1 line
38 KiB
Plaintext
1 line
38 KiB
Plaintext
{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,1,22]],"date-time":"2024-01-22T10:19:46Z","timestamp":1705918786426},"reference-count":108,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,3,26]],"date-time":"2023-03-26T00:00:00Z","timestamp":1679788800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"operational program ESF Saxony-Anhalt WISSENSCHAFT Chancengleichheit with funds from the European Union"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Organotin(IV) carboxylates are a class of compounds explored as alternatives to platinum-containing chemotherapeutics due to propitious in vitro and in vivo results, and distinct mechanisms of action. In this study, triphenyltin(IV) derivatives of non-steroidal anti-inflammatory drugs (indomethacin (HIND) and flurbiprofen (HFBP)) are synthesized and characterized, namely [Ph3Sn(IND)] and [Ph3Sn(FBP)]. The crystal structure of [Ph3Sn(IND)] reveals penta-coordination of the central tin atom with almost perfect trigonal bipyramidal geometry with phenyl groups in the equatorial positions and two axially located oxygen atoms belonging to two distinct carboxylato (IND) ligands leading to formation of a coordination polymer with bridging carboxylato ligands. Employing MTT and CV probes, the antiproliferative effects of both organotin(IV) complexes, indomethacin, and flurbiprofen were evaluated on different breast carcinoma cells (BT-474, MDA-MB-468, MCF-7 and HCC1937). [Ph3Sn(IND)] and [Ph3Sn(FBP)], unlike the inactive ligand precursors, were found extremely active towards all examined cell lines, demonstrating IC50 concentrations in the range of 0.076\u20130.200 \u00b5M. Flow cytometry was employed to examine the mode of action showing that neither apoptotic nor autophagic mechanisms were triggered within the first 48 h of treatment. However, both tin(IV) complexes inhibited cell proliferation potentially related to the dramatic reduction in NO production, resulting from downregulation of nitric oxide synthase (iNOS) enzyme expression.<\/jats:p>","DOI":"10.3390\/biom13040595","type":"journal-article","created":{"date-parts":[[2023,3,27]],"date-time":"2023-03-27T07:31:48Z","timestamp":1679902308000},"page":"595","source":"Crossref","is-referenced-by-count":2,"title":["Triphenyltin(IV) Carboxylates with Exceptionally High Cytotoxicity against Different Breast Cancer Cell Lines"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"http:\/\/orcid.org\/0000-0003-2178-6332","authenticated-orcid":false,"given":"Ivana","family":"Predarska","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry, Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, 04103 Leipzig, Germany"},{"name":"Department of Engineering and Natural Sciences, University of Applied Sciences Merseburg, Eberhard Leibnitz-Str. 2, 06217 Merseburg, Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0003-0749-8692","authenticated-orcid":false,"given":"Mohamad","family":"Saoud","sequence":"additional","affiliation":[{"name":"Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0002-4032-2691","authenticated-orcid":false,"given":"Ibrahim","family":"Morgan","sequence":"additional","affiliation":[{"name":"Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0003-1335-0897","authenticated-orcid":false,"given":"Peter","family":"L\u00f6nnecke","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry, Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, 04103 Leipzig, Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0001-5168-1000","authenticated-orcid":false,"given":"Goran N.","family":"Kalu\u0111erovi\u0107","sequence":"additional","affiliation":[{"name":"Department of Engineering and Natural Sciences, University of Applied Sciences Merseburg, Eberhard Leibnitz-Str. 2, 06217 Merseburg, Germany"},{"name":"Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0003-4267-0603","authenticated-orcid":false,"given":"Evamarie","family":"Hey-Hawkins","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry, Faculty of Chemistry and Mineralogy, Leipzig University, Johannisallee 29, 04103 Leipzig, Germany"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3029","DOI":"10.1002\/cncr.33587","article-title":"The ever-increasing importance of cancer as a leading cause of premature death worldwide","volume":"127","author":"Bray","year":"2021","journal-title":"Cancer"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"209","DOI":"10.3322\/caac.21660","article-title":"Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries","volume":"71","author":"Sung","year":"2021","journal-title":"CA Cancer J. Clin."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Hawash, M. (2022). Recent advances of tubulin inhibitors targeting the colchicine binding site for cancer therapy. Biomolecules, 12.","DOI":"10.3390\/biom12121843"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2070","DOI":"10.1016\/j.ccr.2009.01.028","article-title":"Mechanistic insight into the cellular uptake and processing of cisplatin 30 years after its approval by FDA","volume":"253","author":"Arnesano","year":"2009","journal-title":"Coord. Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1219","DOI":"10.1002\/1097-0142(197405)33:5<1219::AID-CNCR2820330505>3.0.CO;2-U","article-title":"Diaminodichloroplatinum: A phase I study showing responses in testicular and other tumors","volume":"33","author":"Higby","year":"1974","journal-title":"Cancer"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2467","DOI":"10.1021\/cr980421n","article-title":"Structure, recognition, and processing of cisplatin-DNA adducts","volume":"99","author":"Jamieson","year":"1999","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1007\/s00280-016-2976-z","article-title":"Platinum-based drugs: Past, present and future","volume":"77","author":"Dilruba","year":"2016","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3436","DOI":"10.1021\/acs.chemrev.5b00597","article-title":"The next generation of platinum drugs: Targeted Pt(II) agents, nanoparticle delivery, and Pt(IV) prodrugs","volume":"116","author":"Johnstone","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1021\/acs.chemrev.8b00271","article-title":"Toward multi-targeted platinum and ruthenium drugs\u2014A new paradigm in cancer drug treatment regimens?","volume":"119","author":"Kenny","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1038\/nrd1691","article-title":"Cellular processing of platinum anticancer drugs","volume":"4","author":"Wang","year":"2005","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"6645","DOI":"10.1039\/C8DT00838H","article-title":"The side effects of platinum-based chemotherapy drugs: A review for chemists","volume":"47","author":"Oun","year":"2018","journal-title":"Dalton Trans."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"119","DOI":"10.4155\/fmc-2018-0248","article-title":"Metal-based antitumor compounds: Beyond cisplatin","volume":"11","author":"Simpson","year":"2019","journal-title":"Future Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1016\/j.jinorgbio.2019.02.003","article-title":"Anti-proliferative and antitumor activity of organotin(IV) compounds. An overview of the last decade and future perspectives","volume":"194","author":"Banti","year":"2019","journal-title":"J. Inorg. Biochem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3131","DOI":"10.2174\/1568026617666171004155437","article-title":"Multi-target metal-based anticancer agents","volume":"17","author":"Chen","year":"2017","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_15","first-page":"140284","article-title":"On the discovery, biological effects, and use of cisplatin and metallocenes in anticancer chemotherapy","volume":"2012","year":"2012","journal-title":"Bioinorg. Chem. Appl."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1021\/ic401529u","article-title":"Rhodium, iridium, and ruthenium half-sandwich picolinamide complexes as anticancer agents","volume":"53","author":"Almodares","year":"2014","journal-title":"Inorg. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1016\/j.drudis.2009.02.002","article-title":"Organometallic compounds in oncology: Implications of novel organotins as antitumor agents","volume":"14","author":"Alama","year":"2009","journal-title":"Drug Discov. Today"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"26","DOI":"10.5530\/srp.2019.1.5","article-title":"Synthesis and biological activities of organotin(IV) carboxylates: A review","volume":"10","author":"Hadi","year":"2019","journal-title":"Syst. Rev. Pharm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"657599","DOI":"10.3389\/fchem.2021.657599","article-title":"Cellular basis of organotin(IV) derivatives as anticancer metallodrugs: A review","volume":"9","author":"Kamaludin","year":"2021","journal-title":"Front. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"e4651","DOI":"10.1002\/aoc.4651","article-title":"Design, synthesis and characterization of tin-based cancer chemotherapy drug entity: In vitro DNA binding, cleavage, induction of cancer cell apoptosis by triggering DNA damage-mediated P53 phosphorylation and molecular docking","volume":"33","author":"Esmail","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1002\/cmdc.201100432","article-title":"Study of the anticancer properties of tin(IV) carboxylate complexes on a panel of human tumor cell lines","volume":"7","author":"Prashar","year":"2012","journal-title":"ChemMedChem"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1294","DOI":"10.1016\/j.jinorgbio.2005.03.002","article-title":"Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptosis","volume":"99","author":"Pellerito","year":"2005","journal-title":"J. Inorg. Biochem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1733","DOI":"10.1016\/j.jorganchem.2005.12.025","article-title":"Biological activity studies on organotin(IV)n+ complexes and parent compounds","volume":"691","author":"Pellerito","year":"2006","journal-title":"J. Organomet. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1016\/j.ccr.2007.12.026","article-title":"Antiproliferative and anti-tumor activity of organotin compounds","volume":"253","author":"Hadjikakou","year":"2009","journal-title":"Coord. Chem. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1016\/S0162-0134(03)00178-8","article-title":"Synthesis, structural characterization and in vitro cytotoxicity of organotin(IV) derivatives of heterocyclic thioamides, 2-mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, 3-methyl-2-mercaptobenzothiazole and 2-mercaptonicotinic acid","volume":"96","author":"Xanthopoulou","year":"2003","journal-title":"J. Inorg. Biochem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/j.ejmech.2007.03.028","article-title":"Biological studies of new organotin(IV) complexes of thioamide ligands","volume":"43","author":"Xanthopoulou","year":"2008","journal-title":"Eur. J. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1021\/ic061601f","article-title":"Synthesis, structural characterization, and biological studies of six- and five-coordinate organotin(iv) complexes with the thioamides 2-mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, and 2-mercaptobenzoxazole","volume":"46","author":"Xanthopoulou","year":"2007","journal-title":"Inorg. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1007\/s11172-007-0115-z","article-title":"Biological studies of organotin(IV) complexes with 2-mercaptopyrimidine","volume":"56","author":"Xanthopoulou","year":"2007","journal-title":"Russ. Chem. Bull."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1002\/aoc.465","article-title":"Synthesis, properties and crystal structural characterization of diorganotin(IV) derivatives of 2-mercapto-6-nitrobenzothiazole","volume":"17","author":"Ma","year":"2003","journal-title":"Appl. Organomet. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1002\/aoc.508","article-title":"Syntheses and crystal structures of diorganotin(IV) bis(2-pyridinethiolato-N-oxide) complexes","volume":"17","author":"Ma","year":"2003","journal-title":"Appl. Organomet. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1002\/aoc.1441","article-title":"Tin dithiocarbamates: Applications and structures","volume":"22","author":"Tiekink","year":"2008","journal-title":"Appl. Organomet. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/0010-8545(89)80003-7","article-title":"Organotin compounds and cancer chemotherapy","volume":"95","author":"Saxena","year":"1989","journal-title":"Coord. Chem. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1016\/S0223-5234(00)80030-6","article-title":"Synthesis and evaluation of the in vivo trypanocidal activity of water soluble organotin compounds","volume":"34","author":"Susperregui","year":"1999","journal-title":"Eur. J. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/S0010-8545(01)00399-X","article-title":"Organotin(IV)n+ complexes formed with biologically active ligands: Equilibrium and structural studies, and some biological aspects","volume":"224","author":"Pellerito","year":"2002","journal-title":"Coord. Chem. Rev."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4850","DOI":"10.1016\/j.jorganchem.2006.08.005","article-title":"Synthesis and characterization of bis[dicarboxylatotetraorganodistannoxane] units involving 5-[(E)-2-(Aryl)-1-Diazenyl]-2-hydroxybenzoic acids: An investigation of structures by X-ray diffraction, NMR, electrospray ionisation MS and assessment of in vitro cytotoxicity","volume":"691","author":"Rynjah","year":"2006","journal-title":"J. Organomet. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1646","DOI":"10.1016\/j.jinorgbio.2005.05.006","article-title":"Synthesis, characterization and biological activity of triorganotin 2-phenyl-1,2,3-triazole-4-carboxylates","volume":"99","author":"Tian","year":"2005","journal-title":"J. Inorg. Biochem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/S0162-0134(02)00369-0","article-title":"Synthesis and characterization of water-insoluble and water-soluble dibutyltin(IV) porphinate complexes based on the tris(pyridinyl) porphyrin moiety, their anti-tumor activity in vitro and interaction with DNA","volume":"91","author":"Han","year":"2002","journal-title":"J. Inorg. Biochem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2087","DOI":"10.1016\/j.jinorgbio.2008.07.009","article-title":"Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes","volume":"102","author":"Prashar","year":"2008","journal-title":"J. Inorg. Biochem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1016\/j.jinorgbio.2009.12.006","article-title":"On the bioreactivity of triorganotin aminobenzoates. Investigation of trialkyl and triarylyltin(IV) esters of 3-amino and 4-aminobenzoic acids","volume":"104","author":"Tzimopoulos","year":"2010","journal-title":"J. Inorg. Biochem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1002\/aoc.331","article-title":"Review: Organotin compounds and their therapeutic potential: A report from the Organometallic Chemistry Department of the Free University of Brussels","volume":"16","author":"Gielen","year":"2002","journal-title":"Appl. Organomet. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Gielen, M., and Tiekink, E.R.T. (2005). Metallotherapeutic Drugs and Metal-Based Diagnostic Agents: The Use of Metals in Medicine, Wiley.","DOI":"10.1002\/0470864052"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/S1734-1140(10)70262-0","article-title":"COX-2 as a target for cancer chemotherapy","volume":"62","author":"Ghosh","year":"2010","journal-title":"Pharmacol. Rep."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1002\/mc.20326","article-title":"The cyclooxygenase-2-mediated prostaglandin signaling is causally related to epithelial carcinogenesis","volume":"46","year":"2007","journal-title":"Mol. Carcinog."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Hawash, M., Jaradat, N., Abualhasan, M., \u015e\u00fck\u00fcro\u011flu, M.K., Qaoud, M.T., Kahraman, D.C., Daraghmeh, H., Maslamani, L., Sawafta, M., and Ratrout, A. (2023). Design, synthesis, molecular docking studies and biological evaluation of thiazole carboxamide derivatives as COX inhibitors. BMC Chem., 17.","DOI":"10.1186\/s13065-023-00924-3"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"342","DOI":"10.1007\/s13205-022-03408-8","article-title":"Molecular docking studies and biological evaluation of isoxazole-carboxamide derivatives as COX inhibitors and antimicrobial agents","volume":"12","author":"Hawash","year":"2022","journal-title":"3 Biotech"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"738","DOI":"10.1016\/j.inoche.2011.02.024","article-title":"Chemical, spectroscopic characterization and antibacterial activities in vitro of a novel gold(I)-ibuprofen complex","volume":"14","author":"Fiori","year":"2011","journal-title":"Inorg. Chem. Commun."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.inoche.2014.03.039","article-title":"Synthesis, spectroscopic studies and in vitro antibacterial activity of ibuprofen and its derived metal complexes","volume":"45","author":"Carballo","year":"2014","journal-title":"Inorg. Chem. Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"10701","DOI":"10.1039\/C7NR01582H","article-title":"Diruthenium(II,III) metallodrugs of ibuprofen and naproxen encapsulated in intravenously injectable polymer-lipid nanoparticles exhibit enhanced activity against breast and prostate cancer cells","volume":"9","author":"Abbasi","year":"2017","journal-title":"Nanoscale"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"8253","DOI":"10.1039\/C7NJ00247E","article-title":"Four monomeric copper(II) complexes of non-steroidal anti-inflammatory drug ibuprofen and N-donor ligands: Syntheses, characterization, crystal structures and cytotoxicity studies","volume":"41","author":"Kumar","year":"2017","journal-title":"New J. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1016\/j.ica.2015.04.010","article-title":"A novel bioactive Cd(II) polymeric complex with mefenamic acid: Synthesis, crystal structure and biological evaluations","volume":"432","author":"Tabrizi","year":"2015","journal-title":"Inorg. Chim. Acta"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1361","DOI":"10.1016\/j.jinorgbio.2004.04.016","article-title":"Synthesis, X-ray crystal structure, anti-fungal and anti-cancer activity of [Ag2(NH3)2(salH)2] (salH2 = salicylic acid)","volume":"98","author":"Coyle","year":"2004","journal-title":"J. Inorg. Biochem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.poly.2012.05.012","article-title":"Synthesis and characterization of a diruthenium(II,III)-ketoprofen compound and study of the in vitro effects on CRC cells in comparison to the naproxen and ibuprofen derivatives","volume":"42","author":"Santos","year":"2012","journal-title":"Polyhedron"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"5157","DOI":"10.1016\/j.ejmech.2010.08.028","article-title":"[Cyclopentadienyl]metalcarbonyl complexes of acetylsalicylic acid as neo-anticancer agents","volume":"45","author":"Rubner","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1016\/j.jinorgbio.2010.10.008","article-title":"The triphenyltin(VI) complexes of NSAIDs and derivatives. Synthesis, crystal structure and antiproliferative activity. Potent anticancer agents","volume":"105","author":"Dokorou","year":"2011","journal-title":"J. Inorg. Biochem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"e5283","DOI":"10.1002\/aoc.5283","article-title":"Organotin(IV) complexes of NSAID, ibuprofen, X-ray structure of Ph3Sn(IBF), binding and cleavage interaction with DNA and in vitro cytotoxic studies of several organotin complexes of drugs","volume":"34","author":"Kumari","year":"2020","journal-title":"Appl. Organomet. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Panteli\u0107, N.\u0110., Bo\u017ei\u0107, B., Zmejkovski, B.B., Banjac, N.R., Doj\u010dinovi\u0107, B., Wessjohann, L.A., and Kalu\u0111erovi\u0107, G.N. (2021). In vitro evaluation of antiproliferative properties of novel organotin(IV) carboxylate compounds with propanoic acid derivatives on a panel of human cancer cell lines. Molecules, 26.","DOI":"10.3390\/molecules26113199"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1002\/aoc.1366","article-title":"Synthesis, structural characterization and cytotoxic activity of organotin derivatives of indomethacin","volume":"22","author":"Toscano","year":"2008","journal-title":"Appl. Organomet. Chem."},{"key":"ref_58","first-page":"657","article-title":"Synthesis, characterization and biological applications of organotin(IV) derivatives of 2-(2-Fluoro-4-biphenyl)propanoic acid","volume":"27","author":"Mahmood","year":"2003","journal-title":"Turk. J. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1038\/35021093","article-title":"Molecular portraits of human breast tumours","volume":"406","author":"Perou","year":"2000","journal-title":"Nature"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1150","DOI":"10.1002\/cmdc.201402074","article-title":"Conjugates of cisplatin and cyclooxygenase inhibitors as potent antitumor agents overcoming cisplatin resistance","volume":"9","author":"Neumann","year":"2014","journal-title":"ChemMedChem"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1039\/D1DT03265H","article-title":"Cisplatin-cyclooxygenase inhibitor conjugates, free and immobilised in mesoporous silica SBA-15, prove highly potent against triple-negative MDA-MB-468 breast cancer cell line","volume":"51","author":"Predarska","year":"2022","journal-title":"Dalton Trans."},{"key":"ref_62","unstructured":"CrysAlisPro data reduction software package."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2014Integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. A"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with It SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Mercury CSD 2.0\u2014New features for the visualization and investigation of crystal structures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Crystallogr."},{"key":"ref_66","first-page":"35","article-title":"The expression patterns of ER, PR, HER2, CK5\/6, EGFR, Ki-67 and AR by immunohistochemical analysis in breast cancer cell lines","volume":"4","author":"Subik","year":"2010","journal-title":"Breast Cancer"},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Khan, M.F., Nasr, F.A., Noman, O.M., Alyhya, N.A., Ali, I., Saoud, M., Rennert, R., Dube, M., Hussain, W., and Green, I.R. (2020). Cichorins D\u2013F: Three new compounds from Cichorium intybus and their biological effects. Molecules, 25.","DOI":"10.3390\/molecules25184160"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"111383","DOI":"10.1016\/j.jinorgbio.2021.111383","article-title":"Antitumor potential of cisplatin loaded into SBA-15 mesoporous silica nanoparticles against B16F1 melanoma cells: In vitro and in vivo studies","volume":"217","author":"Edeler","year":"2021","journal-title":"J. Inorg. Biochem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2292","DOI":"10.1080\/01480545.2021.1935397","article-title":"The impact of filtered water-pipe smoke on healthy versus cancer cells and their neurodegenerative role on AMPA receptor","volume":"45","author":"Hawash","year":"2022","journal-title":"Drug Chem. Toxicol."},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Krajnovi\u0107, T., Maksimovi\u0107-Ivani\u0107, D., Mijatovi\u0107, S., Dra\u010da, D., Wolf, K., Edeler, D., Wessjohann, L.A., and Kalu\u0111erovi\u0107, G.N. (2018). Drug delivery system for emodin based on mesoporous silica SBA-15. Nanomaterials, 8.","DOI":"10.3390\/nano8050322"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"2842","DOI":"10.1016\/j.ica.2009.01.003","article-title":"Organotin(IV) 4-methoxyphenylethanoates: Synthesis, spectroscopic characterization, X-ray structures and in vitro anticancer activity against human prostate cell lines (PC-3)","volume":"362","author":"Muhammad","year":"2009","journal-title":"Inorg. Chim. Acta"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2490","DOI":"10.1021\/ic00235a004","article-title":"Pentacoordinated molecules. 65. Discrete, dimeric, and polymeric structures of triphenyltin esters of chlorobenzoic acids","volume":"25","author":"Holmes","year":"1986","journal-title":"Inorg. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1016\/0022-328X(89)87144-X","article-title":"Organotin esters of 3-benzoylpropionic acid. Crystal structure of triphenyltin(IV) 3-benzoylpropionate, (C6H5)3SnOC(O)(CH2)2C(O)C6H5","volume":"364","author":"Syed","year":"1989","journal-title":"J. Organomet. Chem."},{"key":"ref_74","first-page":"81","article-title":"Crystal structure of catena-poly-(\u03bc-dichloroacetato)triphenyltin, [Ph3Sn(O2CHCl2)]n","volume":"215","author":"Smyth","year":"2000","journal-title":"Z. Krist. New Cryst. Struct."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1007\/s10904-005-7875-4","article-title":"The synthesis and characterization of triorganotin carboxylates of 2-mercapto-4-methyl-5-thiazoleacetic acid: X-ray crystal structures of polymeric Me3Sn[O2CCH2(C4H3NS)S]SnMe3 and Ph3Sn[O2CCH2(C4H3NS)S]SnPh3","volume":"15","author":"Ma","year":"2005","journal-title":"J. Inorg. Organomet. Polym. Mater."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1883","DOI":"10.1016\/j.jorganchem.2010.04.029","article-title":"Synthesis, characterization and biological studies of 1-D polymeric triphenyltin(IV) carboxylates","volume":"695","author":"Paschke","year":"2010","journal-title":"J. Organomet. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","unstructured":"\u015aliwka, L., Wiktorska, K., Suchocki, P., Milczarek, M., Mielczarek, S., Lubelska, K., Cierpia\u0142, T., \u0141y\u017cwa, P., Kie\u0142basi\u0144ski, P., and Jaromin, A. (2016). The comparison of MTT and CVS assays for the assessment of anticancer agent interactions. PLoS ONE, 11.","DOI":"10.1371\/journal.pone.0155772"},{"key":"ref_78","first-page":"2515","article-title":"Tetrazolium-based assays for cellular viability: A critical examination of selected parameters affecting formazan production","volume":"51","author":"Vistica","year":"1991","journal-title":"Cancer Res."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1016\/j.jep.2004.04.011","article-title":"Reduction of MTT by aqueous herbal extracts in the absence of cells","volume":"93","author":"Shoemaker","year":"2004","journal-title":"J. Ethnopharmacol."},{"key":"ref_80","doi-asserted-by":"crossref","unstructured":"Wang, P., Henning, S.M., and Heber, D. (2010). Limitations of MTT and MTS-based assays for measurement of antiproliferative activity of green tea polyphenols. PLoS ONE, 5.","DOI":"10.1371\/journal.pone.0010202"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1055\/s-2002-32073","article-title":"Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay","volume":"68","author":"Bruggisser","year":"2002","journal-title":"Planta Med."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/0022-1759(95)00072-I","article-title":"A Novel assay for apoptosis. flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V","volume":"184","author":"Vermes","year":"1995","journal-title":"J. Immunol. Methods"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"111031","DOI":"10.1039\/C6RA22596A","article-title":"SBA-15 mesoporous silica particles loaded with cisplatin induce senescence in B16F10 Cells","volume":"6","author":"Edeler","year":"2016","journal-title":"RSC Adv."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1038\/bjc.1994.14","article-title":"The role of apoptosis in cell killing by cisplatin: A flow cytometric study","volume":"69","author":"Ormerod","year":"1994","journal-title":"Br. J. Cancer"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1007\/s002800050413","article-title":"Cis-diamminedichloroplatinum(II)-induced cell death through apoptosis in sensitive and resistant human ovarian carcinoma cell lines","volume":"37","author":"Ormerod","year":"1996","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"7265","DOI":"10.1038\/sj.onc.1206933","article-title":"Cisplatin: Mode of cytotoxic action and molecular basis of resistance","volume":"22","author":"Siddik","year":"2003","journal-title":"Oncogene"},{"key":"ref_87","doi-asserted-by":"crossref","unstructured":"Predarska, I., Saoud, M., Dra\u010da, D., Morgan, I., Komazec, T., Eichhorn, T., Mihajlovi\u0107, E., Dun\u0111erovi\u0107, D., Mijatovi\u0107, S., and Maksimovi\u0107-Ivani\u0107, D. (2022). Mesoporous silica nanoparticles enhance the anticancer efficacy of platinum(IV)-phenolate conjugates in breast cancer cell lines. Nanomaterials, 12.","DOI":"10.3390\/nano12213767"},{"key":"ref_88","doi-asserted-by":"crossref","unstructured":"Choi, Y.-M., Kim, H.-K., Shim, W., Anwar, M.A., Kwon, J.-W., Kwon, H.-K., Kim, H.J., Jeong, H., Kim, H.M., and Hwang, D. (2015). Mechanism of cisplatin-induced cytotoxicity is correlated to impaired metabolism due to mitochondrial ROS generation. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0135083"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1038\/s41419-019-2081-4","article-title":"Direct impact of cisplatin on mitochondria induces ROS production that dictates cell fate of ovarian cancer cells","volume":"10","author":"Kleih","year":"2019","journal-title":"Cell Death Dis."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1186\/s12943-021-01488-3","article-title":"The crosstalk between reactive oxygen species and noncoding RNAs: From cancer code to drug role","volume":"21","author":"Zuo","year":"2022","journal-title":"Mol. Cancer"},{"key":"ref_91","first-page":"109","article-title":"Nitric oxide: Physiology, pathophysiology, and pharmacology","volume":"43","author":"Moncada","year":"1991","journal-title":"Pharmacol. Rev."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1016\/j.freeradbiomed.2008.03.020","article-title":"The chemical biology of nitric oxide: Implications in cellular signaling","volume":"45","author":"Thomas","year":"2008","journal-title":"Free Radic. Biol. Med."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"381","DOI":"10.2174\/138161210790232149","article-title":"Nitric oxide and cancer therapy: The emperor has no clothes","volume":"16","author":"Hickok","year":"2010","journal-title":"Curr. Pharm. Des."},{"key":"ref_94","doi-asserted-by":"crossref","unstructured":"Khan, F.H., Dervan, E., Bhattacharyya, D.D., McAuliffe, J.D., Miranda, K.M., and Glynn, S.A. (2020). The role of nitric oxide in cancer: Master regulator or not?. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21249393"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1038\/sj.cr.7290133","article-title":"The role of nitric oxide in cancer","volume":"12","author":"Xu","year":"2002","journal-title":"Cell Res."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.cell.2011.06.006","article-title":"Glioma stem cell proliferation and tumor growth are promoted by nitric oxide synthase-2","volume":"146","author":"Eyler","year":"2011","journal-title":"Cell"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1002\/1096-9896(200106)194:2<194::AID-PATH851>3.0.CO;2-S","article-title":"Inducible nitric oxide synthase expression in benign and malignant cutaneous melanocytic lesions","volume":"194","author":"Massi","year":"2001","journal-title":"J. Pathol."},{"key":"ref_98","first-page":"334","article-title":"Frequent nitric oxide synthase-2 expression in human colon adenomas: Implication for tumor angiogenesis and colon cancer progression","volume":"58","author":"Ambs","year":"1998","journal-title":"Cancer Res."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1002\/ijc.27644","article-title":"NOS2 Enhances KRAS-induced lung carcinogenesis, inflammation and MicroRNA-21 expression","volume":"132","author":"Okayama","year":"2013","journal-title":"Int. J. Cancer"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1038\/bjc.1995.274","article-title":"Nitric oxide synthase activity in human breast cancer","volume":"72","author":"Thomsen","year":"1995","journal-title":"Br. J. Cancer"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"3843","DOI":"10.1172\/JCI42059","article-title":"Increased NOS2 predicts poor survival in estrogen receptor-negative breast cancer patients","volume":"120","author":"Glynn","year":"2010","journal-title":"J. Clin. Investig."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1007\/s00428-005-1250-2","article-title":"Significance of inducible nitric oxide synthase expression in benign and malignant breast epithelium: An immunohistochemical study of 151 cases","volume":"447","author":"Bulut","year":"2005","journal-title":"Virchows Arch."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/j.ejca.2004.07.010","article-title":"The role of early expression of inducible nitric oxide synthase in human breast cancer","volume":"41","author":"Loibl","year":"2005","journal-title":"Eur. J. Cancer"},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1186\/s13058-015-0527-x","article-title":"Inhibition of iNOS as a novel effective targeted therapy against triple-negative breast cancer","volume":"17","author":"Liu","year":"2015","journal-title":"Breast Cancer Res."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1023\/A:1011020132140","article-title":"Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages","volume":"18","author":"Hinz","year":"2001","journal-title":"Pharm. Res."},{"key":"ref_106","first-page":"160","article-title":"Study the effect of indomethacin administration on breast tumor growth and INOS gene expression in tumor-bearing mice","volume":"7","year":"2019","journal-title":"Int. J. Adv. Biol. Biomed. Res."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1038\/sj.cdd.4402233","article-title":"Oxidative stress induces autophagic cell death independent of apoptosis in transformed and cancer cells","volume":"15","author":"Chen","year":"2008","journal-title":"Cell Death Differ."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1038\/s41420-020-00315-w","article-title":"Induction of STK11-dependent cytoprotective autophagy in breast cancer cells upon honokiol treatment","volume":"6","author":"Muniraj","year":"2020","journal-title":"Cell Death Discov."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/13\/4\/595\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,27]],"date-time":"2023-03-27T10:39:53Z","timestamp":1679913593000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/13\/4\/595"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,26]]},"references-count":108,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["biom13040595"],"URL":"http:\/\/dx.doi.org\/10.3390\/biom13040595","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":["Molecular Biology","Biochemistry"],"published":{"date-parts":[[2023,3,26]]}}} |