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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

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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
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1735
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