Synthesis and structural characterization of nano‐sized metal complexes of 3‐(1‐methyl‐4‐hydroxy‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)‐2‐nitro‐3‐oxopropanoic acid. XRD, thermal, 3D modeling, and antitumor activity studies
Abstract:New Co(II), Ni(II), Cu(II), Zn(II), and Fe(III) complexes of the ligand 3-(1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-2-nitro-3-oxopropanoic acid (H 3 L) were synthesized and characterized by various analytical and spectroscopic techniques. The obtained data confirmed the formation of 1:1 (M:L) stoichiometry for Fe(III), Co(II) complexes and 2:1 (M:L) stoichiometry for Ni(II), Cu(II), Zn(II) complexes, and the ligand, H 3 L, acts as mono-, bi-, tribasic bis-, tris-and tetradentate towards the metal ion… Show more
“…The Cu( ii ) complex 6a is characterized by the distorted octahedral geometry of the coordination core, which is corroborated by the bent bond angles O(2)–Cu(1)–O(6), O(2)–Cu(1)–O(7), O(3)–Cu(1)–O(6), O(3)–Cu(1)–O(7) due to steric congestion created by the ligand molecules (Table S4, ESI†). The lengths of Cu–N bonds in the complexes 1a–6a fall within the range of 1.97–2.08 Å, whereas the Cu–O bond lengths are 1.91–1.96 Å, which is in accordance with the previously reported data 50,51 (Table S4, ESI†).…”
Phenolic Schiff bases and their Cu(ii) complexes have been synthesized and characterized by physicochemical methods. The complexes exhibit low cell toxicity and high antioxidant and antibacterial activity, as evidenced by molecular docking studies.
“…The Cu( ii ) complex 6a is characterized by the distorted octahedral geometry of the coordination core, which is corroborated by the bent bond angles O(2)–Cu(1)–O(6), O(2)–Cu(1)–O(7), O(3)–Cu(1)–O(6), O(3)–Cu(1)–O(7) due to steric congestion created by the ligand molecules (Table S4, ESI†). The lengths of Cu–N bonds in the complexes 1a–6a fall within the range of 1.97–2.08 Å, whereas the Cu–O bond lengths are 1.91–1.96 Å, which is in accordance with the previously reported data 50,51 (Table S4, ESI†).…”
Phenolic Schiff bases and their Cu(ii) complexes have been synthesized and characterized by physicochemical methods. The complexes exhibit low cell toxicity and high antioxidant and antibacterial activity, as evidenced by molecular docking studies.
“…[13] On the other side, several metal complexes have been applied as potential chemotherapeutic, anti-inflammatory, neurological, antibacterial, and anticancer drugs in pharmaceutical chemistry as well as highly significant economic applications. [14][15][16] Furthermore, nanosized metal chelates have received rising attention as a result of their fantastic magnetic, optical, electrical, and catalytic characteristics, [17,18] and hence, such compounds are essentially applied in bioinorganic chemistry because of their high biological efficiency. [19][20][21] Sulfafurazole, an FDA-approved oral antibiotic, has been identified as an excellent inhibitor of small extracellular vesicle secretion from breast cancer cells, which provide cancer sufferers with therapeutic benefits.…”
A new azo dye ligand (abbreviated as H 3 L) derived from coupling of sulfafurazole diazonium salt with 2,4-dihydroxybenzaldehyde was prepared and characterized applying different spectroscopic and analytical techniques.The novel nanosized trivalent Cr and Fe alongside with divalent Mn, Co, Ni, and Cd complexes with H 3 L have been synthesized for further promising pharmaceutical uses. All complexes were totally characterized by investigating various analytical and spectral tools such as microanalysis, FT-IR, 1 H NMR, UV-Vis, powder XRD, and TEM spectra as well as magnetic moment and molar conductance measurements. Microanalysis, TGA, and conductance studies confirmed the formation of all metal complexes in 1:1 (L: M) molar ratio with covalent mode. The FT-IR and 1 H NMR investigation asserted the chelation of H 3 L to different metal ions through azo nitrogen and phenolic deprotonated hydroxy oxygen in the o-position. UV-Vis, ESR, and magnetic moment studies revealed octahedral geometry around Cr and Fe ions, whereas Mn, Co, Ni, and Cd complexes displayed tetrahedral configurations. XRD patterns and TEM images proved homogeneous distribution over the chelates surfaces and nanometric size of complexes particles. Molecular modeling was used to optimize the complexes' geometric structure showing good harmonity with the experimental results. The antifungal and antibacterial efficiencies were strongly enhanced upon complex formation. Cr(III) and Ni(II) complexes showed the strongest and promising anticancer activities (IC 50 = 7.64 and 6.99 μg/ml) among the tested compounds, whereas Cd(II) complex showed moderate anticancer efficiency (IC 50 = 12.10 μg/ml), compared with the 5-fluorouracil (applied standard drug) with IC 50 = 6.44 μg/ ml.
“…The local tetragonal axes are parallel or just slightly misaligned if G > 4.0, while a substantial exchange coupling and misalignment is noticeable if G < 4.0 42 . The estimated G-value for the Cu(II) complex 5 was 1.94, indicating that the exchange coupling effects were operative between Cu(II) centers in the current Cu(II) complex 43 . Figure 5 X-band ESR spectra of Mn(II) complex 2 ( a ), Co(II) complex 3 ( b ), Cu(II) complex 5 ( c ), and the standard (DPPH) ( d ).…”
New Schiff base ligand, derived from antiviral valacyclovir, and its novel Cr(III), Mn(II), Co(II), Ni(II), Cu(II), Zn(II) complexes have been synthesized. By using a variety of analytical and spectroscopic techniques, the type of bonding between the ligand and the metal ions in the recently formed complexes was clarified. The Schiff base ligand act as a bidentate and coordinated with the metal ions through the azomethine-N and the phenolic-O centers, in a mono-deprotonated form. Except for the Zn(II) complex, which displayed a tetrahedral geometry, all complexes displayed octahedral geometry. The TGA findings supported that the stability and decomposition properties of the metal complexes were entirely distinct from one another. The thermogram showed decomposition of all investigated metal complexes above 200 °C in three, four or five steps, and indicated the high thermal stability of these complexes. According to XRD patterns, the particles of these complexes were located at the nanoscale. Moreover, for all the samples analyzed, the TEM images showed uniform and homogeneous surface morphology. The biological activity revealing the high efficiencies of the screened complexes as antibacterial and antitumor agents. The antimicrobial activity of the ligand and its complexes was examined against a variety of pathogenic bacteria and fungi including Escherichia coli, Staphylococcus aureus and Candida albicans. The data obtained revealed that the metal ion in the complexes enhanced the antimicrobial activity compared to the free ligand. The high efficiencies toward S. aureus, E. coli, and C. albicans appeared by Cu(II) complex 23, Ni(II) complex 20, and Ni(II) complex 19, respectively. The antitumor activity of the ligand and its complexes was tested against Hepatocellular carcinoma cell line (HepG-2 cells), the residue 28 which produced after heating the Cu(II) complex 25 at 200 °C for 1 h, exhibited strong inhibition of HepG-2 cell growth. The results of the DNA cleavage investigation demonstrated the ability of investigated Cu(II) complex to degrade DNA. The docking findings showed strong interactions of both the ligand and its examined Cu(II) complex, revealing their ability to cleavage DNA and their potent inhibitory effects on tumor cells. The electrical conductivity study confirmed that the ligand and its investigated complexes had semiconducting properties.
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