Phototransformation of sulfamethoxazole under simulated sunlight: Transformation products and their antibacterial activity toward Vibrio fischeri

Sulfamethoxazole (SMX) is a bacteriostatic antibiotic ubiquitously found in the aquatic environment. Since conventional biological wastewater treatment is not efficient to remove SMX, photolysis in natural waters can represent an important transformation pathway. It was recently shown that SMX transformation products can retain antibiotic activity. Therefore, it is crucial to better understand photochemical processes occurring in natural water just as the formation of active transformation products (TPs). During long-term SMX photolysis experiments (one week), nine TPs were identified by reference standards. Moreover, five further TPs of photodecomposition of SMX were found. For the first time, a TP with m/z 271 [M+H]+ was observed during photolysis and tentatively confirmed as 4,x-dihydroxylated SMX. The DOC mass balance clearly showed that only around 5 to 10% were mineralized during the experiment emphasizing the need to elucidate the fate of TPs. Bacterial bioassays confirmed that the mixture retains its antibiotic toxicity toward luminescence (24h) and that there is no change over the treatment time on EC50. In contrast, growth inhibition activity was found to slightly decrease over the irradiation time. However, this decrease was not proportional to the transformation of the parent compound SMX. [Display omitted] •During SMX photolysis experiments, nine TPs were identified by reference standards.•Six further TPs of SMX phototransformation were found.•A TP with a m/z 271 was tentatively confirmed as 4-,x-dihydroxylated SMX.•The mixture exhibitsluminescence inhibition without changes over the irradiation time.•Growth inhibition was found to slightly decrease over the irradiation time.