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, VukadinRodić, 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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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 ligandsSource:
European Journal of Inorganic Chemistry, 2015, 5, 882-895Publisher:
- 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
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IHTMTY - 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 . .