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, NevenaZlatar, Matija
Novaković, Irena T.

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://cherry.chem.bg.ac.rs/handle/123456789/4857
- Related crystallographic data (CCDC 2110386): https://cherry.chem.bg.ac.rs/handle/123456789/4859
- Related crystallographic data (CCDC 2110387): https://cherry.chem.bg.ac.rs/handle/123456789/4860
- Related crystallographic data (CCDC 2110388): https://cherry.chem.bg.ac.rs/handle/123456789/4861
Related info:
- Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4857 - Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4859 - Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4860 - Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4861
Collections
Institution/Community
Hemijski fakultetTY - DATA AU - Stevanović, Nevena AU - Zlatar, Matija AU - Novaković, Irena T. 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 - http://cherry.chem.bg.ac.rs/handle/123456789/4858 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 T. 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. T., 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 IT, 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 T., 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; Srdić-Rajić, Tatjana; Radanović, Dušanka D.; Radulović, Siniša; Pelizzi, Giancarlo; Anđelković, Katarina K. (Elsevier Science Inc, New York, 2010) -
Synthesis and characterization of a novel Pd(II) complex with the condensation product of 2-(diphenylphosphino) benzaldehyde and ethyl hydrazino acetate. Cytotoxic activity of the synthesized complex and related Pd(II) and Pt(II) complexes
Malesevic, Nevenka; Srdić, Tatjana; Radulović, Siniša; Sladić, Dušan; Radulovic, Vesna; Brčeski, Ilija; Anđelković, Katarina K. (Elsevier Science Inc, New York, 2006) -
Transition metal complexes with thiosemicarbazide-based ligands. part 37. Synthesis and study of the first thiosemi-carbazide-derived copper(I) complexes: Crystal structure of [2-(diphenylphosphino)benzaldehyde thiosemicarbazonato(-l)] copper(I)nitrate-me
Argay, C; Kalman, A; Parkanyi, L; Leovac, Vukadin M.; Brčeski, Ilija; Radivojsa, PN (Taylor & Francis Ltd, Abingdon, 2000)