{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,2]],"date-time":"2026-05-02T04:24:51Z","timestamp":1777695891958,"version":"3.51.4"},"reference-count":67,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2023,9,15]],"date-time":"2023-09-15T00:00:00Z","timestamp":1694736000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["22-73-00160"],"award-info":[{"award-number":["22-73-00160"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The synthesis of the first conjugates of acridine with cobalt bis(dicarbollide) are reported. A novel 9-azido derivative of acridine was prepared through the reaction of 9-methoxyacridine with N3CH2CH2NH2, and its solid-state molecular structure was determined via single-crystal X-ray diffraction. The azidoacridine was used in a copper (I)-catalyzed azide-alkyne cycloaddition reaction with cobalt bis(dicarbollide)-based terminal alkynes to give the target 1,2,3-triazoles. DNA interaction studies via absorbance spectroscopy showed the weak binding of the obtained conjugates with DNA. The antiproliferative activity (IC50) of the boronated conjugates against a series of human cell lines was evaluated through an MTT assay. The results suggested that acridine derivatives of cobalt bis(dicarbollide) might serve as a novel scaffold for the future development of new agents for boron neutron capture therapy (BNCT).<\/jats:p>","DOI":"10.3390\/molecules28186636","type":"journal-article","created":{"date-parts":[[2023,9,15]],"date-time":"2023-09-15T04:06:13Z","timestamp":1694750773000},"page":"6636","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["New Boron Containing Acridines: Synthesis and Preliminary Biological Study"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2368-4148","authenticated-orcid":false,"given":"Anna A.","family":"Druzina","sequence":"first","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-3309","authenticated-orcid":false,"given":"Nadezhda V.","family":"Dudarova","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6867-7534","authenticated-orcid":false,"given":"Ivan V.","family":"Ananyev","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskii pr., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anastasia A.","family":"Antonets","sequence":"additional","affiliation":[{"name":"Department of Chemistry, M.V. Lomonosov Moscow State University, 1\/3 Leninskie Gory, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7090-3334","authenticated-orcid":false,"given":"Dmitry N.","family":"Kaluzhny","sequence":"additional","affiliation":[{"name":"V.A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov Str., 11991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5821-1658","authenticated-orcid":false,"given":"Alexey A.","family":"Nazarov","sequence":"additional","affiliation":[{"name":"Department of Chemistry, M.V. Lomonosov Moscow State University, 1\/3 Leninskie Gory, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5442-367X","authenticated-orcid":false,"given":"Igor B.","family":"Sivaev","sequence":"additional","affiliation":[{"name":"A.N. 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Isot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3987","DOI":"10.1158\/1078-0432.CCR-05-0035","article-title":"Boron neutron capture therapy of cancer: Current status and future prospects","volume":"11","author":"Barth","year":"2005","journal-title":"Clin. Cancer Res."},{"key":"ref_4","unstructured":"Hosmane, N.S. (2012). Boron Science: New Technologies and Applications, CRC Press."},{"key":"ref_5","first-page":"36","article-title":"A realistic appraisal of boron neutron capture therapy as a cancer treatment modality","volume":"38","author":"Barth","year":"2018","journal-title":"Cancer Commun."},{"key":"ref_6","first-page":"35","article-title":"Boron delivery agents for neutron capture therapy of cancer","volume":"38","author":"Barth","year":"2018","journal-title":"Cancer Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1135\/cccc19990783","article-title":"Chemistry of cobalt bis(dicarbollides). A review","volume":"64","author":"Sivaev","year":"1999","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_8","first-page":"849","article-title":"Cobalt bis(dicarbollide) anion and its derivatives","volume":"170","author":"Dash","year":"2017","journal-title":"J. Organomet. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"17239","DOI":"10.1002\/chem.201803178","article-title":"Metallacarboranes on the road to anticancer therapies: Cellular uptake, DNA interaction, and biological evaluation of cobaltabisdicarbollide [COSAN]\u2212","volume":"24","author":"Fuentes","year":"2018","journal-title":"Chem. Eur. J."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"7804","DOI":"10.1038\/srep07804","article-title":"Biological interaction of living cells with COSAN-based synthetic vesicles","volume":"5","author":"Canetta","year":"2015","journal-title":"Sci. Rep."},{"key":"ref_11","first-page":"62","article-title":"Toxicity of functional derivatives of polyhedral carboranes","volume":"26","author":"Spryshkova","year":"1981","journal-title":"Med. Radiol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"25112","DOI":"10.1039\/C7CP04207H","article-title":"Fast flip-flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane","volume":"19","author":"Rokitskaya","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6700","DOI":"10.1039\/c4cc01283f","article-title":"Amphiphilic COSAN and I2-COSAN crossing synthetic lipid membranes: Planar bilayers and liposomes","volume":"50","author":"Alcaraz","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"11790","DOI":"10.1021\/acs.joc.9b01688","article-title":"High-affinity binding of metallacarborane cobalt bis(dicarbollide) anions to cyclodextrins and application to membrane translocation","volume":"84","author":"Assaf","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/0167-8140(94)90414-6","article-title":"Radiation dose heterogeneity in receptor and antigen mediated boron neutron capture therapy","volume":"31","author":"Hartman","year":"1994","journal-title":"Radiother. Oncol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"14","DOI":"10.2307\/3577018","article-title":"The Monte Carlo simulation of the biological effect of the 10B(n,\u03b1)7Li reaction in cells and tissue and its implication for Boron Neutron Capture Therapy","volume":"111","author":"Gabel","year":"1987","journal-title":"Radiat. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"303","DOI":"10.2174\/138955707780059808","article-title":"Boronated DNA-binding compounds as potential agents for Boron Neutron Capture Therapy","volume":"7","author":"Crossley","year":"2007","journal-title":"Mini-Rev. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6905","DOI":"10.1016\/0040-4039(96)01512-2","article-title":"Synthesis of para- and nido-carboranyl phenanthridinium compounds for neutron capture therapy","volume":"37","author":"Tjarks","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"17519","DOI":"10.1016\/S0040-4020(97)10200-9","article-title":"Synthesis of boronated phenanthridinium derivatives for potential use in boron neutron capture therapy (BNCT)","volume":"53","author":"Ghaneolhosseini","year":"1997","journal-title":"Tetrahedron"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Mishima, Y. (1996). Cancer Neutron Capture Therapy, Springer.","DOI":"10.1007\/978-1-4757-9567-7"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"298","DOI":"10.3891\/acta.chem.scand.53-0298","article-title":"Synthesis of a boronated naphthalimide for potential use in boron neutron capture therapy (BNCT)","volume":"53","author":"Ghaneolhosseini","year":"1999","journal-title":"Acta Chem. Scand."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"103432","DOI":"10.1016\/j.bioorg.2019.103432","article-title":"Synthesis of naphthalimide-carborane and metallacarborane conjugates: Anticancer activity, DNA binding ability","volume":"94","author":"Nekvinda","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Rykowski, S., Gurda-Wo\u017ana, D., Orlicka-P\u0142ocka, M., Fedoruk-Wyszomirska, A., Giel-Pietraszuk, M., Wyszko, E., Kowalczyk, A., St\u0105czek, P., Bak, A., and Kiliszek, A. (2021). Design, synthesis, and evaluation of novel 3-carboranyl-1,8-naphthalimide derivatives as potential anticancer agents. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22052772"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"122186","DOI":"10.1016\/j.jorganchem.2021.122186","article-title":"Synthesis of naphthalimide derivatives of closo-dodecaborate and nido-carborane","volume":"959","author":"Laskova","year":"2021","journal-title":"J. Organomet. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2528","DOI":"10.1039\/D1CC07075D","article-title":"Nematicidal activity of naphthalimide\u2013boron cluster conjugates","volume":"58","author":"Rykowski","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Rykowski, S., Gurda-Wo\u017ana, D., Orlicka-P\u0142ocka, M., Fedoruk-Wyszomirska, A., Giel-Pietraszuk, M., Wyszko, E., Kowalczyk, A., St\u0105czek, P., Biniek-Antosiak, K., and Rypniewski, W. (2022). Design of DNA intercalators based on 4-carboranyl-1,8-naphthalimides: Investigation of their DNA-binding ability and anticancer activity. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23094598"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2171028","DOI":"10.1080\/14756366.2023.2171028","article-title":"Carboranyl-1,8-naphthalimide intercalators induce lysosomal membrane permeabilization and ferroptosis in cancer cell lines","volume":"38","author":"Rykowski","year":"2023","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_28","first-page":"203","article-title":"Boron compounds in cancer therapy","volume":"Volume 1","author":"McCloskey","year":"1964","journal-title":"Progress in Boron Chemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"730","DOI":"10.1021\/jm00316a047","article-title":"Carboranes. III. Boron-containing acridines","volume":"10","author":"Davis","year":"1967","journal-title":"J. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3877","DOI":"10.1016\/S0040-4020(98)00114-8","article-title":"Synthesis of novel boronated acridines- and spermidines as possible agents for BNCT","volume":"54","author":"Ghaneolhosseini","year":"1998","journal-title":"Tetrahedron"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"e202200666","DOI":"10.1002\/cmdc.202200666","article-title":"Acridine\/acridone\u2013carborane conjugates as strong DNA-binding agents with anticancer potential","volume":"18","author":"Kowalczyk","year":"2023","journal-title":"ChemMedChem"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Cebula, J., Fink, K., Goldeman, W., Szermer-Olearnik, B., Nasulewicz-Goldeman, A., Psurski, M., Cuprych, M., K\u0119dziora, A., Dudek, B., and Bugla-P\u0142osko\u0144ska, G. (2023). Structural patterns enhancing the antibacterial activity of metallacarborane-based antibiotics. ChemRxiv.","DOI":"10.26434\/chemrxiv-2022-t2g39-v2"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6956","DOI":"10.1016\/j.bmcl.2010.09.128","article-title":"Design and synthesis of threading intercalators to target DNA","volume":"20","author":"Howell","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"792","DOI":"10.1002\/cmdc.201200060","article-title":"Synthesis of small molecules targeting multiple DNA structures using click chemistry","volume":"7","author":"Howell","year":"2012","journal-title":"ChemMedChem"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1021\/jm00345a015","article-title":"Potential antitumor agents. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents","volume":"25","author":"Denny","year":"1982","journal-title":"J. Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/j.antiviral.2011.05.005","article-title":"Acridine derivatives as anti-BVDV agents","volume":"91","author":"Tonelli","year":"2011","journal-title":"Antiv. Res."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5610","DOI":"10.1039\/C9RA09510A","article-title":"CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: Review","volume":"10","author":"Rani","year":"2020","journal-title":"RSC Adv."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3679","DOI":"10.1021\/acs.organomet.0c00478","article-title":"Cu(I)-catalyzed cycloaddition of vinylacetylene ortho-carborane and arylazides in the design of 1,2,3-triazolyl-modified vinylcarborane fluorophores","volume":"39","author":"Smyshliaeva","year":"2020","journal-title":"Organometalics"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"370","DOI":"10.1002\/aoc.1521","article-title":"Novel types of boronated chlorine e6 conjugates via \u00abclick chemistry\u00bb","volume":"23","author":"Bregadze","year":"2009","journal-title":"Appl. Organometal. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"10675","DOI":"10.1002\/chem.200801053","article-title":"\u201cChemical ligation\u201d: A versatile method for nucleoside modification with boron clusters","volume":"14","author":"Wojtczak","year":"2008","journal-title":"Chem. Eur. J."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1070\/RCR5000","article-title":"Cyclic oxonium derivatives of cobalt and iron bis (dicarbollide)s and their use in organic synthesis","volume":"90","author":"Druzina","year":"2021","journal-title":"Russ. Chem. Rev."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","article-title":"The Cambridge Structural Database","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"m1318","DOI":"10.1107\/S1600536810037499","article-title":"Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato) cuprate(II) trihydrate","volume":"66","author":"Aghabozorg","year":"2010","journal-title":"Acta Cryst. E"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"m1411","DOI":"10.1107\/S1600536811036981","article-title":"Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato-\u03ba3O2,N,O6)manganate(II) trihydrate","volume":"67","author":"Mirzaei","year":"2011","journal-title":"Acta Cryst. E"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"o657","DOI":"10.1107\/S160053681401023X","article-title":"9-Aminoacridin-10-ium 4-aminobenzoate dihydrate","volume":"70","author":"Dhanabalan","year":"2014","journal-title":"Acta Cryst. E"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"m761","DOI":"10.1107\/S1600536812020247","article-title":"9-Aminoacridinium bis(pyridine-2,6-dicarboxylato-\u03ba3O2,N,O6)ferrate(III) tetrahydrate","volume":"68","author":"Mirzaei","year":"2012","journal-title":"Acta Cryst. E"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"m355","DOI":"10.1107\/S1600536812005764","article-title":"Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) trihydrate","volume":"68","author":"Mirzaei","year":"2012","journal-title":"Acta Cryst. E"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing noncovalent interactions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"9362","DOI":"10.1002\/chem.200700408","article-title":"Bond paths as privileged exchange channels","volume":"13","author":"Pendas","year":"2007","journal-title":"Chem. Eur. J."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2213","DOI":"10.1002\/jcc.26390","article-title":"Interatomic exchange-correlation interaction energy from a measure of quantum theory of atoms in molecules topological bonding: A diatomic case","volume":"41","author":"Anisimov","year":"2020","journal-title":"J. Comput. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1607","DOI":"10.1002\/jcc.25235","article-title":"Estimations of energy of noncovalent bonding from integrals over interatomic zero-flux surfaces: Correlation trends and beyond","volume":"39","author":"Romanova","year":"2018","journal-title":"J. Comput. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1111\/j.1600-0749.1989.tb00196.x","article-title":"New thermal neutron capture therapy for malignant melanoma: Melanogenesis-seeking 10B molecule-melanoma cell interaction from in vitro to first clinical trial","volume":"2","author":"Mishima","year":"1989","journal-title":"Pigm. Cell Res."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1007\/s11172-013-0069-2","article-title":"Synthesis of 1,4-disubstituted 1,2,3-triazoles based on cobalt bis (1,2-dicarbollide)","volume":"62","author":"Kosenko","year":"2013","journal-title":"Russ. Chem. Bull."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"8575","DOI":"10.3390\/molecules27238575","article-title":"New azido coumarins as potential agents for fluorescent labeling and their \u201cclick\u201d chemistry reactions for the conjugation with closo-dodecaborate anion","volume":"27","author":"Laskova","year":"2022","journal-title":"Molecules"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3847","DOI":"10.1021\/acs.bioconjchem.8b00678","article-title":"Anthranilic acid as a versatile fluorescent tag and linker for functional glycomics","volume":"29","author":"Zhu","year":"2018","journal-title":"Bioconjugate Chem."},{"key":"ref_57","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. Cryst. A"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"Appl. Cryst."},{"key":"ref_59","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 09, Revision D.01, Gaussian, Inc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1039\/b508541a","article-title":"Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1057","DOI":"10.1039\/b515623h","article-title":"Accurate Coulomb-fitting basis sets for H to Rn","volume":"8","author":"Weigend","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"9982","DOI":"10.1063\/1.472933","article-title":"Rationale for mixing exact exchange with density functional approximations","volume":"105","author":"Perdew","year":"1996","journal-title":"J. Chem. Phys."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"6158","DOI":"10.1063\/1.478522","article-title":"Toward reliable density functional methods without adjustable parameters: The PBE0 model","volume":"110","author":"Adamo","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"154104","DOI":"10.1063\/1.3382344","article-title":"A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu","volume":"132","author":"Grimme","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_65","first-page":"1456","article-title":"Effect of the damping function in dispersion corrected density functional theory","volume":"132","author":"Grimme","year":"2011","journal-title":"J. Chem. Phys."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_67","unstructured":"Keith, T.A. (2019). AIMAll (Version 19.10.12), TK Gristmill Software."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/18\/6636\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:51:27Z","timestamp":1760129487000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/18\/6636"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,9,15]]},"references-count":67,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2023,9]]}},"alternative-id":["molecules28186636"],"URL":"https:\/\/doi.org\/10.3390\/molecules28186636","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,9,15]]}}}