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Antibacterial activity of amidodithiophosphonato nickel(II) complexes: an experimental and theoretical approach

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
1420-3049
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
14a14e34-7d30-440d-83d6-004332a23a0e
Arca, Massimiliano
f90b59f6-4dfb-471d-912e-3515e6507165
Atzeni, Giulia
e8e92233-1f16-4584-a3cd-504037724b08
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Ibba, Antonella
325c195d-a0f5-4b0b-9259-c222c9139c6d
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
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.
2aaa7a46-7c0a-45eb-a46b-3623db83407d

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).

Record type: Article

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.

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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
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 21 May 2020 16:30
Last modified: 22 May 2020 00:26

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Contributors

Author: Enrico Podda
Author: Massimiliano Arca
Author: Giulia Atzeni
Author: Simon J. Coles ORCID iD
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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