Article
Biochemical Research Methods
Mate Dobo, Mohammadhassan Foroughbakhshfasaei, Peter Horvath, Zoltan-Istvan Szabo, Gergo Toth
Summary: The enantioseparation of four oxazolidinone and one biosimilar thiazolidine derivatives was performed on seven different polysaccharide-type chiral stationary phases, with Amylose-based columns providing the highest enantioselectivities. Replacing an oxygen with a sulfur atom in the backbone of the studied analytes significantly alters the enantiomer recognition mechanism. Additionally, reversal of enantiomer elution order and hysteresis of retention and enantioselectivity were observed, which can be further utilized for fine-tuning chiral separation performance of the studied columns.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Article
Chemistry, Analytical
Khadidja Addadi, Khaled Sekkoum, Nasser Belboukhari, Zeid A. ALOthman, Ahmed M. Aljuwayid, Mika Sillanpaa, Imran Ali
Summary: In this study, the enantio-separation of three chiral sulfoxide drugs was achieved on a Chiralpak AS-3R column using acetonitrile-water as the mobile phase. The chiral separation was validated properly with LOD and LOQ values of 9.70-14.16 and 29.39-42.91 μg/mL, respectively. The enantiomer elution order was confirmed through experimental and theoretical methods. A simple, fast, reliable, and thermodynamically stable HPLC method was developed for the separation and determination of enantiomer elution order of the chiral sulfoxide drugs.
MICROCHEMICAL JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Mohammadhassan Foroughbakhshfasaei, Mate Dobo, Francisc Boda, Zoltan-Istvan Szabo, Gergo Toth
Summary: The study investigated the enantioseparation of four phthalimide derivatives using different polysaccharide-type stationary phases and polar organic mobile phases. It found that only Chiralcel OJ-H column with MeOH was successful for baseline-separation of all investigated drugs, and observed that enantioselectivity depends on the direction from which the composition of the eluent is approached, regardless of the eluent pair used.
Review
Engineering, Environmental
Qingsong Cheng, Hebing Pei, Qian Ma, Ruibin Guo, Nijuan Liu, Zunli Mo
Summary: This paper reviews the progress of chiral graphene materials for enantiomer separation, discussing their synthesis strategies, separation mechanism, and applications, as well as exploring related issues and future prospects.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Biochemical Research Methods
Roberto Dallocchio, Alessandro Dessi, Barbara Sechi, Bezhan Chankvetadze, Giorgi Jibuti, Sergio Cossu, Victor Mamane, Paola Peluso
Summary: In this study, the enantioseparation of 14 planar chiral ferrocenes was investigated using cellulose tris(4-methylbenzoate) (CMB) and cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) chiral columns. Baseline enantioseparations were achieved for nine analytes with the CMB column, compared to only three with the CDMPC column, under the same elution conditions. The impact of analyte and chiral stationary phase (CSP) structure, as well as mobile phase (MP) polarity, on the enantioseparation was evaluated.
Article
Biochemical Research Methods
Mari-Luiza Konjaria, Rusudan Kakava, Alessandro Volonterio, Bezhan Chankvetadze, Gerhard K. E. Scriba
Summary: This study evaluated the enantioseparation of 16 chiral compounds using capillary electrophoresis with charged cyclodextrins as chiral selectors. It found that randomly substituted cyclodextrins showed good separation ability for the model analytes. The study also discovered the influence of complexation constants and complex mobilities on the migration order of enantiomers.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Article
Biochemical Research Methods
Wenhui Li, Yu Huang, Yuqian Xiang, Xiaohui Yan, Yanshuo Li, Dapeng Wu
Summary: A vacuum-assisted thermal bonding method was proposed for the covalent coupling of beta-cyclodextrin (CD-CSP), hexamethylene diisocyanate cross-linked beta-CD (HDI-CSP) and 3, 5-dimethylphenyl isocyanate modified beta-CD (DMPI-CSP) onto isocyanate silane modified silica gel. The method avoided side reactions under vacuum conditions and achieved optimal temperature and time of 160 degrees C and 3 h. The three CSPs exhibited good chromatographic performance, with CD-CSP achieving separation of all 7 flavanones enantiomers and HDI-CSP showing good separation performance for triazoles enantiomers with one chiral center.
JOURNAL OF CHROMATOGRAPHY A
(2023)
Review
Chemistry, Inorganic & Nuclear
Qingsong Cheng, Qian Ma, Hebing Pei, Hao Liang, Xuejiao Zhang, Xuening Jin, Nijuan Liu, Ruibin Guo, Zunli Mo
Summary: Chirality is a fascinating natural property involved in the origin and evolution of life. Pure enantiomers are crucial for the safety and health of organisms. Chiral metal-organic frameworks have shown great potential in racemic resolution.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Biochemical Research Methods
Roberto Dallocchio, Barbara Sechi, Alessandro Dessi, Bezhan Chankvetadze, Sergio Cossu, Victor Mamane, Robin Weiss, Patrick Pale, Paola Peluso
Summary: This study investigated the enantioseparation of 2'-(4-pyridyl)- and 2'-(4-hydroxyphenyl)-TCIBPs on various chiral columns, exploring the factors influencing the selectivity between enantiomers, including the polymer backbone and side chain substituent properties. Findings showed that the cellulose and amylose tris(3,5-dimethylphenylcarbamate) influenced the elution order of analytes, highlighting the importance of polysaccharide backbone in enantioseparation.
Article
Chemistry, Analytical
Gaia Pulitelli, Francesca Romana Mammone, Daniele Sadutto, Damiano Tanini, Roberto Cirilli
Summary: Chromatographic enantioseparation on polysaccharide-based chiral stationary phases has become an important method for separating chiral compounds. In this study, the enantioselective and retention properties of Chiralpak IG-U chiral stationary phase were explored using eugenol derivatives as references. The results showed that hydrogen bonding plays a leading role in achieving high enantioseparation. A retention map model was proposed to describe virtual chiral recognition under extreme elution conditions. This approach opens up new possibilities for understanding the performance of polysaccharide-based chiral stationary phases.
ANALYTICA CHIMICA ACTA
(2023)
Article
Biochemical Research Methods
Alessia Rosetti, Rosella Ferretti, Claudio Villani, Marco Pierini, Roberto Cirilli
Summary: A simple and green high-performance liquid chromatography method has been developed for the separation of paroxetine from its enantiomeric and diastereomeric impurities, allowing baseline separation without interference from other chiral and achiral impurities.
JOURNAL OF CHROMATOGRAPHY A
(2021)
Article
Biochemical Research Methods
Petra Vankatova, Anna Kubickova, Kveta Kalikova
Summary: A study was conducted on the effects of mobile phase composition and column temperature on enantiomer elution order using chiral rod-like liquid crystalline materials. The results showed that factors such as type and content of cosolvent, as well as temperature, could influence the elution order of enantiomers.
Article
Chemistry, Analytical
Chiara Cantatore, Marcus Korb, Heinrich Lang, Roberto Cirilli
Summary: The study demonstrated an ON/OFF switching of receptor-like chiral discrimination through the use of different alcohols as mobile phases. The differences in retention times between the enantiomers of nine planar chiral 1,2-ferrocenes were significantly influenced by the choice of alcohol.
ANALYTICA CHIMICA ACTA
(2022)
Review
Chemistry, Analytical
Mohammad Mahdi Moein
Summary: Chiral recognition mechanism based on molecularly imprinted polymers has greatly enhanced the enatioseparation abilities of chemical and electrochemical analytical sample preparation techniques. Over the past decade, significant progress has been made in the preparation and application of various CMIPs in different formats, as well as in the development of CMIPs-based sensor fields.
Article
Chemistry, Analytical
Yiqun Li, Lin Zhao, Jiayi Li, Shanshan Xie, Ning Liang
Summary: A gamma-Cyclodextrin based metal-organic framework with D-Histidine as a chiral ligand was synthesized for the selective enrichment of S-Naproxen enantiomer. Computer simulations predicted intermolecular binding patterns and the difference in affinity due to the differentiation in pi-lone pair miscellaneous and hydrogen bonding force capacities. This chiral adsorption material shows great potential as a chiral resolution agent.
MICROCHEMICAL JOURNAL
(2023)
Article
Chemistry, Analytical
Chiara Cantatore, Paola Bertocchi, Daniela De Orsi, Alessia Panusa, Roberto Cirilli
Summary: Normal-phase and reversed-phase high-performance liquid chromatography methods were developed to separate the active pharmaceutical ingredient escitalopram from its (R)-enantiomer impurity. Both methods used ethanol as a cosolvent and achieved complete enantioseparation without interference from other associated chiral impurities.
JOURNAL OF SEPARATION SCIENCE
(2022)
Article
Chemistry, Analytical
Chiara Cantatore, Giuseppe La Regina, Rosella Ferretti, Romano Silvestri, Roberto Cirilli
Summary: This study developed a direct method for separating the enantiomers of the pain medicine tramadol and its active metabolite in a single run. Through optimizing the normal-phase and reversed-phase conditions and using ethanol as a solvent, the simultaneous separation of the enantiomers was achieved. The use of an ethanol-water-diethylamine mobile phase showed promising performance for the separation.
SEPARATION SCIENCE PLUS
(2022)
Article
Chemistry, Medicinal
Gerardo Salinas, Filippo Malacarne, Giorgia Bonetti, Roberto Cirilli, Tiziana Benincori, Serena Arnaboldi, Alexander Kuhn
Summary: A microfluidic valve based on chemically responsive materials is reported, which is triggered by bipolar electrochemistry and chiral recognition. The valve can be opened and closed by reversible deflection of a conducting polymer actuator, allowing the release of dye from a reservoir. The device works well even in the presence of chemically different chiral analytes in the same solution, opening up new possibilities in microfluidics, including controlled drug delivery applications.
Article
Biochemistry & Molecular Biology
Francesca Romana Mammone, Leo Zanitti, Michela Puxeddu, Giuseppe La Regina, Romano Silvestri, Anna Borioni, Roberto Cirilli
Summary: A direct and highly selective ultra-high-performance liquid chromatographic method was developed and validated for determining the content of rosuvastatin calcium salt (RSV) in medicinal products. The method achieved baseline separation of all organic related substances listed in the European Pharmacopoeia monograph for RSV tablets in less than 15 minutes. The method was proven to be linear, precise, and accurate for determining RSV and related chiral substances in tablet formulations according to the guidelines of the International Conference on Harmonization (ICH).
Article
Biochemistry & Molecular Biology
Simona Rizzo, Tiziana Benincori, Francesca Fontana, Dario Pasini, Roberto Cirilli
Summary: The chiral resolving ability of commercially available amylose-based chiral stationary phase (CSP) towards four representative chiral probes with different stereogenicity (central, axial, helical, and planar) was investigated. The results showed that the amylose-based CSP is effective in separating chiral compounds containing any kind of stereogenic element. The experimental retention and enantioselectivity behavior, as well as the established enantiomer elution order, can provide key information on the enantiorecognition mechanism of the amylose-based CSP.
Article
Chemistry, Multidisciplinary
Alessia Rosetti, Giulio Apolloni, Claudio Villani, Tiziana Benincori, Roberto Cirilli
Summary: In this study, a new atropisomeric C-2-symmetry chiral monomer based on the 3,3'-bithiophene core was synthesized and resolved by high-performance liquid chromatography (HPLC). The enantioseparation was optimized using a cellulose-type Chiralpak IB-3 column and a specific mobile phase. Scale-up of the enantioseparation process led to notable deformations in the HPLC profile, which were investigated and addressed. The optimized chromatographic conditions were then used to obtain milligram amounts of enantiopure sample for further characterization studies.
APPLIED SCIENCES-BASEL
(2023)
Article
Biochemistry & Molecular Biology
Francesca Polli, Gabriele Cianfoni, Rem Elnahas, Laura Mangiardi, Francesca A. Scaramuzzo, Silvia Cammarone, Deborah Quaglio, Andrea Calcaterra, Marco Pierini, Franco Mazzei, Robertino Zanoni, Bruno Botta, Francesca Ghirga
Summary: A practical supramolecular Ab conjugation strategy based on resorc[4]arene modifiers was developed to immobilize antibodies onto the surface of carbon nanotubes (CNTs) for selective binding to target antigens (Ags). The study utilized host-guest approach and synthesized resorc[4]arene linkers R1 and R2 to improve the orientation of antibodies on CNTs and optimize the Ab/Ag interaction, showing potential applicability in label-free immunosensor development.
Article
Chemistry, Analytical
Silvia Cauteruccio, Valentina Pelliccioli, Sara Grecchi, Roberto Cirilli, Emanuela Licandro, Serena Arnaboldi
Summary: In this study, a wireless miniaturized stereoselective light-emitting system was designed to qualitatively detect chiral contaminants in reduced volumes. By mixing an inherently chiral inductor with a chiral probe in micro-solutions of a commercial ionic liquid, an asymmetric environment was created. The synergy between the inductor, the applied electric field, and the chiral pollutant was transduced by the light emission produced from a miniaturized light-emitting diode (LED) used as a bipolar electrode.
Article
Chemistry, Organic
Fabio Buonsenso, Marta Colombo, Andrea Marchesi, Francesca Romana Mammone, Francesco Sannicolo, Roberto Cirilli, Marco Pierini
Summary: An experimental and theoretical study was conducted to analyze the configurational lability of drugs with a non-planar seven-membered cycloheptadiene ring, which confers chirality to these compounds. The study investigated the energy barrier opposing the inversion of the chiral tricyclic scaffold, which is dependent on appropriate substituents on the external cycles. Structural changes were made to accurately control the stereolability of the tricyclic framework, providing interesting insights.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Giulia Mazzoccanti, Roberta Franzini, Alessia Ciogli, Marco Pierini, Fabio Buonsenso, Cristina Faggi, Antonio Francioso, Simone Manetto, Claudio Villani
Summary: This study investigates the chirality of dibenzocyclooctynes through theoretical and experimental methods. Computational analysis is conducted and used as a guide for experimental investigation. An array of different experiments is then used to elucidate the structure, including HPLC, chiroptical spectroscopy, and X-ray diffraction. The study demonstrates the chirality and conformational behavior of dibenzocyclooctynes and their derivatives with azides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Anna Borioni, Francesca Romana Mammone, Roberta Risoluti, Alessia Panusa, Marco Pierini, Roberto Cirilli
Summary: This study reports the kinetics and complete structural characterization of the degradation of rosuvastatin, a lipid-lowering drug. The study also reveals that rosuvastatin can form multiple degradation products, which may have potential toxic effects and impact the quantification of related substances.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Daniele Sadutto, Paolo Guglielmi, Simone Carradori, Daniela Secci, Roberto Cirilli
Summary: The study investigates the tautomerization process of the imine moiety of the isoxazoline ring in the presence of a basic catalyst. The results can be used to control the stereointegrity of pharmacologically active compounds and guide the synthesis towards the desired tautomer.
Article
Chemistry, Organic
Macarena Martinez-Bailen, Camilla Matassini, Francesca Clemente, Cristina Faggi, Andrea Goti, Francesca Cardona
Summary: This study presents a novel stereoselective synthetic method for pentahydroxyazepaneiminosugars. The approach involves a crucial osmium-catalyzed aminohydroxylation reaction of allylic alcohols derived from the addition of vinylmagnesium bromide to a d-mannose-derived aldehyde. This reaction forms a new C-N bond with complete regio- and stereocontrol based on the tethering approach, followed by intramolecular reductive amination to obtain the desired azepanes. This is the first application of the osmium-catalyzed tethered aminohydroxylation reaction in the synthesis of iminosugars.
Correction
Biochemical Research Methods
Yong Wang, Suhua Yu, Rui Li, Jing Wan, Yuheng Wang, Zongli Huo, Chunyong Wu, Li Mi, Songqin Liu
JOURNAL OF CHROMATOGRAPHY A
(2024)
Review
Biochemical Research Methods
Israel D. Souza, Maria Eugenia C. Queiroz
Summary: Organic-silica hybrid monolithic materials have gained significant attention in separation science and sample preparation due to their unique properties. This review summarizes the characteristics, current status, and recent developments of these materials, as well as discusses synthesis methods, characterization techniques, and strategies for improving extraction efficiency in various applications.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Bhagwat Upreti, Bhanu Prasad Vempatapu, Jagdish Kumar, Pankaj K. Kanaujia
Summary: Lubricating oils are essential for the effective performance of internal combustion engines. This study presents a new HPLC method for determining additives in finished lubricating oils and polar substances in used engine oils.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Zongqing Huang, Haoju Hua, Xiuzhen Du, Zipeng Zhen, Wei Zhao, Jun Feng, Ji-an Li
Summary: This study successfully isolated VHHs against the SUMO protein for the first time using biopanning of an immune camelid nanobody library. The VHHs were coupled to agarose resins to form affinity chromatography resins, allowing for one-step purification of various SUMO fusions.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Xueting Qiu, Xuben Hou, Yue Yang, Hao Fang, Fei Cui, Xinying Yang
Summary: In this study, a new method based on electrophoretically mediated microanalysis was developed for the investigation of PTPRO enzymatic activity. The method was successfully used to determine the kinetics of PTPRO and the inhibitory concentration of PTPRO inhibitors. The method exhibited improved accuracy and reduced consumption compared to traditional methods.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Feifei Luo, Mengmeng Hao, Lei Zhang, Yangguo Xie, Wei Hou, Hongya Wang, Zhongli Zhang
Summary: In this study, a comprehensive screening and structure elucidation of 23 nonvolatile organic compounds (NVOCs) in two antibody drugs was conducted. Seven previously unreported compounds were identified. A quantitative method with high sensitivity, accuracy, and precision was developed for evaluating the safety of NVOCs in drug products.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Zuzana Vosahlova, Kveta Kalfkova, Martin Gilar, Jakub Szymarek, Maria Mazurkiewicz-Beldzinska, Sylwia Studzi
Summary: A hydrophilic interaction liquid chromatography method was developed for the separation and identification of oligonucleotide impurities and metabolites, and successfully applied to the analysis of serum samples from Spinraza-treated patients.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Aswanidevi Kongasseri, Thirumalai Madhesan, Sangeetha Krishna Kumar, Sushmitha Pedugu Sivaraman, Suchashrita Mitra, Pitchaiah Kancharlapalli Chinaraga, C. V. S. Brahmmananda Rao, Sivaraman Nagarajan, Prabhakaran Deivasigamani, Akhila Maheswari Mohan
Summary: This study focuses on the sequential separation of trivalent lanthanides using modified C-18 silica-packed supports and reversed-phase HPLC technique. By tuning the column modifiers and separation parameters, the researchers achieved systematic separation of Ln(3+). The results showed that the choice of column modifiers and fine-tuning of the modification procedure were crucial for achieving excellent separation.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Raquel Perez-Robles, Szabolcs Fekete, Robert Kormany, Natalia Navas, Davy Guillarme
Summary: There is a mismatch between the sample diluent and the mobile phase in HILIC analysis, leading to analyte breakthrough and peak distortion. Adding a weak solvent for pre-injection can effectively prevent these issues and improve sensitivity.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Oleg Pokrovskiy, Irina Rostovschikova, Konstantin Ustinovich, Ilya Voronov, Dmitry Kosyakov
Summary: A chromatography-like propagation of water through the material bed was observed during supercritical fluid extraction of aroma plants with high moisture content, which could be significant for modeling the kinetics of supercritical fluid extraction of non-volatile compounds.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Yasar Kemal Recepoglu, Ozguer Arar, Asli Yuksel
Summary: Biosorption using phosphorylated hazelnut shell waste (FHS) is a promising method for lithium removal and recovery. This study investigated the performance of a continuous-flow packed-bed column system using FHS for ultra-low level lithium removal. The results showed that the lihium biosorption capacity of the FHS column was unaffected by the bed height, but decreased with increasing flow rate.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Jian Sun, Zheheng Zheng, Zixiao Jia, Jiabin Wang, Xucong Lin
Summary: In this study, an ionic covalent organic framework (iCOF) surface grafting monolithic sorbent was prepared for in-tube solid-phase microextraction (SPME) of aristolochic acids (AAs) in various samples. The density of quaternary ammonium ions in the iCOF was modulated for enhanced adsorption of AAs. The iCOF surface grafting monolithic sorbent was confirmed by different means. Several operating conditions were optimized to develop the online in-tube SPME-HPLC method, which showed good linearity, low limits of detection, and high recoveries for AAs in serum samples. This study presents a feasible approach for the application of COF-based monolithic sorbents in sample preparation.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Zeng Wen, Ruihan Peng, Die Gao, Jing Lin, Jia Zeng, Zhou Li, Famin Ke, Zhining Xia, Dandan Wang
Summary: A chitosan-alginate sponge with multiple cross-linking networks was developed for adsorption and enrichment of anionic dyes from food samples. The sponge showed better three-dimensional network structure, mechanical behavior, and stability compared to pure chitosan and alginate sponges. The adsorption performance and selectivity of the sponge were systematically studied, and it maintained high adsorption capacity and selectivity for anionic dyes. The sponge also showed satisfactory reusability and was successfully combined with high-performance liquid chromatography for the enrichment and detection of anionic dyes in candy and cocktail samples.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Hairong Zhang, Xiaojuan Jiang, Dandan Zhang, Yuexin Yang, Qiang Xie, Caisheng Wu
Summary: Analysis of in vivo exposure to traditional Chinese medicine using mass spectrometry is helpful for identifying effective ingredients and developing new drugs. This study focused on Forsythia suspensa (Lian Qiao) and used metabolomics technology to explore its in vivo exposure. By comparing the differences before and after administration, a complete set of nontargeted analysis strategies for TCM exposure was established. The study identified 393 Lian Qiao-related chemical components in mice after administration, including prototypes and metabolites. This study provides a reference for research on the active ingredients of Lian Qiao in vivo.
JOURNAL OF CHROMATOGRAPHY A
(2024)
Article
Biochemical Research Methods
Oscar Castejon-Musulen, Ricardo Lopez, Ignacio Ontan, Vicente Ferreira
Summary: A quantitative analytical method was developed and validated in this study to determine the concentrations of 81 aroma-relevant wine volatiles. The method utilizes stir bar sorptive extraction and multidimensional gas chromatography with flame ionization detector or mass spectrometer. The method demonstrated good linearity, reproducibility, and recovery, and was successfully applied to analyze 20 wine samples.
JOURNAL OF CHROMATOGRAPHY A
(2024)