Antibacterial activity of amidodithiophosphonato nickel(II) complexes: an experimental and theoretical approach
Antibacterial activity of amidodithiophosphonato nickel(II) complexes: an experimental and theoretical approach
The reactions of 2,4-bis(4-methoxyphenyl)-1,3-dithio-2,4-diphosphetane-2,4-disulfide (Lawesson’s Reagent, LR) with benzylamine (BzNH2) and 4-phenylbutylamine (PhBuNH2) yield benzylammonium P-(4-methoxyphenyl)-N-benzyl-amidodithiophosphonate (BzNH3)(BzNH-adtp) and 4-phenylbutylammonium P-(4-methoxyphenyl)-N-(4-phenylbutyl)-amidodithiophosphonate (PhBuNH3)(PhBuNH-adtp). The relevant nickel complexes [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] and the corresponding hydrolysed derivatives (BzNH3)2[Ni(dtp)2] and (PhBuNH3)2[Ni(dtp)2] were prepared and fully characterized. The antimicrobial activity of the aforementioned amidodithiophosphonates against a set of Gram-positive and Gram-negative pathogen bacteria was evaluated, and [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] showed antiproliferative activity towards Staphylococcus aureus and Staphylococcus haemolyticus strains. density functional theory (DFT) calculations were performed to shed some light on the activity of reported compounds related to their tendency towards P–N bond cleavage.
Amidodithiophosphonate, Antibacterial activity, Density functional theory (DFT), Nickel complexes, P–N cleavage, X-ray diffraction
Podda, Enrico
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Arca, Massimiliano
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Atzeni, Giulia
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Coles, Simon J.
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Ibba, Antonella
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Isaia, Francesco
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Lippolis, Vito
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Orrù, Germano
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Orton, James B.
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Pintus, Anna
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Tuveri, Enrica
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Carla Aragoni, M.
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1 May 2020
Podda, Enrico
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Arca, Massimiliano
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Atzeni, Giulia
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Coles, Simon J.
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Ibba, Antonella
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Isaia, Francesco
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Lippolis, Vito
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Orrù, Germano
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Orton, James B.
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Pintus, Anna
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Tuveri, Enrica
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Carla Aragoni, M.
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Podda, Enrico, Arca, Massimiliano, Atzeni, Giulia, Coles, Simon J., Ibba, Antonella, Isaia, Francesco, Lippolis, Vito, Orrù, Germano, Orton, James B., Pintus, Anna, Tuveri, Enrica and Carla Aragoni, M.
(2020)
Antibacterial activity of amidodithiophosphonato nickel(II) complexes: an experimental and theoretical approach.
Molecules, 25 (9), [2052].
(doi:10.3390/molecules25092052).
Abstract
The reactions of 2,4-bis(4-methoxyphenyl)-1,3-dithio-2,4-diphosphetane-2,4-disulfide (Lawesson’s Reagent, LR) with benzylamine (BzNH2) and 4-phenylbutylamine (PhBuNH2) yield benzylammonium P-(4-methoxyphenyl)-N-benzyl-amidodithiophosphonate (BzNH3)(BzNH-adtp) and 4-phenylbutylammonium P-(4-methoxyphenyl)-N-(4-phenylbutyl)-amidodithiophosphonate (PhBuNH3)(PhBuNH-adtp). The relevant nickel complexes [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] and the corresponding hydrolysed derivatives (BzNH3)2[Ni(dtp)2] and (PhBuNH3)2[Ni(dtp)2] were prepared and fully characterized. The antimicrobial activity of the aforementioned amidodithiophosphonates against a set of Gram-positive and Gram-negative pathogen bacteria was evaluated, and [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] showed antiproliferative activity towards Staphylococcus aureus and Staphylococcus haemolyticus strains. density functional theory (DFT) calculations were performed to shed some light on the activity of reported compounds related to their tendency towards P–N bond cleavage.
Text
Antibacterial Activity of Amidodithiophosphonato
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Accepted/In Press date: 24 April 2020
e-pub ahead of print date: 28 April 2020
Published date: 1 May 2020
Keywords:
Amidodithiophosphonate, Antibacterial activity, Density functional theory (DFT), Nickel complexes, P–N cleavage, X-ray diffraction
Identifiers
Local EPrints ID: 440878
URI: http://eprints.soton.ac.uk/id/eprint/440878
ISSN: 1420-3049
PURE UUID: 5d61c72d-c5fd-4265-8e0a-c3384436f21c
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Date deposited: 21 May 2020 16:30
Last modified: 18 Mar 2024 02:50
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Contributors
Author:
Enrico Podda
Author:
Massimiliano Arca
Author:
Giulia Atzeni
Author:
Antonella Ibba
Author:
Francesco Isaia
Author:
Vito Lippolis
Author:
Germano Orrù
Author:
James B. Orton
Author:
Anna Pintus
Author:
Enrica Tuveri
Author:
M. Carla Aragoni
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