Evaluation of meso-substituted cationic corroles as potential antibacterial agents

Cationic derivatives of 5,10,15-tris[4-(pyridin-4-ylsulphanyl)-2,3,5,6-tetrafluorophenyl]-corrolategallium(III)pyridine and 5,10,15-tris[4-(pyridin-2-ylsulfanyl)-2,3,5,6-tetrafluorophenyl]-correlategallium(III)pyridine were synthesized and their photosensitizing properties against the naturally bioluminescent Gram-negative bacterium Allivibrio fischeri were evaluated. The cationic corrole derivatives exhibited antibacterial activity at micromolar concentrations against this Gram-negative bacterium strain.

Key words:
Allivibrio fischeri; corroles; photosensitizer; PDI; bioluminescence

Authorship

TERESA A.F. CARDOTE

Química Orgânica, Produtos Naturais e Agroalimentares/QOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalUniversity of AveiroPortugalAveiro, PortugalQuímica Orgânica, Produtos Naturais e Agroalimentares/QOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

JOANA F.B. BARATA

CICECO (Aveiro Institute of Materials), Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalUniversity of AveiroPortugalAveiro, PortugalCICECO (Aveiro Institute of Materials), Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal

CAROLINA AMADOR

ELIANA ALVES

Centro de Estudos do Ambiente e do Mar/CESAM, Department of Biology, University of Aveiro, 3810-193 Aveiro, Portugal University of AveiroPortugalAveiro, PortugalCentro de Estudos do Ambiente e do Mar/CESAM, Department of Biology, University of Aveiro, 3810-193 Aveiro, Portugal

MARIA GRAÇA P.M.S. NEVES

JOSÉ A.S. CAVALEIRO

ÂNGELA CUNHA

ADELAIDE ALMEIDA

MARIA AMPARO F. FAUSTINO

Correspondence to: Joana F.B. Barata E-mail: jbarata@ua.pt Adelaide Almeida E-mail: aalmeida@ua.pt Maria Amparo Ferreira Faustino E-mail: faustino@ua.pt

*
Contribution to the centenary of the Brazilian Academy of Sciences.

SCIMAGO INSTITUTIONS RANKINGS

Figures

Figures (6)

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Figure 1
Reaction of gallium(III) complex of 5,10,15-tris(pentafluorophenyl)corrole 1 with adequate pyridine derivatives.

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Figure 2
Structures of the 5,10,15-tris[2,3,5,6-tetrafluoro-4-(1-methylpyridinium-4-sulfanyl)phenyl]corrolatogallium(III)(pyridine) tri-iodide 2b and 5,10,15-tris[2,3,5,6-tetrafluoro-4-(1-methylpyridinium-2-sulfanyl)phenyl]corrolatogallium(III)(pyridine) tri-iodide 3b.

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Figure 3
Normalized UV-Vis spectra of compounds 1 and 3b in DMSO.

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Figure 4
Time dependent photodecomposition of DPBF (50 mM) photosensitized by corroles derivatives 2a,b and 3a,b in DMF upon irradiation with a LED array with an emission peak centred at 640 nm and a bandwidth at half maximum of ± 20 nm (9.0 mW cm⁻²) with or without PS (0.5 μM).

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Figure 5
Bioluminescence monitoring of A. fischeri treated with 10 mM of cationic PSs 2b and 3b and Tetra-Py ⁺ -Me after irradiation with white light (400-800 nm) at an irradiance of 100 mW cm^-2 during 120 min. Each value represents the mean ± standard deviation of three independent experiments, with two replicates each. Error bars indicate the standard deviation.

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Figure 6
Bioluminescence monitoring of A. fischeri treated with 10 mM of neutral corroles 2a and 3a and 5,10,15,20-tetra(4-pyridyl)porphyrin (Tetra-Py) after irradiation with white light (400-800 nm) at an irradiance of 100 mW cm^-2 during 120 min. Each value represents the mean ± standard deviation of three independent experiments, with two replicates each. Error bars indicate the standard deviation.

Figure 1 Reaction of gallium(III) complex of 5,10,15-tris(pentafluorophenyl)corrole 1 with adequate pyridine derivatives.

Figure 2 Structures of the 5,10,15-tris[2,3,5,6-tetrafluoro-4-(1-methylpyridinium-4-sulfanyl)phenyl]corrolatogallium(III)(pyridine) tri-iodide 2b and 5,10,15-tris[2,3,5,6-tetrafluoro-4-(1-methylpyridinium-2-sulfanyl)phenyl]corrolatogallium(III)(pyridine) tri-iodide 3b.

Figure 3 Normalized UV-Vis spectra of compounds 1 and 3b in DMSO.

Figure 4 Time dependent photodecomposition of DPBF (50 mM) photosensitized by corroles derivatives 2a,b and 3a,b in DMF upon irradiation with a LED array with an emission peak centred at 640 nm and a bandwidth at half maximum of ± 20 nm (9.0 mW cm⁻²) with or without PS (0.5 μM).

Figure 5 Bioluminescence monitoring of A. fischeri treated with 10 mM of cationic PSs 2b and 3b and Tetra-Py ⁺ -Me after irradiation with white light (400-800 nm) at an irradiance of 100 mW cm^-2 during 120 min. Each value represents the mean ± standard deviation of three independent experiments, with two replicates each. Error bars indicate the standard deviation.

Figure 6 Bioluminescence monitoring of A. fischeri treated with 10 mM of neutral corroles 2a and 3a and 5,10,15,20-tetra(4-pyridyl)porphyrin (Tetra-Py) after irradiation with white light (400-800 nm) at an irradiance of 100 mW cm^-2 during 120 min. Each value represents the mean ± standard deviation of three independent experiments, with two replicates each. Error bars indicate the standard deviation.

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Evaluation of meso-substituted cationic corroles as potential antibacterial agents

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[1] Correspondence to: Joana F.B. Barata E-mail: jbarata@ua.pt Adelaide Almeida E-mail: aalmeida@ua.pt Maria Amparo Ferreira Faustino E-mail: faustino@ua.pt