{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T06:25:30Z","timestamp":1788675930900,"version":"build-2803163510"},"reference-count":31,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2020,8,4]],"date-time":"2020-08-04T00:00:00Z","timestamp":1596499200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Canadian Environmental Protection Act funding"}],"content-domain":{"domain":["acsess.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J of Env Quality"],"published-print":{"date-parts":[[2020,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Chlortetracycline (CTC), an antimicrobial administered as a feed additive to cattle, swine, and poultry, is present in the corresponding manure. Land application of raw or processed (composted or stockpiled) manure provides a mechanism by which CTC (and other antimicrobials) enters the environment and becomes available for transport to surface receiving waters via rainfall or snowmelt runoff. Chlortetracycline has been detected in Canadian surface waters, but little has been reported on its fate in aquatic ecosystems. To address this knowledge gap, the dissipation of CTC\u2010enol was monitored in deionized water and water typical of wetlands within the prairie region of Canada. In deionized water, CTC\u2010enol tautomerized to CTC\u2010keto, and both tautomers epimerized to 4\u2010epi\u2010CTC\u2010enol and 4\u2010epi\u2010CTC\u2010keto, respectively. Irreversible isomerization to <jats:italic>iso<\/jats:italic>\u2010CTC occurred, which then epimerized to 4\u2010epi\u2010<jats:italic>iso<\/jats:italic>\u2010CTC. In wetland water, although tauterization of CTC\u2010enol to CTC\u2010keto occurred, there was no evidence of the formation of the 4\u2010epimers of either CTC\u2010enol or CTC\u2010keto. The major product formed in the wetland water was <jats:italic>iso<\/jats:italic>\u2010CTC, some of which epimerized to 4\u2010epi\u2010<jats:italic>iso<\/jats:italic>\u2010CTC. Although CTC\u2010enol was shown to tautomerize to CTC\u2010keto, the concentration of CTC\u2010keto remained low in both deionized and wetland water, suggesting that the isomerization of CTC\u2010enol to <jats:italic>iso<\/jats:italic>\u2010CTC most likely occurred via CTC\u2010keto. The dissipation of CTC\u2010enol in wetland water was described by pseudo first\u2010order kinetics with a DT<jats:sub>50<\/jats:sub> (time required for 50% dissipation) value of 4.8 h. The short DT<jats:sub>50<\/jats:sub> value of CTC and reduced antimicrobial activity of <jats:italic>iso<\/jats:italic>\u2010CTC and 4\u2010epi\u2010<jats:italic>iso<\/jats:italic>\u2010CTC suggest a lower probability for selection for CTC\u2010resistant bacteria in Canadian Prairie aquatic ecosystems.<\/jats:p>","DOI":"10.1002\/jeq2.20079","type":"journal-article","created":{"date-parts":[[2020,4,8]],"date-time":"2020-04-08T05:53:58Z","timestamp":1586325238000},"page":"1435-1444","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Isomerization of chlortetracycline in prairie wetland water"],"prefix":"10.1002","volume":"49","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7365-9928","authenticated-orcid":false,"given":"Allan J.","family":"Cessna","sequence":"first","affiliation":[{"name":"Agriculture and Agri\u2010Food Canada Research Centre  107 Science Place Saskatoon SK S7N 0X2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandra L.","family":"Kuchta","sequence":"additional","affiliation":[{"name":"Toxicology Graduate Program Univ. of Saskatchewan  Saskatoon SK S7N 5B3 Canada"},{"name":"Current address Health Canada  269 Laurier Ave. West Ottawa ON K1A 0K9 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan","family":"Bailey","sequence":"additional","affiliation":[{"name":"Environment and Climate Change Canada National Hydrology Research Centre  Saskatoon SK S7N 3H5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marley","family":"Waiser","sequence":"additional","affiliation":[{"name":"Environment and Climate Change Canada National Hydrology Research Centre  Saskatoon SK S7N 3H5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vijay","family":"Tumber","sequence":"additional","affiliation":[{"name":"Environment and Climate Change Canada National Hydrology Research Centre  11 Innovation Blvd. Saskatoon SK S7N 3H5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,8,4]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/177433a0"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2013.02.0039"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jhazmat.2008.08.019"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2164(08)70405-2"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2005.0462"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/jeq2.20034"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2010.0079"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2008.0128"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2013.09.119"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1001-0742(11)60775-4"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2007.0392"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01540093"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.4296\/cwrj3601001"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00244-001-0017-2"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/03601230902801075"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2009.04.047"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2005.11.015"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.2134\/jeq2007.0230"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.envpol.2006.11.035"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01568a050"},{"key":"e_1_2_8_22_1","unstructured":"Mitscher L. 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