Synthesis and antibacterial activity of novel cationic BODIPY photosensitizers

Abstract

BODIPYs are versatile dyes never tested before in photodynamic application against prokaryotes. We specifically synthesized two cationic BODIPYs (compounds 3 and 4) with structural features suitable for this pourpose. The novel BODIPYs are both characterized by the presence of one pyridinium cationic group on position 8 and two iodine atoms on 2,6-positions of the dipyrrolylmethene structure, thus ensuring solubility in 1/1 water/organic solvent mixture and a good singlet oxygen formation rate. These two photosensitizers differ only in the moiety linked on pyridine nitrogen atom as 3 and 4 bear a methyl and a benzyl group, respectively. BODIPYs 3 and 4 were tested against two bacterial model strains, the Gram positive Staphylococcus xylosus and the Gram negative Escherichia coli. Despite the small structural modification between 3 and 4, a remarkable difference in photocatalyzed efficacy against the model microorganisms was observed. In particular methylated compound 3 was found much more efficient with respect to the benzylated one (4). As consequence, in-depth examination of the antibacterial activity was performed using the more efficient compound 3. A high degree of phototoxicity (>6 log units) was observed with the photosensitizer 0.5 μM against S. xylosus and 5.0 μM against E. coli, following 5 min irradiation with a green LED device (light dose 1.38 J/cm(2)). No dark toxicity was observed up to 40 μM. Further studies indicate that the phototoxic efficacy induced by BODIPY 3 depends both on its concentration and on light dose, which can be specifically modulated to achieve the eradication of the tester strains.