Chiral recognition of penicillamine enantiomers based on a vancomycin membrane electrode

Wang, Yonghua; Han, Qian; Zhang, Qing; Huang, Yihan; Guo, Lingyu; Fu, Yingzi

doi:10.1039/c3ay40882e

Cited by 12 publications

(5 citation statements)

References 41 publications

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“…Many biochemical processes, to function correctly, also require a particular handedness enantiomer. This is observed in the metabolism of pharmaceuticals such as thalidomide ( 4 ) and penicillamine ( 5 ), wherein one enantiomer produces medicinal effects and the other toxicity. Thus, enantiomer discrimination techniques such as circular dichroism (CD) spectroscopy are essential for minimizing the toxic effects of medications ( 6 , 7 ), developing effective treatments for diseases ( 8 , 9 ), and probing the nature of chiral systems ( 10 ).…”

Section: Introductionmentioning

confidence: 99%

Microscopic origin of the chiroptical response of optical media

et al. 2019

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The potential for enhancing the optical activity of natural chiral media using engineered nanophotonic components has been central in the quest toward developing next-generation circular-dichroism spectroscopic techniques. Through confinement and manipulation of optical fields at the nanoscale, ultrathin optical elements have enabled a path toward achieving order-of-magnitude enhancements in the chiroptical response. Here, we develop a model framework to describe the underlying physics governing the origin of the chiroptical response in optical media. The model identifies optical activity to originate from electromagnetic coupling to the hybridized eigenstates of a coupled electron-oscillator system, whereas differential absorption of opposite handedness light, though resulting in a far-field chiroptical response, is shown to have incorrectly been identified as optical activity. We validate the model predictions using experimental measurements and show them to also be consistent with observations in the literature. The work provides a generalized framework for the design and study of chiroptical systems.

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Section: Introductionmentioning

confidence: 99%

Microscopic origin of the chiroptical response of optical media

et al. 2019

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“…On the other hand, L-Pen enantiomer is known to be toxic and can inhibit the production of vitamin B6. 27 We synthesized isoreticular MOFs comprised of Co(II), L-GG: glycyl-L(S)-glutamate, and either bipy: 4,4ʹ-bipyridyl or bipy-type pillar linkers to test the enantioselective adsorption of DL-Pen. These MOFs are made of one-dimensional dipeptide ladders connected by bipy-type linkers of varying size and functionality, enabling the generation of homochiral MOFs with adjustable porosity (Figure 2a).…”

Section: Introductionmentioning

confidence: 99%

Tuning Enantioselective Drug Adsorption in Isoreticular Homochiral Metal-Peptide Frameworks through Proximity Pore Interactions

Ho,

Yadav,

Gładysiak

et al. 2023

Preprint

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Pharmaceutical research places great importance on the stereochemistry and enantioseparation of racemic drugs due to the potential variations in pharmacological and toxicological properties displayed by different enantiomers as they interact with the body’s metabolic pathway. Metal-organic frameworks (MOFs) are porous adsorbents that can be designed to possess homochirality within their structures, enabling tunable porosity and enantioselective adsorption. In our study, we present the synthesis of five novel and homochiral Co-L-GG(R) MOFs (where L-GG = glycyl-L(S)-glutamic acid and R = bipyridyl (bipy) pillar ligands). These isoreticular MOFs were synthesized using the ligand extension strategy. This approach allowed us to systematically control the pore sizes of the MOFs, enabling fine-tuning of the enantioselective adsorption of racemic drugs, primarily DL-Penicillamine (Pen). Our findings reveal that the pore size greatly influences enantioselective adsorption, where too large or too small pores hinder the proximity-driven dispersive interactions between the drug and the pore surface, resulting in poor enantioselective adsorption of Pen. We achieved an enantiomeric excess (ee) of 60.1% (L over D), increasing to a maximum 76.1% ee using Co-L-GGvinylbipy by tuning proximity interactions in saturated pores. These results were accomplished by controlling the drug saturation within the MOF pores, promoting favorable interactions.

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“…D-penicillamine (D-Pen) can treat Wilson’s disease and rheumatoid arthritis [ 18 , 19 , 20 ], and it has been used as an antidote for poisoning from copper and lead, among others [ 21 , 22 , 23 ]. In contrast, studies have found that L-penicillamine (L-Pen) is toxic and can cause neuritis and marrow damage [ 24 , 25 ]. Currently, the methods for detection and isolation of penicillamine involve flow injection [ 26 ], chromatography [ 27 , 28 , 29 ], spectrometry [ 30 , 31 , 32 ], colorimetric method [ 33 ], and electrochemical method [ 34 , 35 , 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

“…The dsDNA sequences were dsDNA 1 (AAAAAAAAAAAA-TTTTTTTTTTTT), dsDNA 2 (ACACACACACAC-TGTGTGTGTGTG), dsDNA 3 (AGAGAGAGAGAG-TCTCTCTCTCTC), dsDNA 4 (ATATATATATAT-TATATATATATA) and dsDNA 5 (CGCGCGCGCGCG-GCGCGCGCGCGC) respectively; Figure S2: The effect embedding time of 1.0 × 10 −5 mol/L of L-Pen embedded in different dsDNA in 0.005 mol/L of K 4 [Fe(CN) 6 ]/K 3 [Fe(CN) 6 ] (contain 0.1 mol/L KCl) solution over a potential range from +0.6 V to −0.2 V, with a scan rate of 50 mV/s and pulse amplitude of 50 mV; Figure S3: Characterization of L-Pen treated by each double-stranded DNA by AGE (a: dsDNA 1 , b: dsDNA 2 , c: dsDNA 3 , d: dsDNA 4 , e: dsDNA 5 , f: dsDNA 1 -L-Pen, g: dsDNA 2 -L-Pen, h: dsDNA 3 -L-Pen, i: dsDNA 4 -L-Pen, j: dsDNA 5 -L-Pen, k: DNA marker); Figure S4: The formation of MIPs/dsDNA via electropolymerization (Scan rate:50 mV/s; cycle number: 15; working potential: 0~0.8 V); Figure S5: The Effect of eluent pH value on MIP/dsDNA sensor recognition of L-Pen; Table S1: DNA base sequences; Table S2: Comparison of performance between this method and other methods for detecting L-Pen. References [ 24 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ] are cited in the Supplementary Materials.…”

mentioning

confidence: 99%

DNA-Immobilized Special Conformation Recognition of L-Penicillamine Using a Chiral Molecular Imprinting Technique

et al. 2022

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A new chiral molecularly imprinted polymer (MIP) sensor with dual recognition ability was developed for the highly selective separation of enantiomers with toxic side effects in drugs. The sensor contains double-stranded deoxyribonucleic acid (dsDNA) as the element that immobilizes the chiral molecular conformation: the dsDNA enables the imprinted cavities to match the three-dimensional structure and functional groups from the chiral molecule. By embedding the spatial orientation of dsDNA in MIPs, one can accurately capture and immobilize the molecular conformation, eliminating the influence of interfering analogues. Herein, L-penicillamine (L-Pen) was selected as the chiral template molecule and embedded into dsDNA to form dsDNA-L-Pen complex, which was then embedded into the MIPs by electropolymerization. After elution, the stereo-selective imprinted cavities were obtained. The ATATATATATAT-TATATATATATA base sequence showed a high affinity for the embedded L-Pen, which endowed the imprinted cavities with a larger number of sites and improved the selectivity toward Pen enantiomers. Under the optimal working conditions, the current response of the MIP/dsDNA sensor exhibited a positive linear relationship with the logarithm of the L-Pen concentration in the range of 3.0 × 10−16 to 3.0 × 10−13 mol/L, and the detection limit was 2.48 × 10−16 mol/L. After the introduction of dsDNA into the MIP, the selectivity of the sensor toward D-Pen increased by 6.4 times, and the sensor was successfully applied in the analysis of L-Pen in penicillamine tablets.

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Chiral recognition of penicillamine enantiomers based on a vancomycin membrane electrode

Cited by 12 publications

References 41 publications

Microscopic origin of the chiroptical response of optical media

Microscopic origin of the chiroptical response of optical media

Tuning Enantioselective Drug Adsorption in Isoreticular Homochiral Metal-Peptide Frameworks through Proximity Pore Interactions

DNA-Immobilized Special Conformation Recognition of L-Penicillamine Using a Chiral Molecular Imprinting Technique

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