Skip to main content
SpringerLink
Log in

Photochemical persistence of sulfa drugs in aqueous medium: kinetic study and mathematical simulations

  • Advanced Oxidation/Reduction Technologies: An Perspective from Iberoamerican Countries
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

This study aimed at investigating the photochemical behavior of sulfa drugs containing five and six-membered heterocyclic substituents (sulfamethoxazole (SMX) and sulfadiazine (SDZ), respectively), in an aqueous medium. Despite their importance, studies devoted to the use of photochemical models to predict the environmental phototransformation of pollutants in surface waters, by combining laboratory results and natural aquatic systems parameters, are still scarce in the scientific literature. In this work, the second-order reaction rate constants of SDZ and SMX with hydroxyl radicals (●OH), singlet oxygen (1O2), and triplet excited states of chromophoric dissolved organic matter (3CDOM*) were experimentally determined at pH 7, using the competition kinetics approach. The results show that ●OH and 3CDOM* are the key species involved in sulfonamide degradation, with anionic SMX, most prevalent at pH 6–9, being degraded much slower than the anionic form of SDZ. Moreover, SDZ and SMX photodegradation in natural water samples (spring-fed natural pond, public supply reservoir, and sea water) was significantly enhanced relative to depletion in pure water. Finally, from mathematical simulations of the sunlight-driven sulfonamide degradation, half-life times were predicted for these drugs varying from less than 2 to about 90 days, depending on the water depth, concentration of key species (DOC, HCO3−, NO2−, CO32−) in natural aqueous systems, as well as on the particular heterocyclic substituent.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data availability

All data generated or analyzed during this study are included in this published article [and its supplementary information files].

References

  • Arques A, Bianco Prevot A (2015) Soluble bio-based substances isolated from urban wastes: environmental applications. Springer International Publishing

  • Batista APS, Teixeira A, Cooper WJ, Cottrell BA (2016) Correlating the chemical and spectroscopic characteristics of natural organic matter with the photodegradation of sulfamerazine. Water Res 93:20–29

    Article  CAS  Google Scholar 

  • Bianco A, Fabbri D, Minella M, Brigante M, Mailhot G, Maurino V, Minero C, Vione D (2015) New insights into the environmental photochemistry of 5-chloro-2-(2,4-dichlorophenoxy)phenol (triclosan): reconsidering the importance of indirect photoreactions. Water Res 72:271–280

    Article  CAS  Google Scholar 

  • Bodrato M, Vione D (2014) APEX (aqueous photochemistry of environmentally occurring xenobiotics): a free software tool to predict the kinetics of photochemical processes in surface waters. Environ Sci-Proc Imp 16:732–740

    CAS  Google Scholar 

  • Boreen AL, Arnold WA, McNeill K (2004) Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic 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 

  • Carena L, Puscasu CG, Comis S, Sarakha M, Vione D (2019) Environmental photodegradation of emerging contaminants: a reexamination of the importance of triplet-sensitised processes, based on the use of 4-carboxybenzophenone as proxy for the chromophoric dissolved organic matter. Chemosphere 237:124476

    Article  CAS  Google Scholar 

  • De Laurentiis E, Prasse C, Ternes TA, Minella M, Maurino V, Minero C, Sarakha M, Brigante M, Vione D (2014) Assessing the photochemical transformation pathways of acetaminophen relevant to surface waters: transformation kinetics, intermediates, and modelling. Water Res 53:235–248

    Article  Google Scholar 

  • Fabbri D, Minella M, Maurino V, Minero C, Vione D (2015) A model assessment of the importance of direct photolysis in the photo-fate of cephalosporins in surface waters: possible formation of toxic intermediates. Chemosphere 134:452–458

    Article  CAS  Google Scholar 

  • Ge LK, Zhang P, Halsall C, Li YY, Chen CE, Li J, Sun HL, Yao ZW (2019) The importance of reactive oxygen species on the aqueous phototransformation of sulfonamide antibiotics: kinetics, pathways, and comparisons with direct photolysis. Water Res 149:243–250

    Article  CAS  Google Scholar 

  • Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD, Barber LB, Buxton HT (2002) Pharmaceuticals, hormones, and other organic wastewater contaminants in US streams, 1999-2000: a national reconnaissance. Environ Sci Technol 36:1202–1211

    Article  CAS  Google Scholar 

  • Lastre-Acosta AM, Barberato B, Parizi MPS, Teixeira A (2019) Direct and indirect photolysis of the antibiotic enoxacin: kinetics of oxidation by reactive photo-induced species and simulations. Environ Sci Pollut Res 26:4337–4347

    Article  CAS  Google Scholar 

  • Li YJ, Wei XX, Chen JW, Xie HB, Zhang YN (2015) Photodegradation mechanism of sulfonamides with excited triplet state dissolved organic matter: a case of sulfadiazine with 4-carboxybenzophenone as a proxy. J Hazard Mater 290:9–15

    Article  CAS  Google Scholar 

  • Marchetti G, Minella M, Maurino V, Minero C, Vione D (2013) Photochemical transformation of atrazine and formation of photointermediates under conditions relevant to sunlit surface waters: laboratory measures and modelling. Water Res 47:6211–6222

    Article  CAS  Google Scholar 

  • Minella M, Rapa L, Carena L, Pazzi M, Maurino V, Minero C, Brigante M, Vione D (2018) An experimental methodology to measure the reaction rate constants of processes sensitised by the triplet state of 4-carboxybenzophenone as a proxy of the triplet states of chromophoric dissolved organic matter, under steady-state irradiation conditions. Environ Sci Process Impacts 20:1007–1019

    Article  CAS  Google Scholar 

  • Montoneri E, Boffa V, Savarino P, Perrone D, Ghezzo M, Montoneri C, Mendichi R (2011) Acid soluble bio-organic substances isolated from urban bio-waste. Chemical composition and properties of products. Waste Manag 31:10–17

    Article  CAS  Google Scholar 

  • Oliveira C, Lima DLD, Silva CP, Calisto V, Otero M, Esteves VI (2019) Photodegradation of sulfamethoxazole in environmental samples: the role of pH, organic matter and salinity. Sci Total Environ 648:1403–1410

    Article  CAS  Google Scholar 

  • Parizi MPS, Acosta AML, Ishiki HM, Rossi RC, Mafra RC, Teixeira A (2019) Environmental photochemical fate and UVC degradation of sodium levothyroxine in aqueous medium. Environ Sci Pollut Res 26:4393–4403

    Article  CAS  Google Scholar 

  • Passananti M, Temussi F, Iesce MR, Previtera L, Mailhot G, Vione D, Brigante M (2014) Photoenhanced transformation of nicotine in aquatic environments: involvement of naturally occurring radical sources. Water Res 55:106–114

    Article  CAS  Google Scholar 

  • Perisa M, Babic S, Skoric 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 Pollut Res 20:8934–8946

    Article  CAS  Google Scholar 

  • Schwarzenbach RP (2003) Environmental organic chemistry, 2nd edn. Wiley & Sons, Inc., Hoboken

    Google Scholar 

  • Shemer H, Sharpless CM, Elovitz MS, Linden KG (2006) Relative rate constants of contaminant candidate list pesticides with hydroxyl radicals. Environ Sci Technol 40:4460–4466

    Article  CAS  Google Scholar 

  • Silva MP, Mostafa S, McKay G, Rosario-Ortiz FL, Teixeira A (2015) Photochemical fate of amicarbazone in aqueous media: laboratory measurement and simulations. Environ Eng Sci 32:730–740

    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 (2020) A critical view of the application of the APEX software (aqueous photochemistry of environmentally-occurring xenobiotics) to predict photoreaction kinetics in surface freshwaters. Molecules 25:1–34

    Google Scholar 

  • Vione D, Maddigapu PR, De Laurentiis E, Minella M, Pazzi M, Maurino V, Minero C, Kouras S, Richard C (2011) Modelling the photochemical fate of ibuprofen in surface waters. Water Res 45:6725–6736

    Article  CAS  Google Scholar 

  • Vione D, Fabbri D, Minella M, Canonica S (2018) Effects of the antioxidant moieties of dissolved organic matter on triplet-sensitized phototransformation processes: implications for the photochemical modeling of sulfadiazine. Water Res 128:38–48

    Article  CAS  Google Scholar 

  • Wenk J, von Gunten U, Canonica S (2011) Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical. Environ Sci Technol 45:1334–1340

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to Prof. N. Y. M. Iha (Laboratory of Photochemistry and Energy Conversion, Institute of Chemistry, University of São Paulo, Brazil), for the disposal of the solar simulator, and to Prof. J. A. S. Tenório (Laboratory of Recycling, Waste Treatment and Extraction-LAREX, Department of Chemical Engineering, Escola Politécnica, University of São Paulo, Brazil) for the characterization of natural water samples.

Funding

This work was financially supported by São Paulo Research Foundation (FAPESP) grant #2016/03695-8; Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Brasil (CAPES) Finance Code 001 and post-doc grant #88887.340964/2019-00; and National Council for Scientific and Technological Development (CNPq).

Author information

Authors and Affiliations

  1. Research Group in Advanced Oxidation Processes (AdOx), Department of Chemical Engineering, University of São Paulo, Av. Prof. Luciano Gualberto, tr. 3, 380, São Paulo, SP, Brazil

    Arlen Mabel Lastre-Acosta, Bruno Segawa Cristofoli & Antonio Carlos Silva Costa Teixeira

  2. Chemical Systems Engineering Center, Department of Chemical Engineering, University of São Paulo, Av. Prof. Luciano Gualberto, tr. 3, 380, São Paulo, SP, Brazil

    Arlen Mabel Lastre-Acosta & Claudio Augusto Oller do Nascimento

  3. Energy Engineering Department, São Paulo State University (UNESP), Av. Dos Barrageiros, 1881, Rosana, SP, Brazil

    Marcela Prado Silva Parizi

Authors
  1. Arlen Mabel Lastre-Acosta
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bruno Segawa Cristofoli
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marcela Prado Silva Parizi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Claudio Augusto Oller do Nascimento
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Antonio Carlos Silva Costa Teixeira
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

AMLA: conceptualization, methodology, validation, formal analysis, investigation, writing—original draft, visualization

BSC: methodology, investigation

MPSP: conceptualization, methodology

CAON: resources, supervision, funding acquisition

ACSCT: conceptualization, validation, resources, writing—original draft, writing—review and editing, supervision, funding acquisition

All authors read and approved the final manuscript.

Corresponding author

Correspondence to Arlen Mabel Lastre-Acosta.

Ethics declarations

Competing interests

The authors declare that they have no competing interests.

Ethics approval and consent to participate

Not applicable.

Consent for publication

Not applicable.

Additional information

Responsible Editor: Vítor Pais Vilar

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

ESM 1

(DOCX 22 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lastre-Acosta, A.M., Cristofoli, B.S., Parizi, M.P.S. et al. Photochemical persistence of sulfa drugs in aqueous medium: kinetic study and mathematical simulations. Environ Sci Pollut Res 28, 23887–23895 (2021). https://doi.org/10.1007/s11356-020-11715-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-020-11715-x

Keywords

Search

Navigation