In silico, In Vitro and docking applications for some novel complexes derived from new quinoline derivatives

Ali, Ibrahim A. I.; El-Sakka, Sahar S.; Soliman, M. F.; Mohamed, Omayma El-Sayed Abdel-Basset

doi:10.1016/j.molstruc.2019.06.053

Cited by 19 publications

(27 citation statements)

References 32 publications

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“…The observed spectral features of the Zn(II) complex observed at 231 and 259 were assigned to π → π* and 303 and 393 to n → π* transitions, and those of the Cu(II) complex at the spectral band of 255 nm was assigned to the n → π* transition. 29 , 73 − 75 Additionally, the broad band observed at 351 nm for Cu(II) may be assigned to the ligand-to-metal charge transfer (LMCT), in line with our DFT calculations ( Figure 2 ), which showed the presence of electron transitions from the highest occupied molecular orbital (HOMO) of the ligand to the lowest unoccupied molecular orbital (LUMO) of the metal center. 24 , 71 , 74 , 76 There is no d → d transition band for the Cu(II) complex; however, ligand-to-metal charge transfer (LMCT) was observed to be dominant, in agreement with the literature.…”

Section: Resultssupporting

confidence: 85%

“…The HOMO–LUMO energy gap ( E g ) can be associated with the antibacterial and antioxidant activities. 29 , 61 Accordingly, the energy gaps ( E g = E LUMO – E HOMO ) for possible electron transitions were calculated to be 3.533, 3.580, and 2.973 eV for the H 2 L and Zn(II) and Cu(II) complexes ( Table 5 ), respectively. These band gap energy values were found to be in line with the experimentally found antioxidant activity of the complexes: Cu(II) > Zn(II) ( Figure 7 ).…”

Section: Resultsmentioning

confidence: 99%

“…Based on this, it is deduced that the Cu(II) complex is more reactive than the Zn(II)complex, in line with previously reported studies. 29 , 61 Moreover, the reaction between copper and the ligand has reduced the HOMO–LUMO energy gap of the Cu(II) complex, an indication of improved biological activities. Accordingly, from the band gap and dipole moment results, the metal complexes showed better biological activities than the free ligand, also in line with the experimental biological activities.…”

Section: Resultsmentioning

confidence: 99%

“… 27 Another study also indicated that the zinc(II) complex of a quinoline derivative showed antibacterial activity against E. coli , P. aeruginosa , and S. aureus . 28 Similarly, copper(II) complexes of quinoline derivatives also showed moderate antibacterial activity against E. coli ( 29 ) but showed higher antibacterial activities than the parent ligand. 15 The efficiencies of metal complexes having biological activities depend on the nature of both metal ions and the ligands that the complexes are made from.…”

Section: Introductionmentioning

confidence: 99%

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Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Damena

Alem

Zeleke³

et al. 2022

ACS Omega

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In the present work, two novel complexes of zinc(II) and copper(II) were synthesized from the ligand 2-((2-hydroxyethyl)amino)quinoline-3-carbaldehyde ( H 2 L ) in a 1:2 metal-to-ligand ratio in methanol. The complexes were characterized by UV–visible spectroscopy, fluorescence spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy-energy-dispersive X-ray spectroscopy (SEM-EDX), mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, and thermogravimetric analysis (TGA) experimental techniques and density functional theory (DFT) calculations. The spectral data revealed that the mono-deprotonated ( HL ) ligand acted as a bidentate ligand, which bound to both Zn(II) and Cu(II) ions via the nitrogen atom of the amine (N–H) and the hydroxyl (O–H) groups through the deprotonated oxygen atom. Formation constants and thermal analysis indicated that both metal complexes are stable up to 100 °C with thermodynamically favored chemical reactions. The Cu(II) complex showed antibacterial activities with the zones of inhibition of 20.90 ± 2.00 mm against Pseudomonas aeruginosa , 19.69 ± 0.71 mm against Staphylococcus aureus , and 18.58 ± 1.04 mm against Streptococcus pyogenes . These results are relatively higher compared with the Zn(II) complex at the same concentration. The minimum inhibitory concentration (MIC) results for the complexes also showed similar trends against the three bacteria. On the other hand, radical scavenging activities of both Cu(II) and Zn(II) complexes showed half-maximal inhibitory concentrations (IC 50 ) of 4.72 and 8.2 μg/mL, respectively, while ascorbic acid (a positive control) has a value of 4.28 μg/mL. The Cu(II) complex exhibited better communication with the positive control, indicating its potential use for biological activities. The calculated and in silico molecular docking results also strongly support the experimental results.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Damena

Alem

Zeleke³

et al. 2022

ACS Omega

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“…Furthermore, the metal complexes of Cu, Ni, and Co with quinoline derivatized ligand 129 (Figure 18) have been investigated for their antifungal properties, revealing noteworthy inhibitory properties against A. niger strain. [ 74 ] Compared with fluconazole (15 mm), a copper complex of ligand 129 exhibited a moderate A. niger inhibitory activity (7 mm). Besides, the complexation of ligands with metals has substantially enhanced antifungal properties as compared with the ligand.…”

Section: Antifungal Activitymentioning

confidence: 99%

Recent update on antibacterial and antifungal activity of quinoline scaffolds

Dorababu¹

2020

Archiv der Pharmazie

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Although most of the heterocycles have been reported to possess a significant pharmacological activity, only a few of them, namely quinoline derivatives, have exhibited the finest biological activities. Despite the few medicinal properties of the plain quinoline molecule, its derivatives exhibit diverse pharmacological properties such as anticancer, anti‐inflammatory, antibacterial, antiviral, antifungal, antiprotozoal activities, and so on. The potential antimicrobial properties of the quinoline derivatives are evident from the decades of research on these derivatives. Owing to limitations like drug resistance, high cost, severe side effects, and less bioavailability of previously synthesized antimicrobial agents, these drugs have become obsolete in recent years. Hence, the design of more efficient antimicrobial drugs must be given topmost priority. A breakthrough in drug discovery is a must to prevent malevolent microbial diseases. Addressing all these issues, researchers have been continuously contributing to antimicrobial drug discovery. Herein, a short description of the pharmacology of antimicrobial agents such as antibacterials and antifungals synthesized recently is provided. The versatile derivatization of the quinoline moiety leading to significant antimicrobial potencies is discussed, considering the structure–activity relationship.

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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

El-ghamry

El‐Shafiy

2021

Applied Organom Chemis

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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 ions via the oxygen of quinolinonate, the enolic/ketonic of β-ketoacid, and carboxylate besides of the nitro groups. All complexes showed tetrahedral geometry, except Fe(III) complex which exhibited an octahedral geometry. The X-ray diffractograms of the ligand, H 3 L, and its metal complexes revealed a series of sharp and intense diffraction peaks which indicate their crystalline characteristic with the particle size in the nano-scale range. Geometrical optimizations of the ligand, H 3 L, and its metal complexes were performed at the B3LYP/6-311G(d, p) level using density functional theory (DFT) implemented in the Gaussian 09 program.The data obtained were correlated with the experimental results and suggested that the Zn(II) complex may exhibit extremely bio-efficiency than other compounds. The antimicrobial screening results showed enhancement in the efficiency of the free ligand, H 3 L, on coordination with the metal ions. The antitumor activity was evaluated in vitro against Hepatocellular carcinoma cell line (HepG-2 cells). The ligand, H 3 L, and its Zn(II) complex showed strong antitumor activities, especially nano-sized Zn(II) complex that exhibited IC 50 value (2.90 μg/ml) smaller than the well-known standard antitumor drug cisplatin (IC 50~3 .27 μg/ml), prominent it as an antitumor agent towards HepG-2 cells.

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In silico, In Vitro and docking applications for some novel complexes derived from new quinoline derivatives

Cited by 19 publications

References 32 publications

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Recent update on antibacterial and antifungal activity of quinoline scaffolds

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

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