Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide
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2013
Authors
Cobeljić, Božidar
Pevec, Andrej
Turel, Iztok

Swart, Marcel

Mitić, Dragana

Milenković, Marina

Marković, Ivanka

Jovanović, Maja
Sladić, Dušan

Jeremić, Marko

Anđelković, Katarina

Article (Published version)

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A Schiff base of 3-acetylpyridine with semicarbazide as well as the corresponding tetrahedral Zn(II) complex were synthesized and characterized by X-ray crystal structure analysis and spectroscopic methods. It is interesting to note that the ligand coordinated as a monodentate although there are several donor atoms in it. Computational studies showed that such structure is more stable than the hypothetical structure with one ligand bound as a bidentate. The complex exibited moderate antibacterial, antifungal and cytotoxic activities while the ligand was mostly inactive. The complex strongly induced formation of reactive oxygen species in tumor cell lines. It also influenced cell cycle progression in tumor cell lines, and induced autophagy. The latter effect is, at least in part, a protective one.
Keywords:
Zn(II) complex / Schiff base / DFT calculations / Biological activitySource:
Inorganica Chimica Acta, 2013, 404, 5-12Publisher:
- Elsevier Science Sa, Lausanne
Funding / projects:
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
- ICREA
DOI: 10.1016/j.ica.2013.04.017
ISSN: 0020-1693
WoS: 000320651900002
Scopus: 2-s2.0-84878219485
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PharmacyTY - JOUR AU - Cobeljić, Božidar AU - Pevec, Andrej AU - Turel, Iztok AU - Swart, Marcel AU - Mitić, Dragana AU - Milenković, Marina AU - Marković, Ivanka AU - Jovanović, Maja AU - Sladić, Dušan AU - Jeremić, Marko AU - Anđelković, Katarina PY - 2013 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1964 AB - A Schiff base of 3-acetylpyridine with semicarbazide as well as the corresponding tetrahedral Zn(II) complex were synthesized and characterized by X-ray crystal structure analysis and spectroscopic methods. It is interesting to note that the ligand coordinated as a monodentate although there are several donor atoms in it. Computational studies showed that such structure is more stable than the hypothetical structure with one ligand bound as a bidentate. The complex exibited moderate antibacterial, antifungal and cytotoxic activities while the ligand was mostly inactive. The complex strongly induced formation of reactive oxygen species in tumor cell lines. It also influenced cell cycle progression in tumor cell lines, and induced autophagy. The latter effect is, at least in part, a protective one. PB - Elsevier Science Sa, Lausanne T2 - Inorganica Chimica Acta T1 - Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide VL - 404 SP - 5 EP - 12 DO - 10.1016/j.ica.2013.04.017 ER -
@article{ author = "Cobeljić, Božidar and Pevec, Andrej and Turel, Iztok and Swart, Marcel and Mitić, Dragana and Milenković, Marina and Marković, Ivanka and Jovanović, Maja and Sladić, Dušan and Jeremić, Marko and Anđelković, Katarina", year = "2013", abstract = "A Schiff base of 3-acetylpyridine with semicarbazide as well as the corresponding tetrahedral Zn(II) complex were synthesized and characterized by X-ray crystal structure analysis and spectroscopic methods. It is interesting to note that the ligand coordinated as a monodentate although there are several donor atoms in it. Computational studies showed that such structure is more stable than the hypothetical structure with one ligand bound as a bidentate. The complex exibited moderate antibacterial, antifungal and cytotoxic activities while the ligand was mostly inactive. The complex strongly induced formation of reactive oxygen species in tumor cell lines. It also influenced cell cycle progression in tumor cell lines, and induced autophagy. The latter effect is, at least in part, a protective one.", publisher = "Elsevier Science Sa, Lausanne", journal = "Inorganica Chimica Acta", title = "Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide", volume = "404", pages = "5-12", doi = "10.1016/j.ica.2013.04.017" }
Cobeljić, B., Pevec, A., Turel, I., Swart, M., Mitić, D., Milenković, M., Marković, I., Jovanović, M., Sladić, D., Jeremić, M.,& Anđelković, K.. (2013). Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide. in Inorganica Chimica Acta Elsevier Science Sa, Lausanne., 404, 5-12. https://doi.org/10.1016/j.ica.2013.04.017
Cobeljić B, Pevec A, Turel I, Swart M, Mitić D, Milenković M, Marković I, Jovanović M, Sladić D, Jeremić M, Anđelković K. Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide. in Inorganica Chimica Acta. 2013;404:5-12. doi:10.1016/j.ica.2013.04.017 .
Cobeljić, Božidar, Pevec, Andrej, Turel, Iztok, Swart, Marcel, Mitić, Dragana, Milenković, Marina, Marković, Ivanka, Jovanović, Maja, Sladić, Dušan, Jeremić, Marko, Anđelković, Katarina, "Synthesis, characterization, DFT calculations and biological activity of derivatives of 3-acetylpyridine and the zinc(II) complex with the condensation product of 3-acetylpyridine and semicarbazide" in Inorganica Chimica Acta, 404 (2013):5-12, https://doi.org/10.1016/j.ica.2013.04.017 . .