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)

Thumbnail

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

Thumbnail

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.

Thumbnail

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

Thumbnail

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).

Thumbnail

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.

Thumbnail

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.

How to cite

copy

Academia Brasileira de Ciências Rua Anfilófio de Carvalho, 29, 3º andar, 20030-060 Rio de Janeiro RJ Brasil, Tel: +55 21 3907-8100 - Rio de Janeiro - RJ - Brazil
E-mail: aabc@abc.org.br

Stay informed of issues for this journal through your RSS reader

PDF version for download

PDF

English

Google
Google Scholar

Versões e tradução automática

Versão original do texto

English

Tradução automática

Google Translator
Microsoft Translator

Como citar

RIS

BIBTEX

Outros formatos de citação e exportação:

SciELO - Scientific Electronic Library Online
Rua Dr. Diogo de Faria, 1087 – 9º andar – Vila Clementino 04037-003 São Paulo/SP - Brasil
E-mail: scielo@scielo.org

Read our Open Access Statement

Metrics

Evaluation of meso-substituted cationic corroles as potential antibacterial agents

PlumX

Mensagem

[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