Amphiphilic meso(sulfonate ester fluoroaryl)porphyrins: refining the substituents of porphyrin derivatives for phototherapy and diagnostics

作者：Simoes Ana V C; Adamowicz Agnieszka; Dabrowski Janusz M^*; Calvete Mario J F; Abreu Artur R; Stochel Grazyna; Arnaut Luis G; Pereira Mariette M

来源：Tetrahedron, 2012, 68(42): 8767-8772.

DOI：10.1016/j.tet.2012.08.007

• Porphyrins
• Anticancer agents
• Imaging agents
• Singlet oxygen
• Photodynamic therapy
• Photosensitizers

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 mu s and 102 mu s), high singlet oxygen quantum yields (0.74 %26lt;= FD %26lt;= 1.00), low fluorescence quantum yields (%26lt;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.

• 出版日期2012-10-21