear equations of Ip (μA) = 11.40 CL-Tyr (mM) + 0.28 (R2 = 0.99147) and Ip (μA) = 7.96 CD-Tyr (mM) + 0.22 (R2 = 0.99583) in the concentration range 0.01–1.00 mM have been obtained. The limits of detection (S/N=3) for L-Tyr and D-Tyr were 4.81 and 6.89 µM, respectively. An interesting phenomenon was that the value of IL-Tyr/ID-Tyr (1.51) in this work was slightly higher than the value of IL-Trp/ID-Trp (1.49) reported in our previous study, where tryptophan (Trp) enantiomers were electrochemically recognized by Nafion (NF)-stabilized BPNSs-G2-β-CD composite. The two similar sensors fabricated by different methods showed different recognition ability toward either Tyr or Trp enantiomers, and the underlying mechanism was discussed in detail. More importantly, the proposed chiral sensor enables prediction of the percentages of D-Tyr in racemic Tyr mixtures. The chiral sensor may provide a novel approach for the fabrication of novel chiral platforms in the practical detection of L- or D-enantiomer in racemic Tyr mixtures. Graphical abstract
Wu D., Pan F., Gao L., Tao Y., Kong Y.
Analytical Chemistry scimago Q1 wos Q1
2020-09-22 citations by CoLab: 22 Abstract  
Although an increasing number of researchers are developing electroanalytical protocols for the chiral recognition of amino acids, the electroactive units of the tested isomers still need to provide corresponding electrical signals. In this study, a supramolecular system was developed for the chiral electroanalysis of amino acids regardless of electroactive units. As a model system, an enantiopure electroactive molecule Fc-(S,S)-1 that includes a ferrocenyl group was synthesized and acted as a guest. Moreover, hydrophobic cyclobis-(paraquat-p-phenylene) (CBPQT4+-2) was used as the host. In the presence of π-π stacking and the attraction of π-electrons, CBPQT4+-2 can encapsulate Fc-(S,S)-1 into its cavity. Next, a screen-printed electrode was utilized for electrochemical chiral recognition. The host was fixed on the surface of the working electrode, and the guest was used as the electroactive chiral selector to support electron transfer. Once different configurations of amino acids (threonine, histidine, glutamine, and leucine) were mixed with the guest, regardless of whether they contained electroactive units, differences in the cyclic voltammetry results of the probe enantiomers could be observed, namely, in the peak currents or peak potentials. However, glutamine was an exception because the L-isomer had a stronger binding affinity with Fc-(S,S)-1 + Cu(II), which would limit the transport of the complex into the cavity of CBPQT4+-2, thereby resulting in a low peak current. Thus, an inverse phenomenon was observed with glutamine. In summary, we believe that this work can increase the testing scope for the chiral recognition of different kinds of isomers using electrochemical tools.
Hu M., Feng H., Yuan Y., Zheng Y., Tang B.Z.
Coordination Chemistry Reviews scimago Q1 wos Q1
2020-08-01 citations by CoLab: 228 Abstract  
• Chiral AIE compounds are recently developed very rapidly. • Chiral AIEgens display excellent chiral recognition, ee analysis and CPL properties. • Review paper about preparation of chiral AIEgens and their applications is scarce. Due to immense potential in using as chemo/biosensors and solid emitters, aggregation-induced emission (AIE) phenomenon is attracting huge interest in scientific community. After endowed with chirality, the resultant chiral AIE luminogens (AIEgen), just like a tiger with added wings, can display more and stronger promising functionalities. Moreover, many classic luminophores can be transformed into AIEgens from notorious aggregation-caused quenching (ACQ) compounds as soon as they are attached with chiral groups. Compared with other chiral fluorescent receptors and chiral emitter, chiral AIEgens have displayed unique and outstanding advantages. Firstly, chiral AIEgen can differentiate two enantiomers of chiral analyte by 1.68 × 10 4 fold difference and get a chiral magnification up to 2.5 × 10 3 times due to aggregation. In addition, two enantiomers of up to 18 chiral carboxylic acids can be recognized just by using only one chiral AIEgen receptor and enantiomeric excess (ee) of chiral analytes at uM level can be measured. Furthermore, accurate ee analysis was carried out for the first time from fluorescence wavelength change rather than intensity change of the chiral AIEgen receptor. Therefore, the chiral AIEgens show unprecedentedly high selectivity, high sensitivity, high applicability, and high accuracy. Secondly, in the area of organic circularly polarized luminescence (CPL) materials, the CPL dissymmetry factor (g lum ) of chiral AIEgen can get to 1.42 that is near to the theoretical value of 2, making a breakthrough progress while the |g lum | of previous organic luminophores is generally between 10 −5 and 10 −2 . Furthermore, the highly efficient circularly polarized organic light-emitting diodes (CPOLEDs) are constructed for the first time by chiral AIEgens. Thirdly, chiral AIEgens enable novel display technology under different lighting conditions to be possible. More importantly, due to AIE effect, AIEgens are very beneficial for disclosing the mechanism of chiral transfer and magnification between molecules, which is thought to be the key for evolution of homochirality in natural world and preparation of chiral materials with hierarchical structures. For the above reason, chiral AIEgens have been brought to extensive attention and a large number of research works about them are reported. To take an overall view on chiral AIEgens and facilitate the development of chiral AIEgens, it is necessary to make a full review on the chiral AIEgens. This review covers the following contents: (1) construction of chiral AIEgens including propeller-like chiral AIEgens, chiral AIEgens with optically pure groups, polymer chiral AIEgens and supramolecular chiral AIEgen system; (2) chiral recognition and ee determination of chiral carboxylic acids, chiral amines, α-amino acids, and chiral neutral molecules by chiral AIEgens; (3) performance of chiral AIEgens in circular dichroism (CD), CPL and CPOLEDs; (4) other versatile application researches related to chiral AIEgens.
Zou J., Yu J.
2020-07-01 citations by CoLab: 49 Abstract  
In this work, we have fabricated nafion (NF) stabilized black phosphorus nanosheets (BPNSs) and 6-O-α-maltosyl-β-cyclodextrin (G2-β-CD) composite (BPNSs-G2-β-CD) as novel electrochemical sensoring platform for chiral recognition of tryptophan (Trp) enantiomers. BPNSs-G2-β-CD composite modified glassy carbon electrode (BPNSs-G2-β-CD/GCE) was further coated with NF which served as a protective film to immobilize BPNSs-G2-β-CD on the electrode surface to achieve high stability. Under the optimum conditions, the oxidation peak current ratio of L-Trp to D-Trp (IL/ID) and the difference between the peak potential (ΔEp = ED - EL) were observed to be 1.49 and 20 mV at NF/BPNSs-G2-β-CD/GCE by square wave voltammetry (SWV). In addition, a linear calibration curve could be obtained for peak current versus Trp enantiomers in the concentration range 0.01–1.00 mM with detection limits of 1.07 μM and 1.71 μM for L-Trp and D-Trp (signal-to-noise ratio of 3, S/N = 3), respectively. The chiral recognition mechanism was also proposed, and the intermolecular hydrogen bonding interactions as well as the hydrophobic-cavity-triggered embedding effect dominated the effective chiral recognition. Moreover, the proposed NF/BPNSs-G2-β-CD/GCE showed excellent stability, good reproducibility and anti-interference capability. Therefore, the designed chiral sensor is expected to be practically applied for the sensitive recognition of Trp enantiomers in real samples.
Niu X., Yang X., Mo Z., Wang J., Pan Z., Liu Z., Shuai C., Liu G., Liu N., Guo R.
Bioelectrochemistry scimago Q2 wos Q2
2020-02-01 citations by CoLab: 32 Abstract  
We report a novel chiral interface based on polysaccharides that was integrated via an amidation reaction between the COOH of sodium alginate and the NH2 of chitosan to form a chiral selector (SA-CS) with three dimensional N-doped graphene-CNT (NGC) as the substrate material. This interface was used for chiral discrimination of tryptophan (Trp) enantiomers via electrochemical measurements. The FT-IR, SEM, TEM and XPS characterization showed that the chiral selector and substrate materials were prepared successfully. Compared with individual SA-CS and NGC, the integrated polysaccharides/3D NGC showed higher enantioselectivity for L-Trp than D-Trp due to the smaller steric hindrance for D-Trp during the formation of three-point interactions between the two diastereoisomeric enantiomer-selector complexes, which allowed L-Trp to more easily detach from the electrode modification layer and approach the electrode surface, facilitating its approach and confirming that SA-CS had a higher constant for L-Trp when applied to real samples.
Ye Q., Yin Z., Wu H., Wu D., Tao Y., Kong Y.
Electrochemistry Communications scimago Q1 wos Q2 Open Access
2020-01-01 citations by CoLab: 30 Abstract  
Cu and Pt nanoparticles (NPs) were simultaneously integrated with glutathione (GSH), and the resultant Cu-Pt NPs decorated GSH (GSH-Cu/Pt) was characterized by FT-IR and X-ray photoelectron spectroscopy (XPS). Next, the GSH-Cu/Pt was used for electrochemical chiral sensing of tyrosine (Tyr) enantiomers, and the results show that the recognition efficiency, indicated by peak current ratio of L-Tyr to D-Tyr and peak potential separation, of the GSH-Cu/Pt is superior to those of GSH, Cu NPs decorated GSH (GSH-Cu) and Pt NPs decorated GSH (GSH-Pt). The higher affinity of GSH-Cu/Pt to L-Tyr than D-Tyr is further confirmed by density functional theory (DFT) and UV spectra.
Singh S.K., Savoy A.W.
Journal of Molecular Liquids scimago Q1 wos Q1
2020-01-01 citations by CoLab: 851 Abstract  
Over the past two decades, ionic liquids (ILs) have had a wide range and cutting-edge impact, generating promising science and technologies and have also expanded exponentially in terms of their publications. They have been utilized for both academic and industrial applications. They are potential candidates for solving some of the major issues society is currently faced with by emerging as a clean, efficient, and eco-friendly alternative resource of volatile organic solvents along with many more significant benefits due to their unique thermal, physical, chemical and biological properties. Furthermore, these properties could be modified depending on their application by altering the combination of cations and anions. However, their synthesis and purification require standard synthesis methods to certify their consistent reproducibility. The yields from ILs at large scales for the industrial applications along with their synthesis, toxicity and environmentally friendly nature have become the main concerns. The aim of this review is to investigate the current literature that describes the cutting-edge-knowledge regarding the synthesis of various classes of homogeneous (task specific-ILs, chiral-ILs, switchable polarity solvent ILs, bio-ILs, poly-ILs, energetic-ILs and many more) and heterogeneous (supported-ILs) ILs. Fundamental aspects of ILs such as the green aspects, environmental impacts and purity of ILs are also discussed. The potential applications of ILs in electro-chemistry, solvent, engineering, catalysis, biological aid, physical chemistry, analytical chemistry and many more are briefly explained. In addition, the explanations based on purifications and recovery of ILs by using single or combined methods along with their physico-chemical properties were also reviewed. Moreover, the comprehensive study summarizes the latest progress on assorted classes of ILs along with discussing their prospective applications in the first half. The synthesis of homo/heterogeneous ILs is thoroughly elaborated in the second half. Finally, the future prospective medical applications of ILs are also mentioned.
Stoian I., Iacob B., Oprean R., Bodoki E.
Electrochimica Acta scimago Q1 wos Q1
2024-09-01 citations by CoLab: 2 Abstract  
The present study aims to explore the interaction mechanisms between propranolol (PRNL) enantiomers and bare and L/D-Cysteine modified gold nanoparticles (L/D-Cys−AuNPs) surfaces, using electrochemical (cyclic voltammetry, differential pulse voltammetry, electrochemical impedance spectroscopy) and microcalorimetric (isothermal titration calorimetry) techniques. In the absence of a chiral environment, PRNL enantiomers are strongly physisorbed on the AuNPs modified surface, yet no significant difference was recorded in the oxidation peak potential (+0.778 V R(+)-PRNL versus +0.78 V for S(-)-PRNL). Upon decorating AuNPs with L-Cys, an ∼40 mV anodic shift is recorded for S(-)-PRNL due to a more favored orientation of its diastereoisomer on the electrode's surface towards electron transfer. Interestingly, by altering the conformation of the diastereoisomeric chiral selector (replacing L-Cys with D-Cys), the enantioselective nature of the recorded electrochemical signals fades out. Additionally, the potential synergistic effects of a dual chiral system, based on the covalently bound L-/D-Cys−AuNPs and β-cyclodextrin (β-CD), a free, host-guest type chiral selector, added to the electrolyte, has also been studied.
Yang M., Su T., Zhao J., Gao Z., Song Y., Guo J., Zhao C.
Analytica Chimica Acta scimago Q1 wos Q1
2024-09-01 citations by CoLab: 0 Abstract  
Chirality, an inherent characteristic of natural substances (such as sugars, peptides, proteins, and nucleic acid), plays a vital role in human metabolism and exerts substantial impacts. In general, chiral drugs can display diverse pharmacological and pharmacokinetic properties. One enantiomer may exhibit therapeutic effects, while the other could cause adverse reactions. Selective recognition of enantiomers is thus a significant task in the biomolecular and pharmaceutical fields. Despite the development of several chiral identification techniques, low-cost enantioselective sensing methods remain highly desirable. Here, we designed and developed an electrochemical sensing device for reductive enantiomer identification using natural wood channels as the substrate. The wood channels were endowed with oxidase-like activity through the in-situ growth of cerium oxide nanoparticles (CeO
Zhang X., Zhou X., Hu Z., Lu D., Chen Y., Feng L.
2024-08-01 citations by CoLab: 0 Abstract  
The recognition and separation of stereoselective molecules with similar chemical properties and structures are of great biological significance. Developing a highly effective chiral recognition platform is crucial for further research on chiral molecules. Herein, a chiral aptamer-modified gold nanoclusters functionalized electrochemical device that exhibits an ideal platform for enantioselective recognition is reported. Its electrochemical current restriction amplification strategy enables stereoselective signal amplification on an electrode. It is found that introducing chiral aptamers into the gold nanoclusters would result in a nice chiral tyrosinamide recognition. This work has a liner range ranging from 1 nM to 10 μM. Furthermore, the ratio of the peak current change was 4. This study might provide a useful strategy for designing sensitive chiral recognition devices with chiral aptamer-modified materials and restricting their electrochemical currents.
Hosseini F., Dashtian K., Golzani M., Ejraei Z., Zare-Dorabei R.
Analytica Chimica Acta scimago Q1 wos Q1
2024-08-01 citations by CoLab: 2 Abstract  
Monitoring the levels of L-Tryptophan(L-Trp) in body fluids is crucial due to its significant role in metabolism and protein synthesis, which ultimately affects neurological health. Herein, we have developed a novel magneto-responsive electrochemical enantioselective sensor for the recognition of L-Trp based on oriented biochar derived from Loofah, Fe3O4 nanoparticles, and molecularly imprinted polydopamine (MIPDA) in xanthan hydrogel. The successful synthesis of these materials has been confirmed through physicochemical and electrochemical characterization. Various operational factors such as pH, response time, loading sample volume, and loading of active materials were optimized. As a result, the sensor exhibited an affordable linear range of 1.0-60.0 μM, with a desirable limit of detection of 0.44 μM. Furthermore, the proposed electrochemical sensor demonstrated good reproducibility and desirable selectivity for the determination of L-Trp, making it suitable for analyzing L-Trp levels in human plasma and serum samples. The development presented offers an appealing, easily accessible, and efficient strategy. It utilizes xanthan hydrogel to improve mass transfer and adhesion, biochar-stabilized Fe3O4 to facilitate magnetic orientation and accelerate mass transfer and sensitivity, and polydopamine MIP to enhance selectivity. This approach enables on-site evaluation of L-Trp levels, which holds significant value for healthcare monitoring and early detection of related conditions.
Di Filippo I., Anfar Z., Magna G., Pranee P., Monti D., Stefanelli M., Oda R., Di Natale C., Paolesse R.
Nanoscale Advances scimago Q1 wos Q2 Open Access
2024-07-19 citations by CoLab: 2 PDF Abstract  
An enantioselective array comprised of chiral silica nanohelices grafted with porphyrins shows the capability of recognizing enantiomers with high classification accuracies.
Satapathy S., Kumar S., Kurmi B., Gupta G., Patel P.
Chirality scimago Q2 wos Q2
2024-07-04 citations by CoLab: 3 Abstract  
ABSTRACTChirality, the property of molecules having mirror‐image forms, plays a crucial role in pharmaceutical and biomedical research. This review highlights its growing importance, emphasizing how chiral drugs and nanomaterials impact drug effectiveness, safety, and diagnostics. Chiral molecules serve as precise diagnostic tools, aiding in accurate disease detection through unique biomolecule interactions. The article extensively covers chiral drug applications in treating cardiovascular diseases, CNS disorders, local anesthesia, anti‐inflammatories, antimicrobials, and anticancer drugs. Additionally, it explores the emerging field of chiral nanomaterials, highlighting their suitability for biomedical applications in diagnostics and therapeutics, enhancing medical treatments.
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.

Top-30

Journals

1
2
3
4
1
2
3
4

Publishers

2
4
6
8
10
12
14
16
2
4
6
8
10
12
14
16
  • We do not take into account publications without a DOI.
  • Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Share
Cite this
GOST | RIS | BibTex
Found error?