{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:44:25Z","timestamp":1760233465261,"version":"build-2065373602"},"reference-count":76,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2021,1,20]],"date-time":"2021-01-20T00:00:00Z","timestamp":1611100800000},"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":["20-73-00228"],"award-info":[{"award-number":["20-73-00228"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Novel zwitter-ionic nido-carboranyl azide 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was prepared by the reaction of 9-Cl(CH2)3Me2N-nido-7,8-C2B9H11 with NaN3. The solid-state molecular structure of nido-carboranyl azide was determined by single-crystal X-ray diffraction. 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenylacetylene, alkynyl-3\u03b2-cholesterol and cobalt\/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The nido-carborane-cholesterol conjugate 9-3\u03b2-Chol-O(CH2)C-CH-N3(CH2)3Me2N-nido-7,8-C2B9H11 with charge-compensated group in a linker can be used as a precursor for preparation of liposomes for Boron Neutron Capture Therapy (BNCT). A series of novel zwitter-ionic boron-enriched cluster compounds bearing a 1,2,3-triazol-metallacarborane-carborane conjugated system was synthesized. Prepared conjugates contain a large amount of boron atom in the biomolecule and potentially can be used for BNCT.<\/jats:p>","DOI":"10.3390\/molecules26030530","type":"journal-article","created":{"date-parts":[[2021,1,20]],"date-time":"2021-01-20T12:16:18Z","timestamp":1611144978000},"page":"530","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis and Structure of Nido-Carboranyl Azide and Its \u201cClick\u201d Reactions"],"prefix":"10.3390","volume":"26","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., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Olga B.","family":"Zhidkova","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nadezhda V.","family":"Dudarova","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irina D.","family":"Kosenko","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ivan V.","family":"Ananyev","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6699-7910","authenticated-orcid":false,"given":"Sergey V.","family":"Timofeev","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vladimir I.","family":"Bregadze","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,20]]},"reference":[{"key":"ref_1","unstructured":"Grimes, R.N. (2016). Carboranes, Academic Press. [3rd ed.]."},{"key":"ref_2","unstructured":"Michael, D., Mingos, P., and Crabtree, R.H. (2007). Comprehensive Organometallic Chemistry III., Elsevier."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"950","DOI":"10.1002\/anie.199309501","article-title":"The role of chemistry in the development of boron neutron capture therapy of cancer","volume":"32","author":"Hawthorne","year":"1993","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/S0010-8545(02)00087-5","article-title":"The medicinal chemistry of carboranes","volume":"232","author":"Valliant","year":"2002","journal-title":"Coord. Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Armstrong, A.F., and Valliant, J.F. (2007). The bioinorganic and medicinal chemistry of carboranes: From new drug discovery to molecular imaging and therapy. Dalton Trans., 4240\u20134251.","DOI":"10.1039\/b709843j"},{"key":"ref_6","unstructured":"Hosmane, N.S. (2012). Medicinal application of carboranes: Inhibition of HIV protease. Boron Science: New Technologies and Applications, CRC Press."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1135\/cccc20020913","article-title":"Polyhedral boron compounds as potential linkers for attachment of radiohalogens to targeting proteins and peptides. A review","volume":"67","author":"Tolmachev","year":"2002","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_8","unstructured":"Hosmane, N.S. (2012). New Opportunities in Boron Chemistry for Medical Applications. Boron Science: New Technologies and Applications, CRC Press."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1433","DOI":"10.1002\/ejic.200900003","article-title":"Polyhedral boranes for medical applications: Current status and perspectives","volume":"11","author":"Sivaev","year":"2009","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1007\/s11172-020-2805-8","article-title":"Determination of boron by inductively coupled plasma atomic emission spectroscopy. Biodistribution of 10B in tumor-bearing mice","volume":"69","author":"Tsygankova","year":"2020","journal-title":"Russ. Chem. Bull."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1676","DOI":"10.1135\/cccc20071676","article-title":"Synthesis of Functional Derivatives of 7,8-Dicarba-nido-undecaborate Anion by Ring-Opening of Its Cyclic Oxonium Derivatives","volume":"72","author":"Stogniy","year":"2007","journal-title":"Collect. Czechoslov. Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1007\/s11172-013-0095-0","article-title":"Synthesis of podands with nido-carboranyl groups as a basis for construction of crown ethers with an incorporated metallacarborane moiety","volume":"62","author":"Stogniy","year":"2013","journal-title":"Russ. Chem. Bull."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"196","DOI":"10.1016\/j.jorganchem.2015.05.012","article-title":"Synthesis of crown ethers with the incorporated cobalt bis(dicarbollide) fragment","volume":"798","author":"Kazakov","year":"2015","journal-title":"J. Organomet. Chem."},{"key":"ref_14","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_15","doi-asserted-by":"crossref","first-page":"5044","DOI":"10.1039\/C3DT52845F","article-title":"A new approach to the synthesis of functional derivatives of nido-carborane: Alkylation of [9-MeS-nido-7,8-C2B9H11]\"","volume":"43","author":"Zakharova","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4436","DOI":"10.1002\/ejic.201700785","article-title":"Synthesis of 10-methylsulfide and 10-alkylmethylsulfonium nido-carborane derivatives: B\u2013H\u00b7\u00b7\u00b7\u03c0 Interactions between the B\u2013H\u2013B hydrogen atom and alkyne group in 10-RC\u2261CCH2S(Me)-7,8-C2B9H11","volume":"38\u201339","author":"Anufriev","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1643","DOI":"10.1007\/s11172-017-1936-z","article-title":"New carborane-containing acids and amines","volume":"66","author":"Anufriev","year":"2017","journal-title":"Russ. Chem. Bull."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.poly.2018.07.009","article-title":"Experimental crystal structure determination","volume":"153","author":"Erokhina","year":"2018","journal-title":"Polyhedron."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.jorganchem.2014.01.026","article-title":"Direct synthesis of nido-carborane derivatives with pendant functional groups by copper-promoted reactions with dimethylalkylamines","volume":"757","author":"Timofeev","year":"2014","journal-title":"J. Organomet. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"17958","DOI":"10.1039\/C8NJ04192J","article-title":"Nucleophilic addition reactions to the ethylnitrilium derivative of nido-carborane 10-EtC\ue002N-7,8-C2B9H11","volume":"42","author":"Stogniy","year":"2018","journal-title":"New J. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1002\/9780470559277.ch110148","article-title":"Copper-catalyzed azide-alkyne click chemistry for bioconjugation","volume":"3","author":"Stanislav","year":"2011","journal-title":"Curr. Protoc. Chem. Biol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2933","DOI":"10.1016\/j.ccr.2011.06.028","article-title":"The copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) \u201cclick\u201d reaction and its applications. An overview","volume":"255","author":"Liang","year":"2011","journal-title":"Coord. Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"e85","DOI":"10.1002\/cpch.85","article-title":"Azide-Terminated RAFT Polymers for Biological Applications","volume":"12","author":"Jiang","year":"2020","journal-title":"Curr. Protoc. Chem. Biol."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Meldal, M., and Diness, F. (2020). Recent Fascinating Aspects of the CuAAC Click Reaction. Trends Chemistry.","DOI":"10.1016\/j.trechm.2020.03.007"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3086","DOI":"10.1021\/acs.chemrev.5b00408","article-title":"Cu-Catalyzed Click Reaction in Carbohydrate Chemistry","volume":"116","author":"Tiwari","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_26","unstructured":"Gribble, G.W., and Joule, J.A. (2020). Five-Membered Ring Systems: With More than One N Atom. Progress in Heterocyclic Chemistry, Elsevier."},{"key":"ref_27","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_28","doi-asserted-by":"crossref","first-page":"111700","DOI":"10.1016\/j.ejmech.2019.111700","article-title":"1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships","volume":"183","author":"Xu","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3511","DOI":"10.1016\/j.bmc.2019.07.005","article-title":"1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview","volume":"27","author":"Bozorov","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3472","DOI":"10.1016\/j.bmcl.2018.09.019","article-title":"Synthesis, biological evaluation and molecular modeling of a novel series of fused 1,2,3-triazoles as potential anti-coronavirus agents","volume":"28","author":"Karypidou","year":"2018","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1016\/j.ejmech.2019.02.055","article-title":"Comprehensive review on the anti-bacterial activity of 1,2,3-triazole hybrids","volume":"168","author":"Zhang","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"El Malah, T., Nour, H.F., Satti, A.A.E., Hemdan, B.A., and ElSayed, W.A. (2020). Design, synthesis and antimicrobial activities of 1,2,3- triazole glycoside clickamers. Molecules, 25.","DOI":"10.3390\/molecules25040790"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1134\/S1068162018020097","article-title":"Design, synthesis, antioxidant and antibacterial activities of novel 2-((1-benzyl-1h-1,2,3-triazol-4- yl)methyl)-5-(2hchromen- 3-yl)-2h-tetrazoles","volume":"44","author":"Srinivas","year":"2018","journal-title":"Russ. J. Bioorg. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2400","DOI":"10.1002\/jhet.3956","article-title":"Synthesis, antibacterial and antioxidant activities of naphthyl-linked disubstituted 1,2,3-triazoles","volume":"57","author":"Kaushik","year":"2020","journal-title":"J. Heterocycl. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"370","DOI":"10.1002\/aoc.1521","article-title":"Novel types of boronated chlorine6conjugates via \u2018click chemistry\u2019","volume":"23","author":"Bregadze","year":"2009","journal-title":"Appl. Organomet. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6571","DOI":"10.1021\/bi9007726","article-title":"\u201cClick\u201d chemistry and bioorthogonal reactions: Unprecedented selectivity in the labeling of biological molecules","volume":"48","author":"Best","year":"2009","journal-title":"Biochemistry"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"121007","DOI":"10.1016\/j.jorganchem.2019.121007","article-title":"Synthesis of novel carboranyl azides and \u201cclick\u201d reactions thereof","volume":"904","author":"Stogniy","year":"2019","journal-title":"J. Organomet. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1016\/j.jorganchem.2008.12.024","article-title":"Synthesis of closo-dodecaborate based nucleoside conjugates","volume":"694","author":"Semioshkin","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1717","DOI":"10.1135\/cccc20071717","article-title":"An effective approach to 1,2,3-triazole-containing 12-vertex closo-dodecaborates","volume":"72","author":"Semioshkin","year":"2007","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Allen, B.J., Moore, D.E., and Harrington, B.V. (1992). In Vitro Biological Efficacy of Boronated Low Density Lipoproteins for NCT. Progress in Neutron Capture Therapy for Cancer, Plenum Press.","DOI":"10.1007\/978-1-4615-3384-9"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"11177","DOI":"10.1016\/S0040-4020(99)00640-7","article-title":"Synthesis of boron-containing cholesterol derivatives for incorporation into unilamellar liposomes and evaluation as potential agents for BNCT","volume":"55","author":"Feakes","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1016\/S0960-894X(02)00426-2","article-title":"Synthesis of cholesterol-carborane conjugate for targeted drug delivery","volume":"12","author":"Ji","year":"2002","journal-title":"Bioorgan. Med. Chem. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"S3","DOI":"10.1016\/j.apradiso.2009.03.102","article-title":"Boron neutron capture therapy at the crossroads: Challenges and opportunities","volume":"67","author":"Barth","year":"2009","journal-title":"Appl. Radiat. Isot."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.addr.2012.10.002","article-title":"The EPR effect for macromolecular drug delivery to solid tumors: Improvement of tumor uptake, lowering of systemic toxicity, and distinct tumor imaging in vivo","volume":"65","author":"Maeda","year":"2013","journal-title":"Adv. Drug. Deliv. Rev."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1016\/j.colsurfb.2014.09.029","article-title":"Liposomes as carriers of hydrophilic small molecule drugs: Strategies to enhance encapsulation and delivery","volume":"123","author":"Eloy","year":"2014","journal-title":"Colloids. Surf. B Biointerfaces"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"44","DOI":"10.2174\/1566524018666180416101522","article-title":"Advances in tumor targeted liposomes","volume":"18","author":"Jain","year":"2018","journal-title":"Curr. Mol. Med."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"628","DOI":"10.1016\/j.mencom.2019.11.007","article-title":"\u2018Click\u2019 synthesis of cobalt bis(dicarbollide)\u2013cholesterol conjugates","volume":"29","author":"Druzina","year":"2019","journal-title":"Mendeleev Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2658","DOI":"10.1002\/ejic.202000388","article-title":"Novel cobalt bis(dicarbollide) based on terminal alkynes and their \u201cclick\u201d reactions","volume":"27","author":"Druzina","year":"2020","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1080","DOI":"10.1007\/s11172-020-2870-z","article-title":"Synthesis of conjugates of closo-dodecaborate dianion with cholesterol using a \u201cclick\u201d reaction","volume":"69","author":"Druzina","year":"2020","journal-title":"Russ. Chem. Bull."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"13832","DOI":"10.1002\/chem.201905083","article-title":"Boron-containing lipids and liposomes: New conjugates of cholesterol with polyhedral boron hydrides","volume":"26","author":"Bregadze","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Dubey, R.D., Sarkar, A., Shen, Z., Bregadze, V.I., Sivaev, I.B., Druzina, A.A., Zhidkova, O.B., Shmal\u2019ko, A.V., Kosenko, I.D., and Sreejyothi, P. (2020). Effects of linkers on the development of liposomal formulation of cholesterol conjugated cobalt bis(dicarbollides). J. Pharm. Sci.","DOI":"10.1016\/j.xphs.2020.12.017"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1016\/j.bbrc.2019.11.144","article-title":"PEGylated liposome encapsulating nido-carborane showed significant tumor suppression in boron neutron capture therapy (BNCT)","volume":"522","author":"Lee","year":"2020","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4405","DOI":"10.1016\/j.bmcl.2015.09.019","article-title":"Difluoromethyl ketones: Potent inhibitors of wild type and carbamate-insensitive G119S mutant anopheles gambiae acetylcholinesterase","volume":"25","author":"Aly","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1599","DOI":"10.1016\/j.jorganchem.2008.10.059","article-title":"Syntheses of C-substituted icosahedral dicarbaboranes bearing the 8-dioxane-cobalt bisdicarbollide moiety","volume":"694","author":"Teixidor","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_55","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_56","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1186\/s40880-018-0299-7","article-title":"Boron delivery agents forb neutron capture therapy of cancer","volume":"38","author":"Barth","year":"2018","journal-title":"Cancer Commun."},{"key":"ref_57","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_58","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":"J. Sci. Rep."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"5298","DOI":"10.1002\/anie.201100410","article-title":"A theta-shaped amphiphilic cobaltabisdicarbollide anion: Transition from monolayer vesicles to micelles","volume":"50","author":"Bauduin","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3088","DOI":"10.1002\/anie.201913257","article-title":"Atomistic simulations of COSAN: Amphiphiles without a head-and-tail design display \u00abhead and tail\u00bb surfactant behavior","volume":"59","author":"Malaspina","year":"2020","journal-title":"J. Angew. Chem. Int. Ed."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"11613","DOI":"10.1073\/pnas.0801763105","article-title":"The effect of particle design on cellular internalization pathways","volume":"105","author":"Gratton","year":"2008","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"105708","DOI":"10.1088\/0957-4484\/22\/10\/105708","article-title":"The role of surface charge on the uptake and biocompatibility of hydroxyapatite nanoparticles with osteoblast cells","volume":"22","author":"Chen","year":"2011","journal-title":"Nanotechnology"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"6606","DOI":"10.1021\/la401074y","article-title":"Effect of functionalized gold nanoparticles on floating lipid bilayers","volume":"29","author":"Tatur","year":"2013","journal-title":"Langmuir"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1571","DOI":"10.1039\/C4DT03015J","article-title":"Synthesis and the structure of 8-tetrahydrofuronium and 8-tetrahydropyronium derivatives of iron bis(dicarbollide)(-I) and their cleavage reactions","volume":"44","author":"Lobanova","year":"2015","journal-title":"Dalton Trans."},{"key":"ref_65","doi-asserted-by":"crossref","unstructured":"Matta, C.F., and Boyd, R.J. (2007). The Quantum Theory of Atoms in Molecules: From Solid State to DNA, Drug Design, Wiley-VCH Verlag GmbH & Co. KgaA.","DOI":"10.1002\/9783527610709"},{"key":"ref_66","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_67","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_68","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing non-covalent iinteractions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_69","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_70","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_71","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_72","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_73","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_74","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_75","doi-asserted-by":"crossref","first-page":"1456","DOI":"10.1002\/jcc.21759","article-title":"Effect of the damping function in dispersion corrected density functional theory","volume":"32","author":"Grimme","year":"2011","journal-title":"J. Comput. Chem."},{"key":"ref_76","unstructured":"Keith, T.A. (2019). AIMAll, TK Gristmill Software. version 13.05.06."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/530\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:13:11Z","timestamp":1760159591000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/530"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,20]]},"references-count":76,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26030530"],"URL":"https:\/\/doi.org\/10.3390\/molecules26030530","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2021,1,20]]}}}