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Degradation of typical macrolide antibiotic roxithromycin by hydroxyl radical: kinetics, products, and toxicity assessment

  • Wei LiEmail author
  • Xiujuan Xu
  • Baoling Lyu
  • Ying Tang
  • Yinlong ZhangEmail author
  • Fang Chen
  • Gregory Korshin
Research Article
  • 21 Downloads

Abstract

The degradation of roxithromycin (ROX) by hydroxyl radical (·OH) generated by UV/H2O2 was systematically investigated in terms of degradation kinetics, effects of water chemistry parameters, oxidation products, as well as toxicity evaluation. The degradation of ROX by UV/H2O2 with varying light irradiation intensity, initial ROX concentration, and H2O2 concentration in pure water and wastewater all followed pseudo-first-order kinetics. The second-order rate constant for reaction between ROX and ·OH is 5.68 ± 0.34 × 109/M/s. The degradation rate of ROX increased with the pH; for instance, the apparent degradation rates were 0.0162 and 0.0309/min for pH 4 and pH 9, respectively. The presence of natural organic matter (NOM) at its concentrations up to 10 mg C/L did not significantly affect the removal of ROX. NO3 and NO2 anions inhibited the degradation of ROX due to the consumption of ·OH in reactions with these ions. Fe3+, Cu2+, and Mg2+ cations inhibited the degradation of ROX, probably because of the formation of ROX-metal chelates. A total of ten degradation products were tentatively identified by HPLC/LTQ-Orbitrap XL MS, which mainly derived from the attack on the oxygen linking the lactone ring and the cladinose moiety, tertiary amine and oxime side chain moiety by ·OH. The toxicity evaluation revealed that UV/H2O2 treatment of ROX induced the toxicity to bioluminescent bacteria increased.

Keywords

Emerging contaminants Advanced oxidation process Reaction kinetics Water matrix effects Degradation products Toxicity assessment 

Notes

Funding information

This work was financially supported by the National Science Fund for Colleges and Universities of Jiangsu Province (15KJB610006), the Natural Science Foundation of Jiangsu Province (BK20160930), China Postdoctoral Science Foundation (2016 M590461), Jiangsu Postdoctoral Science Foundation (1501008B), and the National Natural Science Foundation of China (31700441, 41501514).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11356_2019_4713_MOESM1_ESM.doc (425 kb)
ESM 1 (DOC 425 kb)

References

  1. Al-Mustafa J (2002) Magnesium, calcium and barium perchlorate complexes of ciprofloxacin and norfloxacin. Acta Chim Slov 49(3):457–466Google Scholar
  2. Bang H, Slokar YM, Ferrero G, Kruithof JC, Kennedy MD (2016) Removal of taste and odor causing compounds by UV/H2O2 treatment: effect of the organic and inorganic water matrix. Desalin Water Treat 57:27485–27494Google Scholar
  3. Bensalah N, Khodary A, Abdel-Wahab A (2011) Kinetic and mechanistic investigations of mesotrione degradation in aqueous medium by Fenton process. J Hazard Mater 189:479–485CrossRefGoogle Scholar
  4. Bolobajev J, Trapido M, Goi A (2016) Effect of iron ion on doxycycline photocatalytic and Fenton-based autocatalytic decomposition. Chemosphere 153:220–226CrossRefGoogle Scholar
  5. Bu Q, Wang B, Huang J, Deng S, Yu G (2013) Pharmaceuticals and personal care products in the aquatic environment in China: a review. J Hazard Mater 262:189–211CrossRefGoogle Scholar
  6. Chiou CS, Chen YH, Chang CT, Chang CY, Shie JL, Li YS (2006) Photochemical mineralization of di-n-butyl phthalate with H2O2/Fe3+. J Hazard Mater B 135:344–349CrossRefGoogle Scholar
  7. Choi K, Kim Y, Jung J, Kim M, Kim C, Kim N, Park J (2008) Occurrences and ecological risks of roxithromycin, trimethoprim, and chloramphenicol in the Han River, Korea. Environ Toxicol Chem 27:711–719CrossRefGoogle Scholar
  8. Dalrymple RM, Carfagno AK, Sharpless CM (2010) Correlations between dissolved organic matter optical properties and quantum yields of singlet oxygen and hydrogen peroxide. Environ Sci Technol 44:5824–5829CrossRefGoogle Scholar
  9. De la Cruz N, Esquius L, Grandjean D, Magnet A, Tungler A, de Alencastro LF, Pulgarin C (2013) Degradation of emergent contaminants by UV, UV/H2O2 and neutral photo-Fenton at pilot scale in a domestic wastewater treatment plant. Water Res 47:5836–5845CrossRefGoogle Scholar
  10. Ding J, Lu G, Liu J, Zhang Z (2015) Evaluation of the potential for trophic transfer of roxithromycin along an experimental food chain. Environ Sci Pollut R 22(14):10592–10600CrossRefGoogle Scholar
  11. Dodd MC, Buffle MO, Von Gunten U (2006) Oxidation of antibacterial molecules by aqueous ozone: moiety-specific reaction kinetics and application to ozone-based wastewater treatment. Environ Sci Technol 40:1969–1977CrossRefGoogle Scholar
  12. Dong H, Yuan X, Wang W, Qiang Z (2016) Occurrence and removal of antibiotics in ecological and conventional wastewater treatment processes: a field study. J Environ Manag 178:11–19CrossRefGoogle Scholar
  13. El-Rjoob AW, Taha ZA, Al-Mustafa J, Ajlouni AM (2012) A thermodynamic study of complexation of iron ions with clarithromycin and roxithromycin in methanol using a conductometric method. J Solut Chem 41:1079–1087CrossRefGoogle Scholar
  14. Esplugas S, Bila DM, Krause LGT, Dezotti M (2007) Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J Hazard Mater 149:631–642CrossRefGoogle Scholar
  15. Gao L, Shi Y, Li W, Niu H, Liu J, Cai Y (2012) Occurrence of antibiotics in eight sewage treatment plants in Beijing, China. Chemosphere 86:665–671CrossRefGoogle Scholar
  16. Gomes J, Costa R, Quinta-Ferreira RM, Martins RC (2017) Application of ozonation for pharmaceuticals and personal care products removal from water. Sci Total Environ 586:265–283CrossRefGoogle Scholar
  17. Hamdan II (2003) Comparative in-vitro investigations of the interaction between some macrolides and Cu(II), Zn(II) and Fe(II). Pharmazie 58:223–224Google Scholar
  18. Huber MM, Canonica S, Park G, Von Gunten U (2003) Oxidation of pharmaceuticals during ozonation and advanced oxidation processes. Environ Sci Technol 37:1016–1024CrossRefGoogle Scholar
  19. Jiang Y, Li M, Guo C, An D, Xu J, Zhang Y, Xi B (2014) Distribution and ecological risk of antibiotics in a typical effluent-receiving river (Wangyang River) in North China. Chemosphere 112:267–274CrossRefGoogle Scholar
  20. Keen OS, Linden KG (2013) Degradation of antibiotic activity during UV/H2O2 advanced oxidation and photolysis in wastewater effluent. Environ Sci Technol 47:13020–13030CrossRefGoogle Scholar
  21. Kim I, Yamashita N, Tanaka H (2009) Performance of UV and UV/H2O2 processes for the removal of pharmaceuticals detected in secondary effluent of a sewage treatment plant in Japan. J Hazard Mater 166:1134–1140CrossRefGoogle Scholar
  22. Kummerer K (2009) Antibiotics in the aquatic environment—a review—part I. Chemosphere 75:417–434CrossRefGoogle Scholar
  23. Kwiecień A, Krzek J, Zmudzki P, Matoga U, Dlugosz M, Szczubialka K, Nowakowska M (2014) Roxithromycin degradation by acidic hydrolysis and photocatalysis. Anal Methods 6:6414–6423CrossRefGoogle Scholar
  24. Li X, Shen T, Wang D, Yue X, Liu X, Yang Q, Cao J, Zheng W, Zheng G (2012) Photodegradation of amoxicillin by catalyzed Fe3+/H2O2 process. J Environ Sci-China 24:269–275CrossRefGoogle Scholar
  25. Li W, Nanaboina V, Zhou Q, Korshin GV (2013) Changes of excitation/emission matrixes of wastewater caused by Fenton- and Fenton-like treatment and their associations with the generation of hydroxyl radicals, oxidation of effluent organic matter and degradation of trace-level organic pollutants. J Hazard Mater 244-245:698–708CrossRefGoogle Scholar
  26. Liao CH, Lu MC, Su SH (2001) Role of cupric ions in the H2O2/UV oxidation of humic acids. Chemosphere 44:913–919CrossRefGoogle Scholar
  27. Lin T, Yu S, Chen W (2016) Occurrence, removal and risk assessment of pharmaceutical and personal care products (PPCPs) in an advanced drinking water treatment plant (ADWTP) around Taihu Lake in China. Chemosphere 152:1–9CrossRefGoogle Scholar
  28. Liu Y, He X, Fu Y, Dionysiou DD (2016) Degradation kinetics and mechanism of oxytetracycline by hydroxyl radical-based advanced oxidation processes. Chem Eng J 284:1317–1327CrossRefGoogle Scholar
  29. Liu P, Zhang H, Feng Y, Yang F, Zhang J (2014) Removal of trace antibiotics from wastewater: a systematic study of nanofiltration combined with ozone-based advanced oxidation processes. Chem Eng J 240:211–220CrossRefGoogle Scholar
  30. Loganathan B, Phillips M, Mowery H, Jones-Lepp TL (2009) Contamination profiles and mass loadings of macrolide antibiotics and illicit drugs from a small urban wastewater treatment plant. Chemosphere 75:70–77CrossRefGoogle Scholar
  31. Luo C, Ma J, Jiang J, Liu Y, Song Y, Yang Y, Guan Y, Wu D (2015) Simulation and comparative study on the oxidation kinetics of atrazine by UV/H2O2, UV/HSO5 and UV/S2O8 2−. Water Res 80:99–108CrossRefGoogle Scholar
  32. Luo Y, Xu L, Rysz M, Wang Y, Zhang H, Alvarez PJJ (2011) Occurrence and transport of tetracycline, sulfonamide, quinolone, and macrolide antibiotics in the Haihe river basin, China. Environ Sci Technol 45:1827–1833CrossRefGoogle Scholar
  33. Mao L, Meng C, Zeng C, Ji Y, Yang X, Gao S (2011) The effect of nitrate, bicarbonate and natural organic matter on the degradation of sunscreen agent p-aminobenzoic acid by simulated solar irradiation. Sci Total Environ 409:5376–5381CrossRefGoogle Scholar
  34. Miralles-Cuevas S, Darowna D, Wanag A, Mozia S, Malato S, Oller I (2017) Comparison of UV/H2O2, UV/S2O8 2−, solar/Fe(II)/H2O2 and solar/Fe(II)/S2O8 2− at pilot plant scale for the elimination of micro-contaminants in natural water: An economic assessment. Chem Eng J 310:514–524CrossRefGoogle Scholar
  35. Radjenovicc J, Godehardt M, Petrovic M, Hein A, Farre M, Jekel M, Barcelo D (2009) Evidencing generation of persistent ozonation products of antibiotics roxithromycin and trimethoprim. Environ Sci Technol 43:6808–6815CrossRefGoogle Scholar
  36. Rizzo L, Manaia C, Merlin C, Schwartz T, Dagot C, Ploy MC, Michael I, Fattakassinos D (2013) Urban wastewater treatment plants as hotspots for antibiotic resistant bacteria and genes spread into the environment: a review. Sci Total Environ 447:345–360CrossRefGoogle Scholar
  37. Tewari S, Jindal R, Kho YL, Eo S, Choi K (2013) Major pharmaceutical residues in wastewater treatment plants and receiving waters in Bangkok, Thailand, and associated ecological risks. Chemosphere 91:697–704CrossRefGoogle Scholar
  38. Velo-Gala I, Pirán-Montañ JA, Rivera-Utrilla J, Sánchez-Polo M, Mota AJ (2017) Advanced oxidation processes based on the use of UVC and simulated solar radiation to remove the antibiotic tinidazole from water. Chem Eng J 323:605–617CrossRefGoogle Scholar
  39. Vione D, Feitosa-Felizzola J, Minero C, Chiron S (2009) Phototransformation of selected human-used macrolides in surface water: kinetics, model predictions and degradation pathways. Water Res 43:1959–1967CrossRefGoogle Scholar
  40. Wang D, Duan X, He X, Dionysiou DD (2016) Degradation of dibutyl phthalate (DBP) by UV-254 nm/H2O2 photochemical oxidation: kinetics and influence of various process parameters. Environ Sci Pollut R 23:23772–23780CrossRefGoogle Scholar
  41. Wang F, Wang W, Yuan S, Wang W, Hu Z (2017a) Comparison of UV/H2O2 and UV/PS processes for the degradation of thiamphenicol in aqueous solution. J Photoch Photobio A 348:79–88CrossRefGoogle Scholar
  42. Wang J, Song M, Chen B, Wang L, Zhu R (2017b) Effect of pH and H2O2 on ammonia, nitrite and nitrate transformations during UV254nm irradiation: implications to nitrogen removal and analysis. Chemosphere 184:1003–1011CrossRefGoogle Scholar
  43. Wang WL, Wu QY, Huang N, Xu ZB, Lee MY, Hu HY (2018) Potential risks from UV/H2O2 oxidation and UV photocatalysis: a review of toxic, assimilable, and sensory-unpleasant transformation products. Water Res 141:109–125Google Scholar
  44. Wei X, Chen J, Xie Q, Zhang S, Li Y, Zhang Y, Xie H (2015) Photochemical behavior of antibiotics impacted by complexation effects of concomitant metals: a case for ciprofloxacin and Cu(II). Environ Sci Proc impacts 17:1220–1227CrossRefGoogle Scholar
  45. Westerhoff P, Mezyk SP, Cooper WJ, Minakata D (2007) Electron pulse radiolysis determination of hydroxyl radical rate constants with Suwannee river fulvic acid and other dissolved organic matter isolates. Environ Sci Technol 41:4640–4646CrossRefGoogle Scholar
  46. Yang LH, Ying GG, Su HC, Stauber JL, Adams MS, Binet MT (2008) Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata. Environ Toxicol Chem 27:1201–1208CrossRefGoogle Scholar
  47. Yang JF, Ying GG, Zhao JL, Tan T, Su HC, Liu YS (2011) Spatial and seasonal distribution of selected antibiotics in surface waters of the Pearl Rivers, China. J Environ Sci Health B 46:272–280CrossRefGoogle Scholar
  48. Yuan F, Hu C, Hu X, Wei D, Chen Y, Qu J (2011) Photodegradation and toxicity changes of antibiotics in UV and UV/H2O2 process. J Hazard Mater 185:1256–1263CrossRefGoogle Scholar
  49. Zhan M, Yang X, Xian Q, Kong L (2006) Photosensitized degradation of bisphenol A involving reactive oxygen species in the presence of humic substances. Chemosphere 63:378–386CrossRefGoogle Scholar
  50. Zhang QQ, Ying GG, Pan CG, Liu YS, Zhao JL (2015) Comprehensive evaluation of antibiotics emission and fate in the river basins of China: source analysis, multimedia modeling, and linkage to bacterial resistance. Environ Sci Technol 49:6772–6782CrossRefGoogle Scholar
  51. Zhu X, Zhou D, Cang L, Wang Y (2012) TiO2 photocatalytic degradation of 4-chlorobiphenyl as affected by solvents and surfactants. J Soils Sediments 12:376–385CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Co-Innovation center for sustainable Forestry in Southern China, College of Biology and the EnvironmentNanjing Forestry UniversityNanjingChina
  2. 2.Advanced Analysis and Testing CenterNanjing Forestry UniversityNanjingChina
  3. 3.School of Resources and MaterialsNortheastern University at QinhuangdaoQinhuangdaoChina
  4. 4.Department of Civil and Environmental EngineeringUniversity of WashingtonSeattleUSA

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