Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives
authors Moura, NMM; Ramos, CIV; Linhares, I; Santos, SM; Faustino, MAF; Almeida, A; Cavaleiro, JAS; Amado, FML; Lodeiro, C; Neves, MGPMS
nationality International
journal RSC ADVANCES
keywords BIOLUMINESCENT ESCHERICHIA-COLI; PHOTODYNAMIC INACTIVATION; ANTIMICROBIAL PHOTOINACTIVATION; MASS-SPECTROMETRY; THERAPY; PHOTOSENSITIZERS; INSIGHT; VIRUS; MECHANISMS; STRATEGIES
abstract A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Krohnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.
publisher ROYAL SOC CHEMISTRY
issn 2046-2069
year published 2016
volume 6
issue 112
beginning page 110674
ending page 110685
digital object identifier (doi) 10.1039/c6ra25373c
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000389463600025
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journal impact factor 2.936
5 year journal impact factor 3.096
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