Enhanced Synthesis and Photodynamic Anticancer and Antimicrobial Activities of Tetra(pentafluorophenyl)bacteriochlorin
Аннотация
The potential utility of meso-pentafluorobacteriochlorin (PentaBChl), a readily synthesized porphyrin analogue that absorbs significantly in the near-infrared region, for photodynamic therapy (PDT) and photodynamic antimicrobial chemotherapy (PACT) was investigated. Identifying suitable dyes that absorb significantly in the 700−800 nm region is particularly important from an African perspective, since melanin significantly limits the penetration of laser light into human tissue in the 600−700 nm region, where first- and second-generation photosensitizer dyes usually absorb. A modified solvent-free synthetic approach was developed to prepare PentaBChl from the commercially available meso-pentafluoroporphyrin (PentaP) parent dye in high yield. The in vitro PDT activities of PentaP and PentaBChl were compared against MCF-7 breast cancer cells through 30 min of irradiation with M595L3 (2.7 J/cm2) and M730L4 (1.7 J/cm2) Thorlabs light-emitting diodes (LEDs). An IC50 value of 7.6 µM was obtained for PentaBChl, comparable to values reported previously for tetraarylchlorins, despite a significantly lower singlet oxygen quantum yield of 0.21. In vitro PACT activity studies were conducted against S. aureus and E. coli, as typical examples of Gram-(+) and Gram-(−) bacterial strains, through 60 min of irradiation with M595L3 (5.4 J/cm2) and M730L4 (3.4 J/cm2) Thorlabs LEDs. Log10 reduction values of 3.49 and 5.89 were observed for PentaBChl against S. aureus and E. coli, respectively, after incubation at 80 µM. These results demonstrate that the PDT and PACT activity properties of tetraarylbacteriochlorins merit further in-depth investigation.
Литература
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