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Antibiotics in the environment could undergo various processes with formation of transformation products, but little has been known about their occurrence and (eco)toxicological consequences. Here we investigated the occurrence and fate of nine transformation products of four tetracyclines (tetracycline, oxytetracycline, chlortetracycline and doxycycline) in three municipal wastewater treatment plants (WWTPs) in Guangzhou, China. The results showed the detection of all the tetracyclines and their transformation products in the WWTPs, with mean concentrations ranging from 17.8 ng/L (anhydrotetracycline) to 49.1 ng/L (oxytetracycline) in influent, 3.03 ng/L (tetracycline) to 6.94 ng/L (4-epi-chlortetracycline) in effluent, and 19.8 ng/g (isochlortetracycline) to 503 ng/g (4-epi-tertracycline) in sludge, respectively. The transformation products of tetracycline, oxytetracycline, chlortetracycline and doxycycline accounted for 73%-83%, 26%-52%, 70%-73% and 69%-74% of total concentrations, respectively. The aqueous removal rates of tetracyclines and their transformation products in the three WWTPs ranged from 18.4% (demethyl-chlortetracycline) to 93.7% (oxytetracycline). Mass balance analysis based on both aqueous and solid phase showed that their removals were mainly attributed to the sludge adsorption. Residual tetracyclines and their transformation products in the effluents would pose no obvious ecological risks to three aquatic organisms (green algae, daphnia and fish). However, 43.5% of sludge samples had high risks from these tetracyclines and transformation products, especially the compounds with poor biodegradability. The results from this study suggest that transformation products should be included in future environmental monitoring and control.

Cyclophosphamide (CP) is a broad-spectrum anticancer drug and has been frequently detected in aquatic environments due to its incomplete removal by wastewater treatment facilities and slow degradation in waters. Its toxicity in fish remains largely unknown. In this study, zebrafish eggs4 h post fertilization (hpf) were exposed to CP at the concentrations from 0.5 to 50.0 μg/L until 168 hpf, and its toxicity was evaluated by biochemical, transcriptomic, and behavioral approaches. The results showed that malformation and mortality rates increased with CP concentrations. The 7-day malformation EC