{"title":"二价锌的新型四氮杂环席夫碱配合物:微波辅助绿色合成、光谱表征、密度泛函理论计算、分子对接研究、体外抗菌和抗癌活性。","authors":"Mamta, Ashu Chaudhary","doi":"10.1007/s10534-024-00616-y","DOIUrl":null,"url":null,"abstract":"<div><p>In the present manuscript, novel macrocyclic Schiff base complexes [Zn(N<sub>4</sub>MacL<sub>1</sub>)Cl<sub>2</sub>–Zn(N<sub>4</sub>MacL<sub>3</sub>)Cl<sub>2</sub>] were synthesized by the reaction of ZnCl<sub>2</sub> and macrocyclic ligands (N<sub>4</sub>MacL<sub>1</sub>–N<sub>4</sub>MacL<sub>3</sub>) derived from diketone and diamines under microwave irradiation method and conventional method. The structures of the obtained complexes were identified by various spectrometric methods such as Fourier transformation infra-red (FT-IR), nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), powder X-ray diffraction, molar conductivity, and UV–vis. The structures of the synthesized compounds were optimized by using the def2–TZV/J and def2–SVP/J Coulomb fitting basis sets at B3LYP level in density functional theory (DFT) calculations. The macrocyclic Schiff base complexes exhibited higher activities against Gram-positive bacteria (<i>Staphylococcus aureus</i> and <i>Bacillus cereus</i>), Gram-negative bacteria (<i>Escherichia coli</i> and <i>Xanthomonas campestris</i>), and fungal strains (<i>Fusarium oxysporum</i> and <i>Candida albicans</i>) in comparison to macrocyclic Schiff base ligands. Furthermore, the newly synthesized macrocyclic compounds were assessed for their anticancer activity against three cell lines: A549 (human alveolar adenocarcinoma epithelial cell line), HT-29 (human colorectal adenocarcinoma cell line), and MCF-7 (human breast adenocarcinoma cell line) using the MTT assay. The obtained results showed that the macrocyclic complex [Zn(N<sub>4</sub>MacL<sub>3</sub>)Cl<sub>2</sub>] displayed the highest cytotoxic activity (2.23 ± 0.25 µM, 6.53 ± 0.28 µM, and 7.40 ± 0.45 µM for A549, HT-29, and MCF-7 cancer cell lines, respectively). Additionally, molecular docking investigations were conducted to elucidate potential molecular interactions between the synthesized macrocyclic compounds and target proteins. The results revealed a consistent agreement between the docking calculations and the experimental data.</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":491,"journal":{"name":"Biometals","volume":"37 6","pages":"1431 - 1456"},"PeriodicalIF":4.1000,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Novel tetraaza macrocyclic Schiff base complexes of bivalent zinc: microwave-assisted green synthesis, spectroscopic characterization, density functional theory calculations, molecular docking studies, in vitro antimicrobial and anticancer activities\",\"authors\":\"Mamta, Ashu Chaudhary\",\"doi\":\"10.1007/s10534-024-00616-y\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In the present manuscript, novel macrocyclic Schiff base complexes [Zn(N<sub>4</sub>MacL<sub>1</sub>)Cl<sub>2</sub>–Zn(N<sub>4</sub>MacL<sub>3</sub>)Cl<sub>2</sub>] were synthesized by the reaction of ZnCl<sub>2</sub> and macrocyclic ligands (N<sub>4</sub>MacL<sub>1</sub>–N<sub>4</sub>MacL<sub>3</sub>) derived from diketone and diamines under microwave irradiation method and conventional method. The structures of the obtained complexes were identified by various spectrometric methods such as Fourier transformation infra-red (FT-IR), nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), powder X-ray diffraction, molar conductivity, and UV–vis. The structures of the synthesized compounds were optimized by using the def2–TZV/J and def2–SVP/J Coulomb fitting basis sets at B3LYP level in density functional theory (DFT) calculations. The macrocyclic Schiff base complexes exhibited higher activities against Gram-positive bacteria (<i>Staphylococcus aureus</i> and <i>Bacillus cereus</i>), Gram-negative bacteria (<i>Escherichia coli</i> and <i>Xanthomonas campestris</i>), and fungal strains (<i>Fusarium oxysporum</i> and <i>Candida albicans</i>) in comparison to macrocyclic Schiff base ligands. Furthermore, the newly synthesized macrocyclic compounds were assessed for their anticancer activity against three cell lines: A549 (human alveolar adenocarcinoma epithelial cell line), HT-29 (human colorectal adenocarcinoma cell line), and MCF-7 (human breast adenocarcinoma cell line) using the MTT assay. The obtained results showed that the macrocyclic complex [Zn(N<sub>4</sub>MacL<sub>3</sub>)Cl<sub>2</sub>] displayed the highest cytotoxic activity (2.23 ± 0.25 µM, 6.53 ± 0.28 µM, and 7.40 ± 0.45 µM for A549, HT-29, and MCF-7 cancer cell lines, respectively). Additionally, molecular docking investigations were conducted to elucidate potential molecular interactions between the synthesized macrocyclic compounds and target proteins. The results revealed a consistent agreement between the docking calculations and the experimental data.</p><h3>Graphical abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":491,\"journal\":{\"name\":\"Biometals\",\"volume\":\"37 6\",\"pages\":\"1431 - 1456\"},\"PeriodicalIF\":4.1000,\"publicationDate\":\"2024-06-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Biometals\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10534-024-00616-y\",\"RegionNum\":3,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biometals","FirstCategoryId":"99","ListUrlMain":"https://link.springer.com/article/10.1007/s10534-024-00616-y","RegionNum":3,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Novel tetraaza macrocyclic Schiff base complexes of bivalent zinc: microwave-assisted green synthesis, spectroscopic characterization, density functional theory calculations, molecular docking studies, in vitro antimicrobial and anticancer activities
In the present manuscript, novel macrocyclic Schiff base complexes [Zn(N4MacL1)Cl2–Zn(N4MacL3)Cl2] were synthesized by the reaction of ZnCl2 and macrocyclic ligands (N4MacL1–N4MacL3) derived from diketone and diamines under microwave irradiation method and conventional method. The structures of the obtained complexes were identified by various spectrometric methods such as Fourier transformation infra-red (FT-IR), nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), powder X-ray diffraction, molar conductivity, and UV–vis. The structures of the synthesized compounds were optimized by using the def2–TZV/J and def2–SVP/J Coulomb fitting basis sets at B3LYP level in density functional theory (DFT) calculations. The macrocyclic Schiff base complexes exhibited higher activities against Gram-positive bacteria (Staphylococcus aureus and Bacillus cereus), Gram-negative bacteria (Escherichia coli and Xanthomonas campestris), and fungal strains (Fusarium oxysporum and Candida albicans) in comparison to macrocyclic Schiff base ligands. Furthermore, the newly synthesized macrocyclic compounds were assessed for their anticancer activity against three cell lines: A549 (human alveolar adenocarcinoma epithelial cell line), HT-29 (human colorectal adenocarcinoma cell line), and MCF-7 (human breast adenocarcinoma cell line) using the MTT assay. The obtained results showed that the macrocyclic complex [Zn(N4MacL3)Cl2] displayed the highest cytotoxic activity (2.23 ± 0.25 µM, 6.53 ± 0.28 µM, and 7.40 ± 0.45 µM for A549, HT-29, and MCF-7 cancer cell lines, respectively). Additionally, molecular docking investigations were conducted to elucidate potential molecular interactions between the synthesized macrocyclic compounds and target proteins. The results revealed a consistent agreement between the docking calculations and the experimental data.
期刊介绍:
BioMetals is the only established journal to feature the important role of metal ions in chemistry, biology, biochemistry, environmental science, and medicine. BioMetals is an international, multidisciplinary journal singularly devoted to the rapid publication of the fundamental advances of both basic and applied research in this field. BioMetals offers a forum for innovative research and clinical results on the structure and function of:
- metal ions
- metal chelates,
- siderophores,
- metal-containing proteins
- biominerals in all biosystems.
- BioMetals rapidly publishes original articles and reviews.
BioMetals is a journal for metals researchers who practice in medicine, biochemistry, pharmacology, toxicology, microbiology, cell biology, chemistry, and plant physiology who are based academic, industrial and government laboratories.