Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones
Authors
Rodríguez-Castillo, MaríaMonge, Miguel
Holló, Berta Barta
Padrón, José M.

Puerta, Adrián
Sousa, Sérgio F.
Fernandes, Henrique S.
Blagojević, Vladimir

Višnjevac, Aleksandar
Olszewski, Mateusz
Maciejewska, Natalia
Araškov, Jovana

Article (Published version)

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Thiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral Zn(II) complexes (1–3) with pyridine-based TH ligands HLS1‒3 in order to investigate the influence of the ligands charge on the structure and intermolecular interactions in the solid state, and consequently photophysical properties. The deprotonation of the ligands mainly affects the relative energies of electronic levels in the complexes, compared to cationic counterparts, resulting in similar photoluminescence mechanisms and quantum yields with a small shift in emission energy. The influence of the substitution at the ligands’ periphery on the selected quantum... molecular descriptors of the complexes is localized to the substitution site. Also, the substituents did not considerably influence the redox responses of the complexes. However, predominant spectral changes were observed in the course of the first reduction and oxidation processes which caused distinct spectral color changes indicating their possible functionality for electrochromic applications. In addition, complex 1 showed antiproliferative activity with GI50 values below 2 µM on all tested cancer cell lines.
Keywords:
TD-DFT / Spectroelectrochemistry / Photoluminescence / Intermolecular interactions / Anticancer activitySource:
Journal of Molecular Structure, 2023, 1281, 135157-Publisher:
- Elsevier
Funding / projects:
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200125 (University of Novi Sad, Faculty of Science) (RS-200125)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200116 (University of Belgrade, Faculty of Agriculture) (RS-200116)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200168 (University of Belgrade, Faculty of Chemistry) (RS-200168)
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Rodríguez-Castillo, María AU - Monge, Miguel AU - Holló, Berta Barta AU - Padrón, José M. AU - Puerta, Adrián AU - Sousa, Sérgio F. AU - Fernandes, Henrique S. AU - Blagojević, Vladimir AU - Višnjevac, Aleksandar AU - Olszewski, Mateusz AU - Maciejewska, Natalia AU - Araškov, Jovana PY - 2023 UR - http://cherry.chem.bg.ac.rs/handle/123456789/5885 AB - Thiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral Zn(II) complexes (1–3) with pyridine-based TH ligands HLS1‒3 in order to investigate the influence of the ligands charge on the structure and intermolecular interactions in the solid state, and consequently photophysical properties. The deprotonation of the ligands mainly affects the relative energies of electronic levels in the complexes, compared to cationic counterparts, resulting in similar photoluminescence mechanisms and quantum yields with a small shift in emission energy. The influence of the substitution at the ligands’ periphery on the selected quantum molecular descriptors of the complexes is localized to the substitution site. Also, the substituents did not considerably influence the redox responses of the complexes. However, predominant spectral changes were observed in the course of the first reduction and oxidation processes which caused distinct spectral color changes indicating their possible functionality for electrochromic applications. In addition, complex 1 showed antiproliferative activity with GI50 values below 2 µM on all tested cancer cell lines. PB - Elsevier T2 - Journal of Molecular Structure T1 - Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones VL - 1281 SP - 135157 DO - 10.1016/j.molstruc.2023.135157 ER -
@article{ author = "Rodríguez-Castillo, María and Monge, Miguel and Holló, Berta Barta and Padrón, José M. and Puerta, Adrián and Sousa, Sérgio F. and Fernandes, Henrique S. and Blagojević, Vladimir and Višnjevac, Aleksandar and Olszewski, Mateusz and Maciejewska, Natalia and Araškov, Jovana", year = "2023", abstract = "Thiazolyl-hydrazones (THs) exhibit a wide spectrum of biological activity that can be enhanced by complexation with various metal ions. Zn(II) complexes with α-pyridine-1,3-TH ligands may represent an alternative to the standard platinum-based chemotherapeutics. In addition, they show photoluminescence properties and thus can be regarded as multifunctional materials. In this study, we synthesized and characterized three neutral Zn(II) complexes (1–3) with pyridine-based TH ligands HLS1‒3 in order to investigate the influence of the ligands charge on the structure and intermolecular interactions in the solid state, and consequently photophysical properties. The deprotonation of the ligands mainly affects the relative energies of electronic levels in the complexes, compared to cationic counterparts, resulting in similar photoluminescence mechanisms and quantum yields with a small shift in emission energy. The influence of the substitution at the ligands’ periphery on the selected quantum molecular descriptors of the complexes is localized to the substitution site. Also, the substituents did not considerably influence the redox responses of the complexes. However, predominant spectral changes were observed in the course of the first reduction and oxidation processes which caused distinct spectral color changes indicating their possible functionality for electrochromic applications. In addition, complex 1 showed antiproliferative activity with GI50 values below 2 µM on all tested cancer cell lines.", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones", volume = "1281", pages = "135157", doi = "10.1016/j.molstruc.2023.135157" }
Rodríguez-Castillo, M., Monge, M., Holló, B. B., Padrón, J. M., Puerta, A., Sousa, S. F., Fernandes, H. S., Blagojević, V., Višnjevac, A., Olszewski, M., Maciejewska, N.,& Araškov, J.. (2023). Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones. in Journal of Molecular Structure Elsevier., 1281, 135157. https://doi.org/10.1016/j.molstruc.2023.135157
Rodríguez-Castillo M, Monge M, Holló BB, Padrón JM, Puerta A, Sousa SF, Fernandes HS, Blagojević V, Višnjevac A, Olszewski M, Maciejewska N, Araškov J. Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones. in Journal of Molecular Structure. 2023;1281:135157. doi:10.1016/j.molstruc.2023.135157 .
Rodríguez-Castillo, María, Monge, Miguel, Holló, Berta Barta, Padrón, José M., Puerta, Adrián, Sousa, Sérgio F., Fernandes, Henrique S., Blagojević, Vladimir, Višnjevac, Aleksandar, Olszewski, Mateusz, Maciejewska, Natalia, Araškov, Jovana, "Structural, physicochemical and anticancer study of Zn complexes with pyridyl-based thiazolyl-hydrazones" in Journal of Molecular Structure, 1281 (2023):135157, https://doi.org/10.1016/j.molstruc.2023.135157 . .