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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 (O-1(2)) generation, water solubility and uptake properties.
Keywords
BIOLUMINESCENT ESCHERICHIA-COLI, VITRO PHOTODYNAMIC ACTIVITIES, GRAM-NEGATIVE BACTERIA, CATIONIC PORPHYRINS, SILICON(IV) PHTHALOCYANINES, EFFICIENT PHOTOSENSITIZERS, ZINC(II) PHTHALOCYANINES, PHOTOCHEMICAL PROPERTIES, METAL PHTHALOCYANINES, CANCER-CELLS

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Citation

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Chicago
Lourenço, Leandro MO, Andreina Sousa, Maria C Gomes, Maria AF Faustino, Adelaide Almeida, Artur MS Silva, Maria GPMS Neves, José AS Cavaleiro, Ângela Cunha, and João Tomé. 2015. “Inverted Methoxypyridinium Phthalocyanines for PDI of Pathogenic Bacteria.” Photochemical & Photobiological Sciences 14 (10): 1853–1863.
APA
Lourenço, L. M., Sousa, A., Gomes, M. C., Faustino, M. A., Almeida, A., Silva, A. M., Neves, M. G., et al. (2015). Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 14(10), 1853–1863.
Vancouver
1.
Lourenço LM, Sousa A, Gomes MC, Faustino MA, Almeida A, Silva AM, et al. Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES. 2015;14(10):1853–63.
MLA
Lourenço, Leandro MO et al. “Inverted Methoxypyridinium Phthalocyanines for PDI of Pathogenic Bacteria.” PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES 14.10 (2015): 1853–1863. Print.
@article{7139989,
  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 (O-1(2)) generation, water solubility and uptake properties.},
  author       = {Louren\c{c}o, Leandro MO and Sousa, Andreina and Gomes, Maria C and Faustino, Maria AF and Almeida, Adelaide and Silva, Artur MS and Neves, Maria GPMS and Cavaleiro, Jos{\'e} AS and Cunha, {\^A}ngela and Tom{\'e}, Jo{\~a}o},
  issn         = {1474-905X},
  journal      = {PHOTOCHEMICAL \& PHOTOBIOLOGICAL SCIENCES},
  language     = {eng},
  number       = {10},
  pages        = {1853--1863},
  title        = {Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria},
  url          = {http://dx.doi.org/10.1039/c5pp00145e},
  volume       = {14},
  year         = {2015},
}

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