{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,22]],"date-time":"2026-07-22T23:33:57Z","timestamp":1784763237125,"version":"3.55.0"},"reference-count":66,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2022,4,16]],"date-time":"2022-04-16T00:00:00Z","timestamp":1650067200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007514","name":"University of Pisa","doi-asserted-by":"publisher","award":["Ateneo 2020-2021"],"award-info":[{"award-number":["Ateneo 2020-2021"]}],"id":[{"id":"10.13039\/501100007514","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007514","name":"University of Pisa","doi-asserted-by":"publisher","award":["PRA_2020_39 and PRA_2020_58"],"award-info":[{"award-number":["PRA_2020_39 and PRA_2020_58"]}],"id":[{"id":"10.13039\/501100007514","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007514","name":"University of Pisa","doi-asserted-by":"publisher","award":["Progetti di Ricerca di Ateneo PRA_2020_32"],"award-info":[{"award-number":["Progetti di Ricerca di Ateneo PRA_2020_32"]}],"id":[{"id":"10.13039\/501100007514","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Beneficentia Stiftung (Vaduz)","award":["BEN2020\/34 and BEN2019\/48"],"award-info":[{"award-number":["BEN2020\/34 and BEN2019\/48"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Auranofin (AF, hereafter) is an orally administered chrysotherapeutic agent approved for the treatment of rheumatoid arthritis that is being repurposed for various indications including bacterial infections. Its likely mode of action involves the impairment of the TrxR system through the binding of the pharmacophoric cation [AuPEt3]+. Accordingly, a reliable strategy to expand the medicinal profile of AF is the replacement of the thiosugar moiety with different ligands. Herein, we aimed to prepare the AF analogue bearing the acetylcysteine ligand (AF-AcCys, hereafter) and characterize its anti-staphylococcal activity. Biological studies revealed that AF-AcCys retains an antibacterial effect superimposable with that of AF against Staphylococcus aureus, whereas it is about 20 times less effective against Staphylococcus epidermidis. Bioinorganic studies confirmed that upon incubation with human serum albumin, AF-AcCys, similarly to AF, induced protein metalation through the [AuPEt3]+ fragment. Additionally, AF-AcCys appeared capable of binding the dodecapeptide Ac-SGGDILQSGCUG-NH2, corresponding to the tryptic C-terminal fragment (488\u2013499) of hTrxR. To shed light on the pharmacological differences between AF and AF-AcCys, we carried out a comparative experimental stability study and a theoretical estimation of bond dissociation energies, unveiling the higher strength of the Au\u2013S bond in AF-AcCys. From the results, it emerged that the lower lipophilicity of AF-AcCys with respect to AF could be a key feature for its different antibacterial activity. The differences and similarities between AF and AF-AcCys are discussed, alongside the opportunities and consequences that chemical structure modifications imply.<\/jats:p>","DOI":"10.3390\/molecules27082578","type":"journal-article","created":{"date-parts":[[2022,4,19]],"date-time":"2022-04-19T01:03:01Z","timestamp":1650330181000},"page":"2578","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Anti-Staphylococcal Activity of the Auranofin Analogue Bearing Acetylcysteine in Place of the Thiosugar: An Experimental and Theoretical Investigation"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4857-9819","authenticated-orcid":false,"given":"Lorenzo","family":"Chiaverini","sequence":"first","affiliation":[{"name":"Department of Pharmacy, University of Pisa, Via Bonanno Pisano, 6, 56126 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9553-9943","authenticated-orcid":false,"given":"Alessandro","family":"Pratesi","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry (DCCI), University of Pisa, Via G. Moruzzi, 13, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9175-9562","authenticated-orcid":false,"given":"Damiano","family":"Cirri","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Industrial Chemistry (DCCI), University of Pisa, Via G. Moruzzi, 13, 56124 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arianna","family":"Nardinocchi","sequence":"additional","affiliation":[{"name":"Department of Biology, University of Pisa, Via San Zeno 35\u201339, 56100 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9700-5331","authenticated-orcid":false,"given":"Iogann","family":"Tolbatov","sequence":"additional","affiliation":[{"name":"Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, 43007 Tarragona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8311-8172","authenticated-orcid":false,"given":"Alessandro","family":"Marrone","sequence":"additional","affiliation":[{"name":"Dipartimento di Farmacia, Universit\u00e0 degli Studi \u201cG. D\u2019Annunzio\u201d Chieti-Pescara, Via dei Vestini, 66100 Chieti, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mariagrazia","family":"Di Luca","sequence":"additional","affiliation":[{"name":"Department of Biology, University of Pisa, Via San Zeno 35\u201339, 56100 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2567-3637","authenticated-orcid":false,"given":"Tiziano","family":"Marzo","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Pisa, Via Bonanno Pisano, 6, 56126 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4193-7612","authenticated-orcid":false,"given":"Diego","family":"La Mendola","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Pisa, Via Bonanno Pisano, 6, 56126 Pisa, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,4,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1016\/S0140-6736(21)02724-0","article-title":"Global burden of bacterial antimicrobial resistance in 2019: A systematic analysis","volume":"399","author":"Murray","year":"2022","journal-title":"Lancet"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1038\/s41598-017-00261-1","article-title":"Modeling Nosocomial Infections of Methicillin-Resistant Staphylococcus aureus with Environment Contamination*","volume":"7","author":"Wang","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"12888","DOI":"10.1039\/D0SC04082G","article-title":"Metallodrugs are unique: Opportunities and challenges of discovery and development","volume":"11","author":"Anthony","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4540","DOI":"10.1021\/cr400460s","article-title":"Metallodrugs in medicinal inorganic chemistry","volume":"114","author":"Mjos","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"6333","DOI":"10.1039\/c2dt90061k","article-title":"Application of inorganic chemistry for non-cancer therapeutics","volume":"41","author":"Franz","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5106","DOI":"10.1039\/c3cc41143e","article-title":"Exploration of the medical periodic table: Towards new targets","volume":"49","author":"Barry","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"371","DOI":"10.1038\/nrmicro3028","article-title":"Antimicrobial activity of metals: Mechanisms, molecular targets and applications","volume":"11","author":"Lemire","year":"2013","journal-title":"Nat. Rev. Microbiol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1038\/s41598-017-01017-7","article-title":"Synergistic Antimicrobial Effects of Silver\/Transition-metal Combinatorial Treatments","volume":"7","author":"Castillo","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Marzo, T., and Mendola, D. (2021). La Strike a Balance: Between Metals and Non-Metals, Metalloids as a Source of Anti-Infective Agents. Inorganics, 9.","DOI":"10.3390\/inorganics9060046"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"111382","DOI":"10.1016\/j.msec.2020.111382","article-title":"Organic and inorganic antibacterial approaches in combating bacterial infection for biomedical application","volume":"118","author":"Saidin","year":"2021","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"108272","DOI":"10.1016\/j.intimp.2021.108272","article-title":"Auranofin: Past to Present, and repurposing","volume":"101","author":"Yamashita","year":"2021","journal-title":"Int. Immunopharmacol."},{"key":"ref_12","first-page":"409","article-title":"Repurposing auranofin as a Clostridioides difficile therapeutic","volume":"75","author":"Hutton","year":"2020","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1007\/s40268-015-0083-y","article-title":"Auranofin: Repurposing an Old Drug for a Golden New Age","volume":"15","author":"Roder","year":"2015","journal-title":"Drugs R D"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Cirri, D., Bartoli, F., Pratesi, A., Baglini, E., Barresi, E., and Marzo, T. (2021). Strategies for the Improvement of Metal-Based Chemotherapeutic Treatments. Biomedicines, 9.","DOI":"10.3390\/biomedicines9050504"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1007\/s12672-021-00439-0","article-title":"The gold complex auranofin: New perspectives for cancer therapy","volume":"12","author":"Abdalbari","year":"2021","journal-title":"Discov. Oncol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4","DOI":"10.3389\/fcimb.2017.00004","article-title":"Repurposing Approach Identifies Auranofin with Broad Spectrum Antifungal Activity That Targets Mia40-Erv1 Pathway","volume":"7","author":"Thangamani","year":"2017","journal-title":"Front. Cell. Infect. Microbiol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"22571","DOI":"10.1038\/srep22571","article-title":"Antibacterial activity and mechanism of action of auranofin against multi-drug resistant bacterial pathogens","volume":"6","author":"Thangamani","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2448","DOI":"10.1002\/cmdc.201800498","article-title":"Auranofin and its Analogues Show Potent Antimicrobial Activity against Multidrug-Resistant Pathogens: Structure-Activity Relationships","volume":"13","author":"Marzo","year":"2018","journal-title":"ChemMedChem"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1016\/j.ijantimicag.2015.12.016","article-title":"Repurposing auranofin for the treatment of cutaneous staphylococcal infections","volume":"47","author":"Thangamani","year":"2016","journal-title":"Int. J. Antimicrob. Agents"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"550","DOI":"10.1002\/med.20168","article-title":"Gold compounds as anticancer agents: Chemistry, cellular pharmacology, and preclinical studies","volume":"30","author":"Nobili","year":"2010","journal-title":"Med. Res. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1321","DOI":"10.1073\/pnas.1915202117","article-title":"An anticancer gold(III)-activated porphyrin scaffold that covalently modifies protein cysteine thiols","volume":"117","author":"Tong","year":"2020","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4035","DOI":"10.1128\/JB.00164-09","article-title":"Inhibition of selenium metabolism in the oral pathogen Treponema denticola","volume":"191","author":"Self","year":"2009","journal-title":"J. Bacteriol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"656","DOI":"10.1021\/acsmedchemlett.9b00007","article-title":"Replacement of the Thiosugar of Auranofin with Iodide Enhances the Anticancer Potency in a Mouse Model of Ovarian Cancer","volume":"10","author":"Marzo","year":"2019","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"213905","DOI":"10.1016\/j.ccr.2021.213905","article-title":"Proteomics as a tool to disclose the cellular and molecular mechanisms of selected anticancer gold compounds","volume":"438","author":"Gamberi","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"ref_25","first-page":"65","article-title":"N-acetylcysteine overdose after acetaminophen poisoning","volume":"8","author":"Mahmoudi","year":"2015","journal-title":"Int. Med. Case Rep. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2835787","DOI":"10.1155\/2018\/2835787","article-title":"Biological activities and potential oral applications of N-acetylcysteine: Progress and prospects","volume":"2018","author":"Pei","year":"2018","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1007\/s00214-021-02718-z","article-title":"Molecular dynamics simulation of the Pb(II) coordination in biological media via cationic dummy atom models","volume":"140","author":"Tolbatov","year":"2021","journal-title":"Theor. Chem. Acc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"111533","DOI":"10.1016\/j.jinorgbio.2021.111533","article-title":"Reactivity of antitumor coinage metal-based N-heterocyclic carbene complexes with cysteine and selenocysteine protein sites","volume":"223","author":"Tolbatov","year":"2021","journal-title":"J. Inorg. Biochem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"398","DOI":"10.1007\/978-3-030-87016-4_30","article-title":"Multilayered Modelling of the Metallation of Biological Targets","volume":"12958","author":"Tolbatov","year":"2021","journal-title":"Lect. Notes Comput. Sci."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7751","DOI":"10.1021\/acs.jmedchem.9b00550","article-title":"Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens","volume":"62","author":"Wu","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0169-409X(00)00129-0","article-title":"Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings","volume":"46","author":"Lipinski","year":"2001","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1007\/s10534-019-00210-7","article-title":"The leading established metal-based drugs: A revisitation of their relevant physico-chemical data","volume":"32","author":"Cirri","year":"2019","journal-title":"BioMetals"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1007\/978-1-4939-2272-7_3","article-title":"Getting across the cell membrane: An overview for small molecules, peptides, and proteins","volume":"1266","author":"Yang","year":"2015","journal-title":"Methods Mol. Biol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"120297","DOI":"10.1016\/j.ica.2021.120297","article-title":"Protein metalation by two structurally related gold(I) carbene complexes: An ESI MS study","volume":"520","author":"Zoppi","year":"2021","journal-title":"Inorg. Chim. Acta"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1007\/s00775-006-0103-z","article-title":"A mass spectrometric investigation of the binding of gold antiarthritic agents and the metabolite [Au(CN)2]- to human serum albumin","volume":"11","author":"Talib","year":"2006","journal-title":"J. Biol. Inorg. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"10507","DOI":"10.1021\/acs.inorgchem.8b02177","article-title":"Reactions of Auranofin and Its Pseudohalide Derivatives with Serum Albumin Investigated through ESI-Q-TOF MS","volume":"57","author":"Pratesi","year":"2018","journal-title":"Inorg. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"28042","DOI":"10.18632\/oncotarget.25556","article-title":"Antiproliferative effects of two gold(I)-N-heterocyclic carbene complexes in A2780 human ovarian cancer cells: A comparative proteomic study","volume":"9","author":"Magherini","year":"2018","journal-title":"Oncotarget"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1039\/C4DT03105A","article-title":"Gold(I) thiotetrazolates as thioredoxin reductase inhibitors and antiproliferative agents","volume":"44","author":"Serebryanskaya","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/j.jinorgbio.2014.01.009","article-title":"Insights on the mechanism of thioredoxin reductase inhibition by Gold N-heterocyclic carbene compounds using the synthetic linear Selenocysteine containing C-terminal peptide hTrxR(488-499): An ESI-MS investigation","volume":"136","author":"Pratesi","year":"2014","journal-title":"J. Inorg. Biochem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"581648","DOI":"10.3389\/fchem.2020.581648","article-title":"Reactions of Medicinal Gold(III) Compounds With Proteins and Peptides Explored by Electrospray Ionization Mass Spectrometry and Complementary Biophysical Methods","volume":"8","author":"Massai","year":"2020","journal-title":"Front. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1002\/cmdc.201800672","article-title":"A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies","volume":"14","author":"Fabbrini","year":"2018","journal-title":"ChemMedChem"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Braccini, S., Rizzi, G., Biancalana, L., Pratesi, A., Zacchini, S., Pampaloni, G., Chiellini, F., and Marchetti, F. (2021). Anticancer Diiron Vinyliminium Complexes: A Structure\u2013Activity Relationship Study. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13081158"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"118983","DOI":"10.1016\/j.ica.2019.118983","article-title":"The cisplatin\/serum albumin system: A reappraisal","volume":"495","author":"Massai","year":"2019","journal-title":"Inorg. Chim. Acta"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"5906","DOI":"10.1039\/D0DT00283F","article-title":"ESI MS studies highlight the selective interaction of Auranofin with protein free thiols","volume":"49","author":"Zoppi","year":"2020","journal-title":"Dalton Trans."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"812","DOI":"10.3389\/fchem.2020.00812","article-title":"Mechanistic Insights Into the Anticancer Properties of the Auranofin Analog Au(PEt3)I: A Theoretical and Experimental Study","volume":"8","author":"Tolbatov","year":"2020","journal-title":"Front. Chem."},{"key":"ref_46","first-page":"351","article-title":"Antitumor Metallodrugs that Target Proteins","volume":"18","author":"Sullivan","year":"2018","journal-title":"Met. Ions Life Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1692","DOI":"10.1016\/j.ccr.2009.02.026","article-title":"Thioredoxin reductase: A target for gold compounds acting as potential anticancer drugs","volume":"253","author":"Bindoli","year":"2009","journal-title":"Coord. Chem. Rev."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.freeradbiomed.2018.03.043","article-title":"Significance of the mitochondrial thioredoxin reductase in cancer cells: An update on role, targets and inhibitors","volume":"127","author":"Scalcon","year":"2018","journal-title":"Free Radic. Biol. Med."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"eaaf7444","DOI":"10.1126\/scitranslmed.aaf7444","article-title":"Irreversible inhibition of cytosolic thioredoxin reductase 1 as a mechanistic basis for anticancer therapy","volume":"10","author":"Stafford","year":"2018","journal-title":"Sci. Transl. Med."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1111\/j.1365-2672.2004.02181.x","article-title":"Adhesion of Staphylococcus aureus and Staphylococcus epidermidis to the Episkin\u00ae reconstructed epidermis model and to an inert 304 stainless steel substrate","volume":"97","author":"Lerebour","year":"2004","journal-title":"J. Appl. Microbiol."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Liu, Y., Lu, Y., Xu, Z., Ma, X., Chen, X., and Liu, W. (2022). Repurposing of the gold drug auranofin and a review of its derivatives as antibacterial therapeutics. Drug Discov. Today.","DOI":"10.1016\/j.drudis.2022.02.010"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1515\/znb-2007-0321","article-title":"Introduction of phosphine-gold(I) precursors into a Cys-modified enkephalin neuropeptide as part of solid phase peptide synthesis","volume":"62","author":"Caddy","year":"2007","journal-title":"Z. Fur Naturforsch.\u2014Sect. B J. Chem. Sci."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2936","DOI":"10.1021\/ic00162a034","article-title":"Gold-197 Moessbauer studies of some gold(I) thiolates and their phosphine complexes including certain antiarthritic gold drugs","volume":"22","author":"Hill","year":"2002","journal-title":"Inorg. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"997","DOI":"10.1021\/acsmedchemlett.7b00162","article-title":"Auranofin, Et3PAuCl, and Et3PAuI Are Highly Cytotoxic on Colorectal Cancer Cells: A Chemical and Biological Study","volume":"8","author":"Marzo","year":"2017","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"96062","DOI":"10.18632\/oncotarget.21708","article-title":"Selection and characterization of a human ovarian cancer cell line resistant to auranofin","volume":"8","author":"Landini","year":"2017","journal-title":"Oncotarget"},{"key":"ref_56","unstructured":"(2012). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically. Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, CLSI. [9th ed.]. Approved Standard."},{"key":"ref_57","unstructured":"(2021, November 03). Citation|Gaussian.com. Available online: https:\/\/gaussian.com\/citation\/."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"6776","DOI":"10.1039\/D0DT00923G","article-title":"Double addition of phenylacetylene onto the mixed bridge phosphinito-phosphanido Pt(i) complex [(PHCy2)Pt(\u03bc-PCy2){\u03ba2: P, O -\u03bc-P(O)Cy2}Pt(PHCy2)](Pt-Pt)","volume":"49","author":"Todisco","year":"2020","journal-title":"Dalton Trans."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"9643","DOI":"10.1039\/D1DT01492G","article-title":"Two mixed valence diruthenium(II,III) isomeric complexes show different anticancer properties","volume":"50","author":"Barresi","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"14520","DOI":"10.1039\/D0DT02527E","article-title":"A mixed-valence diruthenium(ii,iii) complex endowed with high stability: From experimental evidence to theoretical interpretation","volume":"49","author":"Barresi","year":"2020","journal-title":"Dalton Trans."},{"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":"211","DOI":"10.1016\/S0166-1280(98)00553-3","article-title":"The IEF version of the PCM solvation method: An overview of a new method addressed to study molecular solutes at the QM ab initio level","volume":"464","author":"Tomasi","year":"1999","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"084106","DOI":"10.1063\/1.2834918","article-title":"Systematic optimization of long-range corrected hybrid density functionals","volume":"128","author":"Chai","year":"2008","journal-title":"J. Chem. Phys."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1007\/s00214-020-02694-w","article-title":"Reactivity of arsenoplatin complex versus water and thiocyanate: A DFT benchmark study","volume":"139","author":"Tolbatov","year":"2020","journal-title":"Theor. Chem. Acc."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"19928","DOI":"10.1002\/anie.202106906","article-title":"Probing the Paradigm of Promiscuity for N-Heterocyclic Carbene Complexes and their Protein Adduct Formation","volume":"60","author":"Sullivan","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"4220","DOI":"10.1021\/acs.jctc.5b00601","article-title":"A Comprehensive Comparison of the IEFPCM and SS(V)PE Continuum Solvation Methods with the COSMO Approach","volume":"11","author":"Klamt","year":"2015","journal-title":"J. Chem. 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