New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies
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2023
Authors
Lađarević, Jelena
Radovanović, Lidija
Božić, Bojan

Mašulović, Aleksandra

Lunić, Tanja
Radovanović, Željko

Rogan, Jelena

Mijin, Dušan

Article (Published version)

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Two azo dye ligands, bearing different substituents (chlorine atom or methoxy group) in the para-position of the phenyl ring, were employed for the synthesis of two Cu(II) chelates. Full structural affirmation of complexes was assessed. X-ray diffraction measurements revealed that the coordination geometry for Cu atoms in both complexes is square-pyramidal with a ligand:metal ratio of 2:1 where dyes behave as monobasic bidentate ligands. Thermogravimetric analyses of the complexes and their starting dyes were performed to study their thermal stabilities and decomposition behavior confirming the thermal stability of both dyes and complexes. Antioxidative activity of the complexes has been assigned and compared with their parent ligands revealing that the presence of the electron–donor, methoxy group, in the phenyl ring, in both dye and complex, is responsible for the activity (IC50 values of 1.54 for the dye and 1.30 mM for the complex). It should be stated that the complexation of the ...methoxy-substituted dye leads to enhanced antioxidative activity concurrent to a standard antioxidant molecule of ascorbic acid, making this molecule a promising antioxidant agent. Docking study with vascular endothelial growth factor receptor 2 and Aurora kinase A proteins indicate that complexes exhibit higher binding affinities to proteins than the starting ligand dyes. The most promising structure exhibiting the best docking potential toward both proteins is the complex-bearing methoxy group. The presented results represent a promising start for further investigations of these compounds as potential therapeutic candidates for the treatment of various types of cancer.
Keywords:
azo pyridone dyes / copper(II) complex / crystal structure / molecular docking / thermal analysisSource:
Applied Organometallic Chemistry, 2023Publisher:
- John Wiley and Sons Ltd.
Funding / projects:
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-200135)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200178 (University of Belgrade, Faculty of Biology) (RS-200178)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-200287)
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Tehnološko-metalurški fakultetTY - JOUR AU - Lađarević, Jelena AU - Radovanović, Lidija AU - Božić, Bojan AU - Mašulović, Aleksandra AU - Lunić, Tanja AU - Radovanović, Željko AU - Rogan, Jelena AU - Mijin, Dušan PY - 2023 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6604 AB - Two azo dye ligands, bearing different substituents (chlorine atom or methoxy group) in the para-position of the phenyl ring, were employed for the synthesis of two Cu(II) chelates. Full structural affirmation of complexes was assessed. X-ray diffraction measurements revealed that the coordination geometry for Cu atoms in both complexes is square-pyramidal with a ligand:metal ratio of 2:1 where dyes behave as monobasic bidentate ligands. Thermogravimetric analyses of the complexes and their starting dyes were performed to study their thermal stabilities and decomposition behavior confirming the thermal stability of both dyes and complexes. Antioxidative activity of the complexes has been assigned and compared with their parent ligands revealing that the presence of the electron–donor, methoxy group, in the phenyl ring, in both dye and complex, is responsible for the activity (IC50 values of 1.54 for the dye and 1.30 mM for the complex). It should be stated that the complexation of the methoxy-substituted dye leads to enhanced antioxidative activity concurrent to a standard antioxidant molecule of ascorbic acid, making this molecule a promising antioxidant agent. Docking study with vascular endothelial growth factor receptor 2 and Aurora kinase A proteins indicate that complexes exhibit higher binding affinities to proteins than the starting ligand dyes. The most promising structure exhibiting the best docking potential toward both proteins is the complex-bearing methoxy group. The presented results represent a promising start for further investigations of these compounds as potential therapeutic candidates for the treatment of various types of cancer. PB - John Wiley and Sons Ltd. T2 - Applied Organometallic Chemistry T1 - New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies DO - 10.1002/aoc.7219 ER -
@article{ author = "Lađarević, Jelena and Radovanović, Lidija and Božić, Bojan and Mašulović, Aleksandra and Lunić, Tanja and Radovanović, Željko and Rogan, Jelena and Mijin, Dušan", year = "2023", abstract = "Two azo dye ligands, bearing different substituents (chlorine atom or methoxy group) in the para-position of the phenyl ring, were employed for the synthesis of two Cu(II) chelates. Full structural affirmation of complexes was assessed. X-ray diffraction measurements revealed that the coordination geometry for Cu atoms in both complexes is square-pyramidal with a ligand:metal ratio of 2:1 where dyes behave as monobasic bidentate ligands. Thermogravimetric analyses of the complexes and their starting dyes were performed to study their thermal stabilities and decomposition behavior confirming the thermal stability of both dyes and complexes. Antioxidative activity of the complexes has been assigned and compared with their parent ligands revealing that the presence of the electron–donor, methoxy group, in the phenyl ring, in both dye and complex, is responsible for the activity (IC50 values of 1.54 for the dye and 1.30 mM for the complex). It should be stated that the complexation of the methoxy-substituted dye leads to enhanced antioxidative activity concurrent to a standard antioxidant molecule of ascorbic acid, making this molecule a promising antioxidant agent. Docking study with vascular endothelial growth factor receptor 2 and Aurora kinase A proteins indicate that complexes exhibit higher binding affinities to proteins than the starting ligand dyes. The most promising structure exhibiting the best docking potential toward both proteins is the complex-bearing methoxy group. The presented results represent a promising start for further investigations of these compounds as potential therapeutic candidates for the treatment of various types of cancer.", publisher = "John Wiley and Sons Ltd.", journal = "Applied Organometallic Chemistry", title = "New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies", doi = "10.1002/aoc.7219" }
Lađarević, J., Radovanović, L., Božić, B., Mašulović, A., Lunić, T., Radovanović, Ž., Rogan, J.,& Mijin, D.. (2023). New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies. in Applied Organometallic Chemistry John Wiley and Sons Ltd... https://doi.org/10.1002/aoc.7219
Lađarević J, Radovanović L, Božić B, Mašulović A, Lunić T, Radovanović Ž, Rogan J, Mijin D. New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies. in Applied Organometallic Chemistry. 2023;. doi:10.1002/aoc.7219 .
Lađarević, Jelena, Radovanović, Lidija, Božić, Bojan, Mašulović, Aleksandra, Lunić, Tanja, Radovanović, Željko, Rogan, Jelena, Mijin, Dušan, "New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies" in Applied Organometallic Chemistry (2023), https://doi.org/10.1002/aoc.7219 . .