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Environmental behavior of sulfadiazine, sulfamethazine, and their metabolites

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Abstract

Sulfonamides are one of the most frequently used antibiotics worldwide. Therefore, processes that determine their fate in the environment are of great interest. In the present work, biodegradation as biotic process and hydrolysis and photolysis as abiotic processes were investigated. In biodegradation experiments, it was found out that sulfonamides (sulfadiazine and sulfamethazine) and their N 4-acetylated metabolites were not readily biodegradable. The results showed that decrease of concentrations were in the range from 4% for sulfadiazine to 22% for N 4-acetylsulfamethazine. Hydrolytic experiments examined at pH values normally found in the environment also showed their resistance. However, photolysis proved to be significant process for decreasing concentrations of sulfonamides and their metabolites in three various aqueous matrices (Milli-Q water, river water, and synthetic wastewater). In addition, influence of ubiquitous water constituents (Cl, NO3 , SO4 2−, PO4 3−, and humic acids) was also investigated, showing their different impact on photolysis of investigated pharmaceuticals. The results showed that photolysis followed first-order kinetics in all cases. The obtained results are very important for assesing the environmental fate of sulfonamides and their metabolites in the aquatic environment.

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References

  • Adamek E, Baran W, Sobczak A (2016) Assessment of the biodegradability of selected sulfa drugs in two polluted rivers in Poland: effects of seasonal variations, accidental contamination, turbidity and salinity. J Hazard Mater 313:147–158

    Article  CAS  Google Scholar 

  • Alexy R, Kummerer K (2006) Antibiotics for human use. In: Reemtsma T, Jekel M (eds) Organic pollutants in the water cycle—properties, occurrence, analysis and environmental relevance of polar compounds. Wiley-VCH, Weinheim

    Google Scholar 

  • Alexy R, Kumpel T, Kummerer K (2004) Assessment of degradation of 18 antibiotics in the closed bottle test. Chemosphere 57:505–512

    Article  CAS  Google Scholar 

  • Andreozzi R, Raffaele M, Nicklas P (2003) Pharmaceuticals in STP effluents and their solar photodegradation in aquatic environment. Chemosphere 50:1319–1330

    Article  CAS  Google Scholar 

  • Babić S, Mutavdžić Pavlović D, Ašperger D, Periša M, Zrnčić M, Horvat AJM, Kaštelan-Macan M (2010) Determination of multi-class pharmaceuticals in wastewater by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem 398:1185–1194

    Article  Google Scholar 

  • Babić S, Periša M, Škorić I (2013) Photolytic degradation of norfloxacin, enrofloxacin and ciprofloxacin in various aqueous media. Chemosphere 91:1635–1642

    Article  Google Scholar 

  • Bahnmuller S, von Gunten U, Canonica S (2014) Sunlight-induced transformation of sulfadiazine and sulfamethoxazole in surface waters and wastewater effluents. Water Res 57:183–192

    Article  CAS  Google Scholar 

  • Baran W, Adamek E, Ziemianska J, Sobczak A (2011) Effects of the presence of sulfonamides in the environment and their influence on human health. J Hazard Mater 196:1–15

    Article  CAS  Google Scholar 

  • Batchu SR, Panditi VR, O’Shea KE, Gardinali PR (2014) Photodegradation of antibiotics under simulated solar radiation: implications for their environmental fate. Sci Total Environ 470-471:299–310

    Article  CAS  Google Scholar 

  • Bialk-Bielinska A, Stolte S, Matzke M, Fabianska A, Maszkowska J, Kolodziejska M, Liberek B, Stepnowski P, Kumirska J (2012) Hydrolysis of suplhonamides in aqueous solutions. J Hazard Mater 221-222:264–274

    Article  CAS  Google Scholar 

  • Boreen AL, Arnold WA, McNeill K (2004) Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclin groups. Environ Sci Technol 38:3933–3940

    Article  CAS  Google Scholar 

  • Boreen AL, Arnold WA, McNeill K (2005) Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct. Environ Sci Technol 39:3630–3638

    Article  CAS  Google Scholar 

  • Chen Y, Hu C, Qu J, Yang M (2008) Photodegradation of tetracycline and formation of reactive oxygen species in aqueous tetracycline solution under simulated sunlight irradiation. J Photoch Photobio A 197:81–87

    Article  CAS  Google Scholar 

  • Chen Y, Zhang K, Zuo Y (2013) Direct and indirect photodegradation of estriol in the presence of humic acid, nitrate and iron complexes in water solutions. Sci Total Environ 463-464:802–809

    Article  CAS  Google Scholar 

  • Cizmas L, Sharma VK, Gray CM, McDonald TJ (2015) Pharmaceuticals and personal care products in waters: occurrence, toxicity, and risk. Environ Chem Lett 13:381–394

    Article  CAS  Google Scholar 

  • Diaz-Cruz MS, Garcia-Galan MJ, Barcelo D (2008) Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry. J Chromatogr A 1193:50–59

    Article  CAS  Google Scholar 

  • Ding S-L, Wang X-K, Jiang W-Q, Meng X, Zhao R-S, Wang C, Wang X (2013) Photodegradation of the antimicrobial triclocarban in aqueous systems under ultraviolet radiation. Environ Sci Poll Res 20:3195–3201

    Article  CAS  Google Scholar 

  • Drillia P, Dokianakis SN, Fountoulakis MS, Kornaros M (2005) On the occasional biodegradation of pharmaceuticals in the activated sludge process: the example of the antibiotic sulfamethoxazole. J Hazard Mater 122:259–265

    Article  CAS  Google Scholar 

  • Fatta-Kassinos D, Vasquez MI, Kummerer K (2011) Transformation products of pharmaceuticals in surface waters and wastewater formed during photolysis and advanced oxidation processes—degradation, elucidation of byproducts and assessment of their biological potency. Chemosphere 85:693–709

    Article  CAS  Google Scholar 

  • Garcia-Galan MJ, Diaz-Cruz MS, Barcelo D (2008) Identification and determination of metabolites and degradation products of sulfonamide antibiotics. Trends Anal Chem 27:1008–1022

    Article  CAS  Google Scholar 

  • Garcia-Galan MJ, Garrido T, Fraile J, Ginebreda A, Díaz-Cruz MS, Barcelo D (2010) Simultaneous occurrence of nitrates and sulfonamide antibiotics in two groundwater bodies of Catalonia (Spain). J Hydrol 383:93–101

    Article  CAS  Google Scholar 

  • Garcia-Galan MJ, Diaz-Cruz MS, Barcelo D (2012) Kinetic studies and characterization of photolytic products of sulfamethazine, sulfapyridine and their acetylated metabolites in water under simulated solar irradiation. Water Res 46:711–722

    Article  CAS  Google Scholar 

  • Gauthier H, Yargeau V, Cooper DG (2010) Biodegradation of pharmaceuticals by Rhodococcus rhodochrous and Aspergillus niger by co-metabolism. Sci Total Environ 408:1701–1706

    Article  CAS  Google Scholar 

  • Gobel A, McArdell CS, Suter MJ-F, Giger W (2004) Trace determination of macrolide and sulfonamide antimicrobials, a human sulfonamide metabolite, and trimethoprim in wastewater using liquid chromatography coupled to electrospray tandem mass spectrometry. Anal Chem 76:4756–4764

    Article  Google Scholar 

  • Halling-Sorensen B, Nielsen SN, Lanzky PF, Ingerslev F, Lutzhoft HCH, Jorgensen SE (1998) Occurrence, fate and effects of pharmaceutical substances in the environment—a review. Chemosphere 36:357–393

    Article  CAS  Google Scholar 

  • Hilton MJ, Thomas KV (2003) Determination of selected human pharmaceutical compounds in effluent and surface water samples by high-performance liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr A 1015:129–141

    Article  CAS  Google Scholar 

  • Hirsch R, Ternes T, Haberer K, Kratz KL (1999) Occurrence of antibiotics in the aquatic environment. Sci Total Environ 225:190–118

    Article  Google Scholar 

  • Ingerslev F, Halling-Sorensen B (2000) Biodegrability properties of sulfonamides in activated sludge. Environ Toxicol Chem 19:2467–2473

    Article  CAS  Google Scholar 

  • Ingerslev F, Torang L, Loke M-L, Halling-Sorensen B, Nyholm N (2008) Primary biodegradation of veterinary antibiotics in aerobic and anaerobic surface water simulation systems. Chemosphere 44:865–872

    Article  Google Scholar 

  • Kummerer K (2008) Pharmaceuticals in the environment. Springer, Berlin

    Book  Google Scholar 

  • Kummerer K (2009) Antibiotics in the aquatic environment—a review—part I. Chemosphere 75:417–434

    Article  Google Scholar 

  • Lai H-T, Hou J-H (2008) Light and microbial effects on the transformation of four sulfonamides in eel pond water and sediment. Aquaculture 283:50–55

    Article  CAS  Google Scholar 

  • Lai H-T, Wang T-S, Chou C-C (2011) Implication of light sources and microbial activities on degradation of sulfonamides in water and sediment from a marine shrimp pond. Bioresource Technol 102:5017–5023

    Article  CAS  Google Scholar 

  • Lam MW, Mabury SA (2005) Photodegradation of the pharmaceuticals atorvastatin, carbamazpine, levofloxacin and sulfamethoxazole in natural waters. Aquat Sci 67:177–188

    Article  CAS  Google Scholar 

  • Li WC (2014) Occurrence, sources, and fate of pharmaceuticals in aquatic environment and soil. Environ Poll 187:193–201

    Article  CAS  Google Scholar 

  • Li Y, Niu J, Wang W (2011) Photolysis of enrofloxacin in aqueous systems under simulated sunlight irradiation: kinetics, mechanism and toxicity of photolysis products. Chemosphere 85:892–897

    Article  CAS  Google Scholar 

  • Liao CH, Kang SF, Wu A (2001) Hydroxyl radical scavenging role of chloride and bicarbonate ions in the H2O2/UV process. Chemosphere 44:1193–1200

    Article  CAS  Google Scholar 

  • Loftin KA, Adams CO, Meyer MT, Surampalli R (2008) Effects of ionic strength, temperature and pH on selected antibiotics. J Environ Qual 37:378–386

    Article  CAS  Google Scholar 

  • Maszkowska J, Stolte S, Kumirska J, Lukaszewicz P, Mioduszewska K, Puckowski A, Caban M, Wagil M, Stepnowski P, Bialk-Bielinska A (2014) Beta-blockers in the environment: part I. Mobility and hydrolysis study. Sci Total Environ 493:1112–1121

    Article  CAS  Google Scholar 

  • Mompelat S, Le Bot B, Thomas O (2009) Occurrence and fate of pharmaceutical products and by-products, from resource to drinking water. Environ Int 35:803–814

    Article  CAS  Google Scholar 

  • Muller E, Schussler W, Horn H, Lemmer H (2013) Aerobic biodegradation of the sulfonamide antibiotic sulfamethoxazole by activated sludge applied as co-substrate and sole carbon and nitrogen. Chemosphere 92:969–978

    Article  CAS  Google Scholar 

  • OECD (2004) Test no. 111: hydrolysis as a function of pH

  • O'Grady D, Evangelista S, Yargeau V (2009) Removal of aqueous 17α-ethinylestradiol by Rhodococcus species. Environ Eng Sci 26:1393–1400

    Article  Google Scholar 

  • Onesios KM, Yu JT, Bouwer EJ (2009) Biodegradation and removal of pharmaceuticals and personal care products in treatment systems: a review. Biodegradation 20:441–466

    Article  CAS  Google Scholar 

  • Periša M, Babić S (2014) Simultaneous determination of pharmaceuticals and some of their metabolites in wastewater by high performance liquid chromatography with tandem mass spectrometry. J Sep Sci 37:1289–1296

    Article  Google Scholar 

  • Periša M, Babić S, Škorić I, Fromel T, Knepper TP (2013) Photodegradation of sulfonamides and their N 4-acetylated metabolites in water by simulated sunlight irradiation: kinetics and identification of photoproducts. Environ Sci Poll Res 20:8934–8946

    Article  Google Scholar 

  • Prabhakaran D, Sukul P, Lamshoft M, Maheswari MA, Zuhlke S, Spiteller M (2009) Photolysis of difloxacin and sarafloxacin in aqueous systems. Chemosphere 77:739–746

    Article  CAS  Google Scholar 

  • Radjenović J, Perez S, Petrović M, Barcelo D (2008) Identification and structural characterization of biodegradation products of atenolol and glibnclamide by liquid chromatography coupled to hybrid quadrupole time-of-flight and quadrupole ion trap mass spectrometry. J Chromatogr A 1210:142–153

    Article  Google Scholar 

  • Radke E, Lauwigi C, Heinkele G, Murdter TE, Letze M (2009) Fate of the antibiotic sulfamethoxazole and its two major human metabolites in a water sediment test. Environ Sci Technol 43:3135–3141

    Article  CAS  Google Scholar 

  • Ryan CC, Tan DT, Arnold WA (2011) Direct and indirect photolysis of sulfamethoxazole and trimethoprim in wastewater treatment plant effluent. Water Res 45:1280–1286

    Article  CAS  Google Scholar 

  • Santos LHMLM, Araujo AN, Fachini A, Pena A, Delerue-Matos C, Montenegro MCBSM (2010) Ecotoxicological aspects related to the presence of pharmaceuticals in the aquatic environment. J Hazard Mater 175:45–95

    Article  CAS  Google Scholar 

  • Shaojun J, Shourong Z, Daqiang Y, Lianhong W, Liangyan C (2008) Aqueous oxytetracycline degradation and the toxicity change of degradation compounds in photoirradiation process. J Environ Sci 20:806–813

    Article  Google Scholar 

  • Sharma VK, Johnson N, Cizmas L, McDonald TJ, Kim H (2016) A review of the influence of treatment strategies on antibiotic resistant bacteria and antibiotic resistance genes. Chemosphere 150:702–714

    Article  CAS  Google Scholar 

  • Sukul P, Lamshoft M, Zuhlke S, Spiteller M (2008) Photolysis of 14C-sulfadiazine in water and manure. Chemosphere 71:717–725

    Article  CAS  Google Scholar 

  • Tamtam F, Mercier F, Le Bot B, Eurin J, Tuc Dinh Q, Clement M, Chevreuil M (2008) Occurrence and fate of antibiotics in the Seine River in various hydrological conditions. Sci Total Environ 393:84–95

    Article  CAS  Google Scholar 

  • Tong L, Eichhorn P, Perez S, Wang Y, Barcelo D (2011) Photodegradation of azithromycin in various systems under simulated and solar radiation: kinetics and identification of photoproducts. Chemosphere 83:340–348

    Article  CAS  Google Scholar 

  • Trovo AG, Nogueira RFP, Aguera A, Sirtori C, Fernandez-Alba AR (2009) Photodegradation of sulfamethoxazole in various aqueous media: persistence, toxicity and photoproducts assessment. Chemosphere 77:1292–1298

    Article  CAS  Google Scholar 

  • Vione D, Calza P, Fabbri D, Santoro V, Medana C (2015) The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxycinnamate (EHMC) in surface waters. Sci Total Environ 537:58–68

    Article  CAS  Google Scholar 

  • Walse SS, Morgan SL, Kong L, Ferry JL (2004) Role of dissolved organic matter, nitrate, and bicarbonate in the photolysis of aqueous fipronil. Environ Sci Technol 38:3908–3915

    Article  CAS  Google Scholar 

  • Wawryniuk M, Pietrzak A, Nalecz-Jawecki G (2015) Evaluation of direct and indirect photodegradation of mianserin with high-performance liquid chromatography and short-term bioassays. Ecotox Environ Safe 115:144–151

    Article  CAS  Google Scholar 

  • Xu B, Mao D, Luo Y, Xu L (2011) Sulfamethoxazole biodegradation and biotransformation in the water-sediment system of a natural river. Bioresource Technol 102:7069–7076

    Article  CAS  Google Scholar 

  • Xu J, Hao Z, Guo C, Zhang Y, He Y, Meng W (2014) Photodegradation of sulfapyridine under simulated sunlight irradiation: kinetics, mechanism and toxicity evolvement. Chemosphere 99:186–191

    Article  CAS  Google Scholar 

  • Yang C-W, Hsiao W-C, Chang B-V (2016) Biodegradation of sulfonamide antibiotics in sludge. Chemosphere 150:559–565

    Article  CAS  Google Scholar 

  • Yuan H, Zhang Y, Zhou X (2012) Degradation of bezafibrate with UV/H2O2 in surface water and wastewater treatment plant effluent. Clean–Soil, Air, Water 40(3):239–245

    Article  CAS  Google Scholar 

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Acknowledgement

This study has been partly supported by the Croatian Science Foundation under the project Fate of pharmaceuticals in the environment and during advanced wastewater treatment (PharmaFate) (IP-09-2014-2353).

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Correspondence to Martina Biošić.

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Responsible editor: Ester Heath

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Biošić, M., Mitrevski, M. & Babić, S. Environmental behavior of sulfadiazine, sulfamethazine, and their metabolites. Environ Sci Pollut Res 24, 9802–9812 (2017). https://doi.org/10.1007/s11356-017-8639-8

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  • DOI: https://doi.org/10.1007/s11356-017-8639-8

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