Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]
Two novel complexes, [Cu(T4)Cl2] and [Zn(T4)Cl2], were synthesized from 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] (T4), and copper(II) and zinc(II) chloride, respectively. The structures of these complexes were confirmed using ESI-MS, IR and 1H NMR spectra. The re...
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International Union of Crystallography
2025-01-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989024011617 |
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| author | Hai Le Thi Hong Hau Nguyen Van Duong Hoang Tuan Hung Tran Quang Tuan Dang Thanh Luc Van Meervelt |
| author_facet | Hai Le Thi Hong Hau Nguyen Van Duong Hoang Tuan Hung Tran Quang Tuan Dang Thanh Luc Van Meervelt |
| author_sort | Hai Le Thi Hong |
| collection | DOAJ |
| description | Two novel complexes, [Cu(T4)Cl2] and [Zn(T4)Cl2], were synthesized from 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] (T4), and copper(II) and zinc(II) chloride, respectively. The structures of these complexes were confirmed using ESI-MS, IR and 1H NMR spectra. The results reveal mononuclear structures in which the central metal atoms are coordinated by two N atoms from the imidazole rings and two Cl ligands. The structure of the CuT4 complex [systematic name: dichlorido{1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]-κ2N,N′}copper(II), [CuCl2(C33H21F3N4)], was confirmed by single-crystal X-ray diffraction. The CuII atom adopts a distorted tetrahedral coordination environment with an N2Cl2 coordination set. The predominant features of the crystal packing are C—H...F, C—H...π and C—F...π interactions. Biological evaluations demonstrated that both complexes exhibit enhanced anticancer activity compared to the free ligand, with IC50 values ranging between 18.93 and 67.06 µM. Notably, the CuII complex displays excellent inhibitory activity against the MCF7 breast cancer cell line (IC50 = 27.99 µM), approximately twice as effective as cisplatin. Conversely, the ZnT4 complex shows greater efficacy against Hep-G2 and A549 lung cancer cell lines, with IC50 values between 18.93 and 24.83 µM. The results suggest that CuII and ZnII complexes of T4 show potential as cancer treatment agents. |
| format | Article |
| id | doaj-art-636c273213c44d1a9a3014eafc6717d2 |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-636c273213c44d1a9a3014eafc6717d22025-01-06T09:23:11ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-01-01811475210.1107/S2056989024011617wm5742Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]Hai Le Thi Hong0Hau Nguyen Van1Duong Hoang Tuan2Hung Tran Quang3Tuan Dang Thanh4Luc Van Meervelt5Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, VietnamDepartment of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, VietnamDepartment of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, VietnamInstitute of Chemistry, Vietnamese Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Hanoi, VietnamInstitute of Chemistry, Vietnamese Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Hanoi, VietnamDepartment of Chemistry, KU Leuven, Biomolecular Architecture, Celestijnenlaan 200F, Leuven (Heverlee), B-3001, BelgiumTwo novel complexes, [Cu(T4)Cl2] and [Zn(T4)Cl2], were synthesized from 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] (T4), and copper(II) and zinc(II) chloride, respectively. The structures of these complexes were confirmed using ESI-MS, IR and 1H NMR spectra. The results reveal mononuclear structures in which the central metal atoms are coordinated by two N atoms from the imidazole rings and two Cl ligands. The structure of the CuT4 complex [systematic name: dichlorido{1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]-κ2N,N′}copper(II), [CuCl2(C33H21F3N4)], was confirmed by single-crystal X-ray diffraction. The CuII atom adopts a distorted tetrahedral coordination environment with an N2Cl2 coordination set. The predominant features of the crystal packing are C—H...F, C—H...π and C—F...π interactions. Biological evaluations demonstrated that both complexes exhibit enhanced anticancer activity compared to the free ligand, with IC50 values ranging between 18.93 and 67.06 µM. Notably, the CuII complex displays excellent inhibitory activity against the MCF7 breast cancer cell line (IC50 = 27.99 µM), approximately twice as effective as cisplatin. Conversely, the ZnT4 complex shows greater efficacy against Hep-G2 and A549 lung cancer cell lines, with IC50 values between 18.93 and 24.83 µM. The results suggest that CuII and ZnII complexes of T4 show potential as cancer treatment agents.https://journals.iucr.org/paper?S2056989024011617crystal structurezn(ii) complexcu(ii) complexanticancer activity |
| spellingShingle | Hai Le Thi Hong Hau Nguyen Van Duong Hoang Tuan Hung Tran Quang Tuan Dang Thanh Luc Van Meervelt Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] Acta Crystallographica Section E: Crystallographic Communications crystal structure zn(ii) complex cu(ii) complex anticancer activity |
| title | Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] |
| title_full | Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] |
| title_fullStr | Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] |
| title_full_unstemmed | Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] |
| title_short | Syntheses, structures and anticancer activities of CuII and ZnII complexes containing 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine] |
| title_sort | syntheses structures and anticancer activities of cuii and znii complexes containing 1 1 3 fluorophenyl methylene bis 3 3 fluorophenyl imidazo 1 5 a pyridine |
| topic | crystal structure zn(ii) complex cu(ii) complex anticancer activity |
| url | https://journals.iucr.org/paper?S2056989024011617 |
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