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Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System
Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pU...C19 plasmid DNA.
Keywords:
Bioinorganic chemistry / Medicinal chemistry / Antitumor agents / DNA cleavage / cytotoxicity / Hydrazones / Copper / N / O ligands
Source:
European Journal of Inorganic Chemistry, 2015, 5, 882-895
TY - JOUR
AU - Leovac, Vukadin
AU - Rodić, Marko V.
AU - Jovanović, Ljiljana S.
AU - Joksovic, Milan D.
AU - Stanojković, Tatjana
AU - Vujčić, Miroslava
AU - Sladić, Dušan
AU - Markovic, Violeta
AU - Vojinovic-Jesic, Ljiljana S
PY - 2015
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/1735
AB - Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.
PB - Wiley-V C H Verlag Gmbh, Weinheim
T2 - European Journal of Inorganic Chemistry
T1 - Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System
IS - 5
SP - 882
EP - 895
DO - 10.1002/ejic.201403050
ER -
@article{
author = "Leovac, Vukadin and Rodić, Marko V. and Jovanović, Ljiljana S. and Joksovic, Milan D. and Stanojković, Tatjana and Vujčić, Miroslava and Sladić, Dušan and Markovic, Violeta and Vojinovic-Jesic, Ljiljana S",
year = "2015",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1735",
abstract = "Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Inorganic Chemistry",
title = "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System",
number = "5",
pages = "882-895",
doi = "10.1002/ejic.201403050"
}
Leovac, V., Rodić, M. V., Jovanović, L. S., Joksovic, M. D., Stanojković, T., Vujčić, M., Sladić, D., Markovic, V.,& Vojinovic-Jesic, L. S. (2015). Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System.
European Journal of Inorganic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(5), 882-895.
https://doi.org/10.1002/ejic.201403050
Leovac V, Rodić MV, Jovanović LS, Joksovic MD, Stanojković T, Vujčić M, Sladić D, Markovic V, Vojinovic-Jesic LS. Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System. European Journal of Inorganic Chemistry. 2015;(5):882-895
Leovac Vukadin, Rodić Marko V., Jovanović Ljiljana S., Joksovic Milan D., Stanojković Tatjana, Vujčić Miroslava, Sladić Dušan, Markovic Violeta, Vojinovic-Jesic Ljiljana S, "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System" European Journal of Inorganic Chemistry, no. 5 (2015):882-895,
https://doi.org/10.1002/ejic.201403050 .
