Fractionation and analysis of veterinary antibiotics and their related degradation products in agricultural soils and drainage waters following swine manure amendment

Science of the Total Environment

Volumn 543, Issue , 2016, Pages 524-535

  Solliec, Morgan ^a   Roy Lachapelle, Audrey ^a   Gasser, Marc Olivier ^b   Coté, Caroline ^b   Généreux, Mylène ^b   Sauvé, Sébastien ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b Institut de recherche et de developpement en agroenvironnement   (Canada)

Author keywords

Drainage waters; LC HRMS; Metabolites; Soils; Veterinary antibiotics

Indexed keywords

AGRICULTURAL ROBOTS; AGRICULTURE; DEGRADATION; FERTILIZERS; LIQUID CHROMATOGRAPHY; MANURES; MASS SPECTROMETRY; METABOLITES; SOILS; TOXICITY;

ANTIBIOTIC RESISTANCE; DEGRADATION PRODUCTS; DRAINAGE WATER; HIGH RESOLUTION MASS SPECTROMETRY; LC-HRMS; TERRESTRIAL ENVIRONMENTS; TETRACYCLINE ANTIBIOTICS; VETERINARY ANTIBIOTIC;

ANTIBIOTICS;

AMOXICILLIN; ANHYDROEPITETRACYCLINE; ANHYDROTETRACYCLINE; ANTIBIOTIC AGENT; CEFTIOFUR; CHLORTETRACYCLINE; DEMECLOCYCLINE; DOXYCYCLINE; EPITETRACYCLINE; ISOCHLORTETRACYCLINE; LINCOMYCIN; MINOCYCLINE; OXYTETRACYCLINE; PENICILLIN G; SIMETON; SPIRAMYCIN; SULFADOXINE; TETRACYCLINE; TRIMETHOPRIM; TYLOSIN; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; FERTILIZER; MANURE; SOIL; SOIL POLLUTANT; VETERINARY DRUG;

AGRICULTURAL SOIL; ANTIBIOTICS; DEGRADATION; DRAINAGE WATER; ENVIRONMENTAL FATE; FRACTIONATION; LIQUID CHROMATOGRAPHY; MANURE; MASS SPECTROMETRY; METABOLITE; TOXICITY;

AGRICULTURAL LAND; AGRICULTURAL SLURRY; ARTICLE; BIODEGRADATION; CONTROLLED STUDY; ECOTOXICITY; FRACTIONATION; LIQUID CHROMATOGRAPHY; MANURE; MASS SPECTROMETRY; PRIORITY JOURNAL; PROCESS DEVELOPMENT; QUANTITATIVE ANALYSIS; SENSITIVITY AND SPECIFICITY; SOIL AMENDMENT; VALIDATION PROCESS; WATER SUPPLY; AGRICULTURE; ANALYSIS; ANIMAL; CHEMISTRY; ENVIRONMENTAL MONITORING; PIG; SOIL; SOIL POLLUTANT;

SUIDAE;

AGRICULTURE; ANIMALS; ANTI-BACTERIAL AGENTS; ENVIRONMENTAL MONITORING; FERTILIZERS; MANURE; SOIL; SOIL POLLUTANTS; SWINE; VETERINARY DRUGS;

EID: 84947710716     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2015.11.061     Document Type: Article

References (60)

1. AFSSA-ANMV Index des médicaments vétérinaires autorisés en France. J. Off. Répub. Française 2009, 244:77.
2. Anderson C.R., Rupp H.S., Wu W.H. Complexities in tetracycline analysis - chemistry, matrix extraction, cleanup, and liquid chromatography. J. Chromatogr. A 2005, 1075:23-32.
3. Berendsen B.J., Wegh R.S., Meijer T., Nielen M.W. The assessment of selectivity in different quadrupole-orbitrap mass spectrometry acquisition modes. J. Am. Soc. Mass Spectrom. 2015, 26:337-346.
4. Berger K., Petersen B., Buningpfaue H. Persistence of drugs occurring in liquid manure in the food-chain. Arch. Leb. 1986, 37:99-102.
5. Blackwell P.A., Lützhoft H.C.H., Ma H.P., Halling-Sørensen B., Boxall A.B.A., Kay P. Ultrasonic extraction of veterinary antibiotics from soils and pig slurry with SPE clean-up and LC-UV and fluorescence detection. Talanta 2004, 64:1058-1064.
6. Chee-Sanford J.C., Aminov R.I., Krapac I.J., Garrigues-Jeanjean N., Mackie R.I. Occurrence and diversity of tetracycline resistance genes in lagoons and groundwater underlying two swine production facilities. Appl. Environ. Microbiol. 2001, 67:1494-1502.
7. Chen W.-R., Huang C.-H. Adsorption and transformation of tetracycline antibiotics with aluminum oxide. Chemosphere 2010, 79:779-785.
8. Chen W.-R., Huang C.-H. Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide. Environ. Pollut. 2011, 159:1092-1100.
9. Cherlet M., De Backer P., Croubels S. Control of the keto-enol tautomerism of chlortetracycline for its straightforward quantitation in pig tissues by liquid chromatography-electrospray ionization tandem mass spectrometry. J. Chromatogr. A 2006, 1133:135-141.
10. Dams R., Huestis M.A., Lambert W.E., Murphy C.M. Matrix effect in bio-analysis of illicit drugs with LC-MS/MS: influence of ionization type, sample preparation, and biofluid. J. Am. Soc. Mass Spectrom. 2003, 14:1290-1294.
11. Du F., Liu T., Shen T., Zhu F., Xing J. Qualitative-(semi) quantitative data acquisition of artemisinin and its metabolites in rat plasma using an LTQ/Orbitrap mass spectrometer. J. Mass Spectrom. 2012, 47:246-252.
12. European Commission Decision EC 2002/657 of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off. J. Eur. Communities 2002, 221.
13. Fedorova G., Randak T., Lindberg R.H., Grabic R. Comparison of the quantitative performance of a Q-Exactive high-resolution mass spectrometer with that of a triple quadrupole tandem mass spectrometer for the analysis of illicit drugs in wastewater. Rapid Commun. Mass Spectrom. 2013, 27:1751-1762.
14. Fenner K., Canonica S., Wackett L.P., Elsner M. Evaluating pesticide degradation in the environment: blind spots and emerging opportunities. Science 2013, 341:752-758.
15. Gu C., Karthikeyan K., Sibley S.D., Pedersen J.A. Complexation of the antibiotic tetracycline with humic acid. Chemosphere 2007, 66:1494-1501.
16. Haller M.Y., Muller S.R., McArdell C.S., Alder A.C., Suter M.J.F. Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry. J. Chromatogr. A 2002, 952:111-120.
17. Halling-Sørensen B. Inhibition of aerobic growth and nitrification of bacteria in sewage sludge by antibacterial agents. Arch. Environ. Contam. Toxicol. 2001, 40:451-460.
18. Halling-Sørensen B., Sengeløv G., Tjørnelund J. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria, including selected tetracycline-resistant bacteria. Arch. Environ. Contam. Toxicol. 2002, 42:263-271.
19. Hirsch R., Ternes T.A., Haberer K., Mehlich A., Ballwanz F., Kratz K.L. Determination of antibiotics in different water compartments via liquid chromatography electrospray tandem mass spectrometry. J. Chromatogr. A 1998, 815:213-223.
20. Hu X.G., Zhou Q.X., Luo Y. Occurrence and source analysis of typical veterinary antibiotics in manure, soil, vegetables and groundwater from organic vegetable bases, northern China. Environ. Pollut. 2010, 158:2992-2998.
21. Ingerslev F., Toräng L., Loke M.-L., Halling-Sørensen B., Nyholm N. Primary biodegradation of veterinary antibiotics in aerobic and anaerobic surface water simulation systems. Chemosphere 2001, 44:865-872.
22. Jacobsen A.M., Halling-Sørensen B. Multi-component analysis of tetracyclines, sulfonamides and tylosin in swine manure by liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2006, 384:1164-1174.
23. Jacobsen A.M., Halling-Sørensen B., Ingerslev F., Hansen S.H. Simultaneous extraction of tetracycline, macrolide and sulfonamide antibiotics from agricultural soils using pressurised liquid extraction, followed by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2004, 1038:157-170.
24. Jezowskabojczuk M., Lambs L., Kozlowski H., Berthon G. Metal Ion-tetracycline interactions in biological-fluids .10. Structural investigations on copper(ii) complexes of tetracycline, oxytetracycline, chlortetracycline, 4-(dedimethylamino)tetracycline, and 6-deoxy-6-demethyltetracycline and discussion of their binding modes. Inorg. Chem. 1993, 32:428-437.
25. Jia A., Xiao Y., Hu J.Y., Asami M., Kunikane S. Simultaneous determination of tetracyclines and their degradation products in environmental waters by liquid chromatography-electrospray tandem mass spectrometry. J. Chromatogr. A 2009, 1216:4655-4662.
26. Kaufmann A., Butcher P., Maden K., Walker S., Widmer M. Reliability of veterinary drug residue confirmation: high resolution mass spectrometry versus tandem mass spectrometry. Anal. Chim. Acta 2015, 856:54-67.
27. Kemper N. Veterinary antibiotics in the aquatic and terrestrial environment. Ecol. Indic. 2008, 8:1-13.
28. Kennedy D.G., McCracken R.J., Carey M.P., Blanchflower W.J., Hewitt S.A. Iso- and epi-iso-chlortetracycline are the principal metabolites of chlortetracycline in the hen's egg. J. Chromatogr. A 1998, 812:327-337.
29. Kim S.C., Carlson K. Quantification of human and veterinary antibiotics in water and sediment using SPE/LC/MS/MS. Anal. Bioanal. Chem. 2007, 387:1301-1315.
30. Kim K.-R., Owens G., Kwon S.-I., So K.-H., Lee D.-B., Ok Y.S. Occurrence and environmental fate of veterinary antibiotics in the terrestrial environment. Water Air Soil Pollut. 2011, 214:163-174.
31. Kuhne M., Ihnen D., Moller G., Agthe O. Stability of tetracycline in water and liquid manure. J. Veterinary Med. Ser. A 2000, 47:379-384.
32. Kümmerer K. Antibiotics in the aquatic environment-a review-part I. Chemosphere 2009, 75:417-434.
33. Liang Y.L., Denton M.B., Bates R.B. Stability studies of tetracycline in methanol solution. J. Chromatogr. A 1998, 827:45-55.
34. Little J.L., Cleven C.D., Brown S.D. Identification of "known unknowns" utilizing accurate mass data and chemical abstracts service databases. J. Am. Soc. Mass Spectrom. 2011, 22:348-359.
35. Mamani M.C.V., Reyes F.G.R., Rath S. Multiresidue determination of tetracyclines, sulphonamides and chloramphenicol in bovine milk using HPLC-DAD. Food Chem. 2009, 117:545-552.
36. Mccormick J.R.D., Fox S.M., Smith L.L., Bitler B.A., Reichenthal J., Origoni V.E., et al. Studies of the reversible epimerization occurring in the tetracycline family - the preparation, properties and proof of structure of some 4-epi-tetracyclines. J. Am. Chem. Soc. 1957, 79:2848-2858.
37. McIlvaine T. A buffer solution for colorimetric comparison. J. Biol. Chem. 1921, 49:183-186.
38. Mellon M.G., Benbrook C., Benbrook K.L. Hogging it: Estimates of Antimicrobial Abuse in Livestock: Union of Concerned Scientists 2001.
39. Englert B. Method 1694: Pharmaceuticals and Personal Care Products in Water, Soil, Sediment, and Biosolids by HPLC/MS/MS 2007, 1-72. US Environmental Protection Agency (EPA).
40. Michalski A., Damoc E., Hauschild J.P., Lange O., Wieghaus A., Makarov A., et al. Mass spectrometry-based proteomics using Q Exactive, a high-performance benchtop quadrupole orbitrap mass spectrometer. Mol. Cell. Proteomics 2011, 10.
41. Mohatt J.L., Hu L., Finneran K.T., Strathmann T.J. Microbially mediated abiotic transformation of the antimicrobial agent sulfamethoxazole under iron-reducing soil conditions. Environ. Sci. Technol. 2011, 45:4793-4801.
42. Nagele E., Moritz R. Structure elucidation of degradation products of the antibiotic amoxicillin with ion trap MSn and accurate mass determination by ESI TOF. J. Am. Soc. Mass Spectrom. 2005, 16:1670-1676.
43. Negreira N., Regueiro J., de Alda M.L., Barceló D. Degradation of the anticancer drug erlotinib during water chlorination: non-targeted approach for the identification of transformation products. Water Res. 2015, 85:103-113.
44. O'Connor S., Aga D.S. Analysis of tetracycline antibiotics in soil: advances in extraction, clean-up, and quantification. TRAC, Trends Anal. Chem. 2007, 26:456-465.
45. Paesen J., Cypers W., Pauwels K., Roets E., Hoogmartens J. Study of the stability of tylosin A in aqueous solutions. J. Pharm. Biomed. Anal. 1995, 13:1153-1159.
46. Pfizer Environmental assessment doramectin 1% injectable solution for the treatment of parasitic infections in cattle. Report No. 141-061EA, on USFDA website 1996.
47. Pils J.R.V., Laird D.A. Sorption of tetracycline and chlortetracycline on K- and Ca-saturated soil clays, humic substances, and clay-humic complexes. Environ. Sci. Technol. 2007, 41:1928-1933.
48. Sarmah A.K., Meyer M.T., Boxall A.B.A. A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere 2006, 65:725-759.
49. Sassman S.A., Lee L.S. Sorption of three tetracyclines by several soils: assessing the role of pH and cation exchange. Environ. Sci. Technol. 2005, 39:7452-7459.
50. Sengeløv G., Agerso Y., Halling-Sørensen B., Baloda S.B., Andersen J.S., Jensen L.B. Bacterial antibiotic resistance levels in Danish farmland as a result of treatment with pig manure slurry. Environ. Int. 2003, 28:587-595.
51. Søeborg T., Ingerslev F., Halling-Sørensen B. Chemical stability of chlortetracycline and chlortetracycline degradation products and epimers in soil interstitial water. Chemosphere 2004, 57:1515-1524.
52. Solliec M., Roy-Lachapelle A., Sauvé S. Quantitative performance of liquid chromatography coupled to Q-Exactive high resolution mass spectrometry (HRMS) for the analysis of tetracyclines in a complex matrix. Anal. Chim. Acta 2015, 853:415-424.
53. Thiele-Bruhn S. Pharmaceutical antibiotic compounds in soils-a review. J. Plant Nutr. Soil Sci. 2003, 166:145-167.
54. Tolls J. Sorption of veterinary pharmaceuticals in soils: a review. Environ. Sci. Technol. 2001, 35:3397-3406.
55. Vartanian V.H., Goolsby B., Brodbelt J.S. Identification of tetracycline antibiotics by electrospray ionization in a quadrupole ion trap. J. Am. Soc. Mass Spectrom. 1998, 9:1089-1098.
56. Wang J., Chow W., Chang J., Wong J.W. Ultrahigh-performance liquid chromatography electrospray ionization Q-orbitrap mass spectrometry for the analysis of 451 pesticide residues in fruits and vegetables: method development and validation. J. Agric. Food Chem. 2014, 62:10375-10391.
57. Wessels J., Ford W., Szymczak W., Schneider S. The complexation of tetracycline and anhydrotetracycline with Mg2+ and Ca2+: a spectroscopic study. J. Phys. Chem. B 1998, 102:9323-9331.
58. Yang S.W., Cha J., Carlson K. Quantitative determination of trace concentrations of tetracycline and sulfonamide antibiotics in surface water using solid-phase extraction and liquid chromatography/ion trap tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2004, 18:2131-2145.
59. Yang S.W., Cha J.M., Carlson K. Simultaneous extraction and analysis of 11 tetracycline and sulfonamide antibiotics in influent and effluent domestic wastewater by solid-phase extraction and liquid chromatography-electro spray ionization tandem mass spectrometry. J. Chromatogr. A 2005, 1097:40-53.
60. Zeng T., Chin Y.-P., Arnold W.A. Potential for abiotic reduction of pesticides in prairie pothole porewaters. Environ. Sci. Technol. 2012, 46:3177-3187.