title: Inverted methoxypyridinium phthalocyanines for PDI of pathogenic bacteria.
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 ((1)O2) generation, water solubility and uptake properties.
authors.affiliation: Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal. jtome@ua.pt.
authors.forename: Leandro M O
authors.initials: LM
authors.lastname: Lourenço
authors.forename: Andreina
authors.initials: A
authors.lastname: Sousa
authors.forename: Maria C
authors.initials: MC
authors.lastname: Gomes
authors.forename: Maria A F
authors.initials: MA
authors.lastname: Faustino
authors.forename: Adelaide
authors.initials: A
authors.lastname: Almeida
authors.forename: Artur M S
authors.initials: AM
authors.lastname: Silva
authors.forename: Maria G P M S
authors.initials: MG
authors.lastname: Neves
authors.forename: José A S
authors.initials: JA
authors.lastname: Cavaleiro
authors.forename: Ângela
authors.initials: Â
authors.lastname: Cunha
authors.forename: João P C
authors.initials: JP
authors.lastname: Tomé
mesh_terms: D004926:Escherichia coli / Q000187:drug effects* / Q000502:physiology / Q000528:radiation effects*; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D054833:Isoindoles; D050296:Microbial Viability / Q000187:drug effects / Q000528:radiation effects; D000442:Octanols / Q000737:chemistry; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000737:chemistry* / Q000494:pharmacology*; D011725:Pyridines / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D007211:Indoles; D054833:Isoindoles; D000442:Octanols; D017319:Photosensitizing Agents; D011725:Pyridines; D014867:Water; D026082:Singlet Oxygen; C023666:pyridine; C013647:phthalocyanine