Amantadine copper(II) chloride conjugate with possible implementation in influenza virus inhibition

Banti, Christina N.; Kourkoumelis, Nikolaos; Hatzidimitriou, Antonios G.; Antoniadou, Ioanna; Dimou, Aikaterini; Rallis, Michail; Hoffmann, Anja; Schmidtke, Michaela; McGuire, Kelly L.; Busath, David D.; Kolocouris, Antonios; Hadjikakou, Sotiris K.

doi:10.1016/j.poly.2020.114590

Cited by 24 publications

(23 citation statements)

References 38 publications

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“…Furthermore, H-bond is considered as a significant factor for RNA structure in biological system and less than 2.3 Å increases the binding affinity. Most significant H-bonds of ligand (H 2 L) with HIS-163, and complex [Cu(L)(phen)]( 1 ) with LEU-262 of amino acid residues of protein in a distance 5.44 Å and 4.23 Å, respectively was identified which is closure to standard antiviral drugs [62] . Instead of conventional hydrogen bonding between ligand and main protease, the other factors (π-bonding, dipole-dipole interactions, electrostatic interactions and hydrophobic interactions) affect the effectiveness of these compounds against the COVID-19 virus.…”

Section: Resultsmentioning

confidence: 98%

“…reported [61] that the copper(II) complex of salicylaldehyde benzoyl hydrazone exhibits significantly better inhibitory activity than does salicylaldehyde benzoyl hydrazone itself and also found relatively non-toxic to mice cells. Adamantanamine hydrochloride is a well-known antiviral drug which a mutation makes influenza virus as amantadine (AdNH2) resistant so a new formalism with copper(II) adamantanamines was found to be effective [62] . Very recently, Andreou et al.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Mohan

Choudhary

2021

Journal of Molecular Structure

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This work deals with the synthesis, crystal structure, computational study and antiviral potential of mixed ligand copper(II) complex [Cu(L)(phen)]( 1 ), (where, H 2 L = ( Z )- N ’-(( E )-2-hydroxy-3,5-diiodobenzylidene)- N,N- dimethylcarbamohydrazonothioic acid, phen = 1,10-phenanthroline). The Schiff base ligand (H 2 L) is coordinated with Cu(II) ion in O, N, S-tridentate mode. The copper complex ( 1 ) crystallized in the monoclinic system of the space group P21/c with eight molecules in the unit cell and reveals a square pyramidal geometry. Furthermore, we also perform quantum chemical calculations to get insights into the structure-property relationship and functional properties of ligand (H 2 L) and its copper (II) complex [Cu(L)(phen)]( 1 ). Complex [Cu(L)(phen)]( 1 ) was also virtually designed in-silico evaluation by Swiss-ADME. Additionally, inspiring by recent developments to find a potential inhibitor for the COVID-19 virus, we have also performed molecular docking study of ligand and its copper complex ( 1 ) to see if our compounds shows an affinity for the main protease (M pro ) of COVID-19 spike protein (PDB ID: 7C8U ). Interestingly, the results are found quite encouraging where the binding affinity and inhibition constant were found to be -7.14 kcal/mol and 5.82 μM for ligand (H 2 L) and -6.18 kcal/mol and 0.76 μM for complex [Cu(L)(phen)]( 1 ) with M pro protein. This binding affinity is reasonably well as compared to recently known antiviral drugs. For instance, the binding affinity of ligand and complex was found to be better than docking results of chloroquine (-6.293 kcal/mol), hydroxychloroquine (-5.573 kcal/mol) and remdesivir (-6.352 kcal/mol) with M pro protein. The present study may offer the technological solutions and potential inhibition to the COVID-19 virus in the ongoing and future challenges of the global community. In the framework of synthesis and characterization of mixed ligand copper (II) complex; the major conclusions can be drawn as follow:

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Mohan

Choudhary

2021

Journal of Molecular Structure

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“…For instance, it is found that the copper(II) complex of salicylaldehyde benzoyl hydrazone exhibits significantly better inhibitory activity than does salicylaldehyde benzoyl hydrazone itself and also found relatively non‐toxic to mice cells [37] . Adamantanamine hydrochloride is a well‐known antiviral drug which a mutation makes influenza virus as amantadine (AdNH2) resistant so a new formalism with copper(II) adamantanamines was found to be effective [38] . Very recently, Andreou et al., [39] have also studied the role of copper and N‐acetylcysteine (NAC) in conjugation with antiviral treatments for SARS‐CoV‐2.…”

Section: Resultsmentioning

confidence: 99%

“…[37] Adamantanamine hydrochloride is a well-known antiviral drug which a mutation makes influenza virus as amantadine (AdNH2) resistant so a new formalism with copper(II) adamantanamines was found to be effective. [38] Very recently, Andreou et al, [39] have also studied the role of copper and N-acetylcysteine (NAC) in conjugation with antiviral treatments for SARS-CoV-2. As our [Cu(II)(Phen) 3 ] + 2 complex is a novel synthesis so it is also pertinent to see its effectiveness as a potential inhibitor against SARS-CoV-2.…”

Section: Molecular Docking Of [Cu(ii)(phen) 3 ] + 2 Complex With M Prmentioning

confidence: 99%

Synthesis of Copper(II) Coordination Complex, Its Molecular Docking and Computational Exploration for Novel Functional Properties: A Dual Approach

et al. 2021

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The present investigation uses a dual approach to study the copper (II) complex [Cu(phen) 3 ]. (ClO 4) 2 .HL.CH 3 CN (1) and its cationic complex-[Cu(II)(phen) 3 ] 2 + (1 a), where, HL = 4-Bromo-2((Z)-(naphthalene-4-ylimino)methyl)phenol, phen = 1,10-phenanthroline. The complex (1) crystallized in the triclinic system of the space group P-1 with two molecules in the unit cell and reveals a distorted octahedral geometry. Inspiring by recent developments to find a potential inhibitor for the COVID-19 virus, we have also performed molecular docking study of [Cu(phen) 3 ] + 2 to see if our novel complex shows an affinity for the main protease (M pro) of COVID-19 spike protein. Interestingly, the results are found quite encouraging where the binding affinity and inhibition constant were found to be À 8.400 kcal/mol and 0.661 μM, respectively, for the bestdocked confirmation of [Cu(II)(Phen) 3 ] + 2 complex with M pro protein. This binding affinity is reasonably well as compared to recently known antiviral drugs. For instance, the binding affinity of [Cu(II)(Phen) 3 ] + 2 complex is found to be better than recently docking results of chloroquine (À 6.293 kcal/mol), hydroxychloroquine (À 5.573 kcal/mol) and remdesivir (À 6.352 kcal/mol) with M pro protein. Thus, we believe the broad-spectrum functional properties of our complex will provoke not only the interest of material chemists in materials designing but also incite the drug designing community.

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“…In vivo toxicity of biomaterials on brine shrimp Artemia salina: A simple and a suitable model for the acute toxicity screening of materials, nanoparticles and metal complexes is the nauplii of the brine shrimp Artemia salina [5,8,15,[32][33][34][35][36]. Artemia salina is a zooplanktonic crustacean [32].…”

Section: Figure 10mentioning

confidence: 99%

Hydrogels containing water soluble conjugates of silver(i) ions with amino acids, metabolites or natural products for non infectious contact lenses

et al. 2021

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Amantadine copper(II) chloride conjugate with possible implementation in influenza virus inhibition

Cited by 24 publications

References 38 publications

Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Synthesis, crystal structure, computational study and anti-virus effect of mixed ligand copper (II) complex with ONS donor Schiff base and 1, 10-phenanthroline

Synthesis of Copper(II) Coordination Complex, Its Molecular Docking and Computational Exploration for Novel Functional Properties: A Dual Approach

Hydrogels containing water soluble conjugates of silver(i) ions with amino acids, metabolites or natural products for non infectious contact lenses

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