{"title":"一种新型水溶性硫代氨基脲希夫碱配体及其配合物作为潜在的抗癌剂和细胞荧光成像","authors":"Sima Feizpour, Seyed Abolfazl Hosseini-Yazdi, Elham Safarzadeh, Behzad Baradaran, Michal Dusek, Morgane Poupon","doi":"10.1007/s00775-023-02001-5","DOIUrl":null,"url":null,"abstract":"<div><p>A novel fluorescent ligand (H<sub>2</sub>LCl?1.5CH<sub>3</sub>OH, <b>1</b>) was synthesized and metal complexes of <b>1</b> with Mn(II), Fe(III), Ni(II), Cu(II), and Zn(II) were obtained as Mn(HL)<sub>2</sub>Cl<sub>2</sub> (<b>2</b>), Fe(HL)<sub>2</sub>Cl<sub>3</sub>?3H<sub>2</sub>O (<b>3</b>), Ni(L)(HL)Cl?8H<sub>2</sub>O (<b>4</b>), Cu(HL)Cl<sub>2</sub>?4H<sub>2</sub>O (<b>5</b>), Zn(H<sub>2</sub>L)Cl<sub>3</sub> (<b>6</b>), respectively. These compounds were identified by spectroscopic methods, elemental analysis, molar conductivity, and single-crystal X-ray crystallography. According to the crystal structure of <b>4</b> nickel (II), center is surrounded by two ligands in a distorted octahedral geometry. The ligand and its complexes are soluble in water and have excellent stability. In vitro anti-proliferative activity of these compounds was evaluated against human breast adenocarcinoma (MCF-7) and human lipo-sarcoma (SW-872) as cancer cells and human fibroblasts (HFF-2) as normal cells by MTT assay. Interestingly, complex <b>5</b> exhibited excellent activity against both cancer cells with low IC<sub>50</sub> value 22.18?±?0.35?μg/mL (35.66?±?0.56?μM) for SW-872 and 79.41?±?3.54?μg/mL (127.6?±?5.69?μM) for MCF-7 among the compounds and in comparison with paclitaxel (PTX) which acts finely. Morphological changes were evaluated by flow cytometry that revealed apoptosis is the main cause of cell death. Likewise, cell cycle studies indicated the cell cycle arrest in the G<sub>1</sub> and S phases for complex <b>5</b> against MCF-7 and SW-872 cancer cells, while complex <b>6</b> could arrest the MCF-7 and SW-872 cells in G<sub>2</sub> and G<sub>1</sub> phases, respectively. All of the compounds are fluorescent which enabled us to monitor the uptake and intracellular distribution in living human cancer cells by fluorescence microscopy.</p><h3>Graphical abstract</h3>\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\n </div>","PeriodicalId":603,"journal":{"name":"JBIC Journal of Biological Inorganic Chemistry","volume":"28 5","pages":"457 - 472"},"PeriodicalIF":2.7000,"publicationDate":"2023-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"A novel water-soluble thiosemicarbazone Schiff base ligand and its complexes as potential anticancer agents and cellular fluorescence imaging\",\"authors\":\"Sima Feizpour, Seyed Abolfazl Hosseini-Yazdi, Elham Safarzadeh, Behzad Baradaran, Michal Dusek, Morgane Poupon\",\"doi\":\"10.1007/s00775-023-02001-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A novel fluorescent ligand (H<sub>2</sub>LCl?1.5CH<sub>3</sub>OH, <b>1</b>) was synthesized and metal complexes of <b>1</b> with Mn(II), Fe(III), Ni(II), Cu(II), and Zn(II) were obtained as Mn(HL)<sub>2</sub>Cl<sub>2</sub> (<b>2</b>), Fe(HL)<sub>2</sub>Cl<sub>3</sub>?3H<sub>2</sub>O (<b>3</b>), Ni(L)(HL)Cl?8H<sub>2</sub>O (<b>4</b>), Cu(HL)Cl<sub>2</sub>?4H<sub>2</sub>O (<b>5</b>), Zn(H<sub>2</sub>L)Cl<sub>3</sub> (<b>6</b>), respectively. These compounds were identified by spectroscopic methods, elemental analysis, molar conductivity, and single-crystal X-ray crystallography. According to the crystal structure of <b>4</b> nickel (II), center is surrounded by two ligands in a distorted octahedral geometry. The ligand and its complexes are soluble in water and have excellent stability. In vitro anti-proliferative activity of these compounds was evaluated against human breast adenocarcinoma (MCF-7) and human lipo-sarcoma (SW-872) as cancer cells and human fibroblasts (HFF-2) as normal cells by MTT assay. Interestingly, complex <b>5</b> exhibited excellent activity against both cancer cells with low IC<sub>50</sub> value 22.18?±?0.35?μg/mL (35.66?±?0.56?μM) for SW-872 and 79.41?±?3.54?μg/mL (127.6?±?5.69?μM) for MCF-7 among the compounds and in comparison with paclitaxel (PTX) which acts finely. Morphological changes were evaluated by flow cytometry that revealed apoptosis is the main cause of cell death. Likewise, cell cycle studies indicated the cell cycle arrest in the G<sub>1</sub> and S phases for complex <b>5</b> against MCF-7 and SW-872 cancer cells, while complex <b>6</b> could arrest the MCF-7 and SW-872 cells in G<sub>2</sub> and G<sub>1</sub> phases, respectively. All of the compounds are fluorescent which enabled us to monitor the uptake and intracellular distribution in living human cancer cells by fluorescence microscopy.</p><h3>Graphical abstract</h3>\\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\\n </div>\",\"PeriodicalId\":603,\"journal\":{\"name\":\"JBIC Journal of Biological Inorganic Chemistry\",\"volume\":\"28 5\",\"pages\":\"457 - 472\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2023-05-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"JBIC Journal of Biological Inorganic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s00775-023-02001-5\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"JBIC Journal of Biological Inorganic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s00775-023-02001-5","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
A novel water-soluble thiosemicarbazone Schiff base ligand and its complexes as potential anticancer agents and cellular fluorescence imaging
A novel fluorescent ligand (H2LCl?1.5CH3OH, 1) was synthesized and metal complexes of 1 with Mn(II), Fe(III), Ni(II), Cu(II), and Zn(II) were obtained as Mn(HL)2Cl2 (2), Fe(HL)2Cl3?3H2O (3), Ni(L)(HL)Cl?8H2O (4), Cu(HL)Cl2?4H2O (5), Zn(H2L)Cl3 (6), respectively. These compounds were identified by spectroscopic methods, elemental analysis, molar conductivity, and single-crystal X-ray crystallography. According to the crystal structure of 4 nickel (II), center is surrounded by two ligands in a distorted octahedral geometry. The ligand and its complexes are soluble in water and have excellent stability. In vitro anti-proliferative activity of these compounds was evaluated against human breast adenocarcinoma (MCF-7) and human lipo-sarcoma (SW-872) as cancer cells and human fibroblasts (HFF-2) as normal cells by MTT assay. Interestingly, complex 5 exhibited excellent activity against both cancer cells with low IC50 value 22.18?±?0.35?μg/mL (35.66?±?0.56?μM) for SW-872 and 79.41?±?3.54?μg/mL (127.6?±?5.69?μM) for MCF-7 among the compounds and in comparison with paclitaxel (PTX) which acts finely. Morphological changes were evaluated by flow cytometry that revealed apoptosis is the main cause of cell death. Likewise, cell cycle studies indicated the cell cycle arrest in the G1 and S phases for complex 5 against MCF-7 and SW-872 cancer cells, while complex 6 could arrest the MCF-7 and SW-872 cells in G2 and G1 phases, respectively. All of the compounds are fluorescent which enabled us to monitor the uptake and intracellular distribution in living human cancer cells by fluorescence microscopy.
期刊介绍：
Biological inorganic chemistry is a growing field of science that embraces the principles of biology and inorganic chemistry and impacts other fields ranging from medicine to the environment. JBIC (Journal of Biological Inorganic Chemistry) seeks to promote this field internationally. The Journal is primarily concerned with advances in understanding the role of metal ions within a biological matrix—be it a protein, DNA/RNA, or a cell, as well as appropriate model studies. Manuscripts describing high-quality original research on the above topics in English are invited for submission to this Journal. The Journal publishes original articles, minireviews, and commentaries on debated issues.
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