{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T04:21:08Z","timestamp":1784521268367,"version":"3.55.0"},"reference-count":55,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2023,7,15]],"date-time":"2023-07-15T00:00:00Z","timestamp":1689379200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Russian Science Foundation","award":["RSF 23-23-00617"],"award-info":[{"award-number":["RSF 23-23-00617"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Site-directed spin labeling followed by investigation using Electron Paramagnetic Resonance spectroscopy is a rapidly expanding powerful biophysical technique to study structure, local dynamics and functions of biomolecules using pulsed EPR techniques and nitroxides are the most widely used spin labels. Modern trends of this method include measurements directly inside a living cell, as well as measurements without deep freezing (below 70 K), which provide information that is more consistent with the behavior of the molecules under study in natural conditions. Such studies require nitroxides, which are resistant to the action of biogenic reductants and have high spin relaxation (dephasing) times, Tm. (1R(S),5R(S),7R(S),8R(S))-1,8-bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl is a unique nitroxide that combines these features. We have developed a convenient method for the synthesis of this radical and studied the ways of its functionalization. Promising spin labels have been obtained, the parameters of their spin relaxation T1 and Tm have been measured, and the kinetics of reduction with ascorbate have been studied.<\/jats:p>","DOI":"10.3390\/ijms241411498","type":"journal-article","created":{"date-parts":[[2023,7,17]],"date-time":"2023-07-17T00:35:04Z","timestamp":1689554104000},"page":"11498","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and Properties of (1R(S),5R(S),7R(S),8R(S))-1,8-Bis(hydroxymethyl)-6-azadispiro[4.1.4.2]tridecane-6-oxyl: Reduction-Resistant Spin Labels with High Spin Relaxation Times"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2923-4241","authenticated-orcid":false,"given":"Yulia V.","family":"Khoroshunova","sequence":"first","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia"},{"name":"Department of Physics, Novosibirsk State University, Pirogova Str. 1, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2403-2843","authenticated-orcid":false,"given":"Denis A.","family":"Morozov","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Danil A.","family":"Kuznetsov","sequence":"additional","affiliation":[{"name":"Department of Physics, Novosibirsk State University, Pirogova Str. 1, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2398-5271","authenticated-orcid":false,"given":"Tatyana V.","family":"Rybalova","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yurii I.","family":"Glazachev","sequence":"additional","affiliation":[{"name":"Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0057-383X","authenticated-orcid":false,"given":"Elena G.","family":"Bagryanskaya","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6033-0368","authenticated-orcid":false,"given":"Igor A.","family":"Kirilyuk","sequence":"additional","affiliation":[{"name":"N.N. 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Nitroxides: Synthesis, Properties and Applications, The Royal Society of Chemistry.","DOI":"10.1039\/9781788019651"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3248289","DOI":"10.1155\/2018\/3248289","article-title":"Site-Directed Spin Labeling EPR for Studying Membrane Proteins","volume":"2018","author":"Sahu","year":"2018","journal-title":"BioMed Res. Int."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1281","DOI":"10.1515\/hsz-2013-0155","article-title":"Site-directed spin labeling EPR spectroscopy in protein research","volume":"394","author":"Klare","year":"2013","journal-title":"Biol. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1002\/cbic.201900291","article-title":"In-Cell EPR: Progress towards Structural Studies Inside Cells","volume":"21","author":"Bonucci","year":"2020","journal-title":"ChemBioChem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.pnmrs.2022.11.001","article-title":"Electron paramagnetic resonance spectroscopy in structural-dynamic studies of large protein complexes","volume":"134\u2013135","author":"Galazzo","year":"2023","journal-title":"Prog. Nucl. Magn. Reson. Spectrosc."},{"key":"ref_7","first-page":"1","article-title":"Tuning the properties of nitroxide spin labels for use in electron paramagnetic resonance spectroscopy through chemical modification of the nitroxide framework","volume":"Volume 25","author":"Chechik","year":"2017","journal-title":"Electron Paramagnetic Resonance"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1476","DOI":"10.1016\/j.bpj.2019.09.002","article-title":"Disulfide Chaperone Knockouts Enable In Vivo Double Spin Labeling of an Outer Membrane Transporter","volume":"117","author":"Nilaweera","year":"2019","journal-title":"Biophys. J."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"16614","DOI":"10.1021\/ja305300m","article-title":"Macromolecular Crowding and Protein Stability","volume":"134","author":"Wang","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3016","DOI":"10.1111\/febs.13744","article-title":"Grasping the nature of the cell interior: From Physiological Chemistry to Chemical Biology","volume":"283","author":"Kyne","year":"2016","journal-title":"FEBS J."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.jmr.2018.12.005","article-title":"Increasing nitroxide lifetime in cells to enable in-cell protein structure and dynamics measurements by electron spin resonance spectroscopy","volume":"299","author":"Singewald","year":"2019","journal-title":"J. Magn. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"78","DOI":"10.3109\/10715762.2014.979409","article-title":"Sterically Shielded Spin Labels for In-Cell EPR Spectroscopy: Analysis of Stability in Reducing Environment","volume":"49","author":"Jagtap","year":"2015","journal-title":"Free Radic. Res."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Jana, S., Evans, E.G.B., Jang, H.S., Zhang, S., Zhang, H., Rajca, A., Gordon, S.E., Zagotta, W.N., Stoll, S., and Mehl, R.A. (2023). Ultra-Fast Bioorthogonal Spin-Labeling and Distance Measurements in Mammalian Cells Using Small, Genetically Encoded Tetrazine Amino Acids. bioRxiv.","DOI":"10.1101\/2023.01.26.525763"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1366","DOI":"10.1002\/anie.201710184","article-title":"Bioresistant Nitroxide Spin Label for In-Cell EPR Spectroscopy: In Vitro and In Oocytes Protein Structural Dynamics Studies","volume":"57","author":"Karthikeyan","year":"2018","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"13142","DOI":"10.1039\/C5CC05014F","article-title":"Site-directed spin labeling of 20-amino groups in RNA with isoindoline nitroxides that are resistant to reduction","volume":"51","author":"Saha","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1035","DOI":"10.1002\/open.201900232","article-title":"gem-Diethyl Pyrroline Nitroxide Spin Labels: Synthesis, EPR Characterization, Rotamer Libraries and Biocompatibility","volume":"8","author":"Bleicken","year":"2019","journal-title":"ChemistryOpen"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"958","DOI":"10.1002\/cbic.201900537","article-title":"Isoindoline-Based Nitroxides as Bioresistant Spin Labels for Protein Labeling through Cysteines and Alkyne-Bearing Noncanonical Amino Acids","volume":"21","author":"Braun","year":"2020","journal-title":"Chembiochem"},{"key":"ref_18","first-page":"100041","article-title":"In situ distance measurements in a membrane transporter using maleimide functionalized orthogonal spin labels and 5-pulse electron-electron double resonance spectroscopy","volume":"10\u201311","author":"Ketter","year":"2022","journal-title":"J. Magn. Reson. Open (Companion Title J. Magn. Reson.)"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Dobrynin, S.A., Usatov, M.S., Zhurko, I.F., Morozov, D.A., Polienko, Y.F., Glazachev, Y.I., Parkhomenko, D.A., Tyumentsev, M.A., Gatilov, Y.V., and Chernyak, E.I. (2021). A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series. Molecules, 26.","DOI":"10.3390\/molecules26195761"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1042\/ETLS20170143","article-title":"The contribution of modern EPR to structural biology","volume":"2","author":"Jeschke","year":"2018","journal-title":"Emerg. Top. Life Sci."},{"key":"ref_21","first-page":"223","article-title":"Measurement of Distances Between Electron Spins Using Pulsed EPR","volume":"Volume 24\/B","author":"Eaton","year":"2005","journal-title":"Biomedical EPR, Part B: Methodology, Instrumentation, and Dynamics"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5778","DOI":"10.1002\/chem.200903102","article-title":"A spirocyclohexyl nitroxide amino acid spin label for pulsed EPR spectroscopy distance measurements","volume":"16","author":"Rajca","year":"2010","journal-title":"Chemistry"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1016\/j.bpj.2015.01.015","article-title":"Room-temperature distance measurements of immobilized spin-labeled protein by DEER\/PELDOR","volume":"108","author":"Meyer","year":"2015","journal-title":"Biophys. J."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"5322","DOI":"10.1021\/ol302506f","article-title":"Synthesis and Reduction Kinetics of Sterically Shielded Pyrrolidine Nitroxides","volume":"14","author":"Paletta","year":"2012","journal-title":"Org. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1038\/s42004-023-00912-7","article-title":"Conformational tuning improves the stability of spirocyclic nitroxides with long paramagnetic relaxation times","volume":"6","author":"Gahlawat","year":"2023","journal-title":"Commun. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jmr.2016.02.014","article-title":"Room-temperature electron spin relaxation of nitroxides immobilized in trehalose: Effect of substituents adjacent to NO-group","volume":"266","author":"Kuzhelev","year":"2016","journal-title":"J. Magn. Reson."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"10688","DOI":"10.1021\/jo3019158","article-title":"Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones","volume":"77","author":"Morozov","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8016","DOI":"10.1021\/jo301235j","article-title":"Synthesis of 2,5-Bis(spirocyclohexane)-Substituted Nitroxides of Pyrroline and Pyrrolidine Series, Including Thiol-Specific Spin Label: An Analogue of MTSSL with Long Relaxation Time","volume":"77","author":"Kirilyuk","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5298","DOI":"10.1021\/ol502449r","article-title":"Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides","volume":"16","author":"Wang","year":"2014","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2036","DOI":"10.3762\/bjoc.15.200","article-title":"Synthesis of 1-azaspiro[4.4]nonan-1-oxyls via intramolecular 1,3-dipolar cycloaddition","volume":"15","author":"Khoroshunova","year":"2019","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5274","DOI":"10.1021\/jo00071a045","article-title":"New Synthesis of Five-Membered Cyclic Nitrones from Tartaric Acid","volume":"58","author":"Cicchi","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6489","DOI":"10.1021\/acs.joc.7b00959","article-title":"Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones","volume":"82","author":"Saruengkhanphasit","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"10399","DOI":"10.1016\/S0040-4020(01)88344-7","article-title":"X = Y \u2212 ZH Systems as potential 1,3-dipoles. Part 37 generation of nitrones from oximes. Tandem intramolecular 1,3-azaprotio cyclotransfer\u2014Intramolecular 1,3-dipolar cycloaddition reactions. Class 4 processes","volume":"48","author":"Grigg","year":"1992","journal-title":"Tetrahedron"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Khoroshunova, Y.V., Morozov, D.A., Taratayko, A.I., Dobrynin, S.A., Eltsov, I.V., Rybalova, T.V., Sotnikova, Y.S., Polovyanenko, D.N., Asanbaeva, N.B., and Kirilyuk, I.A. (2021). The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4. Molecules, 26.","DOI":"10.3390\/molecules26196000"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2564","DOI":"10.1021\/jo982143y","article-title":"Oxidation of Primary Alcohols to Carboxylic Acids with Sodium Chlorite Catalyzed by TEMPO and Bleach","volume":"64","author":"Zhao","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_36","first-page":"397","article-title":"Proton exchange in stable nitroxyl radicals of the imidazoline and imidazolidine series","volume":"61","author":"Khramtsov","year":"1985","journal-title":"J. Magn. Reson."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"530","DOI":"10.1055\/s-1979-28747","article-title":"Nitroxyls; IV. Synthesis of Spin-Labelled N-(4-Piperidinyloxycarbonyl)-imidazole and 4-Piperidinyloxycarbonyl Azides and Their Reaction with Amino Acid Derivatives","volume":"1979","author":"Hankovszky","year":"1979","journal-title":"Synthesis"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Trofimov, D.G., Glazachev, Y.I., Gorodetsky, A.A., Komarov, D.A., Rybalova, T.V., and Kirilyuk, I.A. (2022). 4-Dialkylamino-2,5-dihydroimidazol-1-oxyls with Functional Groups at the Position 2 and at the Exocyclic Nitrogen: The pH-Sensitive Spin Labels. Gels, 8.","DOI":"10.3390\/gels8010011"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4875","DOI":"10.1039\/C9CP05584C","article-title":"Combining site-directed spin labeling in vivo and in-cell EPR distance determination","volume":"22","author":"Widder","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4523","DOI":"10.1016\/j.bmcl.2014.07.077","article-title":"\u2018Click\u2019 assembly of glycoclusters and discovery of a trehalose analogue that retards A\u03b240 aggregation and inhibits A\u03b240-induced neurotoxicity","volume":"24","author":"Rajaram","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"104687","DOI":"10.1016\/j.bioorg.2021.104687","article-title":"Synthesis, in vitro and computational studies of novel glycosyl-1, 2, 3-1H-triazolyl methyl benzamide derivatives as potential \u03b1-glucosidase inhibitory activity","volume":"109","author":"Shukla","year":"2021","journal-title":"Bioorganic Chem."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"El-Sayed, W.A., Alminderej, F.M., Mounier, M.M., Nossier, E.S., Saleh, S.M., and Kassem, A.F. (2022). Novel 1,2,3-Triazole-Coumarin Hybrid Glycosides and Their Tetrazolyl Analogues: Design, Anticancer Evaluation and Molecular Docking Targeting EGFR, VEGFR-2 and CDK-2. Molecules, 27.","DOI":"10.3390\/molecules27072047"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1069","DOI":"10.1080\/10715760701449302","article-title":"Enzymatic reduction-resistant nitroxyl spin probes with spirocyclohexyl rings","volume":"41","author":"Okazaki","year":"2007","journal-title":"Free. Radic. Res."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1615","DOI":"10.1039\/C7CP07074H","article-title":"Dynamical decoupling of nitroxides in o-terphenyl: A study of temperature, deuteration and concentration effects","volume":"20","author":"Soetbeer","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"5352","DOI":"10.1039\/D1CP00055A","article-title":"Dynamical decoupling in water\u2013glycerol glasses: A comparison of nitroxides, trityl radicals and gadolinium complexes","volume":"23","author":"Soetbeer","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1007\/BF03162452","article-title":"Librational dynamics of nitroxide molecules in a molecular glass studied by echo-detected EPR","volume":"21","author":"Kirilina","year":"2001","journal-title":"Appl. Magn. Reson."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"054502","DOI":"10.1063\/1.2220571","article-title":"On the possible manifestation of harmonic-anharmonic dynamical transition in glassy media in electron paramagnetic resonance of nitroxide spin probes","volume":"125","author":"Dzuba","year":"2006","journal-title":"J. Chem. Phys."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1016\/j.freeradbiomed.2006.11.007","article-title":"Reversible reduction of nitroxides to hydroxylamines: Roles for ascorbate and glutathione","volume":"42","author":"Bobko","year":"2007","journal-title":"Free Radic. Biol. Med."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"9118","DOI":"10.1021\/acs.joc.5b01494","article-title":"Effect of Sterical Shielding on the Redox Properties of Imidazoline and Imidazolidine Nitroxides","volume":"80","author":"Kirilyuk","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_50","unstructured":"Sheldrick, G.M. (2008). SADABS, v. 2008\/1, Bruker AXS, Inc."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A Short History of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2014Integrated space-group and crystal-structure determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_53","first-page":"3","article-title":"Crystal Structure Refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"100092","DOI":"10.1016\/j.jmro.2022.100092","article-title":"A broadband pulse EPR spectrometer for high-throughput measurements in the X-band","volume":"14\u201315","author":"Isaev","year":"2023","journal-title":"J. Magn. Reson. Open"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"911","DOI":"10.1055\/s-1980-29268","article-title":"Nitroxyls; VI1. Synthesis and Reactions of 3-Hydroxymethyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-1-oxyl and 3-Formyl Derivatives","volume":"1980","author":"Hideg","year":"1980","journal-title":"Synthesis"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/14\/11498\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:12:40Z","timestamp":1760127160000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/14\/11498"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,15]]},"references-count":55,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2023,7]]}},"alternative-id":["ijms241411498"],"URL":"https:\/\/doi.org\/10.3390\/ijms241411498","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,15]]}}}