{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:43:15Z","timestamp":1760150595711,"version":"build-2065373602"},"reference-count":55,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2023,12,4]],"date-time":"2023-12-04T00:00:00Z","timestamp":1701648000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Chiral resolution is a technique of choice, making it possible to obtain asymmetric and enantiomerically pure compounds from a racemic mixture. This study investigated the behavior of vancomycin when used as a chiral additive in high-performance liquid chromatography (HPLC) to separate enantiomers of nonsteroidal anti-inflammatory drugs (NSAIDs), including ketoprofen, ibuprofen, flurbiprofen, and naproxen enantiomeric impurities. We compared two achiral stationary phases (C18 and NH2) to assess the impact of mobile phase composition and stationary phase on the vancomycin retention time in the racemic resolution of drug enantiomers. Our results demonstrated the successful enantioseparation of all drugs using vancomycin in the mobile phase (phosphate buffer 0.05 M\/2-propanol, 50\/50) with an NH2 column. This enhanced separation on the NH2 column resulted from the chromatography system\u2019s efficiency and vancomycin dimers\u2019 stereoselective interaction on the NH2 surface. This study underscores the importance of stationary phase selection in the chiral resolution of NSAIDs with vancomycin as a chiral additive. It offers valuable insights for future research and development of NSAID chiral separation methods, highlighting potential vancomycin applications in this context.<\/jats:p>","DOI":"10.3390\/sym15122154","type":"journal-article","created":{"date-parts":[[2023,12,4]],"date-time":"2023-12-04T03:40:58Z","timestamp":1701661258000},"page":"2154","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["The Effect of the Stationary Phase on Resolution in the HPLC-Based Separation of Racemic Mixtures Using Vancomycin as a Chiral Selector: A Case Study with Profen Nonsteroidal Anti-Inflammatory Drugs"],"prefix":"10.3390","volume":"15","author":[{"given":"Dehbiya","family":"Gherdaoui","sequence":"first","affiliation":[{"name":"Laboratory of Experimental Biology and Pharmacology (LBPE), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Madiha Melha","family":"Yahoum","sequence":"additional","affiliation":[{"name":"Materials and Environmental Laboratory (LME), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"},{"name":"Faculty of Sciences, University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Selma","family":"Toumi","sequence":"additional","affiliation":[{"name":"Faculty of Sciences, University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hichem","family":"Tahraoui","sequence":"additional","affiliation":[{"name":"Laboratoire de G\u00e9nie des Proc\u00e9d\u00e9s Chimiques, Department of Process Engineering, University of Ferhat Abbas, Setif 19000, Algeria"},{"name":"Laboratory of Biomaterials and Transport Phenomena (LBMTP), University Yahia Fares, Medea 26000, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fatma","family":"Bouazza","sequence":"additional","affiliation":[{"name":"Laboratory of Experimental Biology and Pharmacology (LBPE), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"},{"name":"Ecole Normale Sup\u00e9rieure, Laboratory of Research on Bio-Active Products and Valorization of Biomasse, Vieux-Kouba, Algiers 16050, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sonia","family":"Lefnaoui","sequence":"additional","affiliation":[{"name":"Laboratory of Experimental Biology and Pharmacology (LBPE), University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"},{"name":"Faculty of Sciences, University of Medea, Nouveau Pole Urbain, Medea 26000, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abdelhamid","family":"Zeghdaoui","sequence":"additional","affiliation":[{"name":"Physics Department, Laboratoire N-Corps et Structure de la Mati\u00e8re, Ecole Normale Sup\u00e9rieure, B.P. 92, Vieux-Kouba, Algiers 16050, Algeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2622-2384","authenticated-orcid":false,"given":"Abdeltif","family":"Amrane","sequence":"additional","affiliation":[{"name":"Univ Rennes, Ecole Nationale Sup\u00e9rieure de Chimie de Rennes, CNRS, ISCR\u2014UMR 6226, 35000 Rennes, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bassem","family":"Jaouadi","sequence":"additional","affiliation":[{"name":"Laboratoire de Biotechnologie Microbienne, Enzymatique et de Biomol\u00e9cules (LBMEB), Centre de Biotechnologie de Sfax (CBS), Universit\u00e9 de Sfax, Sfax 3018, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9745-664X","authenticated-orcid":false,"given":"Jie","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Engineering, Merz Court, Newcastle University, Newcastle upon Tyne NE1 7RU, UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1016\/j.envint.2018.09.041","article-title":"Chiral Pharmaceuticals: Environment Sources, Potential Human Health Impacts, Remediation Technologies and Future Perspective","volume":"121","author":"Zhou","year":"2018","journal-title":"Environ. Int."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0021-9673(00)00532-X","article-title":"Wolfgang. Separation of Enantiomers: Needs, Challenges, Perspectives","volume":"906","author":"Maier","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1007\/s002280100320","article-title":"Clinical Pharmacology of Thalidomide","volume":"57","author":"Eriksson","year":"2001","journal-title":"Eur. J. Clin. Pharmacol."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Batra, S., and Bhushan, R. (2019). Methods and Approaches for Determination and Enantioseparation of (RS)-Propranolol. Biomed. Chromatogr., 33.","DOI":"10.1002\/bmc.4370"},{"key":"ref_5","unstructured":"Fanali, S., Haddad, P.R., Poole, C.F., and Riekkola, M.-L. (2017). Liquid Chromatography, Elsevier. [2nd ed.]."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1002\/chir.23427","article-title":"Chiral Stationary Phases and Applications in Gas Chromatography","volume":"34","author":"Betzenbichler","year":"2022","journal-title":"Chirality"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Teixeira, J., Tiritan, M.E., Pinto, M.M.M., and Fernandes, C. (2019). Chiral Stationary Phases for Liquid Chromatography: Recent Developments. Molecules, 24.","DOI":"10.3390\/molecules24050865"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1007\/978-1-62703-263-6_13","article-title":"Chiral Mobile Phase Additives in HPLC Enantioseparations","volume":"Volume 970","author":"Scriba","year":"2013","journal-title":"Chiral Separations"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"814","DOI":"10.1016\/j.chroma.2009.10.022","article-title":"Chiral Recognition by Enantioselective Liquid Chromatography: Mechanisms and Modern Chiral Stationary Phases","volume":"1217","year":"2010","journal-title":"J. Chromatogr. A"},{"key":"ref_10","first-page":"8","article-title":"Chiral Chromatography and Its Application to the Pharmaceutical Industry: A Review","volume":"2","author":"Mudi","year":"2011","journal-title":"ChemSearch J."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Scriba, G.K.E. (2019). Chiral Separations: Methods and Protocols, Springer. Methods in Molecular Biology.","DOI":"10.1007\/978-1-4939-9438-0"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1007\/s10337-012-2261-1","article-title":"Chiral Recognition Mechanisms in Analytical Separation Sciences","volume":"75","author":"Scriba","year":"2012","journal-title":"Chromatographia"},{"key":"ref_13","first-page":"306","article-title":"Chiral separation of citalopram by reversed phase hplc using sulfated beta cyclodextrin as chiral mobile phase additive","volume":"7","author":"Deshpande","year":"2015","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/S0021-9673(01)94407-3","article-title":"Eluotropic Strength of Solvents: Prediction and Use in Reversed-Phase High-Performance Liquid Chromatography","volume":"389","author":"Patel","year":"1987","journal-title":"J. Chromatogr. A"},{"key":"ref_15","unstructured":"Meyer, V.R. (2013). Practical High-Performance Liquid Chromatography, John Wiley & Sons."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"6551","DOI":"10.1021\/ac0705115","article-title":"Retention Mechanism in Reversed-Phase Liquid Chromatography: A Molecular Perspective","volume":"79","author":"Rafferty","year":"2007","journal-title":"Anal. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Berkecz, R., Tan\u00e1cs, D., P\u00e9ter, A., and Ilisz, I. (2021). Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors. Molecules, 26.","DOI":"10.3390\/molecules26113380"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Hancu, G., Papp, L.A., Szekely-Szentmiklosi, B., and Kelemen, H. (2022). The Use of Antibiotics as Chiral Selectors in Capillary Electrophoresis: A Review. Molecules, 27.","DOI":"10.3390\/molecules27113601"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"496","DOI":"10.1002\/chir.530060609","article-title":"Evaluation of the Macrocyclic Antibiotic Vancomycin as a Chiral Selector for Capillary Electrophoresis","volume":"6","author":"Armstrong","year":"1994","journal-title":"Chirality"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1007\/s13738-016-0951-6","article-title":"Chiral Separation of Ketoprofen on an Achiral NH2 Column by HPLC Using Vancomycin as Chiral Mobile Phase Additive","volume":"13","author":"Gherdaoui","year":"2016","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"7098","DOI":"10.1002\/anie.201208344","article-title":"Nonproteinogenic Amino Acid Building Blocks for Nonribosomal Peptide and Hybrid Polyketide Scaffolds","volume":"52","author":"Walsh","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1134\/S1061934817010075","article-title":"Separation of \u03b2-Blocker and Amino Acid Enantiomers on a Mixed Chiral Sorbent Modified with Macrocyclic Antibiotics Eremomycin and Vancomycin","volume":"72","author":"Fedorova","year":"2017","journal-title":"J. Anal. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1002\/chir.22432","article-title":"Determination of Trantinterol Enantiomers in Human Plasma by High-Performance Liquid Chromatography\u2013Tandem Mass Spectrometry Using Vancomycin Chiral Stationary Phase and Solid Phase Extraction and Stereoselective Pharmacokinetic Application","volume":"27","author":"Qin","year":"2015","journal-title":"Chirality"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1016\/S1074-5521(01)00075-8","article-title":"Direct Interaction of a Vancomycin Derivative with Bacterial Enzymes Involved in Cell Wall Biosynthesis","volume":"8","author":"Yang","year":"2001","journal-title":"Chem. Biol."},{"key":"ref_25","unstructured":"Xiao, L. (2004). Enantiomeric Separations Using Macrocyclic Glycopeptide Based Chiral Stationary Phases, an Application and Mechanism Study. [Ph.D. Thesis, Iowa State University]."},{"key":"ref_26","unstructured":"Riley, C., and Zechinati, B. (2020). Separation of Vancomycin and Its Degradation Products 2020. (WO2020081599A1), Worldwide Applications."},{"key":"ref_27","first-page":"96","article-title":"The Combined Effects of pH and Acetonitrile Composition on the Separation of Two Lincosamide Antibiotics","volume":"7","author":"Vella","year":"2014","journal-title":"Asian J. Pharm. Clin. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"100023","DOI":"10.1016\/j.jcoa.2021.100023","article-title":"Modified Aqueous Mobile Phases: A Way to Improve Retention Behavior of Active Pharmaceutical Compounds and Their Impurities in Liquid Chromatography","volume":"2","author":"Krmar","year":"2022","journal-title":"J. Chromatogr. Open"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1016\/0378-5173(93)90252-B","article-title":"Acid-Base Properties and Proton-Speciation of Vancomycin","volume":"89","year":"1993","journal-title":"Int. J. Pharm."},{"key":"ref_30","first-page":"30","article-title":"Back to Basics: The Role of pH in Retention and Selectivity","volume":"30","author":"Dolan","year":"2017","journal-title":"LCGC Eur."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/S0021-9673(03)00535-1","article-title":"Development and Validation of an Improved Method for the Analysis of Vancomycin by Liquid Chromatography: Selectivity of Reversed-Phase Columns towards Vancomycin Components","volume":"996","author":"Diana","year":"2003","journal-title":"J. Chromatogr. A"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1016\/S0378-4347(00)83049-2","article-title":"Rapid and Specific Method for the Determination of Vancomycin in Plasma by High-Performance Liquid Chromatography on an Aminopropyl Column","volume":"487","author":"Hosotsubo","year":"1989","journal-title":"J. Chromatogr. B Biomed. Sci. Appl."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/S0021-9673(00)93816-0","article-title":"Solvophobic Interactions in Liquid Chromatography with Nonpolar Stationary Phases","volume":"125","author":"Melander","year":"1976","journal-title":"J. Chromatogr. A"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1016\/0021-9673(93)80816-Q","article-title":"Retention in Reversed-Phase Liquid Chromatography as a Function of Mobile-Phase Composition","volume":"656","author":"Snyder","year":"1993","journal-title":"J. Chromatogr. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.chroma.2016.10.068","article-title":"Study of the Slope of the Linear Relationship between Retention and Mobile Phase Composition (Snyder-Soczewi\u00f1ski Model) in Normal Phase Liquid Chromatography with Bonded and Charge-Transfer Phases","volume":"1475","author":"Wu","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_36","unstructured":"Aguilar, M.-I. (2004). HPLC of Peptides and Proteins: Methods and Protocols, Springer. Methods in Molecular BiologyTM."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"430","DOI":"10.1002\/chir.22706","article-title":"New Chiral Stationary Phases Based on Xanthone Derivatives for Liquid Chromatography","volume":"29","author":"Fernandes","year":"2017","journal-title":"Chirality"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0021-9673(98)00727-4","article-title":"Retention in Reversed-Phase Chromatography: Partition or Adsorption?","volume":"829","author":"Vailaya","year":"1998","journal-title":"J. Chromatogr. A"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.jchromb.2014.02.049","article-title":"Enantioseparation of Chiral Pharmaceuticals in Biomedical and Environmental Analyses by Liquid Chromatography: An Overview","volume":"968","author":"Ribeiro","year":"2014","journal-title":"J. Chromatogr. B"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Scriba, G.K.E. (2019). Chiral Separations: Methods and Protocols, Springer. Methods in Molecular Biology.","DOI":"10.1007\/978-1-4939-9438-0"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1007\/s00706-021-02832-5","article-title":"An Overview of Chiral Separations of Pharmaceutically Active Substances by HPLC (2018\u20132020)","volume":"152","author":"Grybinik","year":"2021","journal-title":"Monatshefte Chem.\u2014Chem. Mon."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1067","DOI":"10.1002\/chir.22985","article-title":"Evaluation of the Edman Degradation Product of Vancomycin Bonded to Core-shell Particles as a New HPLC Chiral Stationary Phase","volume":"30","author":"Hellinghausen","year":"2018","journal-title":"Chirality"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"921","DOI":"10.1007\/s13738-015-0635-7","article-title":"Reversed-Phase High-Performance Liquid Chromatographic Separation of Some 2-Arylpropionic Acids Using Vancomycin as Chiral Stationary Phase","volume":"12","author":"Bouchair","year":"2015","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_44","first-page":"531","article-title":"Vancomycin as Chiral Selector for Enantioselective Separation of Selected Profen Nonsteroidal Anti-inflammatory Drugs Incapillary Liquid Chromatography","volume":"18","author":"Coufal","year":"2006","journal-title":"Chirality Pharmacol. Biol. Chem. Conseq. Mol. Asymmetry"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Berthod, A. (2010). Chiral Recognition in Separation Methods: Mechanisms and Applications, Springer.","DOI":"10.1007\/978-3-642-12445-7"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/s41664-022-00222-2","article-title":"Recent Advances on Chiral Mobile Phase Additives: A Critical Review","volume":"6","author":"Li","year":"2022","journal-title":"J. Anal. Test."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1002\/chir.22717","article-title":"Chiral Separation and Modeling of Baclofen, Bupropion, and Etodolac Profens on Amylose Reversed Phase Chiral Column","volume":"29","author":"Ali","year":"2017","journal-title":"Chirality"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"338861","DOI":"10.1016\/j.aca.2021.338861","article-title":"Modelling Approaches for Chiral Chromatography on Polysaccharide-Based and Macrocyclic Antibiotic Chiral Selectors: A Review","volume":"1198","author":"Vanommeslaeghe","year":"2022","journal-title":"Anal. Chim. Acta"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1016\/j.jpba.2005.10.045","article-title":"Chiral Separation of Ketoprofen on an Achiral C8 Column by HPLC Using Norvancomycin as Chiral Mobile Phase Additives","volume":"41","author":"Guo","year":"2006","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1701","DOI":"10.1007\/s13738-021-02408-4","article-title":"The Comparison of Some Chiral Selectors for Enantioselective Separation of Naproxen as a Model Drug in Capillary Electrophoresis: Thermodynamic Analysis of the Separation Mechanism","volume":"19","author":"Naghdi","year":"2022","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Papp, L.-A., Krizbai, S., Dob\u00f3, M., Hancu, G., Szab\u00f3, Z.-I., and T\u00f3th, G. (2022). Determination of Chiral Impurity of Naproxen in Different Pharmaceutical Formulations Using Polysaccharide-Based Stationary Phases in Reversed-Phased Mode. Molecules, 27.","DOI":"10.3390\/molecules27092986"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"397","DOI":"10.2116\/analsci.30.397","article-title":"High-Performance Enantiomer Separation of Nonsteroidal Anti-Inflammatory Drugs (NSAIDs) by 3 \u039cm Reversed-Phase Chiral Columns and Application to the Optical Purity Testing of Naproxen Drug Substances and Its Formulations","volume":"30","author":"Tanaka","year":"2014","journal-title":"Anal. Sci."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1208\/s12249-016-0660-6","article-title":"Two Synthetic Methods for Preparation of Chiral Stationary Phases Using Crystalline Degradation Products of Vancomycin: Column Performance for Enantioseparation of Acidic and Basic Drugs","volume":"18","author":"Abdollahpour","year":"2017","journal-title":"Aaps Pharmscitech"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1289","DOI":"10.1002\/chir.23273","article-title":"Enantioseparation of Mandelic Acid on Vancomycin Column: Experimental and Docking Study","volume":"32","author":"Shahnani","year":"2020","journal-title":"Chirality"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"460687","DOI":"10.1016\/j.chroma.2019.460687","article-title":"Enantioselective Potential of Teicoplanin-and Vancomycin-Based Superficially Porous Particles-Packed Columns for Supercritical Fluid Chromatography","volume":"1612","author":"Kozlov","year":"2020","journal-title":"J. Chromatogr. A"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/15\/12\/2154\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:37:20Z","timestamp":1760132240000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/15\/12\/2154"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,4]]},"references-count":55,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2023,12]]}},"alternative-id":["sym15122154"],"URL":"https:\/\/doi.org\/10.3390\/sym15122154","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2023,12,4]]}}}