Review
Chemistry, Analytical
Xiaoping Wang, Hui Li, Kaijun Quan, Liang Zhao, Hongdeng Qiu, Zuguang Li
Summary: Separation and identification of chiral enantiomers are increasingly important in various fields like pharmaceutical production, chemical intermediates preparation, and biochemistry. Cellulose and its derivatives, with strong chiral recognition ability, large loading capacity and ease of functionalization, have shown excellent performance in enantioseparation, indicating great potential in chiral separation. This review systematically summarizes the types of cellulose derivatives, preparation of cellulose-functionalized chiral stationary phases, and their recent applications in chiral chromatographic separation, aiming to provide a useful reference for researchers and inspire new discoveries in the field.
Article
Chemistry, Analytical
Francesca Romana Mammone, Paola Rotundo, Rosella Ferretti, Michela Puxeddu, Romano Silvestri, Roberto Cirilli
Summary: A direct reversed-phase high-performance liquid chromatographic method was developed for determining the content of the enantiomeric impurity of rosuvastatin calcium salt in tablets. The method offered improved selectivity and reduced analysis times compared to the method in European Pharmacopoeia. The limits of quantitation and detection of the enantiomeric impurity were found to be 0.15 and 0.05 μg/mL.
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
(2023)
Article
Biochemical Research Methods
Eliana A. Agathokleous, Ioannis J. Stavrou, Constantina Kapnissi-Christodoulou
Summary: In this study, various types of chiral stationary phases were utilized for the chiral separations of different clinically and pharmaceutically important compounds in high-performance liquid chromatography. It was found that RN-CF6 was the most suitable and efficient chiral stationary phase for separating a wide range of analytes, including acids, amines, alcohols, and neutral compounds, providing baseline enantioseparation for thyroxine and cetirizine.
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Analytical
Pieter De Gauquier, Jordy Peeters, Kenno Vanommeslaeghe, Yvan Vander Heyden, Debby Mangelings
Summary: This study aims to develop models for predicting the retention, separation, and elution sequence of enantiomers in diverse pharmaceuticals. Quantitative Structure Retention Relationships (QSRR) models are built using molecular descriptors and retention. The models show that only achiral descriptors can accurately predict the global retention, while chiral descriptors are not suitable for predicting enantioseparation and elution sequence. Models with both chiral and achiral descriptors can effectively predict retention, but their ability to predict elution sequence and separation varies for different chromatographic systems.
Article
Chemistry, Analytical
Yu-Ping Yang, Ji-Kai Chen, Ping Guo, Yan-Rui Lu, Cai-Fang Liu, Bang-Jin Wang, Jun-Hui Zhang, Sheng-Ming Xie, Li-Ming Yuan
Summary: A spherical chiral porous organic polymer (POPs) COP-1 was synthesized and used as a novel chiral stationary phase (CSPs) for mixed-mode high-performance liquid chromatography (HPLC) enantioseparation. The COP-1-packed column exhibited excellent separation performance and showed good chiral recognition complementarity with other columns.
Article
Chemistry, Medicinal
Alessia Rosetti, Giovanni Preda, Claudio Villani, Marco Pierini, Dario Pasini, Roberto Cirilli
Summary: The study analyzed two chiral triptycene derivatives on a Chiralpak IB-U column packed with sub-2-micron diameter particles, achieving sub-minute enantioseparations under normal-phase conditions. The evaluation of the compounds' structural elements and chromatographic behavior revealed that hydrogen bond formation is essential for enantiomer separation.
Article
Biochemistry & Molecular Biology
Lajos-Attila Papp, Sarolta Krizbai, Mate Dobo, Gabriel Hancu, Zoltan-Istvan Szabo, Gergo Toth
Summary: A novel reversed-phase chiral HPLC method was developed for the enantiopurity control analysis of naproxen. The method utilized a polysaccharide-type chiral stationary phase and different mobile phase compositions to optimize the enantiomer separation.
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
Materials Science, Paper & Wood
Cuong Viet Bui, Thomas Rosenau, Hubert Hettegger
Summary: A new synthesis strategy for cellulose derivative-based chiral selectors and their immobilization onto silica gel was introduced. The immobilization process did not affect the chiral separation performance, and in some cases, the immobilized chiral stationary phase showed better performance than the coated reference material.
Article
Biochemical Research Methods
Hung-Wei Tsui, Hong-Lin Zhang, Ching-Hung Hsieh
Summary: The study explores the balance between electrostatic interactions and solvophobic interactions in immobilized amylose sorbents, and investigates the retention behaviors of pantolactone enantiomers in both normal and reversed-phase modes. Different types of sorbent interactions and changes in enantiomeric elution order are observed at different IPA concentrations, emphasizing the importance of both electrostatic and solvophobic interactions in chiral recognition.
JOURNAL OF CHROMATOGRAPHY A
(2021)
Article
Biochemistry & Molecular Biology
Zoltan-Istvan Szabo, Agnes Bartalis-Fabian, Gergo Toth
Summary: A high-performance liquid chromatographic method was developed for simultaneous determination of related substances in escitalopram. The optimized parameters achieved baseline separation between all compounds, making the method suitable for routine quality control and enantiomeric purity testing.
Article
Biochemical Research Methods
You -Ping Zhang, Kuan Li, Ling-Xiao Xiong, Bang-Jin Wang, Sheng-Ming Xie, Jun -Hui Zhang, Li -Ming Yuan
Summary: Chiral polyimine macrocycles are a new family of organic macrocycles that have defined cavities, rigid shapes, inherent chirality, and multiple cooperative binding sites, and show great potential in diverse areas. However, their application in high-performance liquid chromatography (HPLC) for enantioseparation is rarely reported. In this study, a novel chiral stationary phase (CSP) for HPLC was prepared by chemically bonding a chiral polyimine macrocycle onto thiolated silica. The CSP exhibited good enantioselectivity in both normal- and reversed-phase HPLC, and showed broader chiral resolution compared to a previously studied chiral macrocycle-based column. It also showed complementary enantioseparation to other popular chiral HPLC columns and demonstrated good stability and reproducibility.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Article
Chemistry, Medicinal
Leonid Asnin, Jana Hercikova, Wolfgang Lindner, Yana Klimova, Daria Ziganshina, Elena Reshetova, Michal Kohout
Summary: In this study, the enantioselectivity of chiral zwitterionic columns (ZWIX (+A) and ZWIX (-A)) on dipeptides under buffer-free reversed-phase conditions was investigated. An electrostatically driven adsorption model was used to analyze the retention characteristics of zwitterionic dipeptides, which showed good fits with both monotonous and U-shaped curves.
Article
Biochemical Research Methods
Yi-Lun Yan, Dong Guo, Jia-Lin Wu, Xi-Hao Tang, Jia-Jun Luo, Shu-Qing Li, Jun Fan, Sheng-Run Zheng, Wei-Guang Zhang, Song-Liang Cai
Summary: This study demonstrates the utilization of stable spherical covalent organic frameworks (SCOFs) as matrixes for the fabrication of new chiral stationary phases (CSPs). The synthesized SCOF-based CSPs exhibit high resolution abilities for enantiomeric separation in high-performance liquid chromatography (HPLC). Compared to silica-based CSPs, the prepared SCOF-based CSPs show superior acid and base stability.
JOURNAL OF CHROMATOGRAPHY A
(2022)
Article
Biochemical Research Methods
Dandan Guo, Tingfeng Tang, Shaohua Huang, Yan Zhu
Summary: A methoxy terminated poly dimethylsiloxane modified silica gel material was proposed as a novel stationary phase for reversed-phase liquid chromatography. The obtained stationary phase demonstrated good separation efficiency and high stability, with a wider polarity separation scale and shorter analysis time compared to traditional columns of the same type.
JOURNAL OF CHROMATOGRAPHY A
(2021)
Article
Biochemistry & Molecular Biology
Desiree Bartolini, Anna Maria Stabile, Carmine Vacca, Alessandra Pistilli, Mario Rende, Antimo Gioiello, Gabriele Cruciani, Francesco Galli
Summary: The NF-kB pathway plays a crucial role in the interaction between SARS-CoV-2 and host cells, regulating cellular stress response and viral replication. The crosstalk between UPR signaling, cellular MAPKs, and NF-kB activity is essential for understanding the pathogenesis of SARS-CoV-2 infection and developing effective therapies.
Article
Biochemistry & Molecular Biology
Rolando Cannalire, Camilla Russo, Paolo Luciano, Bruno Cerra, Antimo Gioiello, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano
Summary: A new Lewis acid promoted reaction was reported, which enables the transformation of Strecker 3-component adducts to 5-aminoimidazole derivatives through isocyanide insertion and cyclization. This synthetic method provides a fast and easy access to this class of compounds, offering important research resources for medicinal chemistry programs.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Analytical
Federica Ianni, Bruno Cerra, Giada Moroni, Ina Varfaj, Alessandro Di Michele, Antimo Gioiello, Andrea Carotti, Roccaldo Sardella
Summary: In this study, the stereoisomers of two tetracyclic quinolines were separated and discriminated using a chiral column. The enantiomeric elution order was determined using an indirect method and confirmed with molecular docking simulations and theoretical calculations. Multiple methods were employed to ensure the accuracy of the results.
SEPARATION SCIENCE PLUS
(2022)
Article
Biochemistry & Molecular Biology
Ina Varfaj, Andrea Carotti, Luciano Mangiapelo, Lina Cossignani, Agnese Taticchi, Antonio Macchiarulo, Federica Ianni, Roccaldo Sardella
Summary: Two LC methods were developed for the analysis of achiral and chiral components of amino acids in a food supplement. Both methods performed well for all eight amino acids, confirming the consistency of amino acid content with manufacturer's declaration. Additionally, a two-dimensional achiral-chiral configuration was proven to be possible in practice, making the methods more environmentally sustainable.
Article
Chemistry, Inorganic & Nuclear
Leonardo Tensi, Anna Dall'Anese, Alfonso Annunziata, Simone Mearini, Vittorio Nofrini, Gabriel Menendez Rodriguez, Andrea Carotti, Roccaldo Sardella, Francesco Ruffo, Alceo Macchioni
Summary: In this study, [Cp*IrLnCl] complexes (L1, L2, and L3) were synthesized and characterized. L1 and L2 exhibit a single diastereoisomer, while L3 exists as interconverting diastereoisomers. These complexes serve as catalysts for the asymmetric transfer hydrogenation of RC(O)C(O)OH in water, showing excellent chemoselectivity and efficiency.
Article
Chemistry, Multidisciplinary
Bruno Cerra, Cecile Blondeau, Rolando Cannalire, Mariateresa Giustiniano, Shiva Tali Shandiz, Antimo Gioiello
Summary: This paper presents a continuous flow approach to address the issues of poor stability and distressing odor of isocyanides, allowing for their synthesis, purification, and in-line reaction.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Biochemistry & Molecular Biology
Luciano Mangiapelo, Francesca Blasi, Federica Ianni, Carolina Barola, Roberta Galarini, Ghaid W. A. Abualzulof, Roccaldo Sardella, Claudia Volpi, Lina Cossignani
Summary: Potato sprouts, an underutilized by-product of potato processing, were found to have potential for the recovery of caffeoyl-quinic acids (CQAs), a family of polyphenols with well-recognized biological activities. The predominant compound 5-CQA was successfully extracted using Ultrasound-Assisted Extraction (UAE) under optimized conditions. The study revealed the critical influence of factors such as solid/solvent ratio, water content, and extraction time on the efficiency of extraction.
Review
Chemistry, Applied
Elena Tomarelli, Bruno Cerra, Francesco Mutti, Antimo Gioiello
Summary: Since their structural elucidation in 1935, steroids have been a popular subject of research for synthetic and medicinal chemists due to their functional groups and steroidal scaffolds. The discovery of steroids with hormonal and pharmacological activity has driven the development of efficient synthetic procedures. However, the preparation of steroidal compounds of pharmaceutical interest still faces challenges and often requires complex synthesis. The use of continuous flow chemistry, such as in photochemistry and biocatalysis, has shown potential to streamline steroid synthesis and improve process efficiency, waste minimization, and safety.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Javier Valverde-Pozo, Jose M. Paredes, Thomas J. Widmann, Carmen Grinan-Lison, Giada Ceccarel, Antimo Gioiello, M. Eugenia Garcia-Rubino, Juan A. . Marchal, Jose M. Alvarez-Pez, Eva M. Talavera
Summary: DPP IV, also known as CD26 lymphocyte T surface antigen, is a transmembrane glycoprotein with a wide range of functions. It is overexpressed in several cancers and can serve as a diagnostic tool. A new near-infrared fluorimetric probe has been designed to detect the activity of DPP IV in living cells and tissues, using zebrafish as a model organism.
Article
Biochemistry & Molecular Biology
Alessandro La Mantia, Federica Ianni, Aurelie Schoubben, Marco Cespi, Klemen Lisjak, Davide Guarnaccia, Roccaldo Sardella, Paolo Blasi
Summary: Cocoa and chocolate antioxidants may contribute to human health by improving blood flow, reducing blood pressure and glycemia, and enhancing cognitive function. However, the polyphenol content in cocoa and chocolate is reduced during the production process. This study investigated the changes in polyphenol content during chocolate production, focusing on roasting. Results showed a bell-shaped curve for the total polyphenol content and antioxidant power, with an increase followed by a decrease at different roasting temperatures. Roasting released epicatechin from oligomers, but also led to epicatechin degradation.
Article
Plant Sciences
Sara Francesconi, Riccardo Ronchetti, Emidio Camaioni, Stefano Giovagnoli, Francesco Sestili, Samuela Palombieri, Giorgio Mariano Balestra
Summary: According to the European Green Deal, the application of imidazole fungicides for managing Fusarium head blight (FHB) and Fusarium crown rot (FCR) will be restricted by 2030. Therefore, a novel and eco-sustainable nanostructured particle formulation (NPF) was developed using cellulose nanocrystals (CNC) and resistant starch as carrier and excipient, chitosan and gallic acid as antifungal and elicitor active principles. The NPF effectively inhibited conidia germination and mycelium growth, reducing FHB and FCR symptoms in susceptible bread wheat genotypes while being biocompatible. Furthermore, the genome of Cadenza SBEIIa showed potential responsiveness to elicitor-like molecules and resistance to FCR fungal spread.
Article
Plant Sciences
Daniele Schiavi, Riccardo Ronchetti, Veronica Di Lorenzo, Riccardo Vivani, Stefano Giovagnoli, Emidio Camaioni, Giorgio M. Balestra
Summary: Nanotechnology is being used in crop protection with a focus on sustainable nanopesticides and nanocarriers for plant pathogen management. Cellulose nanocrystals (CNC) derived from agrofood waste are emerging as innovative antimicrobial materials. This study evaluated new chemical and enzymatic extraction methods for CNC from tomato harvest residues. Both methods were efficient, with the enzymatic method being greener and producing purer CNC at a slightly lower yield. The obtained CNC showed promising antimicrobial activity against plant bacterial pathogens, suggesting their potential in sustainable crop protection strategies.
Article
Chemistry, Analytical
Andrea Carotti, Ina Varfaj, Ilaria Pruscini, Ghaid W. A. Abualzulof, Laura Mercolini, Elisa Bianconi, Antonio Macchiarulo, Emidio Camaioni, Roccaldo Sardella
Summary: A fast HPLC method was developed to study the hydrophobicity extent of pharmaceutically relevant molecular fragments. The method allows for physico-chemical evaluations in drug discovery programs and optimizes the RP-HPLC method for determining log D values. By selecting the & phi;(0) index, log D values can be estimated for fragments unattainable by potentiometric titration. Molecular descriptors such as the number of hydrogen bond donors and index of cohesive interaction are found to correlate with the experimental data.
JOURNAL OF SEPARATION SCIENCE
(2023)
Article
Chemistry, Medicinal
Emiliano Rosatelli, Andrea Carotti, Bruno Cerra, Francesca De Franco, Daniela Passeri, Roberto Pellicciari, Antimo Gioiello
Summary: The activation of TGR5 allows bile acids to modulate nongenomic signaling pathways, leading to physiological actions such as immunosuppression, anti-inflammatory effects, and regulation of glucose metabolism and energy balance. TGR5 agonists have shown promise in drug discovery and preclinical evaluations for the treatment of liver diseases and metabolic syndrome. This study focuses on modifying the chemical structure of bile acids to develop novel chemical tools that can modulate TGR5 in different tissues. The results provide insights into the structure-activity relationships and functional roles of TGR5, uncovering unexpected properties that can be utilized to design selective and potent TGR5 agonists.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)