In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines
The synthesis of novel triphenyltin(IV) compounds, Ph(3)SnLn (n = 1-3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid,...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2021-05, Vol.26 (11), p.3199, Article 3199 |
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| creator | Pantelic, Nebojsa D. Bozic, Bojan Zmejkovski, Bojana B. Banjac, Nebojsa R. Dojcinovic, Biljana Wessjohann, Ludger A. Kaluderovic, Goran N. |
| description | The synthesis of novel triphenyltin(IV) compounds, Ph(3)SnLn (n = 1-3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3, has been performed. The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 mu M. According to the CV assay (IC50 = 0.218 +/- 0.025 mu M), complex Ph(3)SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph(3)SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph(3)SnL1 induces caspase-independent apoptosis in MCF-7 cells. |
| doi_str_mv | 10.3390/molecules26113199 |
| format | Article |
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The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 mu M. According to the CV assay (IC50 = 0.218 +/- 0.025 mu M), complex Ph(3)SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph(3)SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph(3)SnL1 induces caspase-independent apoptosis in MCF-7 cells.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules26113199</identifier><identifier>PMID: 34071809</identifier><language>eng</language><publisher>BASEL: Mdpi</publisher><subject>Acids ; Adenocarcinoma ; Analytical methods ; Animals ; Antiproliferatives ; Apoptosis ; Autophagy ; Biochemistry & Molecular Biology ; Breast cancer ; Carbon ; Carboxylates ; Caspase-3 ; Cell cycle ; Cell division ; Cell Line, Tumor ; Chemistry ; Chemistry, Multidisciplinary ; Cytotoxicity ; Drug Screening Assays, Antitumor - methods ; Embryo fibroblasts ; Female ; Gentian Violet ; HeLa Cells ; HT29 Cells ; Humans ; Hydrogen ; ICP-MS ; In vitro methods and tests ; In Vitro Techniques ; Inductively coupled plasma mass spectrometry ; Inhibitory Concentration 50 ; Investigations ; Life Sciences & Biomedicine ; Ligands ; Liver cancer ; Mass Spectrometry ; Mass spectroscopy ; MCF-7 Cells ; Metals - chemistry ; Mice ; Neoplasms - drug therapy ; NIH 3T3 Cells ; Organotin Compounds - chemistry ; Phagocytosis ; Physical Sciences ; Platinum ; Propionic acid ; Prostate cancer ; Reactive Nitrogen Species ; Reactive Oxygen Species ; Science & Technology ; Triphenyltin ; triphenyltin(IV) ; Tumor cell lines ; Tumors</subject><ispartof>Molecules (Basel, Switzerland), 2021-05, Vol.26 (11), p.3199, Article 3199</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). 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The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 mu M. According to the CV assay (IC50 = 0.218 +/- 0.025 mu M), complex Ph(3)SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph(3)SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph(3)SnL1 induces caspase-independent apoptosis in MCF-7 cells.</description><subject>Acids</subject><subject>Adenocarcinoma</subject><subject>Analytical methods</subject><subject>Animals</subject><subject>Antiproliferatives</subject><subject>Apoptosis</subject><subject>Autophagy</subject><subject>Biochemistry & Molecular Biology</subject><subject>Breast cancer</subject><subject>Carbon</subject><subject>Carboxylates</subject><subject>Caspase-3</subject><subject>Cell cycle</subject><subject>Cell division</subject><subject>Cell Line, Tumor</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor - methods</subject><subject>Embryo fibroblasts</subject><subject>Female</subject><subject>Gentian Violet</subject><subject>HeLa Cells</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Hydrogen</subject><subject>ICP-MS</subject><subject>In vitro methods and tests</subject><subject>In Vitro Techniques</subject><subject>Inductively coupled plasma mass spectrometry</subject><subject>Inhibitory Concentration 50</subject><subject>Investigations</subject><subject>Life Sciences & Biomedicine</subject><subject>Ligands</subject><subject>Liver cancer</subject><subject>Mass Spectrometry</subject><subject>Mass spectroscopy</subject><subject>MCF-7 Cells</subject><subject>Metals - 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The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 mu M. According to the CV assay (IC50 = 0.218 +/- 0.025 mu M), complex Ph(3)SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph(3)SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph(3)SnL1 induces caspase-independent apoptosis in MCF-7 cells.</abstract><cop>BASEL</cop><pub>Mdpi</pub><pmid>34071809</pmid><doi>10.3390/molecules26113199</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0001-5168-1000</orcidid><orcidid>https://orcid.org/0000-0003-1843-9890</orcidid><orcidid>https://orcid.org/0000-0001-9910-2741</orcidid><orcidid>https://orcid.org/0000-0003-1479-8060</orcidid><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_pubmed_primary_34071809 |
| source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; DOAJ Directory of Open Access Journals; Web of Science - Science Citation Index Expanded - 2021<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" />; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Acids Adenocarcinoma Analytical methods Animals Antiproliferatives Apoptosis Autophagy Biochemistry & Molecular Biology Breast cancer Carbon Carboxylates Caspase-3 Cell cycle Cell division Cell Line, Tumor Chemistry Chemistry, Multidisciplinary Cytotoxicity Drug Screening Assays, Antitumor - methods Embryo fibroblasts Female Gentian Violet HeLa Cells HT29 Cells Humans Hydrogen ICP-MS In vitro methods and tests In Vitro Techniques Inductively coupled plasma mass spectrometry Inhibitory Concentration 50 Investigations Life Sciences & Biomedicine Ligands Liver cancer Mass Spectrometry Mass spectroscopy MCF-7 Cells Metals - chemistry Mice Neoplasms - drug therapy NIH 3T3 Cells Organotin Compounds - chemistry Phagocytosis Physical Sciences Platinum Propionic acid Prostate cancer Reactive Nitrogen Species Reactive Oxygen Species Science & Technology Triphenyltin triphenyltin(IV) Tumor cell lines Tumors |
| title | In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-11-30T13%3A27%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=In%20Vitro%20Evaluation%20of%20Antiproliferative%20Properties%20of%20Novel%20Organotin(IV)%20Carboxylate%20Compounds%20with%20Propanoic%20Acid%20Derivatives%20on%20a%20Panel%20of%20Human%20Cancer%20Cell%20Lines&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Pantelic,%20Nebojsa%20D.&rft.date=2021-05-27&rft.volume=26&rft.issue=11&rft.spage=3199&rft.pages=3199-&rft.artnum=3199&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules26113199&rft_dat=%3Cproquest_pubme%3E2539956822%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2539956822&rft_id=info:pmid/34071809&rft_doaj_id=oai_doaj_org_article_d7c8706b268e4df2a3fd191b249e49a8&rfr_iscdi=true |