Isochlortetracycline

Tetracyclines (TCs), broad spectrum antibiotics widely used in the prevention and treatment of infectious diseases, are amphoteric molecules containing several ionizable functional groups that exist predominantly as zwitterions at a given pH value. TCs are reported to undergo a wide variety of reactions at different pH values i.e. TCs form to anhydrotetracyclines at low pH, 4-epitetracyclines at pH 3-5 and isotetracyclines at high pH values. The pH-dependent absorbance and emission properties of tetracycline and its 10 analogs (4-epitetracycline, doxycyline, oxytetracycline, chlortetracycline, 4-epichlortetracycline, isochlortetracycline, methacycline, rolitetracycline, minocycline, and demeclocycline) were investigated and reported in this paper. The main focus of the study was on the pH dependent transformation of epichlortetracycline, chlortetracycline and isotetracycline at basic pH. Absorption, emission and time resolved spectroscopy were used to determine the behavior of the three TC derivatives at this condition. Increasing the buffer's ionic concentration leads to faster transformation to iCTC. A pH dependent transformation of CTC to iCTC was observed and the lifetimes of CTC and iCTC were determined to be 3.0 and 5.89 ns respectively. The distribution factor of CTC to iCTC at basic pH was also reported for the first time.

This work investigated chlortetracycline, tylosin, and tetracycline (plus transformation products), and DNA-based quantitative Campylobacter spp. and Campylobacter tetracycline antibiotic resistant genes (tet(O)) in tile drainage, groundwater, and soil before and following a liquid swine manure (LSM) application on clay loam plots under controlled (CD) and free (FD) tile drainage. Chlortetracycline/tetracycline was strongly bound to manure solids while tylosin dominated in the liquid portion of manure. The chlortetracycline transformation product isochlortetracycline was the most persistent analyte in water. Rhodamine WT (RWT) tracer was mixed with manure and monitored in tile and groundwater. RWT and veterinary antibiotic (VA) concentrations were strongly correlated in water which supported the use of RWT as a surrogate tracer. While CD reduced tile discharge and eliminated application-induced VA movement (via tile) to surface water, total VA mass loading to surface water was not affected by CD. At both CD and FD test plots, the biggest 'flush' of VA mass and highest VA concentrations occurred in response to precipitation received 2d after application, which strongly influenced the flow abatement capacity of CD on account of highly elevated water levels in field initiating overflow drainage for CD systems (when water level <0.3m below surface). VA concentrations in tile and groundwater became very low within 10d following application. Both Campylobacter spp. and Campylobacter tet(O) genes were present in groundwater and soil prior to application, and increased thereafter. Unlike the VA compounds, Campylobacter spp. and Campylobacter tet(O) gene loadings in tile drainage were reduced by CD, in relation to FD.

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.