Provincial Secretariat for Science and Technological Development of Vojvodina

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Provincial Secretariat for Science and Technological Development of Vojvodina

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Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings

Rodić, Marko V.; Leovac, Vukadin M.; Jovanović, Ljiljana S.; Spasojević, Vojislav; Joksović, Milan D.; Stanojković, Tatjana P.; Matić, Ivana Z.; Vojinović-Ješić, Ljiljana S.; Marković, Violeta

(Elsevier, 2016)

TY  - JOUR
AU  - Rodić, Marko V.
AU  - Leovac, Vukadin M.
AU  - Jovanović, Ljiljana S.
AU  - Spasojević, Vojislav
AU  - Joksović, Milan D.
AU  - Stanojković, Tatjana P.
AU  - Matić, Ivana Z.
AU  - Vojinović-Ješić, Ljiljana S.
AU  - Marković, Violeta
PY  - 2016
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/1053
AB  - Three novel copper complexes with tridentate N2O ligand di(2-pyridil) ketone 1-adamantoyl hydrazone (Addpy) of the formula [(Cu2Cu2I)-Cu-II(Addpy)(2)Br-2(mu-Br-4)] (1), catena-poly[CuCl(mu-Addpy)(mu-Cl)CuCl2](n) (2) and [Cu(Addpy)(NCS)(2)] (3) were synthesized. Complexes are characterized by X-ray crystallography, spectral (UV-Vis, FTIR), electrochemical (CV) analyses, and magnetochemical measurements. Investigation of anticancer potential of Cu(II) complexes, mode of cell death, apoptosis, and inhibition of angiogenesis were performed. All tested malignant cell lines (HeLa, LS174, A549, K562, and MDA-MB-231) showed high sensitivity to the examined Cu(II) complexes. It has been shown that the complexes induce apoptosis in the caspase 3-dependent manner, whereas the anti-angiogenic effects of 1, 2, and 3 have been confirmed in EA.hy926 cells using a tube formation assay. (C) 2016 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings
VL  - 115
SP  - 75
EP  - 81
DO  - 10.1016/j.ejmech.2016.03.003
ER  - 
@article{
author = "Rodić, Marko V. and Leovac, Vukadin M. and Jovanović, Ljiljana S. and Spasojević, Vojislav and Joksović, Milan D. and Stanojković, Tatjana P. and Matić, Ivana Z. and Vojinović-Ješić, Ljiljana S. and Marković, Violeta",
year = "2016",
abstract = "Three novel copper complexes with tridentate N2O ligand di(2-pyridil) ketone 1-adamantoyl hydrazone (Addpy) of the formula [(Cu2Cu2I)-Cu-II(Addpy)(2)Br-2(mu-Br-4)] (1), catena-poly[CuCl(mu-Addpy)(mu-Cl)CuCl2](n) (2) and [Cu(Addpy)(NCS)(2)] (3) were synthesized. Complexes are characterized by X-ray crystallography, spectral (UV-Vis, FTIR), electrochemical (CV) analyses, and magnetochemical measurements. Investigation of anticancer potential of Cu(II) complexes, mode of cell death, apoptosis, and inhibition of angiogenesis were performed. All tested malignant cell lines (HeLa, LS174, A549, K562, and MDA-MB-231) showed high sensitivity to the examined Cu(II) complexes. It has been shown that the complexes induce apoptosis in the caspase 3-dependent manner, whereas the anti-angiogenic effects of 1, 2, and 3 have been confirmed in EA.hy926 cells using a tube formation assay. (C) 2016 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings",
volume = "115",
pages = "75-81",
doi = "10.1016/j.ejmech.2016.03.003"
}
Rodić, M. V., Leovac, V. M., Jovanović, L. S., Spasojević, V., Joksović, M. D., Stanojković, T. P., Matić, I. Z., Vojinović-Ješić, L. S.,& Marković, V.. (2016). Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings. in European Journal of Medicinal Chemistry
Elsevier., 115, 75-81.
https://doi.org/10.1016/j.ejmech.2016.03.003
Rodić MV, Leovac VM, Jovanović LS, Spasojević V, Joksović MD, Stanojković TP, Matić IZ, Vojinović-Ješić LS, Marković V. Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings. in European Journal of Medicinal Chemistry. 2016;115:75-81.
doi:10.1016/j.ejmech.2016.03.003 .
Rodić, Marko V., Leovac, Vukadin M., Jovanović, Ljiljana S., Spasojević, Vojislav, Joksović, Milan D., Stanojković, Tatjana P., Matić, Ivana Z., Vojinović-Ješić, Ljiljana S., Marković, Violeta, "Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings" in European Journal of Medicinal Chemistry, 115 (2016):75-81,
https://doi.org/10.1016/j.ejmech.2016.03.003 . .
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Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl

Ivkovic, Sonja A.; Vojinović-Ješić, Ljiljana S.; Leovac, Vukadin M.; Rodić, Marko V.; Novaković, Slađana B.; Bogdanović, Goran A.

(2015)

TY  - JOUR
AU  - Ivkovic, Sonja A.
AU  - Vojinović-Ješić, Ljiljana S.
AU  - Leovac, Vukadin M.
AU  - Rodić, Marko V.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
PY  - 2015
UR  - http://vinar.vin.bg.ac.rs/handle/123456789/360
AB  - A novel pyridoxal thiosemicarbazone (PLTSC) compound, exhibiting ligating properties, of the formula PLTSC center dot HCl center dot 2H(2)O (1) was synthesized and characterized by X-ray analysis. The PLTSC ligand 1 displays significantly different conformation in comparison to the five previously reported compounds of this type. The structural properties of six PLTSC ligands in different conformations were compared in order to establish the structural differences and understand the factors that facilitate particular conformations. The analysis indicated great structural flexibility of the PLTSC ligands. The PLTSC ligand 1 is essentially a planar molecule with the r.m.s deviation of all non-H atoms equal to 0.06 angstrom. Consequently, the molecules of 1 form a layered three-dimensional structure which is stabilized by a variety of hydrogen bonds: O-H center dot center dot center dot O, O-H center dot center dot center dot N, O-H center dot center dot center dot Cl, O-H center dot center dot center dot S, N-H center dot center dot center dot O, N-H center dot center dot center dot N, N-H center dot center dot center dot Cl, N-H center dot center dot center dot S. In addition, the crystal structure of the Fe(III) complex with the ligand 1 of the formula [Fe(PLTSC)Cl-2(H2O)]Cl was resolved by single-crystal X-ray analysis and structural properties of this octahedral complex were discussed and compared to those of uncoordinated PLTSC ligand.
T2  - Structural Chemistry
T1  - Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl
VL  - 26
IS  - 1
SP  - 269
EP  - 277
DO  - 10.1007/s11224-014-0491-6
ER  - 
@article{
author = "Ivkovic, Sonja A. and Vojinović-Ješić, Ljiljana S. and Leovac, Vukadin M. and Rodić, Marko V. and Novaković, Slađana B. and Bogdanović, Goran A.",
year = "2015",
abstract = "A novel pyridoxal thiosemicarbazone (PLTSC) compound, exhibiting ligating properties, of the formula PLTSC center dot HCl center dot 2H(2)O (1) was synthesized and characterized by X-ray analysis. The PLTSC ligand 1 displays significantly different conformation in comparison to the five previously reported compounds of this type. The structural properties of six PLTSC ligands in different conformations were compared in order to establish the structural differences and understand the factors that facilitate particular conformations. The analysis indicated great structural flexibility of the PLTSC ligands. The PLTSC ligand 1 is essentially a planar molecule with the r.m.s deviation of all non-H atoms equal to 0.06 angstrom. Consequently, the molecules of 1 form a layered three-dimensional structure which is stabilized by a variety of hydrogen bonds: O-H center dot center dot center dot O, O-H center dot center dot center dot N, O-H center dot center dot center dot Cl, O-H center dot center dot center dot S, N-H center dot center dot center dot O, N-H center dot center dot center dot N, N-H center dot center dot center dot Cl, N-H center dot center dot center dot S. In addition, the crystal structure of the Fe(III) complex with the ligand 1 of the formula [Fe(PLTSC)Cl-2(H2O)]Cl was resolved by single-crystal X-ray analysis and structural properties of this octahedral complex were discussed and compared to those of uncoordinated PLTSC ligand.",
journal = "Structural Chemistry",
title = "Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl",
volume = "26",
number = "1",
pages = "269-277",
doi = "10.1007/s11224-014-0491-6"
}
Ivkovic, S. A., Vojinović-Ješić, L. S., Leovac, V. M., Rodić, M. V., Novaković, S. B.,& Bogdanović, G. A.. (2015). Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl. in Structural Chemistry, 26(1), 269-277.
https://doi.org/10.1007/s11224-014-0491-6
Ivkovic SA, Vojinović-Ješić LS, Leovac VM, Rodić MV, Novaković SB, Bogdanović GA. Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl. in Structural Chemistry. 2015;26(1):269-277.
doi:10.1007/s11224-014-0491-6 .
Ivkovic, Sonja A., Vojinović-Ješić, Ljiljana S., Leovac, Vukadin M., Rodić, Marko V., Novaković, Slađana B., Bogdanović, Goran A., "Transition metal complexes with thiosemicarbazide-based ligands. Part 61. Comparative analysis of structural properties of the pyridoxal thiosemicarbazone ligands. Crystal structure of PLTSC center dot HCl center dot 2H(2)O and its complex [Fe(PLTSC)Cl-2(H2O)]Cl" in Structural Chemistry, 26, no. 1 (2015):269-277,
https://doi.org/10.1007/s11224-014-0491-6 . .
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