In
this study, two kinds of novel carbazole-based ethynylpyridine
salts: 3,6-bis[2-(1-methylpyridinium)ethynyl]-9-pentyl-carbazole diiodide
(BMEPC) and 3,6-bis[2-(1-methylpyridinium)ethynyl]-9-methyl-carbazole
diiodide (BMEMC) have been employed as photosensitizers owing to their
excellent antibacterial activity. These molecules possess symmetric
A−π–D−π–A-type structures,
which would bring in the unique optical properties. The inhibition
zone measurement of a gradient concentration from 0 to 100 μM
showed BMEPC and BMEMC photoinduced antibacterial activity against Escherichia coli. Diameters of zone of inhibition
were up to 15 and 14 mm under laser irradiations. Under the exposure
of the laser of 442 nm with a power density of 20 mW/cm2, the minimum inhibitory concentrations (MICs) of BMEPC on E. coli were between 3.5 and 6.9 μM and that
of BMEMC were between 9.4 and 18.8 μM, respectively. In the
dark experiments as a control, the MIC value is between 6.9 and 13.8
μM for BMEPC, whereas it is between 187.5 and 225.0 μM
for BMEMC. By the comparison of the MIC values of BMEPC and BMEMC
with laser irradiation and in dark, the laser-induced toxicity on
bacteria is more evident, though both of the derivatives have dark
toxicity. With the laser irradiation duration of 30 s and 10 min for
BMEPC and BMEMC, respectively, the survival rate of E. coli approximates zero. An antibacterial mechanism
has been proposed based on the electron paramagnetic resonance characterization,
which indicates that a nitride radical is generated under laser irradiation.
The carbazole-based ethynylpyridine photosensitizers would provide
high potential for further applications in photodynamic therapy.