Micheal K. Farh , Ikrame Louzi , Hassan Abul-Futouh , Helmar Görls , Norman Häfner , Ingo B. Runnebaum , Wolfgang Weigand
{"title":"β-羟基二硫代酯-二茂铁衍生物介导的铂（II）和钯（II）配合物的合成、表征及抗增殖活性","authors":"Micheal K. Farh , Ikrame Louzi , Hassan Abul-Futouh , Helmar Görls , Norman Häfner , Ingo B. Runnebaum , Wolfgang Weigand","doi":"10.1080/17415993.2022.2152285","DOIUrl":null,"url":null,"abstract":"<div><p>Ferrocene and its derivatives compounds have shown a significant role in medicinal organometallic chemistry as an antiparasitic or antibacterial. Therefore, we herein report on the utilization of dithioesters ferrocenyl derivatives as proligands for the synthesis of heteroleptic platinum(II) and homoleptic palladium(II) complexes bearing a conserved <em>O,S</em> binding moiety. The resulting complexes [Pt(L1)(DMSO)Cl] (<strong>1</strong>), [Pt(L2)(DMSO)Cl] (<strong>2</strong>), [Pt(L3)(DMSO)Cl] (<strong>3</strong>), [Pd(L1)<sub>2</sub>] (<strong>4</strong>), [Pd(L2)<sub>2</sub>] (<strong>5</strong>), and [Pd(L3)<sub>2</sub>] (<strong>6</strong>), in which HL1 = methyl 3-hydroxy-3-ferroceneprop-2-enedithioate, HL2 = ethyl 3-hydroxy-3-ferroceneprop-2-enedithioate and HL3 = propyl 3-hydroxy-3-ferroceneprop-2-enedithioate, were fully characterized employing a variety of analytical techniques (NMR spectroscopy, elemental analysis, and mass spectrometry and X-ray structure determination of complexes <strong>2</strong> and <strong>6</strong>). Cytotoxicity assays of the synthesized ligands as well as the Pt/Pd metal complexes showed low toxicity towards ovarian cancer cells, but the compounds are not affected by cisplatin resistance mechanisms. Pt(II) complexes exhibited the highest activity, and the alkyl substituent strongly influenced the activity of these complexes and the free ligands. The cytotoxic activity increases with the length of the alkyl chain with <strong>3</strong> exhibiting a mean IC<sub>50</sub> of 56 µM.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 320-335"},"PeriodicalIF":2.1000,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Platinum(II) and palladium(II) complexes mediated by β-hydroxy-dithioesters ferrocenyl derivatives: synthesis, characterization and antiproliferative activity\",\"authors\":\"Micheal K. Farh , Ikrame Louzi , Hassan Abul-Futouh , Helmar Görls , Norman Häfner , Ingo B. Runnebaum , Wolfgang Weigand\",\"doi\":\"10.1080/17415993.2022.2152285\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Ferrocene and its derivatives compounds have shown a significant role in medicinal organometallic chemistry as an antiparasitic or antibacterial. Therefore, we herein report on the utilization of dithioesters ferrocenyl derivatives as proligands for the synthesis of heteroleptic platinum(II) and homoleptic palladium(II) complexes bearing a conserved <em>O,S</em> binding moiety. The resulting complexes [Pt(L1)(DMSO)Cl] (<strong>1</strong>), [Pt(L2)(DMSO)Cl] (<strong>2</strong>), [Pt(L3)(DMSO)Cl] (<strong>3</strong>), [Pd(L1)<sub>2</sub>] (<strong>4</strong>), [Pd(L2)<sub>2</sub>] (<strong>5</strong>), and [Pd(L3)<sub>2</sub>] (<strong>6</strong>), in which HL1 = methyl 3-hydroxy-3-ferroceneprop-2-enedithioate, HL2 = ethyl 3-hydroxy-3-ferroceneprop-2-enedithioate and HL3 = propyl 3-hydroxy-3-ferroceneprop-2-enedithioate, were fully characterized employing a variety of analytical techniques (NMR spectroscopy, elemental analysis, and mass spectrometry and X-ray structure determination of complexes <strong>2</strong> and <strong>6</strong>). Cytotoxicity assays of the synthesized ligands as well as the Pt/Pd metal complexes showed low toxicity towards ovarian cancer cells, but the compounds are not affected by cisplatin resistance mechanisms. Pt(II) complexes exhibited the highest activity, and the alkyl substituent strongly influenced the activity of these complexes and the free ligands. The cytotoxic activity increases with the length of the alkyl chain with <strong>3</strong> exhibiting a mean IC<sub>50</sub> of 56 µM.</p></div>\",\"PeriodicalId\":17081,\"journal\":{\"name\":\"Journal of Sulfur Chemistry\",\"volume\":\"44 3\",\"pages\":\"Pages 320-335\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2023-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Sulfur Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1741599323000077\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323000077","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Platinum(II) and palladium(II) complexes mediated by β-hydroxy-dithioesters ferrocenyl derivatives: synthesis, characterization and antiproliferative activity
Ferrocene and its derivatives compounds have shown a significant role in medicinal organometallic chemistry as an antiparasitic or antibacterial. Therefore, we herein report on the utilization of dithioesters ferrocenyl derivatives as proligands for the synthesis of heteroleptic platinum(II) and homoleptic palladium(II) complexes bearing a conserved O,S binding moiety. The resulting complexes [Pt(L1)(DMSO)Cl] (1), [Pt(L2)(DMSO)Cl] (2), [Pt(L3)(DMSO)Cl] (3), [Pd(L1)2] (4), [Pd(L2)2] (5), and [Pd(L3)2] (6), in which HL1 = methyl 3-hydroxy-3-ferroceneprop-2-enedithioate, HL2 = ethyl 3-hydroxy-3-ferroceneprop-2-enedithioate and HL3 = propyl 3-hydroxy-3-ferroceneprop-2-enedithioate, were fully characterized employing a variety of analytical techniques (NMR spectroscopy, elemental analysis, and mass spectrometry and X-ray structure determination of complexes 2 and 6). Cytotoxicity assays of the synthesized ligands as well as the Pt/Pd metal complexes showed low toxicity towards ovarian cancer cells, but the compounds are not affected by cisplatin resistance mechanisms. Pt(II) complexes exhibited the highest activity, and the alkyl substituent strongly influenced the activity of these complexes and the free ligands. The cytotoxic activity increases with the length of the alkyl chain with 3 exhibiting a mean IC50 of 56 µM.
期刊介绍：
The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science.
Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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