In-vitro evaluation studies of 7-chloro-4-aminoquinoline Schiff bases and their copper complexes as cholinesterase inhibitors

Zanon, Vanessa S; Lima, Josélia Alencar; Cuya, Teobaldo; Lima, Flávia Regina Souza; Fonseca, Anna Carolina Carvalho da; Gómez, Jesús Gómez; Ribeiro, Ronny R.; França, Tanos C. C.; Vargas, Maria D.

doi:10.1016/j.jinorgbio.2018.11.019

Cited by 18 publications

(13 citation statements)

References 60 publications

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“…Schiff bases have received much attention due to their wide applications in several fields, ranging from industrial uses such as advanced nanomaterials [7] to chemotherapeutics and new drug development [8,9,10,11]. However, even regarding the chemotherapeutic applications, the reported roles are very divergent, sometimes with proposed roles that could seem contradictory.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

et al. 2019

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Our main interest is the characterization of compounds to support the development of alternatives to currently marketed drugs that are losing effectiveness due to the development of resistance. Schiff bases are promising biologically interesting compounds having a wide range of pharmaceutical properties, including anti-inflammatory, antipyretic, and antimicrobial activities, among others. In this work, we have synthesized 12 Schiff base derivatives of 4-aminoantipyrine. In vitro antimicrobial, antioxidant, and cytotoxicity properties are analyzed, as well as in silico predictive adsorption, distribution, metabolism, and excretion (ADME) and bioactivity scores. Results identify two potential Schiff bases: one effective against E. faecalis and the other with antioxidant activity. Both have reasonable ADME scores and provides a scaffold for developing more effective compounds in the future. Initial studies are usually limited to laboratory in vitro approaches, and following these initial studies, much research is needed before a drug can reach the clinic. Nevertheless, these laboratory approaches are mandatory and constitute a first filter to discriminate among potential drug candidates and chemical compounds that should be discarded.

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Section: Introductionmentioning

confidence: 99%

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

et al. 2019

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“…[2,6] Having known the importance of copper, several Cu(II) complexes both mononuclear and binuclear were synthesized and shown to mimic superoxide dismutase. [7] Cholinesterase inhibition activity of Cu(II) complexes of 7chloro-4-aminoquinoline Schiff bases has been reported by Zanon et al [8] Cu(II) complexes of acetylpyridine ethylthiosemicarbazone and acetylpyrazine methyl thiosemicarbazone were found to inactivate the activity of the enzyme DNA topoisomerase, which can eventually result in apoptosis of cancer cells. [5] Several articles evidence the antimicrobial, DNA cleavage, and anticancer activity of copper complexes containing Schiff bases.…”

Section: Introductionmentioning

confidence: 87%

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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Four copper(II) complexes 1-4 of 3-acetylchromene-2-one and substituted 3-acetylchromene-2-one derived Schiff bases were synthesized and structurally characterized using analytical and spectral techniques. The molecular structure of complex 1 has been confirmed by single crystal X-ray diffraction studies, which revealed that ligand 3-acetylchromene-2-one-4 N-semicarbazone is coordinated to the metal as ONO pincer type ligand. Two nitrate molecules are coordinated to the copper ion through oxygen atoms, of which one nitrate molecule was found to coordinate via two oxygen atoms, thereby achieving six-coordination. Preliminary biological studies like DNA and protein binding analyses indicated the binding of the ligands and complexes to CT-DNA (Calf Thymus DNA) and BSA (Bovine Serum Albumin). We investigated the effects of complexes 1-4 against amyloid-β (Aβ) toxicity using transgenic Caenorhabditis elegans strains expressing muscle-and neuronal-specific human Aβ 1-42 . The results showed that the complexes 2-4 remarkably reduced the Aβ-induced paralysis phenotype, Aβ plaque deposition, and other Alzheimer's disease-associated functional deficits in C. elegans by their potent antioxidant and antiaggregative properties. Complexes 2-4 delayed Alzheimer's disease pathologies, providing a basis for further investigating these effects on higher models.

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“…Quinoline compounds can actively enter the metabolism by binding specific metal targets, including late transition elements like copper and zinc [12]. Iodochlorhydroxyquin (clioquinol) [13] and 7-chloroaminoquinolines [14], for example, are effective Cu(II) scavengers, with potential application against Alzheimer's disease [13][14][15]. Chloroquine and hydroxychloroquine were recently claimed to even exploit antiviral activity against pandemic SARS-CoV2 virions, even though the exact mechanism of action remains to be elucidated [16].…”

Section: Introductionmentioning

confidence: 99%

Unravelling the Chemistry of the [Cu(4,7-Dichloroquinoline)2Br2]2 Dimeric Complex through Structural Analysis: A Borderline Ligand Field Case

et al. 2020

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Large dark prismatic crystals (P 1 ¯ ) consisting of closely packed centrosymmetric [Cu(4,7-dichloroquinoline)2]2Br4 binuclear units are formed when 4,7-dichloroquinoline (DCQ, C9H5NCl2) binds copper(II). Cu2+ adopts a strongly distorted square pyramidal coordination geometry, perturbed by electrostatic interactions with two axial μ–Br ligands acting as highly asymmetric bridges. It is shown that, as electronic states of ligands are higher in energy than the metal ones, antibonding orbitals bear significant ligand-like character and electronic charge is partially transferred from inner-sphere coordinated halogen atoms to copper. Overall, the title compound sits on the Hoffman’s border between main group and transition chemistry, with non-negligible contributions of the ligands to the frontier orbitals. The relative energy placement of metal and ligand states determines an internal redox process, where the metal is slightly reduced at the expense of partial oxidation of the bromide ligands. In fact, the crystal structure is partially disordered due to the substitution of some penta-coordinated Cu(II) centers with tetra-coordinated Cu(I) ions. The geometry of the complex is rationalized in terms of electrostatic-driven distortions from an ideal octahedral prototype. Implications on the reactivity of Cu(II)–quinoline complexes are discussed.

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In-vitro evaluation studies of 7-chloro-4-aminoquinoline Schiff bases and their copper complexes as cholinesterase inhibitors

Cited by 18 publications

References 60 publications

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

Unravelling the Chemistry of the [Cu(4,7-Dichloroquinoline)2Br2]2 Dimeric Complex through Structural Analysis: A Borderline Ligand Field Case

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