Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity
Аутори
Stevanović, NevenaZlatar, Matija
Novaković, Irena T.
Pevec, Andrej
Radanović, Dušanka D.
Matić, Ivana Z.
Đorđić Crnogorac, Marija
Stanojković, Tatjana
Vujčić, Miroslava
Gruden, Maja
Sladić, Dušan
Anđelković, Katarina K.
Turel, Iztok
Čobeljić, Božidar
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
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 structureИзвор:
Dalton Transactions, 2022, 51, 1, 185-196Издавач:
- Royal Society of Chemistry (RSC)
Финансирање / пројекти:
- Slovenian Research Agency (P1-0175)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200043 (Институт за онкологију и радиологију Србије, Београд) (RS-200043)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-200168)
Напомена:
DOI: 10.1039/D1DT03169D
ISSN: 1477-9226; 1477-9234
WoS: 000728802500001
Scopus: 2-s2.0-85121643378
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Stevanović, Nevena AU - Zlatar, Matija AU - Novaković, Irena T. AU - Pevec, Andrej AU - Radanović, Dušanka D. AU - Matić, Ivana Z. AU - Đorđić Crnogorac, Marija AU - Stanojković, Tatjana AU - Vujčić, Miroslava AU - Gruden, Maja AU - Sladić, Dušan AU - Anđelković, Katarina K. AU - Turel, Iztok AU - Čobeljić, Božidar PY - 2022 UR - http://cherry.chem.bg.ac.rs/handle/123456789/4857 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 - Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity VL - 51 IS - 1 SP - 185 EP - 196 DO - 10.1039/D1DT03169D ER -
@article{ author = "Stevanović, Nevena and Zlatar, Matija and Novaković, Irena T. and Pevec, Andrej and Radanović, Dušanka D. and Matić, Ivana Z. and Đorđić Crnogorac, Marija and Stanojković, Tatjana and Vujčić, Miroslava and Gruden, Maja and Sladić, Dušan and Anđelković, Katarina K. 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 = "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity", volume = "51", number = "1", pages = "185-196", doi = "10.1039/D1DT03169D" }
Stevanović, N., Zlatar, M., Novaković, I. T., Pevec, A., Radanović, D. D., Matić, I. Z., Đorđić Crnogorac, M., Stanojković, T., Vujčić, M., Gruden, M., Sladić, D., Anđelković, K. K., Turel, I.,& Čobeljić, B.. (2022). 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)., 51(1), 185-196. https://doi.org/10.1039/D1DT03169D
Stevanović N, Zlatar M, Novaković IT, Pevec A, Radanović DD, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Gruden M, Sladić D, Anđelković KK, Turel I, Čobeljić B. 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;51(1):185-196. doi:10.1039/D1DT03169D .
Stevanović, Nevena, Zlatar, Matija, Novaković, Irena T., Pevec, Andrej, Radanović, Dušanka D., Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina K., 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 . .
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