Enantioseparation on a new synthetic β-cyclodextrin chemically bonded chiral stationary phase and molecular docking study

Li, Meng; Guo, Xingjie; Di, Xin; Jiang, Zhen

doi:10.1007/s00216-021-03344-1

Cited by 15 publications

(8 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The immobilization of the noscapine derivative on azide‐functionalized silica provided 1.399 μmol m −2 selector loading. This amount is more considerable compared to 0.51 and 0.93 μmol m −2 of β‐cyclodextrin, 1.22 μmol m −2 of Whelk‐O1, and 0.46 μmol m −2 vancomycin chiral stationary phase 43–46 . The column capacity for enantioresolution is highly influenced by the bonding density of CSP; thus, the high chiral selector loading for the noscapine derivative will enhance the chromatographic performance.…”

Section: Resultsmentioning

confidence: 99%

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

et al. 2022

View full text Add to dashboard Cite

Noscapine is an isolated compound from the opium poppy, with distinctive chiral structure and chemistry, interacts with other compounds due to having multiple π‐acceptors, hydrogen bond acceptors, and ionic sites. Therefore, it has promising applicability for the enantioselective separation of a wide range of polar, acidic, basic, and neutral compounds. A new noscapine derivative chiral stationary phase (ND‐CSP) has been synthesized by consecutive N‐demethylation, reduction, and N‐propargylation of noscapine followed by attachment of a solid epoxy‐functionalized silica bed through the 1,3‐dipolar Huisgen cycloaddition. The noscapine derivative‐based stationary phase provides a considerable surface coverage, which is greater than some commercial CSPs and can validate better enantioresolution performance. The major advantages inherent to this chiral selector are stability, reproducibility after more than 200 tests, and substantial loading capacity. The characterization by Fourier transform infrared (FTIR) spectroscopy and elemental analysis indicated successful functionalization of the silica surface. Chromatographic method conditions like flow rate and mobile phase composition for enantioseparation of various compounds such as warfarin, propranolol, mandelic acid, and a sulfanilamide derivative were optimized. Comparing the experimental results with docking data revealed a clear correlation between the calculated binding energy of ND‐CSP and each enantiomer with the resolution of enantiomer peaks.

show abstract

Section: Resultsmentioning

confidence: 99%

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

et al. 2022

View full text Add to dashboard Cite

show abstract

“…To date, a number of molecular modelling studies of enantioseparation processes promoted by CDs have been developed in the field of CE, even though some studies on the chiral recognition of CD-based CSP in HPLC − and GC conditions have been also reported. One of the pioneering studies applying MM to the modelling of CE enantioseparation, and involving native CDs as CSs, was reported in 2002 by Chankvetadze and co-authors .…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Peluso

Chankvetadze

2022

Chem. Rev.

View full text Add to dashboard Cite

It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

show abstract

“…After reading the related reports about the separation of flurbiprofen enantiomers, we choose the CHI-RALPAKAAGP column as chiral column to conduct the experiments. The separation methods have been reported include stereospecific capillary zone electrophoresis, 9 enantioselective membrane electrodes modified by different maltodextrins, 10 macrocyclic antibiotics 11 or α-, β-, 2-hydroxyl-3-trimethylammoniopropyl-b-(as chloride salt) and γ-cyclodextrins, 12 pre-column derivatization reversed-phase high-performance liquid chromatography (RP-HPLC), 13 chiral α1-acid glycoprotein column, 14,15 Whelk-O 1 chiral column, 16 chiral stationary phase based on polysaccharide and β-cyclodextrin, [17][18][19] and simulated moving bed chromatography. 20 However, pre-column derivatization and enantioselective membrane electrodes are usually time-consuming for us to operate.…”

Section: Introductionmentioning

confidence: 99%

Comparison of percutaneous permeation profiles of flurbiprofen enantiomers

et al. 2022

View full text Add to dashboard Cite

Flurbiprofen is clinically effective for the treatment of acute or long‐term rheumatoid arthritis and osteoarthritis. Studies showed that S‐flurbiprofen had better anti‐inflammatory effect than R‐flurbiprofen. As flurbiprofen racemates are usually used in the form of transdermal preparations, such as Flurbiprofen Cataplasms (Zepolas), it is of great significance to investigate the percutaneous permeation profiles of flurbiprofen enantiomers for considering whether it is necessary to develop the transdermal preparation with single optical enantiomer. Taking the economy into consideration, the flurbiprofen enantiomers as the mode drug and the CHIRALPAKAAGP column we had as instrument were used to perform the following experiments. On the basis of experiences provided by predecessors, we made some improvements to the analytical conditions, and method validation was developed to verify the feasibility of the method. The results showed that the established method could be used to analyze the percutaneous permeation profiles of flurbiprofen enantiomers in the flurbiprofen cataplasms accurately and effectively, and the percutaneous permeation profiles of flurbiprofen enantiomers had no significantly difference no matter under what conditions (P > 0.05).

show abstract

Enantioseparation on a new synthetic β-cyclodextrin chemically bonded chiral stationary phase and molecular docking study

Cited by 15 publications

References 43 publications

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Comparison of percutaneous permeation profiles of flurbiprofen enantiomers

Contact Info

Product

Resources

About