Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"
Authors
Stevanović, Nevena
Zlatar, Matija

Novaković, Irena

Pevec, Andrej

Radanović, Dušanka

Matić, Ivana Z.

Đorđić Crnogorac, Marija

Stanojković, Tatjana

Vujčić, Miroslava

Gruden, Maja

Sladić, Dušan

Anđelković, Katarina

Turel, Iztok

Čobeljić, Božidar

Dataset (Published version)
Metadata
Show full item recordAbstract
In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavengin...g activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.
Keywords:
Metal complexes / bioinorganic chemistry / hidrazones / Cu(II) complexes / Mn(II) complexes / Zn(II) complexes / coordination chemistry / DFT / Girard’s T reagent / penta-coordinated complexes / binuclear complexes / trigonal-prismatic complexes / theromdiynamic stability / antimicrobial activity / antifungal activity / cytotoxic activity / X-ray structureSource:
Dalton Transactions, 2022Publisher:
- Royal Society of Chemistry (RSC)
Funding / projects:
- Slovenian Research Agency (P1-0175)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-200026)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200043 (Institute of Oncology and Radiology of Serbia, Belgrade) (RS-200043)
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200168 (University of Belgrade, Faculty of Chemistry) (RS-200168)
Note:
- The supporting information for: Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity" in Dalton Transactions, 51, no. 1 (2022):185-196, https://doi.org/10.1039/D1DT03169D
- Published article: https://cer.ihtm.bg.ac.rs/handle/123456789/4901
- Related crystallographic data (CCDC 2110386): https://cer.ihtm.bg.ac.rs/handle/123456789/4903
- Related crystallographic data (CCDC 2110387): https://cer.ihtm.bg.ac.rs/handle/123456789/4904
- Related crystallographic data (CCDC 2110388): https://cer.ihtm.bg.ac.rs/handle/123456789/4905
Related info:
- Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4901 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4903 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4904 - Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4905
Collections
Institution/Community
IHTMTY - DATA AU - Stevanović, Nevena AU - Zlatar, Matija AU - Novaković, Irena AU - Pevec, Andrej AU - Radanović, Dušanka AU - Matić, Ivana Z. AU - Đorđić Crnogorac, Marija AU - Stanojković, Tatjana AU - Vujčić, Miroslava AU - Gruden, Maja AU - Sladić, Dušan AU - Anđelković, Katarina AU - Turel, Iztok AU - Čobeljić, Božidar PY - 2022 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4902 AB - In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin. PB - Royal Society of Chemistry (RSC) T2 - Dalton Transactions T1 - Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity" UR - https://hdl.handle.net/21.15107/rcub_cherry_4858 ER -
@misc{ author = "Stevanović, Nevena and Zlatar, Matija and Novaković, Irena and Pevec, Andrej and Radanović, Dušanka and Matić, Ivana Z. and Đorđić Crnogorac, Marija and Stanojković, Tatjana and Vujčić, Miroslava and Gruden, Maja and Sladić, Dušan and Anđelković, Katarina and Turel, Iztok and Čobeljić, Božidar", year = "2022", abstract = "In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.", publisher = "Royal Society of Chemistry (RSC)", journal = "Dalton Transactions", title = "Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"", url = "https://hdl.handle.net/21.15107/rcub_cherry_4858" }
Stevanović, N., Zlatar, M., Novaković, I., Pevec, A., Radanović, D., Matić, I. Z., Đorđić Crnogorac, M., Stanojković, T., Vujčić, M., Gruden, M., Sladić, D., Anđelković, K., Turel, I.,& Čobeljić, B.. (2022). Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity". in Dalton Transactions Royal Society of Chemistry (RSC).. https://hdl.handle.net/21.15107/rcub_cherry_4858
Stevanović N, Zlatar M, Novaković I, Pevec A, Radanović D, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Gruden M, Sladić D, Anđelković K, Turel I, Čobeljić B. Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity". in Dalton Transactions. 2022;. https://hdl.handle.net/21.15107/rcub_cherry_4858 .
Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"" in Dalton Transactions (2022), https://hdl.handle.net/21.15107/rcub_cherry_4858 .
Related items
Showing items related by title, author, creator and subject.
-
Synthesis, structure and characterization of novel Cd(II) and Zn(II) complexes with the condensation product of 2-formylpyridine and selenosemicarbazide Antiproliferative activity of the synthesized complexes and related selenosemicarbazone complexes
Bjelogrlić, Snežana K.; Todorović, Tamara; Bacchi, Alessia; Zec, Manja; Sladić, Dušan; Srdic-Rajic, Tatjana; Radanović, Dušanka; Radulovic, Sinisa; Pelizzi, Giancarlo; Anđelković, Katarina (Elsevier Science Inc, New York, 2010) -
Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure
Konovalov, Bata; Zivkovic, Marija D.; Milovanovic, Jelena Z.; Đorđević, Dragana B.; Arsenijevic, Aleksandar N.; Vasic, Ivana R.; Janjić, Goran; Franich, Andjela; Manojlović, Dragan; Škrivanj, Sandra; Milovanovic, Marija Z.; Đuran, Miloš; Rajkovic, Snezana (Royal Soc Chemistry, Cambridge, 2018) -
Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid
Vujic, Jelena M.; Kaluđerović, Goran N.; Milovanovic, Marija; Zmejkovski, Bojana; Volarevic, Vladislav; Zivic, Danijela; Durdevic, Predrag; Arsenijevic, Nebojsa; Trifunovic, Srecko R. (Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux, 2011)