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
Čobeljić, BožidarPevec, Andrej
Turel, Iztok
Swart, Marcel
Mitić, Dragana
Milenković, Marina
Marković, Ivanka
Jovanović, Maja
Sladić, Dušan
Jeremić, Marko
Anđelković, Katarina K.
Article (Published version)
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Show full item recordAbstract
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-MESTD-Basic Research (BR or ON)-172055)
- Modulation of intracellular energy balance-controlling signalling pathways in therapy of cancer and neuro-immuno-endocrine disorders (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41025)
- ICREA
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2011-25086/BQU]
- Slovenian Research Agency (ARRS) [P-0175]
- MICINN (Ministry of Science and Innovation, Spain)
- FEDER fund (European Fund for Regional Development) [UNGI08-4E-003]
- DIUE of the Generalitat de Catalunya [2009SGR528]
Note:
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3539
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3540
DOI: 10.1016/j.ica.2013.04.017
ISSN: 0020-1693
WoS: 000320651900002
Scopus: 2-s2.0-84878219485
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Čobeljić, 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 K. PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1367 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 = "Čobeljić, 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 K.", 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" }
Čobeljić, B., Pevec, A., Turel, I., Swart, M., Mitić, D., Milenković, M., Marković, I., Jovanović, M., Sladić, D., Jeremić, M.,& Anđelković, K. 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
Čobeljić B, Pevec A, Turel I, Swart M, Mitić D, Milenković M, Marković I, Jovanović M, Sladić D, Jeremić M, Anđelković KK. 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 .
Čobeljić, Božidar, Pevec, Andrej, Turel, Iztok, Swart, Marcel, Mitić, Dragana, Milenković, Marina, Marković, Ivanka, Jovanović, Maja, Sladić, Dušan, Jeremić, Marko, Anđelković, Katarina 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, 404 (2013):5-12, https://doi.org/10.1016/j.ica.2013.04.017 . .