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Amphiphilic meso(sulfonate ester fluoroaryl)porphyrins: refining the substituents of porphyrin derivatives for phototherapy and diagnostics
Authors:Ana VC Simões  Agnieszka Adamowicz  Janusz M Dąbrowski  Mário JF Calvete  Artur R Abreu  Grażyna Stochel  Luis G Arnaut  Mariette M Pereira
Institution:1. Chemistry Department, University of Coimbra, Rua Larga 3004-535, Coimbra, Portugal;2. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland;3. Edifício Bluepharma, Rua da Bayer, S. Martinho do Bispo, 3045-016 Coimbra, Portugal
Abstract:A set of amphiphilic fluorinated porphyrins appended with sulfonate ester groups were synthesized and fully characterized. The reaction proceeds efficiently, with high yields, with an improved methodology. Their potential use as imaging and phototherapeutic agents was assessed measuring relevant photophysical properties. It is shown that these porphyrins have good photostability, long triplet lifetimes (between 47 μs and 102 μs), high singlet oxygen quantum yields (0.74≤FD≤1.00), low fluorescence quantum yields (<0.04) and sharp 19F NMR peaks. The data on the new meso(sulfonate ester fluoroaryl)porphyrins illustrate the potential of perfluorinated sulfonate esters to improve physical properties relevant for cancer imaging and photodynamic therapy.
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