{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T00:38:44Z","timestamp":1783039124192,"version":"3.54.6"},"reference-count":44,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2023,2,9]],"date-time":"2023-02-09T00:00:00Z","timestamp":1675900800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"RUDN University Strategic Academic Leadership program"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceutics"],"abstract":"<jats:p>The previously demonstrated activity of aqueous solutions of methionine and zinc salts against biofilms of uropathogenic bacteria prompted us to investigate the structure and properties of zinc methionine complex obtained from such solutions. The paper presents the analysis results of zinc coordination complexes with methionine obtained by synthesis (0.034 mol of L-methionine, 0.034 mol of NaOH, 40 mL of H2O, 0.017 mol ZnSO4, 60 \u00b0C) and simple crystallization from water solution (25 mL of a solution containing 134 mmol\/L L-methionine, 67 mmol\/L ZnSO4, pH = 5.74, I = 0.37 mmol\/L, crystallization at room temperature during more than two weeks). IR spectral analysis and X-ray diffraction showed the structural similarity of the substances to each other, in agreement with the data described in the literature. DSC confirmed the formation of a thermally stable (in the range from \u221230 \u00b0C to 180 \u00b0C) chelate compound in both cases and indicated the possible retention of the polymorphic two-dimensional structure inherent in L-methionine with the temperature of phase transition 320 K. The crystallized complex had better solubility in water (100 to 1000 mL per 1.0 g) contra the synthesized analog, which was practically insoluble (more than 10 000 mL per 1.0 g). The results of the solubility assessment, supplemented by the results of the dispersion analysis of solutions by the dynamic light scattering method indicated the formation of zinc-containing nanoparticles (80 nm) in a saturated water solution of a crystallized substance, suggesting the crystallized substance may have higher bioavailability. We predicted a possibility of the equivalent existence of optically active cis and trans isomers in methionine-zinc solutions by the close values of formation enthalpy (\u2212655 kJ\/mol and \u2212657 kJ\/mol for cis and trans forms, respectively) and also illustrated by the polarimetry measurement results (\u2206\u03b1 = 0.4\u00b0, pH = 5.74, C(Met) = 134 mmol\/L; the concentration of metal ion gradually increased from 0 to 134 mmol\/L). The obtained results allowed us to conclude that the compound isolated from the solution is a zinc-methionine chelate with the presence of sulfate groups and underline the role of the synthesis route for the biopharmaceutical characteristics of the resulting substance. We provided some quality indicators that it may be possible to include in the pharmacopeia monographs.<\/jats:p>","DOI":"10.3390\/pharmaceutics15020590","type":"journal-article","created":{"date-parts":[[2023,2,10]],"date-time":"2023-02-10T04:48:03Z","timestamp":1676004483000},"page":"590","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Comparative Analysis of Physical and Chemical Properties of Differently Obtained Zn\u2014Methionine Chelate with Proved Antibiofilm Properties (Part II)"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0174-9489","authenticated-orcid":false,"given":"Alla V.","family":"Marukhlenko","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical and Toxicological Chemistry, Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir N.","family":"Tumasov","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Toxicological Chemistry, Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leonid A.","family":"Butusov","sequence":"additional","affiliation":[{"name":"Institute of Innovative Engineering Technologies, Peoples Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya st., 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Georgy A.","family":"Shandryuk","sequence":"additional","affiliation":[{"name":"Russian Academy of Sciences A.V. Topchiev Institute of Petrochemical Synthesis, 29\/2, Leninsky Prospect, 119071 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1586-2183","authenticated-orcid":false,"given":"Mariya A.","family":"Morozova","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Toxicological Chemistry, Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1038\/s41579-022-00682-4","article-title":"Tolerance and resistance of microbial biofilms","volume":"20","author":"Ciofu","year":"2022","journal-title":"Nat. Rev. Microbiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1186\/s13756-022-01085-z","article-title":"Antimicrobial resistance (AMR) in COVID-19 patients: A systematic review and meta-analysis (November 2019\u2013June 2021)","volume":"11","author":"Kariyawasam","year":"2022","journal-title":"Antimicrob. Resist. Infect. Control"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"114378","DOI":"10.1016\/j.addr.2022.114378","article-title":"Novel antimicrobial agents for combating antibiotic-resistant bacteria","volume":"187","author":"Chang","year":"2022","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_4","first-page":"115","article-title":"Recent advances in nanoparticles as antibacterial agent","volume":"10","author":"Ozdal","year":"2022","journal-title":"ADMET DMPK"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"709","DOI":"10.2116\/analsci.19P413","article-title":"Analysis of complexation interactions between metal ions and drugs under pseudo-physiological pH conditions by a high-throughput screening method using a solid-phase extraction cartridge","volume":"36","author":"Moriwa","year":"2020","journal-title":"Anal. Sci."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.chempr.2019.10.013","article-title":"Classification of metal-based drugs according to their mechanisms of action","volume":"6","author":"Boros","year":"2020","journal-title":"Chem"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Sharmin, E., and Zafar, F. (2017). Spectroscopic Analyses\u2014Developments and Applications, IntechOpen.","DOI":"10.5772\/65617"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1110","DOI":"10.1080\/00958972.2016.1149819","article-title":"Synthesis, characterization and antimicrobial activity of zinc(II) ibuprofen complexes with nitrogen-based ligands","volume":"69","author":"Ali","year":"2016","journal-title":"J. Coord. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Al Sharabati, M., Sabouni, R., and Husseini, G.A. (2022). Biomedical Applications of Metal-Organic Frameworks for Disease Diagnosis and Drug Delivery: A Review. Nanomaterials, 12.","DOI":"10.3390\/nano12020277"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"356","DOI":"10.1080\/03602532.2019.1632887","article-title":"Zinc-based metal\u2013organic frameworks as nontoxic and biodegradable platforms for biomedical applications: Review study","volume":"51","author":"Bahrani","year":"2019","journal-title":"Drug Metab. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"741873","DOI":"10.3389\/fmicb.2021.741873","article-title":"Strategies for Zinc Uptake in Pseudomonas aeruginosa at the Host-Pathogen Interface","volume":"12","author":"Wang","year":"2021","journal-title":"Front. Microbiol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1073\/pnas.1519265113","article-title":"Zinc-dependent mechanical properties of Staphylococcus aureus biofilm-forming surface protein SasG","volume":"113","author":"Speziale","year":"2016","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"233","DOI":"10.3389\/fcimb.2017.00233","article-title":"Increased Zinc Availability Enhances Initial Aggregation and Biofilm Formation of Streptococcus pneumoniae","volume":"7","author":"Brown","year":"2017","journal-title":"Front. Cell. Infect. Microbiol."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Abdelghafar, A., Yousef, N., and Askoura, M. (2022). Zinc oxide nanoparticles reduce biofilm formation, synergize antibiotics action and attenuate Staphylococcus aureus virulence in host; an important message to clinicians. BMC Microbiol., 22.","DOI":"10.1186\/s12866-022-02658-z"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"110319","DOI":"10.1016\/j.msec.2019.110319","article-title":"Biofilm formation to inhibition: Role of zinc oxide-based nanoparticles","volume":"108","author":"Patil","year":"2020","journal-title":"Mater. Sci. Eng. C Mater. Biol. Appl."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Husain, F.M., Qais, F.A., Ahmad, I., Hakeem, M.J., Baig, M.H., Masood Khan, J., and Al-Shabib, N.A. (2022). Biosynthesized Zinc Oxide Nanoparticles Disrupt Established Biofilms of Pathogenic Bacteria. Appl. Sci., 12.","DOI":"10.3390\/app12020710"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"rbac019","DOI":"10.1093\/rb\/rbac019","article-title":"Zinc-based metal organic framework with antibacterial and anti-inflammatory properties for promoting wound healing","volume":"9","author":"Chen","year":"2022","journal-title":"Regen Biomater."},{"key":"ref_18","first-page":"109","article-title":"Ultrasonic synthesis of Zn(II)methionine nanostructures: As a precursor for ZnO nanoparticles and in vitro study","volume":"5","author":"Hakkak","year":"2020","journal-title":"J. Part. Sci. Technol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"388","DOI":"10.22159\/ijap.2018.v10s1.86","article-title":"Synthesis and analysis of zinc methionine, zinc glycine, copper leucine, and copper glycine complexes using atomic absorption spectrophotometry","volume":"10","author":"Nastiti","year":"2018","journal-title":"Int. J. Appl. Pharm."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1667","DOI":"10.1007\/s11814-013-0140-6","article-title":"Synthesis of metal-organic frameworks: A mini review","volume":"30","author":"Lee","year":"2013","journal-title":"Korean J. Chem. Eng."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Marukhlenko, A.V., Morozova, M.A., Mbarga, A.M.J., Antipova, N.V., Syroeshkin, A.V., Podoprigora, I.V., and Maksimova, T.V. (2022). Chelation of Zinc with Biogenic Amino Acids: Description of Properties Using Balaban Index, Assessment of Biological Activity on Spirostomum Ambiguum Cellular Biosensor, Influence on Biofilms and Direct Antibacterial Action. Pharmaceuticals, 15.","DOI":"10.3390\/ph15080979"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"154","DOI":"10.33380\/2305-2066-2021-10-4-154-161","article-title":"Development and Validation of Method for the Quantitative Determination of Zinc in its Chelate Complexes Using Energy Dispersive X-ray Fluorescence Spectroscopy","volume":"10","author":"Marukhlenko","year":"2021","journal-title":"Drug Dev. Regist."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1498","DOI":"10.1021\/ic50172a052","article-title":"Structural characterization of bis(L-methionato)zinc(II), Zn(L-met)2","volume":"16","author":"Wilson","year":"1977","journal-title":"Inorg. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Abendrot, M., Ch\u0119ci\u0144ska, L., Kusz, J., Lisowska, K., Zawadzka, K., Felczak, A., and Kalinowska-Lis, U. (2020). Zinc(II) Complexes with Amino Acids for Potential Use in Dermatology: Synthesis, Crystal Structures, and Antibacterial Activity. Molecules, 25.","DOI":"10.3390\/molecules25040951"},{"key":"ref_25","unstructured":"Council of Europe (2013). The European Pharmacopoeia, Council of Europe. [8th ed.]."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1042\/bj1210549","article-title":"The computed distribution of copper (II) and zinc (II) ions among seventeen amino acids present in human blood plasma","volume":"121","author":"Hallman","year":"1971","journal-title":"Biochem. J."},{"key":"ref_27","unstructured":"Council of Europe (2013). The European Pharmacopoeia, Council of Europe. [8th ed.]."},{"key":"ref_28","unstructured":"Council of Europe (2013). The European Pharmacopoeia, Council of Europe. [8th ed.]."},{"key":"ref_29","unstructured":"Council of Europe (2013). The European Pharmacopoeia, Council of Europe. [8th ed.]."},{"key":"ref_30","unstructured":"(2022, October 23). MolView v2.4. Available online: https:\/\/molview.org\/."},{"key":"ref_31","unstructured":"(2022, October 23). WebMo v22.0.009e. Available online: https:\/\/www.webmo.net\/demoserver\/cgi-bin\/webmo\/login.cgi."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.jscs.2009.12.005","article-title":"Synthesis and spectroscopic, magnetic and cyclic voltammetric characterization of some metal complexes of methionine: [(C5H10NO2S)2MII]; M II = Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II)","volume":"14","author":"Mamun","year":"2010","journal-title":"J. Saudi Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3115","DOI":"10.3382\/ps.2012-02314","article-title":"Bioavailability of organic and inorganic zinc sources in male broilers","volume":"91","author":"Star","year":"2012","journal-title":"Poult. Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1927","DOI":"10.1002\/jps.1143","article-title":"Gastrointestinal persorption and tissue distribution of differently sized colloidal gold nanoparticles","volume":"90","author":"Hillyer","year":"2001","journal-title":"J. Pharm. Sci."},{"key":"ref_35","first-page":"38","article-title":"Synthesis of D-element compounds with amino acids","volume":"2","author":"Golovnev","year":"2006","journal-title":"Vestn. Krasn. Gos. Universiteta. Estestv. Nauk."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2799","DOI":"10.1107\/S0567740873007569","article-title":"Crystal Structures and Molecular Conformations of L-Methionine and L-Norleucine","volume":"29","author":"Tori","year":"1973","journal-title":"Acta Cryst. B"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"9363","DOI":"10.1039\/C6CE02079H","article-title":"Understanding the single-crystal-to-single-crystal solid-state phase transition of DL-methionine","volume":"18","author":"Smets","year":"2016","journal-title":"CrystEngComm"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2221","DOI":"10.1016\/S0022-0248(01)02279-5","article-title":"Polymorphic transformation of dl-methionine crystals in aqueous solutions","volume":"237","author":"Yamanobe","year":"2002","journal-title":"J. Cryst. Growth"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1107\/S0365110X52001015","article-title":"McL. The Crystal Structures of the Dimorphs of DL-Methionine","volume":"5","author":"Mathieson","year":"1952","journal-title":"Acta Cryst."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2000208","DOI":"10.1002\/crat.202000208","article-title":"Polymorphic Control of \u03b1 and \u03b2 dl-Methionine through Swift Cooling Crystallization Process","volume":"56","author":"Suresh","year":"2021","journal-title":"Cryst. Res. Technol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2590","DOI":"10.1063\/1.1696337","article-title":"Infrared Spectra and Normal Coordinate Analysis of Metal Glycino Complexes","volume":"42","author":"Condrate","year":"1965","journal-title":"J. Chem. Phys."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1746","DOI":"10.1246\/bcsj.38.1746","article-title":"Metal complexes of amino acids. I. The circular dichroism of copper(II) complexes with optically active amino acids","volume":"38","author":"Yasui","year":"1965","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2417","DOI":"10.1246\/bcsj.39.2417","article-title":"Metal Complexes of Amino Acids. III. The Circular Dichroism of Cobalt(III) Ammine and Ethylenediamine Complexes with L-Amino Acids","volume":"39","author":"Yasui","year":"1966","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"11146","DOI":"10.1021\/ja0010296","article-title":"Tetrahedral vs Octahedral Zinc Complexes with Ligands of Biological Interest: A DFT\/CDM Study","volume":"112","author":"Dudev","year":"2000","journal-title":"J. Am. Chem. Soc."}],"container-title":["Pharmaceutics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1999-4923\/15\/2\/590\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:28:55Z","timestamp":1760120935000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1999-4923\/15\/2\/590"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,9]]},"references-count":44,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["pharmaceutics15020590"],"URL":"https:\/\/doi.org\/10.3390\/pharmaceutics15020590","relation":{},"ISSN":["1999-4923"],"issn-type":[{"value":"1999-4923","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,9]]}}}