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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

Authorized Users Only
2015
Authors
Leovac, Vukadin
Rodić, Marko V.
Jovanović, Ljiljana S.
Joksovic, Milan D.
Stanojković, Tatjana
Vujčić, Miroslava
Sladić, Dušan
Markovic, Violeta
Vojinovic-Jesic, Ljiljana S
Article (Published version)
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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 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
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-172014)
  • Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
  • Biological response modifiers in physiological and pathological conditions (RS-175011)
  • Provincial Secretariat for Science and Technological Development of Vojvodina

DOI: 10.1002/ejic.201403050

ISSN: 1434-1948

WoS: 000349435300015

Scopus: 2-s2.0-84922475134
[ Google Scholar ]
23
22
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1735
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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  - https://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",
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. in 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. in European Journal of Inorganic Chemistry. 2015;(5):882-895.
doi:10.1002/ejic.201403050 .
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" in European Journal of Inorganic Chemistry, no. 5 (2015):882-895,
https://doi.org/10.1002/ejic.201403050 . .

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