6 results on '"Bagnarelli L."'
Search Results
2. Exploring the Antitumor Potential of Copper Complexes Based on Ester Derivatives of Bis(pyrazol-1-yl)acetate Ligands.
- Author
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Pellei M, Santini C, Bagnarelli L, Battocchio C, Iucci G, Venditti I, Meneghini C, Amatori S, Sgarbossa P, Marzano C, De Franco M, and Gandin V
- Subjects
- Acetates, Cisplatin, Crystallography, X-Ray, Esters pharmacology, Humans, Ligands, Coordination Complexes chemistry, Coordination Complexes pharmacology, Copper chemistry
- Abstract
Bis(pyrazol-1-yl)acetic acid (HC(pz)
2 COOH) and bis(3,5-dimethyl-pyrazol-1-yl)acetic acid (HC(pzMe2 )2 COOH) were converted into the methyl ester derivatives 1 (LOMe ) and 2 (L2OMe ), respectively, and were used for the preparation of Cu(I) and Cu(II) complexes 3 - 10 . The copper(II) complexes were prepared by the reaction of CuCl2 ·2H2 O or CuBr2 with ligands 1 and 2 in methanol solution. The copper(I) complexes were prepared by the reaction of Cu[(CH3 CN)4 ]PF6 and 1,3,5-triaza-7-phosphaadamantane (PTA) or triphenylphosphine with LOMe and L2OMe in acetonitrile solution. Synchrotron radiation-based complementary techniques (XPS, NEXAFS, and XAS) were used to investigate the electronic and molecular structures of the complexes and the local structure around copper ions in selected Cu(I) and Cu(II) coordination compounds. All Cu(I) and Cu(II) complexes showed a significant in vitro antitumor activity, proving to be more effective than the reference drug cisplatin in a panel of human cancer cell lines, and were able to overcome cisplatin resistance. Noticeably, Cu complexes appeared much more effective than cisplatin in 3D spheroid cultures. Mechanistic studies revealed that the antitumor potential did not correlate with cellular accumulation but was consistent with intracellular targeting of PDI, ER stress, and paraptotic cell death induction.- Published
- 2022
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3. A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations.
- Author
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Bagnarelli L, Dolmella A, Santini C, Vallesi R, Giacomantonio R, Gabrielli S, and Pellei M
- Abstract
A new dimeric copper(II) bromide complex, [Cu(L
OHex )Br(μ-Br)]2 ( 1 ), was prepared by a reaction of CuBr2 with the hexyl bis(pyrazol-1-yl)acetate ligand (LOHex ) in acetonitrile solution and fully characterized in the solid state and in solution. The crystal structure of 1 was also determined: the complex is interlinked by two bridging bromide ligands and possesses terminal bromide ligands on each copper atom. The two pyrazolyl ligands in 1 coordinate with the nitrogen atoms to complete the Cu coordination sphere, resulting in a five-coordinated geometry-away from idealized trigonal bipyramidal and square pyramidal geometries-which can better be described as distorted square pyramidal, as measured by the τ and χ structural parameters. The pendant hexyloxy chain is disordered over two arrangements, with final site occupancies refined to 0.705 and 0.295. The newly synthesized complex was evaluated as a catalyst in copper-catalyzed C-H oxidation for allylic functionalization through a Kharasch-Sosnovsky reaction without any external reducing agent. Using 0.5 mol% of this catalyst, and tert- butyl peroxybenzoate (Luperox) as an oxidant, allylic benzoates were obtained with up to 90% yield. The general reaction time was only slightly decreased to 24 h but a very significant decrease in the alkene:Luperox ratio to 3:1 was achieved. These factors show relevant improvements with respect to classical Kharasch-Sosnovsky reactions in terms of rate and amount of reagents. The present study highlights the potential of copper(II) complexes containing functionalized bis(pyrazol-1-yl)acetate ligands as efficient catalysts for allylic oxidations.- Published
- 2021
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- View/download PDF
4. Syntheses and Reactivity of New Zwitterionic Imidazolium Trihydridoborate and Triphenylborate Species.
- Author
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Pellei M, Vallesi R, Bagnarelli L, Dias HVR, and Santini C
- Abstract
In this study, four new N -(alkyl/aryl)imidazolium-borates were prepared, and their deprotonation reactions were investigated. Addition of BH
3 •THF to N -benzylimidazoles and N -mesitylimidazoles leads to imidazolium-trihydridoborate adducts. Ammonium tetraphenylborate reacts with benzyl- or mesityl-imidazoles with the loss of one of the phenyl groups yielding the corresponding imidazolium-triphenylborates. Their authenticity was confirmed by CHN analysis,1 H-NMR,13 C-NMR,11 B-NMR, FT-IR spectroscopy, and electrospray ionization mass spectrometry (ESI-MS). 3-Benzyl-imidazolium-1-yl)trihydridoborate, (HImBn )BH3 , and (3-mesityl-imidazolium-1-yl)trihydridoborate, (HImMes )BH3 , were also characterized by X-ray crystallography. The reactivity of these new compounds as carbene precursors in an effort to obtain borate-NHC complexes was investigated and a new carbene-borate adduct (which dimerizes) was obtained via a microwave-assisted procedure.- Published
- 2020
- Full Text
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5. Synthesis and Cytotoxic Activity Evaluation of New Cu(I) Complexes of Bis(pyrazol-1-yl) Acetate Ligands Functionalized with an NMDA Receptor Antagonist.
- Author
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Pellei M, Bagnarelli L, Luciani L, Del Bello F, Giorgioni G, Piergentili A, Quaglia W, De Franco M, Gandin V, Marzano C, and Santini C
- Subjects
- Antineoplastic Agents chemical synthesis, Cell Line, Tumor, Cells, Cultured, Coordination Complexes chemical synthesis, Humans, Ligands, Molecular Structure, Acetates chemistry, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Coordination Complexes chemistry, Coordination Complexes pharmacology, Copper chemistry, Pyrazoles chemistry, Receptors, N-Methyl-D-Aspartate agonists
- Abstract
In the present article, copper(I) complexes of bis(pyrazol-1-yl) carboxylic acid (LH), bis(3,5-dimethylpyrazol-1-yl) carboxylic acid (L
2 H), and bis(pyrazol-1-yl) acetates conjugated with an N -methyl-d-aspartate (NMDA) receptor antagonist (LNMDA or L2NMDA ) and phosphane ligands (triphenylphosphine or 1,3,5-triaza-7-phosphaadamantane) were synthesized. The selection of an NMDA antagonist for the coupling with LH and L2 H was suggested by the observation that NMDA receptors are expressed and play a role in different types of cancer models. All the new complexes showed a significant antitumor activity on a panel of human tumor cell lines of different histology, with cisplatin-sensitive, cisplatin-resistant, or multi-drug-resistant phenotype. Their half maximal inhibitory concentration (IC50 ) values were in the low- and sub-micromolar range and, in general, significantly lower than that of cisplatin. Interestingly, the fact that all the complexes proved to be significantly more active than cisplatin even in three-dimensional (3D) spheroids of H157 and BxPC3 cancer cells increased the relevance of the in vitro results. Finally, morphological analysis revealed that the most representative complex 8 induced a massive swelling of the endoplasmic reticulum (ER) membrane, which is a clear sign of ER stress.- Published
- 2020
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6. Syntheses and Biological Studies of Cu(II) Complexes Bearing Bis(pyrazol-1-yl)- and Bis(triazol-1-yl)-acetato Heteroscorpionate Ligands.
- Author
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Pellei M, Gandin V, Marchiò L, Marzano C, Bagnarelli L, and Santini C
- Subjects
- Cell Death drug effects, Cell Line, Tumor, Cell Proliferation drug effects, Coordination Complexes chemical synthesis, Coordination Complexes pharmacology, Copper chemistry, Crystallography, X-Ray, Humans, Ligands, Models, Molecular, Molecular Structure, Pyrazoles chemical synthesis, Pyrazoles pharmacology, Spheroids, Cellular drug effects, Triazoles chemical synthesis, Triazoles pharmacology, Coordination Complexes chemistry, Pyrazoles chemistry, Triazoles chemistry
- Abstract
Copper(II) complexes of bis(pyrazol-1-yl)- and bis(triazol-1-yl)-acetate heteroscorpionate ligands have been synthesized. The copper(II) complexes [HC(COOH)(pz
Me2 )2 ]Cu[HC(COO)(pzMe2 )2 ]·ClO4 , [HC(COOH)(pz)2 ]2 Cu(ClO4 )2 (pzMe2 = 3,5-dimethylpyrazole; pz = pyrazole) were prepared by the reaction of Cu(ClO4 )2 ·6H2 O with bis(3,5-dimethylpyrazol-1-yl)acetic acid (HC(COOH)(pzMe2 )2 ) and bis(pyrazol-1-yl)acetic acid (HC(COOH)(pz)2 ) ligands in ethanol solution. The copper(II) complex [HC(COOH)(tz)2 ]2 Cu(ClO4 )2 ·CH3 OH (tz = 1,2,4-triazole) was prepared by the reaction of Cu(ClO4 )2 ·6H2 O with bis(1,2,4-triazol-1-yl)acetic acid (HC(COOH)(tz)2 ) ligand in methanol solution. The synthesized Cu(II) complexes, as well as the corresponding uncoordinated ligands, were evaluated for their cytotoxic activity in monolayer and 3D spheroid cancer cell cultures with different Pt(II)-sensitivity. The results showed that [HC(COOH)(pzMe2 )2 ]Cu[HC(COO)(pzMe2 )2 ]·ClO4 was active against cancer cell lines derived from solid tumors at low IC50 and this effect was retained in the spheroid model. Structure and ultra-structure changes of treated cancer cells analyzed by Transmission Electron Microscopy (TEM) highlighted the induction of a cytoplasmic vacuolization, thus suggesting paraptotic-like cancer cell death triggering.- Published
- 2019
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