Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Mazur, Liliana; Modzelewska-Banachiewicz, Bożena; Paprocka, Renata; Zimecki, Michał; Wawrzyniak, Urszula E.; Kutkowska, Jolanta; Ziółkowska, Grażyna

doi:10.1016/j.jinorgbio.2012.04.021

Cited by 27 publications

(10 citation statements)

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“…Similarly to Cu(II)-TSC complexes, coordination of carboxamidrazones to Cu(II) improved the cytotoxicity. However, there are only several examples of reported Cu(II)-carboxamidrazone complexes [ 31 , 32 , 33 ]. Therefore, we have prepared novel pyridinamidrazone and S-methylisothiosemicarbazone, structurally related to 3-AP, as well as Cu(II) and Fe(III) complexes thereof ( Scheme 1 ) and investigated their potential as anticancer drugs.…”

Section: Introductionmentioning

confidence: 99%

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

et al. 2020

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Thiosemicarbazones continue to attract the interest of researchers as potential anticancer drugs. For example, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, or triapine, is the most well-known representative of this class of compounds that has entered multiple phase I and II clinical trials. Two new triapine derivatives HL1 and HL2 were prepared by condensation reactions of 2-pyridinamidrazone and S-methylisothiosemicarbazidium chloride with 3-N-(tert-butyloxycarbonyl) amino-pyridine-2-carboxaldehyde, followed by a Boc-deprotection procedure. Subsequent reaction of HL1 and HL2 with CuCl2·2H2O in 1:1 molar ratio in methanol produced the complexes [CuII(HL1)Cl2]·H2O (1·H2O) and [CuII(HL2)Cl2] (2). The reaction of HL2 with Fe(NO3)3∙9H2O in 2:1 molar ratio in the presence of triethylamine afforded the complex [FeIII(L2)2]NO3∙0.75H2O (3∙0.75H2O), in which the isothiosemicarbazone acts as a tridentate monoanionic ligand. The crystal structures of HL1, HL2 and metal complexes 1 and 2 were determined by single crystal X-ray diffraction. The UV-Vis and EPR spectroelectrochemical measurements revealed that complexes 1 and 2 underwent irreversible reduction of Cu(II) with subsequent ligand release, while 3 showed an almost reversible electrochemical reduction in dimethyl sulfoxide (DMSO). Aqueous solution behaviour of HL1 and 1, as well as of HL2 and its complex 2, was monitored as well. Complexes 1−3 were tested against ovarian carcinoma cells, as well as noncancerous embryonic kidney cells, in comparison to respective free ligands, triapine and cisplatin. While the free ligands HL1 and HL2 were devoid of antiproliferative activity, their respective metal complexes showed remarkable antiproliferative activity in a micromolar concentration range. The activity was not related to the inhibition of ribonucleotide reductase (RNR) R2 protein, but rather to cancer cell homeostasis disturbance—leading to the disruption of cancer cell signalling.

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Section: Introductionmentioning

confidence: 99%

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

et al. 2020

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“…As illustrated in Figure , CTA is oxidated to form the uniform CEI film encapsulating LNMO. The CEI film can facilitate the lithium-ions diffusion kinetics, obstruct the dissolution of transition metal cations, and resist the erosion of HF. ,, Furthermore, the CEI film with a higher electronic impedence blocks the electronic transmission between the electrolyte solvent and the cathode to ensure the transmission of all electronics between the cathode and anode only via a conductive network and external circuitry at the initial stage of charge–discharge. Concurrently, the stability of the CEI film was strengthened due to increased antioxidative ability under the influence of field-effect from unsaturated aromatics.…”

Section: Resultsmentioning

confidence: 99%

Stabilized Cathode Interphase for Enhancing Electrochemical Performance of LiNi_0.5Mn_1.5O₄-Based Lithium-Ion Battery via cis-1,2,3,6-Tetrahydrophthalic Anhydride

Tan

Cui

et al. 2021

ACS Appl. Mater. Interfaces

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The continuous degradation of carbonate electrolytes and the dissolution of transition metal cations due to parasitic reactions on the cathode-electrolyte interphase (CEI) block the practical application of LiNi0.5Mn1.5O4-based lithium-ion batteries (LNMO-based LIBs) at a high voltage. cis-1,2,3,6-Tetrahydrophthalic anhydride (CTA) has been used as a functional additive in a carbonate baseline electrolyte (BE) for constructing the CEI film to enhance the cyclic stability of LNMO-based LIBs. The LNMO/Li cell with CTA exhibits a preponderant capacity retention of 83.3% compared with those of propionic anhydride (PA) (46.5%) and BE (13.6%) after 500 cycles at the current density of 1 C from 3.5 to 4.9 V. Additionally, the LNMO/graphite full cell with CTA still has a higher capacity retention of 95.46% even after 300 cycles at 1 C. By characterizations, it is reasonably demonstrated that CTA was oxidated to participate in the construction of a CEI film. An unsaturated aromatic group was introduced into the composition of the CEI film along with CTA in the formation process of the CEI film, which further improved the antioxidative activity of the CEI film under the influence of field-effect. Specifically, the CEI film obtains appreciable stability because of its higher antioxidative activity under the influence of field-effect. The stabilized CEI can significantly suppress the parasitic reactions of electrolytes, decrease the consumption of active-Li+, and protect the LNMO cathode structure, thereby enhancing the cyclic compatibility of LNMO-based LIBs with the carbonate electrolytes from 3.5 to 4.9 V.

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“…Dark-red crystals of X-ray diffraction quality were obtained after 3 days. Yield: 0.037 g, 25 [Cu II 4 (L 1 ) 2 (L 2 ) 2 Cl 2 ]Cl 2 •5MeOH (4•5MeOH). To a solution of HL H (0.500 g, 1.54 mmol) in methanol (20 mL) was added a solution of copper(II) chloride dihydrate (0.263 g, 1.54 mmol) in methanol (10 mL) and triethylamine (0.21 mL, 1.54 mmol).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…In this work, we have prepared heterodinuclear Cu(II)–Ru(II) and Cu(II)–Os(II) complexes linked by a morpholine-substituted amidrazone proligand. The amidrazone backbone was chosen due to its coordination capacity, as well as a broad spectrum of biological activities, antimicrobial and antimycobacterial, − anticonvulsant, and anticancer properties. − However, there is only a limited number of literature reports on the metal complexes of amidrazones. − It was shown that coordination of amidrazones to copper(II) yielded complexes with anticancer activity in a low micromolar range. Moreover, these copper(II)–amidrazone complexes were reported to be electrochemically active and were expected to induce ROS in cancer cells …”

Section: Introductionmentioning

confidence: 99%

Redox-Active Organoruthenium(II)– and Organoosmium(II)–Copper(II) Complexes, with an Amidrazone–Morpholine Hybrid and [Cu^ICl₂]⁻ as Counteranion and Their Antiproliferative Activity

et al. 2019

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A novel proligand HLH has been prepared from 2-pyridinamidrazone and 6-(morpholinomethyl)pyridine-2-carboxaldehyde. Subsequently, starting from HLH and CuCl2·2H2O in the presence of triethylamine, a series of homo- and heterometallic complexes with [CuICl2]− as counteranion, namely mononuclear complex [CuIICl(HLOMe)][CuICl2] (1), dinuclear Ru(II)–Cu(II) complex [CuIIRuII(η6-p-cymene)Cl2(LH)][CuICl2]·1.5H2O (2·1.5H2O), Os(II)–Cu(II) complex [CuIIOsII(η6-p-cymene)Cl2(LH)][CuICl2]·H2O (3·H2O), and tetranuclear complex [CuII 4(L1)2(L2)2Cl2]·5MeOH (4·5MeOH), where HLOMe, L1, and L2 are Schiff base ligands derived from HLH, were synthesized. The structures of metal complexes were established by X-ray diffraction. Complexes 1–3 demonstrated quasireversible one-electron reduction of Cu(II) in complex cations and one-electron oxidation of [CuICl2]− counterion, confirmed by UV–vis and EPR spectroelectrochemical measurements. They exhibited moderate antiproliferative activity against ovarian carcinoma and cervical adenocarcinoma cell lines in a micromolar concentration range, which was superior to the activity of HLH, CuCl2, and [CuICl2]−. The observed anticancer effects might be related to the ability of novel complexes to generate ROS, which was established by spin trapping experiments in cell-free media as well as by confocal microscopic imaging in ovarian carcinoma cells.

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Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Cited by 27 publications

References 50 publications

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

Stabilized Cathode Interphase for Enhancing Electrochemical Performance of LiNi_0.5Mn_1.5O₄-Based Lithium-Ion Battery via cis-1,2,3,6-Tetrahydrophthalic Anhydride

Redox-Active Organoruthenium(II)– and Organoosmium(II)–Copper(II) Complexes, with an Amidrazone–Morpholine Hybrid and [Cu^ICl₂]⁻ as Counteranion and Their Antiproliferative Activity

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Synthesis, crystal structure and biological activities of a novel amidrazone derivative and its copper(II) complex — A potential antitumor drug

Cited by 27 publications

References 50 publications

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells

Stabilized Cathode Interphase for Enhancing Electrochemical Performance of LiNi0.5Mn1.5O4-Based Lithium-Ion Battery via cis-1,2,3,6-Tetrahydrophthalic Anhydride

Redox-Active Organoruthenium(II)– and Organoosmium(II)–Copper(II) Complexes, with an Amidrazone–Morpholine Hybrid and [CuICl2]− as Counteranion and Their Antiproliferative Activity

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Product

Resources

About

Stabilized Cathode Interphase for Enhancing Electrochemical Performance of LiNi_0.5Mn_1.5O₄-Based Lithium-Ion Battery via cis-1,2,3,6-Tetrahydrophthalic Anhydride

Redox-Active Organoruthenium(II)– and Organoosmium(II)–Copper(II) Complexes, with an Amidrazone–Morpholine Hybrid and [Cu^ICl₂]⁻ as Counteranion and Their Antiproliferative Activity