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development of novel complexes with cytostatic properties. In this study, we synthesized a set of half-sandwich complexes of platinum-group metal ions (Ru(II), Os(II), Ir(III) and Rh(III)) with an N,N-bidentate ligand comprising a C-glucosaminyl group and a heterocycle, such as pyridine, pyridazine, pyrimidine, pyrazine or quinoline. The sugar-containing ligands themselves are unknown compounds and were obtained by nucleophilic additions of lithiated heterocycles to O-perbenzylated 2-nitro-glucal. Reduction of the adducts and, where necessary, subsequent protecting group manipulations furnished the above C-glucosaminyl heterocycles in their O-perbenzylated, O-perbenzoylated and O-unprotected forms. The derived complexes were tested on A2780 ovarian cancer cells. Pyridine, pyrazine and pyridazine-containing complexes proved to be cytostatic and cytotoxic on A2780 cells, while pyrimidine and quinoline derivatives were inactive. The best complexes contained pyridine as the heterocycle. The metal ion with polyhapto arene\/arenyl moiety also impacted on the biological activity of the complexes. Ruthenium complexes with p-cymene and iridium complexes with Cp* had the best performance in ovarian cancer cells, followed by osmium complexes with p-cymene and rhodium complexes with Cp*. Finally, the chemical nature of the protective groups on the hydroxyl groups of the carbohydrate moiety were also key determinants of bioactivity; in particular, O-benzyl groups were superior to O-benzoyl groups. The IC50 values of the complexes were in the low micromolar range, and, importantly, the complexes were less active against primary, untransformed human dermal fibroblasts; however, the anticipated therapeutic window is narrow. The bioactive complexes exerted cytostasis on a set of carcinomas such as cell models of glioblastoma, as well as breast and pancreatic cancers. Furthermore, the same complexes exhibited bacteriostatic properties against multiresistant Gram-positive Staphylococcus aureus and Enterococcus clinical isolates in the low micromolar range.<\/jats:p>","DOI":"10.3390\/molecules28073058","type":"journal-article","created":{"date-parts":[[2023,3,30]],"date-time":"2023-03-30T01:31:30Z","timestamp":1680139890000},"page":"3058","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Half-Sandwich Type Platinum-Group Metal Complexes of C-Glucosaminyl Azines: Synthesis and Antineoplastic and Antimicrobial Activities"],"prefix":"10.3390","volume":"28","author":[{"given":"Istv\u00e1n","family":"Kacsir","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary"},{"name":"Doctoral School of Chemistry, University of Debrecen, P.O. 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Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"965","DOI":"10.1080\/17425255.2020.1806235","article-title":"Strategies to reduce the risk of platinum containing antineoplastic drug-induced ototoxicity","volume":"16","author":"Mukherjea","year":"2020","journal-title":"Expert Opin. Drug Metab. Toxicol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1469","DOI":"10.1038\/s41598-017-01624-4","article-title":"DNA methylation and Transcriptome Changes Associated with Cisplatin Resistance in Ovarian Cancer","volume":"7","author":"Lund","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"13397","DOI":"10.1021\/acs.jmedchem.0c00950","article-title":"Platinum-Based Combination Therapy: Molecular Rationale, Current Clinical Uses, and Future Perspectives","volume":"63","author":"Yu","year":"2020","journal-title":"J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.semcancer.2020.08.013","article-title":"New approaches for targeting platinum-resistant ovarian cancer","volume":"77","author":"McMullen","year":"2021","journal-title":"Semin. Cancer Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1434","DOI":"10.1038\/bjc.2015.359","article-title":"Molecular targets for anticancer redox chemotherapy and cisplatin-induced ototoxicity: The role of curcumin on pSTAT3 and Nrf-2 signalling","volume":"113","author":"Fetoni","year":"2015","journal-title":"Br. J. Cancer"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1186\/s10020-021-00295-2","article-title":"The role of the microbiome in ovarian cancer: Mechanistic insights into oncobiosis and to bacterial metabolite signaling","volume":"27","author":"Sipos","year":"2021","journal-title":"Mol. Med. (Camb. Mass.)"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2688","DOI":"10.2174\/156802611798040769","article-title":"Polynuclear ruthenium, osmium and gold complexes. The quest for innovative anticancer chemotherapeutics","volume":"11","author":"Hartinger","year":"2011","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5771","DOI":"10.1039\/C7CS00195A","article-title":"The development of anticancer ruthenium(II) complexes: From single molecule compounds to nanomaterials","volume":"46","author":"Zeng","year":"2017","journal-title":"Chem. Soc. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1016\/j.ccr.2019.06.001","article-title":"Non-platinum complexes containing releasable biologically active ligands","volume":"395","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1039\/C7CS00332C","article-title":"Structure\u2013activity relationships for ruthenium and osmium anticancer agents\u2014Towards clinical development","volume":"47","author":"Gerner","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Coverdale, J.P.C., Laroiya-McCarron, T., and Romero-Canel\u00f3n, I. (2019). Designing Ruthenium Anticancer Drugs: What Have We Learnt from the Key Drug Candidates?. Inorganics, 7.","DOI":"10.3390\/inorganics7030031"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1016\/j.jorganchem.2018.04.021","article-title":"Half-sandwich complexes of platinum group metals (Ir, Rh, Ru and Os) and some recent biological and catalytic applications","volume":"866","author":"Gichumbi","year":"2018","journal-title":"J. Organomet. Chem."},{"key":"ref_15","unstructured":"Jaouen, G. (2006). Bioorganometallics, Wiley-VCH Verlag GmbH & Co. KGaA."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"14498","DOI":"10.1039\/D1DT02909F","article-title":"Metal complexes against breast cancer stem cells","volume":"50","author":"Li","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"9934","DOI":"10.1039\/C8DT01858H","article-title":"Anticancer activity of complexes of the third row transition metals, rhenium, osmium, and iridium","volume":"47","author":"Konkankit","year":"2018","journal-title":"Dalton Trans."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1016\/j.drudis.2014.06.016","article-title":"Development of anticancer agents: Wizardry with osmium","volume":"19","author":"Hanif","year":"2014","journal-title":"Drug Discov. Today"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"112483","DOI":"10.1016\/j.ejmech.2020.112483","article-title":"Synthesis, structure and anti-cancer activity of osmium complexes bearing \u03a0-bound arene substituents and phosphane Co-Ligands: A review","volume":"201","author":"Nabiyeva","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1764","DOI":"10.1016\/j.ccr.2013.01.034","article-title":"Bioactive iridium and rhodium complexes as therapeutic agents","volume":"257","author":"Leung","year":"2013","journal-title":"Coord. Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1174","DOI":"10.1021\/ar400266c","article-title":"Organoiridium complexes: Anticancer agents and catalysts","volume":"47","author":"Liu","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"M\u00e1likov\u00e1, K., Masaryk, L., and \u0160tarha, P. (2021). Anticancer Half-Sandwich Rhodium(III) Complexes. Inorganics, 9.","DOI":"10.3390\/inorganics9040026"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1139\/cjpp-2020-0349","article-title":"Redox and apoptotic potential of novel ruthenium complexes in the rat blood and heart","volume":"99","author":"Mihajlovic","year":"2020","journal-title":"Can. J. Physiol. Pharmacol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"9904","DOI":"10.1039\/C9CC04098F","article-title":"Functionalization and cancer-targeting design of ruthenium complexes for precise cancer therapy","volume":"55","author":"Liu","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1262","DOI":"10.2174\/1871520619666190318152726","article-title":"Antitumour and Toxicity Evaluation of a Ru(II)-Cyclopentadienyl Complex in a Prostate Cancer Model by Imaging Tools","volume":"19","author":"Gano","year":"2019","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1082","DOI":"10.1016\/j.biopha.2018.08.051","article-title":"Acute toxic effects of ruthenium (II)\/amino acid\/diphosphine complexes on Swiss mice and zebrafish embryos","volume":"107","author":"Cardoso","year":"2018","journal-title":"Biomed. Pharmacother."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1007\/s10637-014-0179-1","article-title":"Phase I\/II study with ruthenium compound NAMI-A and gemcitabine in patients with non-small cell lung cancer after first line therapy","volume":"33","author":"Leijen","year":"2015","journal-title":"Investig. 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Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"121155","DOI":"10.1016\/j.jorganchem.2020.121155","article-title":"Ruthenium, rhodium and iridium complexes containing pyrimidine based thienyl pyrazoles: Synthesis and antibacterial studies","volume":"911","author":"Lapasam","year":"2020","journal-title":"J. Organomet. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"mfab007","DOI":"10.1093\/mtomcs\/mfab007","article-title":"Osmium-arene complexes with high potency towards Mycobacterium tuberculosis","volume":"13","author":"Coverdale","year":"2021","journal-title":"Metallomics"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/j.jinorgbio.2018.05.009","article-title":"Synthesis and biological characterization of organoruthenium complexes with 8-hydroxyquinolines","volume":"186","author":"Kljun","year":"2018","journal-title":"J. Inorg. Biochem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3434","DOI":"10.1128\/AAC.00452-13","article-title":"Transition Metal-a-Amino Acid Complexes with Antibiotic Activity against Mycobacterium spp.","volume":"57","author":"Karpin","year":"2013","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"530","DOI":"10.1021\/acs.organomet.7b00742","article-title":"Synthesis, Characterization, and Antimicrobial Activity of RhIII and IrIII b-Diketonato Piano-Stool Compounds","volume":"37","author":"DuChane","year":"2018","journal-title":"Organometallics"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1670","DOI":"10.1021\/acs.organomet.1c00166","article-title":"Synthesis, Characterization, and Antimicrobial Activity of RhIII and IrIII N-Heterocyclic Carbene Piano-Stool Complexes","volume":"40","author":"Bernier","year":"2021","journal-title":"Organometallics"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Holzer, I., Desiatkina, O., Anghel, N., Johns, S.K., Boubaker, G., Hemphill, A., Furrer, J., and Paunescu, E. (2022). Trithiolato-Bridged Dinuclear Arene Ruthenium(ll)- Glycoconjugates: Synthesis and Antiparasitic Activity. ChemRxiv Camb. Camb. Open Engag.","DOI":"10.26434\/chemrxiv-2022-kkcth"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1122","DOI":"10.1021\/ic802220w","article-title":"Synthesis, Characterization, and in vitro Antimalarial and Antitumor Activity of New Ruthenium(II) Complexes of Chloroquine","volume":"48","author":"Rajapakse","year":"2009","journal-title":"Inorg. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3867","DOI":"10.1021\/jm300070h","article-title":"Searching for New Chemotherapies for Tropical Diseases: Ruthenium-Clotrimazole Complexes Display High in Vitro Activity against Leishmania major and Trypanosoma cruzi and Low Toxicity toward Normal Mammalian Cells","volume":"55","author":"Carreon","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Chuong, C., DuChane, C.M., Webb, E.M., Rai, P., Marano, J.M., Bernier, C.M., Merola, J.S., and Weger-Lucarelli, J. (2021). Noble Metal Organometallic Complexes Display Antiviral Activity against SARS-CoV-2. Viruses, 13.","DOI":"10.3390\/v13060980"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1594","DOI":"10.1021\/om401096y","article-title":"Synthesis and Biological Evaluation of Organoruthenium Complexes with Azole Antifungal Agents. First Crystal Structure of a Tioconazole Metal Complex","volume":"33","author":"Kljun","year":"2014","journal-title":"Organometallics"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Kacsir, I., Sipos, A., Ujlaki, G., Bugly\u00f3, P., Soms\u00e1k, L., Bai, P., and Bokor, \u00c9. (2021). Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms221910454"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Kacsir, I., Sipos, A., B\u00e9nyei, A., Janka, E., Bugly\u00f3, P., Soms\u00e1k, L., Bai, P., and Bokor, \u00c9. (2022). Reactive oxygen species production is responsible for antineoplastic activity of osmium, ruthenium, iridium and rhodium half-sandwich type complexes with bidentate glycosyl hetero-cyclic ligands in various cancer cell models. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23020813"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"e5896","DOI":"10.1002\/aoc.5896","article-title":"Ruthenium tetrazene complexes bearing glucose moieties on their periphery: Synthesis, characterization, and in vitro cytotoxicity","volume":"34","author":"Hamala","year":"2020","journal-title":"Appl. Organomet. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1507","DOI":"10.1021\/om5013117","article-title":"Diaminohexopyranosides as Ligands in Half-Sandwich Ruthenium(II), Rhodium(III), and Iridium(III) Complexes","volume":"34","author":"Fowelin","year":"2015","journal-title":"Organometallics"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"8442","DOI":"10.1021\/jo401165y","article-title":"Synthesis of 2-Nitroglycals from Glycals Using the Tetrabutylammonium Nitrate-Trifluoroacetic Anhydride-Triethylamine Reagent System and Base-Catalyzed Ferrier Rearrangement of Acetylated 2-Nitroglycals","volume":"78","author":"Dharuman","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3341","DOI":"10.1002\/ejoc.201402001","article-title":"Stereoselective Access to \u03b2-C-Glycosamines by Nitro-Michael Addition of Organolithium Reagents","volume":"2014","author":"Delaunay","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1059","DOI":"10.1021\/ar7002495","article-title":"2-nitroglycals as powerful glycosyl donors: Application in the synthesis of biologically important molecules","volume":"41","author":"Schmidt","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1687","DOI":"10.1021\/acs.chemrev.6b00475","article-title":"C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential","volume":"117","author":"Bokor","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"12281","DOI":"10.1021\/acs.chemrev.7b00234","article-title":"Recent Advances in the Chemical Synthesis of C-Glycosides","volume":"117","author":"Yang","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_54","first-page":"1977","article-title":"Mild debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene as a non-Lewis-basic cation scavenger","volume":"13","author":"Okano","year":"2008","journal-title":"Synlett"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1016\/S0008-6215(02)00481-0","article-title":"Zinc triflate-benzoyl bromide: A versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides","volume":"338","author":"Polat","year":"2003","journal-title":"Carbohydr. Res."},{"key":"ref_56","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 Crystallogr. Sect. B-Struct. Sci. Cryst. Eng. Mater."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1354","DOI":"10.1021\/ja00839a011","article-title":"General definition of ring puckering coordinates","volume":"97","author":"Cremer","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Jaouen, G., and Salmain, M. (2015). Bioorganometallic Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA.","DOI":"10.1002\/9783527673438"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1107\/S2052519213010014","article-title":"Use of intensity quotients and differences in absolute structure refinement","volume":"69","author":"Parsons","year":"2013","journal-title":"Acta Crystallogr. Sect. B-Struct. Sci. Cryst. Eng. Mater."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3753","DOI":"10.4049\/jimmunol.161.7.3753","article-title":"Poly(ADP-ribose) synthetase activation mediates mitochondrial injury during oxidant-induced cell death","volume":"161","author":"Salzman","year":"1998","journal-title":"J. Immunol."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"6408","DOI":"10.1039\/C6AN01596D","article-title":"Accurate quantification of apoptosis progression and toxicity using a dielectrophoretic approach","volume":"141","author":"Henslee","year":"2016","journal-title":"Analyst"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1093\/jnci\/82.13.1107","article-title":"New colorimetric cytotoxicity assay for anticancer-drug screening","volume":"82","author":"Skehan","year":"1990","journal-title":"J. Natl. Cancer Inst."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"27","DOI":"10.3389\/fchem.2013.00027","article-title":"Influence of the \u03c0-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes","volume":"1","author":"Hanif","year":"2013","journal-title":"Front. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"9046","DOI":"10.1002\/chem.200801032","article-title":"In Vitro Anticancer Activity and Biologically Relevant Metabolization of Organometallic Ruthenium Complexes with Carbohydrate-Based Ligands","volume":"14","author":"Berger","year":"2008","journal-title":"Chem. A Eur. J."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"11926","DOI":"10.1039\/C6DT01571A","article-title":"New [(\u03b75-C5H5)Ru(N-N)(PPh3)][PF6] compounds: Colon anticancer activity and GLUT-mediated cellular uptake of carbohydrate-appended complexes","volume":"45","author":"Florindo","year":"2016","journal-title":"Dalton Trans."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"4339","DOI":"10.1021\/acs.jmedchem.5b00403","article-title":"Cyclopentadienyl-Ruthenium(II) and Iron(II) Organometallic Compounds with Carbohydrate Derivative Ligands as Good Colorectal Anticancer Agents","volume":"58","author":"Florindo","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.jorganchem.2013.09.004","article-title":"Synthesis, characterization and cytotoxicity of cyclopentadienyl ruthenium(II) complexes containing carbohydrate-derived ligands","volume":"760","author":"Florindo","year":"2014","journal-title":"J. Organomet. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"3059","DOI":"10.3762\/bjoc.14.284","article-title":"Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents","volume":"14","author":"Yuan","year":"2018","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1080\/09674845.2012.11669916","article-title":"Antibacterial effects on acinetobacter species of commonly employed antineoplastic agents used in the treatment of haematological malignancies: An in vitro laboratory evaluation","volume":"69","author":"McCarron","year":"2012","journal-title":"Br. J. Biomed. Sci."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1277","DOI":"10.1074\/jbc.M110.171124","article-title":"Cisplatin inhibits protein splicing, suggesting inteins as therapeutic targets in mycobacteria","volume":"286","author":"Zhang","year":"2011","journal-title":"J. Biol. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1099\/jmm.0.001172","article-title":"Repurposing bioactive compounds for treating multidrug-resistant pathogens","volume":"69","author":"Hummell","year":"2020","journal-title":"J. Med. Microbiol."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3165","DOI":"10.1002\/cmdc.202100157","article-title":"Platinum Cyclooctadiene Complexes with Activity against Gram-positive Bacteria","volume":"16","author":"Frei","year":"2021","journal-title":"ChemMedChem"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"39748","DOI":"10.1039\/D1RA06559A","article-title":"Pd(ii) and Pt(ii) complexes of tridentate ligands with selective toxicity against Cryptococcus neoformans and Candida albicans","volume":"11","author":"Mansour","year":"2021","journal-title":"RSC Adv."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1720","DOI":"10.1016\/j.jinorgbio.2011.09.021","article-title":"Platinum(II) and palladium(II) complexes with (N,N\u2032) and (C,N,N\u2032)- ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities","volume":"105","author":"Quirante","year":"2011","journal-title":"J. Inorg. Biochem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1704","DOI":"10.1016\/j.jinorgbio.2011.07.018","article-title":"DNA as molecular target of analogous palladium and platinum anti-Trypanosoma cruzi compounds: A comparative study","volume":"105","author":"Vieites","year":"2011","journal-title":"J. Inorg. Biochem."},{"key":"ref_76","doi-asserted-by":"crossref","unstructured":"Hildebrandt, J., H\u00e4fner, N., Kritsch, D., G\u00f6rls, H., D\u00fcrst, M., Runnebaum, I.B., and Weigand, W. (2022). Highly Cytotoxic Osmium(II) Compounds and Their Ruthenium(II) Analogues Targeting Ovarian Carcinoma Cell Lines and Evading Cisplatin Resistance Mechanisms. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23094976"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"112110","DOI":"10.1016\/j.jinorgbio.2022.112110","article-title":"Ruthenium pincer complexes for light activated toxicity: Lipophilic groups enhance toxicity","volume":"240","author":"Sun","year":"2023","journal-title":"J. Inorg. Biochem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1039\/C1RA00998B","article-title":"Synthesis and X-ray diffraction structures of novel half-sandwich Os(II)-and Ru(II)-hydroxamate complexes","volume":"2","author":"Duff","year":"2012","journal-title":"RSC Adv."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1609","DOI":"10.1002\/(SICI)1099-0690(199808)1998:8<1609::AID-EJOC1609>3.0.CO;2-1","article-title":"Convenient glycoside synthesis of amino sugars: Michael-Type addition to 2-nitro-D-galactal","volume":"1998","author":"Das","year":"1998","journal-title":"Eur. J. Org. Chem."},{"key":"ref_80","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. A-Found. Adv."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","article-title":"publCIF: Software for editing, validating and formatting crystallographic information files","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Crystallogr."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1107\/S002188980600731X","article-title":"Mercury: Visualization and analysis of crystal structures","volume":"39","author":"Macrae","year":"2006","journal-title":"J. Appl. Crystallogr."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1107\/S0021889802022112","article-title":"Single-crystal structure validation with the program PLATON","volume":"36","author":"Spek","year":"2003","journal-title":"J. Appl. Crystallogr."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1046\/j.1523-1747.2003.12329.x","article-title":"Role of intracellular calcium mobilization and cell-density-dependent signaling in oxidative-stress-induced cytotoxicity in HaCaT keratinocytes","volume":"121","author":"Bakondi","year":"2003","journal-title":"J. Investig. Dermatol."},{"key":"ref_85","unstructured":"EUCAST (2021, November 04). MIC Determination of Non-Fastidious and Fastidious Organisms. Available online: https:\/\/www.eucast.org\/ast_of_bacteria\/mic_determination\/?no_cache=1."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1111\/j.2517-6161.1964.tb00553.x","article-title":"An analysis of transformations","volume":"26","author":"Box","year":"1964","journal-title":"J. R. Stat. Soc. 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