Voltammetric chiral recognition of naproxen enantiomers by N-tosylproline functionalized chitosan and reduced graphene oxide based sensor

Kabirova, L. R.; Yarkaeva, Yu. A.; Zagitov, Vadim V.; Nazyrov, Marat; Gainanova, Svetlana; Maistrenko, V. N.

doi:10.1016/j.jelechem.2022.116744

Cited by 23 publications

(7 citation statements)

References 47 publications

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“…The GO spectrum indicates that the stretching vibration peaks at 1612 cm −1 and 1726 cm −1 pertain to C=C and C=O, the absorption peaks at 1050 cm −1 and 1240 cm −1 pertain to C-O-C and -OH, and the characteristic peak at 3410 cm −1 pertains to the stretching vibration of -OH. Compared to GO, the disappearance of C=O at 1726 cm −1 for 3D-rGO indicates that GO was successfully reduced [37,38]. Curve 3D-rGO-CS-BSA showed the bending vibration of -NH and the stretching vibration of -CN have two absorption peaks at 1650 cm −1 and 1135 cm −1 , respectively.…”

Section: Ft-ir and Raman Spectra Of Go 3d-rgo And 3d-rgo-cs-bsamentioning

confidence: 96%

Functionalized Three–Dimensional Graphene Containing Chitosan and Bovine Serum Albumin for Recognizing Chiral Drug Intermediates

Yao

Xie

et al. 2023

Chemosensors

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Chiral enantiomer recognition has important research significance in the field of analytical chemistry research. At present, most prepared chiral sensors are used for recognizing amino acids, while they are rarely used in the identification of drug intermediates. This work found that combining CS and reduced graphene oxide can enhance conductivity, increasing the recognition effect by connecting CS with BSA. Based on the above preparation, a new type of chiral sensor (3D−rGO−CS−BSA) was synthesized for the identification of drug intermediates, including the 1−Boc−3−hydroxypyrrolidine enantiomer. An obvious difference was achieved (IR/IS = 2.82) in the oxidation peak currents between the two enantiomers. The detection limits of the R−enantiomer and S−enantiomer were 4.85 nM and 11.76 nM, respectively. The proposed electrochemical sensing platform also has better potential for detecting the percentage content of mixed chiral enantiomer drugs.

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Section: Ft-ir and Raman Spectra Of Go 3d-rgo And 3d-rgo-cs-bsamentioning

confidence: 96%

Functionalized Three–Dimensional Graphene Containing Chitosan and Bovine Serum Albumin for Recognizing Chiral Drug Intermediates

Yao

Xie

et al. 2023

Chemosensors

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“…While a significant number of voltammetry protocols on various electrode surfaces have been proposed for determination of ketoprofen (e. g. [20] and references herein cited), ibuprofen (e. g. [18,19] ) and especially naproxen (e. g. [21][22][23] ) irrespective of the enantiomer configuration, only a few works deal with enantiorecognition, and mostly result in enantiomer current differences, by far less useful, rather than in potential differences. [32][33][34][35][36] In this frame, naproxen and ketoprofen, which have respectively an oxidation and a reduction process observable at conveniently mild potentials (Figures SI.9.1, SI.9.2 and SI.9.3, Table SI.9.1) (while ibuprofen features both an oxidation and a reduction process in the available potential window, both of them however closer to the background, Figure SI.9.4, Table SI.9), have been selected as model chiral profen probes, and tested in their (S)-enantiopure forms on both (R)-and (S)enantiomers of selector oligomer films, a test actually equiv-alent to testing both probe enantiomers on a single enantiopure film, as in the former case.…”

Section: B) Two Examples Of Profens Non-steroidal Anti-inflammatory D...mentioning

confidence: 99%

Designing Powerful Biindole‐Based Inherently Chiral Selectors: Enhancing Enantiodiscrimination by Core Functionalization with Additional Coordination Elements

Grecchi,

Bonetti,

Emanuele

et al. 2024

Chemistry A European J

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Among inherently chiral selectors of axial stereogenicity, usually resulting in very good enantiodiscrimination performances, the biindole‐based family has the additional advantage of very easy functionalization of the two nitrogen atoms with a variety of substituents with desirable properties. Aiming to evaluate the possibility of exploiting such feature to enhance the enantiodiscrimination ability of the archetype structure, a series of three inherently chiral monomers were designed and synthesized, characterised by a 2,2’‐biindole atropisomeric core conjugated to bithiophene wings enabling fast and regular electrooligomerization, and functionalised at the nitrogen atoms with an ethyl, a methoxyethyl, or a hydroxyethyl substituent. Nitrogen alkylation was also exploited to obtain for the first time the chemical resolution of the biindole selectors without employing chiral HPLC. The enantiodiscrimination ability of the selector series was comparatively evaluated in proof‐of‐concept chiral voltammetry experiments with a “benchmark” chiral ferrocenyl probe as well as with chiral non‐steroidal anti‐inflammatory drugs naproxen and ketoprofen. The large enantiomer potential differences for all probes increased in the ethyl < methoxyethyl ≪ hydroxyethyl sequence of selector substituents, supporting our assumption on the beneficial role of an additional coordination element. The powerful hydroxyethyl selector was also applied to ketoprofen in a commercial drug matrix.

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“…[18][19][20] However, the sensor layer obtained by simple application of chiral compound to the electrode is often unstable over time, mechanically fragile, and not sensitive enough to the analyte. One of the options for improving its characteristics can be the use of a combination of chiral selectors and carbon nanomaterials such as carbon nanotubes, 21,22 reduced graphene oxide, 23,24 and carbon black. 25,26 Porous carbon materials are an ideal background for the immobilization of initially chiral modifiers on the electrode due to the large surface area and high electrical conductivity.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective voltammetric sensor based on mesoporous graphitized carbon black Carbopack X and fulvene derivative

et al. 2023

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For medicine and pharmaceuticals, the problem of determining and recognizing the enantiomers of biologically active compounds is an actual issue because the enantiomers of the same substance can have different effects on living organisms. This paper describes the development of an enantioselective voltammetric sensor (EVS) based on a glassy carbon electrode (GCE) modified with mesoporous graphitized carbon black Carbopack X (CpX) and a fulvene derivative (1S,4R)‐2‐cyclopenta‐2,4‐dien‐1‐ylidene‐1‐isopropyl‐4‐methylcyclohexane (CpIPMC) for recognition and determination of tryptophan (Trp) enantiomers. Synthesized CpIPMC was characterized by 1H and 13C nuclear magnetic resonance (NMR), chromatography–mass spectrometry, and polarimetry. The proposed sensor platform was studied by Fourier‐transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), cyclic voltammetry (CV), and electrochemical impedance spectroscopy (EIS). Using the square‐wave voltammetry (SWV), it was established that the developed sensor is an effective chiral platform for the quantitative determination of Trp enantiomers, including in a mixture and in biological fluids like urine and blood plasma, with adequate precision and recovery ranged from 96% to 101%.

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Voltammetric chiral recognition of naproxen enantiomers by N-tosylproline functionalized chitosan and reduced graphene oxide based sensor

Cited by 23 publications

References 47 publications

Functionalized Three–Dimensional Graphene Containing Chitosan and Bovine Serum Albumin for Recognizing Chiral Drug Intermediates

Functionalized Three–Dimensional Graphene Containing Chitosan and Bovine Serum Albumin for Recognizing Chiral Drug Intermediates

Designing Powerful Biindole‐Based Inherently Chiral Selectors: Enhancing Enantiodiscrimination by Core Functionalization with Additional Coordination Elements

Enantioselective voltammetric sensor based on mesoporous graphitized carbon black Carbopack X and fulvene derivative

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