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Issue 10, 2015
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Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria

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Abstract

Phthalocyanines (Pc) are photoactive molecules that can absorb and emit light in a large range of the UV-Vis spectrum with recognized potential for medical applications. Considering the biomedical applications an important limitation of these compounds is their low solubility in water. The use of suitable pyridinium groups on Pc is a good strategy to solve this drawback and to make them more effective to photoinactivate Gram-negative bacteria via a photodynamic inactivation (PDI) approach. Herein, an easy synthetic access to obtain inverted tetra- and octa-methoxypyridinium phthalocyanines (compounds 5 and 6) and also their efficiency to photoinactivate a recombinant bioluminescent strain of Escherichia coli is described. The obtained results were compared with the ones obtained when more conventional thiopyridinium phthalocyanines (compounds 7 and 8) were used. This innovative study comparing thiopyridinium and inverted methoxypyridinium moieties on cationic Pc is reported for the first time taking into account the efficiency of singlet oxygen (1O2) generation, water solubility and uptake properties.

Graphical abstract: Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria

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Publication details

The article was received on 07 Apr 2015, accepted on 06 Jul 2015 and first published on 07 Jul 2015


Article type: Paper
DOI: 10.1039/C5PP00145E
Author version available: Download Author version (PDF)
Citation: Photochem. Photobiol. Sci., 2015,14, 1853-1863
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    Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria

    L. M. O. Lourenço, A. Sousa, M. C. Gomes, M. A. F. Faustino, A. Almeida, A. M. S. Silva, M. G. P. M. S. Neves, J. A. S. Cavaleiro, Â. Cunha and J. P. C. Tomé, Photochem. Photobiol. Sci., 2015, 14, 1853
    DOI: 10.1039/C5PP00145E

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