On the photodegradation of azithromycin, erythromycin and tylosin and their transformation products – A kinetic study

Alatrache, 2010, Tylosin abetement in water by photocatalytic processes, Water Sci. Technol., 62, 435, 10.2166/wst.2010.928 Andreozzi, 1999, Advanced oxidation processes (AOP) for water purification and recovery, Catalysis Today, 53, 51, 10.1016/S0920-5861(99)00102-9 Atkins, 1986, Kinetic studies on the decomposition of erythromycin A in aqueous acidic and neutral buffers, Int. J. Pharm., 30, 199, 10.1016/0378-5173(86)90079-7 Baquero, 2008, Antibiotics and antibiotic resistance in water environments, Curr. Opin. Biotechnol., 19, 260, 10.1016/j.copbio.2008.05.006 Batchu, 2014, Photodegradation of antibiotics under simulated solar radiation: implications for their environmental fate, Sci. Total Environ., 470–471, 299, 10.1016/j.scitotenv.2013.09.057 Bouki, 2013, Detection and fate of antibiotic resistant bacteria in wastewater treatment plants: a review, Ecotoxicol. Environ. Saf., 91, 1, 10.1016/j.ecoenv.2013.01.016 Christian, 2003, Determination of antibiotic residues in manure, soil, and surface waters, Acta Hydrochim. Hydrobiol., 31, 36, 10.1002/aheh.200390014 Debremaeker, 2003, Analysis of unknown compounds in azithromycin bulk samples with liquid chromatography coupled to ion trap mass spectrometry, Rapid Commun. Mass Spectrom., 17, 342, 10.1002/rcm.917 Delaforge, 1983, Dual effects of macrolide antibiotics on rat liver cytochrome P-450, Biochem. Pharmacol., 32, 2309, 10.1016/0006-2952(83)90178-8 Fatta-Kassinos, 2011, Pharmaceutical residues in environmental waters and wastewater: current state of knowledge and future research, Anal. Bioanal. Chem., 399, 251, 10.1007/s00216-010-4300-9 Fiese, 1990, Comparison of the acid stability of azithromycin and erythromycin A, J. Antimicrob. Chemother., 25, 39, 10.1093/jac/25.suppl_A.39 Hansen, 2002, The structures of four macrolide antibiotics bound to the large ribosomal subunit, Mol. Cell, 10, 117, 10.1016/S1097-2765(02)00570-1 Hassanzadeh, 2007, Mechanism for the degradation of erythromycin A and erythromycin A 2′-ethyl succinate in acidic aqueous solution, J. Phys. Chem. A, 111, 10098, 10.1021/jp073030y Hassanzadeh, 2006, Determination of the stereochemistry of anhydroerythromycin A, the principal degradation product of the antibiotic erythromycin A, Org. Biomol. Chem., 4, 1014, 10.1039/b518182h Hatchard, 1956, A new sensitive chemical Actinometer. II. potassium ferrioxalate as a standard chemical actinometer, Proc. R. Soc. A Math, Phys. Eng. Sci., 235, 518 Heit, 1998, Vacuum-UV (172 nm) Actinometry. The quantum yield of the photolysis of water, J. Phys. Chem. A, 5639, 5551, 10.1021/jp980130i Hirsch, 1998, Determination of antibiotics in different water compartments via liquid chromatography-electrospray tandem mass spectrometry, J. Chromatogr. A, 815, 213, 10.1016/S0021-9673(98)00335-5 Jacobsen, 2004, 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. Chromatography A, 1038, 157, 10.1016/j.chroma.2004.03.034 Kim, 2009, Photodegradation characteristics of PPCPs in water with UV treatment, Environ. Int., 35, 793, 10.1016/j.envint.2009.01.003 Kochany, 1991, Of aqueous organic pollutants. 1. EPR spin-trapping technique for the determination of hydroxyl radical rate constants in the photooxidation of chlorophenols following, J. Phys. Chem., 95, 5116, 10.1021/j100166a039 Kochany, 1992, Mechanism of photodegradation of aqueous organic pollutants. 2. Measurement of the primary rate constants for reaction of hydroxyl radicals with benzene and some halobenzenes using an EPR spin-trapping method following the photolysis of hydrogen peroxide, Environ. Sci. Technol., 26, 262, 10.1021/es00026a004 Kuhn, 2005, International Union of pure and applied chemistry chemical actinometry, IUPAC Tech. Rep., 1 Kümmerer, 2009, Antibiotics in the aquatic environment – a review – part I, Chemosphere, 75, 417, 10.1016/j.chemosphere.2008.11.086 Laidler, 1987 Laoufi, 2013, Removal of a persistent pharmaceutical micropollutant by UV/TiO2 process using an immobilized titanium dioxide catalyst: parametric study, Chem. Eng. Trans., 32, 1951 Loke, 2000, Stability of Tylosin A in manure containing test systems determined by high performance liquid chromatography, Chemosphere, 40, 759, 10.1016/S0045-6535(99)00450-6 López-Serna, 2013, Occurrence of 95 pharmaceuticals and transformation products in urban groundwaters underlying the metropolis of Barcelona, Spain, Environmental Pollution, 174, 305, 10.1016/j.envpol.2012.11.022 López-Serna, 2011, Development of a fast instrumental method for the analysis of pharmaceuticals in environmental and wastewaters based on ultra high performance liquid chromatography (UHPLC)-tandem mass spectrometry (MS/MS), Chemosphere, 85, 1390, 10.1016/j.chemosphere.2011.07.071 Lumaret, 2012, A review on the toxicity and non-target effects of macrocyclic lactones in terrestrial and aquatic environments, Curr. Pharm. Biotechnol., 13, 1004, 10.2174/138920112800399257 Mauser, 1974 Mazellier, 2008, Photodegradation of the steroid hormones 17beta-estradiol (E2) and 17alpha-ethinylestradiol (EE2) in dilute aqueous solution, Chemosphere, 73, 1216, 10.1016/j.chemosphere.2008.07.046 Michael, 2013, Urban wastewater treatment plants as hotspots for the release of antibiotics in the environment: a review, Water Res., 47, 957, 10.1016/j.watres.2012.11.027 Mordi, 2000, Acid-catalyzed degradation of clarithromycin and erythromycin B: a comparative study using NMR spectroscopy, J. Med. Chem., 43, 467, 10.1021/jm9904811 Oppenländer, 2003 Parsons, 2004 Prieto-Rodriguez, 2012, Treatment of emerging contaminants in wastewater treatment plants (WWTP) effluents by solar photocatalysis using low TiO2 concentrations, J. Hazard. Mater., 211–212, 131, 10.1016/j.jhazmat.2011.09.008 Ratpukdi, 2014, Degradation of Paracetamol and Norfloxacin in Aqueous Solution Using Vacuum Ultraviolet (VUV) Process, J. Clean. Energy Technol., 2, 168, 10.7763/JOCET.2014.V2.115 Sacher, 2001, Pharmaceuticals in groundwaters analytical methods and results of a monitoring program in Baden-Württemberg, Germany, J. Chromatogr., 938, 199, 10.1016/S0021-9673(01)01266-3 Solomon, 2009, Risks of agricultural pharmaceuticals in surface water systems and soils, ACS Symp. Ser., 1018, 191, 10.1021/bk-2009-1018.ch013 Sui, 2015, Occurrence, sources and fate of pharmaceuticals and personal care products in the groundwater: a review, Emerg. Contam., 1, 14, 10.1016/j.emcon.2015.07.001 Sun, 1996, Determination of the quantum yield for the photochemical generation of hydroxyl radicals in tio 2 suspensions, J. Phys. Chem., 100, 4127, 10.1021/jp9505800 Tassalit, 2011, Photocatalytic deterioration of Tylosin in an aqueous suspension using UV/TiO2, Sci. Adv. Mater., 3, 944, 10.1166/sam.2011.1243 Tong, 2011, Photodegradation of azithromycin in various aqueous systems under simulated and natural solar radiation: kinetics and identification of photoproducts, Chemosphere, 83, 340, 10.1016/j.chemosphere.2010.12.025 Tong, 2009, Analysis of veterinary antibiotic residues in swine wastewater and environmental water samples using optimized SPE-LC/MS/MS, Chemosphere, 74, 1090, 10.1016/j.chemosphere.2008.10.051 World Health Organization, 2014, Antimicrobial resistance – global report on surveillance, Bull. World Health Organ., 61, 383 Wright, 2005, Bacterial resistance to antibiotics: enzymatic degradation and modification, Adv. Drug Deliv. Rev., 57, 1451, 10.1016/j.addr.2005.04.002 Zhang, 2009, Aspects of degradation kinetics of azithromycin in aqueous solution, Chromatographia, 70, 67, 10.1365/s10337-009-1116-x Zoschke, 2014, Vacuum-UV radiation at 185 nm in water treatment-a review, Water Res., 52, 131, 10.1016/j.watres.2013.12.034