Skip to main content
SpringerLink
Log in

Application of Fenton, photo-Fenton, solar photo-Fenton, and UV/H2O2 to degradation of the antineoplastic agent mitoxantrone and toxicological evaluation

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

In the present study, selected advanced oxidation processes (AOPs)—namely, photo-Fenton (with Fe2+, Fe3+, and potassium ferrioxalate—FeOx—as iron sources), solar photo-Fenton, Fenton, and UV/H2O2—were investigated for degradation of the antineoplastic drug mitoxantrone (MTX), frequently used to treat metastatic breast cancer, skin cancer, and acute leukemia. The results showed that photo-Fenton processes employing Fe(III) and FeOx and the UV/H2O2 process were most efficient for mineralizing MTX, with 77, 82, and 90 % of total organic carbon removal, respectively. MTX probably forms a complex with Fe(III), as demonstrated by voltammetric and spectrophotometric measurements. Spectrophotometric titrations suggested that the complex has a 2:1 Fe3+:MTX stoichiometric ratio and a complexation constant (K) of 1.47 × 104 M–1, indicating high MTX affinity for Fe3+. Complexation partially inhibits the involvement of iron ions and hence the degradation of MTX during photo-Fenton. The UV/H2O2 process is usually slower than the photo-Fenton process, but, in this study, the UV/H2O2 process proved to be more efficient due to complexing of MTX with Fe(III). The drug exhibited no cytotoxicity against NIH/3T3 mouse embryonic fibroblast cells when oxidized by UV/H2O2 or by UV/H2O2/FeOx at the concentrations tested.

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
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  • Alberts DS, Peng Y-M, Leigh S, Davis TP, Woodward DL (1985) Disposition of mitoxantrone in cancer patients. Cancer Res 45:1879–1884

    CAS  Google Scholar 

  • American Public Health Association (APHA) (1999) Method 3500-Fe B, phenanthroline method. In: Standard methods for the examination of water and wastewater, 21st edn. American Publish Health Association, Washington, pp 124–130

    Google Scholar 

  • Batista APS, Nogueira RFP (2012) Parameters affecting sulfonamide photo-Fenton degradation—iron complexation and substituent group. J Photochem Photobiol A 232:8–13

    Article  CAS  Google Scholar 

  • Besse J-P, Latour J-F, Garric J (2012) Anticancer drugs in surface waters. What can we say about the occurrence and environmental significance of cytotoxic, cytostatic and endocrine therapy drugs? Environ Int 39:73–86

    Article  CAS  Google Scholar 

  • Bogo D, Matos MFC, Honda NK, Pontes ERJC, Oguma PM, Santos ECS, Carvalho JE, Nomizo A (2010) In vitro antitumour activity of orsellinates. Zeitschrift für Naturforschung. CA J Bioscience 65:43–48

    CAS  Google Scholar 

  • Bolton JR (1995) The photochemical conversion and storage of solar energy: an historical perspective. Solar Energ Mat Solar C 38:543–554

    Article  CAS  Google Scholar 

  • Braun AM, Maurette MT, Oliveiros E (1991) Photochemical technology chischester. Wiley, New York

    Google Scholar 

  • Brett AMO, Macedo TRA, Raimundo D, Marques MH, Serrano SHP (1999) Electrochemical oxidation of mitoxantrone at a glassy carbon electrode. Anal Chim Acta 385:401–408

    Article  Google Scholar 

  • Calvert JG, Pitts JN (1966) Photochemistry. Wiley, New York

    Google Scholar 

  • Carneiro PA, Nogueira RFP, Zanoni MV (2007) Homogeneous photodegradation of C.I. Reactive Blue 4 using a photo-Fenton process under artificial and solar irradiation. Dyes Pigments 74:127–132

    Article  CAS  Google Scholar 

  • Dyke PH, Foan C, Fredler H (2003) PCB and PAH releases from power stations and waste incineration processes in the UK. Chemosphere 50:469–480

    Article  CAS  Google Scholar 

  • Enache M, Bendic C, Volanschi E (2008) Spectroelectrochemistry of the redox activation of anti-cancer drug mitoxantrone. Bioelectrochemistry 72:10–20

    Article  CAS  Google Scholar 

  • Fiallo MML, Garnier-Suillerot A, Matzanke B, Kozlowski H (1999) How Fe3+ binds anthracycline antitumor compounds. The myth and the reality of a chemical sphinx. J Inorg Biochem 75:105–115

    Article  CAS  Google Scholar 

  • Gaya UI, Abdullah AH (2008) Heterogeneous photocatalytic degradation of organic contaminants over titanium dioxide: a review of fundamentals, progress and problems. J Photoch Photobio C 9:1–12

    Article  CAS  Google Scholar 

  • Gebhardt W, Schröder HF (2007) Liquid chromatography–(tandem) mass spectrometry for the follow-up of the elimination of persistent pharmaceuticals during wastewater treatment applying biological wastewater treatment and advanced oxidation. J Chromatogr A 1160:34–43

    Article  CAS  Google Scholar 

  • Ghaly MY, Hartel G, Mayer R, Haseneder R (2001) Photochemical oxidation of p-chlorophenol by UV/H2O2 and photo-Fenton process. A comparative study. Waste Manage 21:41–47

    Article  CAS  Google Scholar 

  • Gogate PR, Pandit AB (2004) A review of imperative technologies for wastewater treatment I: oxidation technologies at ambient conditions. Adv Environ Res 8:501–551

    Article  CAS  Google Scholar 

  • Golabi SM, Hassan-Zadeh V (1996) Polarographic determination of mitoxantrone in pharmaceutical preparations and biological media. Talanta 43:397–406

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Herman EH, Zhang J, Hasinoff BB, Clark JR Jr, Ferrans VJ (1997) Comparison of the structural changes induced by doxorubicin and mitoxantrone in the heart, kidney and intestine and characterization of the Fe(III)–mitoxantrone complex. J Mol Cell Cardiol 29:2415–2430

    Article  CAS  Google Scholar 

  • Kim I, Yamashita N, Tanaka H (2009) Photodegradation of pharmaceuticals and personal care products during UV and UV/H2O2 treatments. Chemosphere 77:518–525

    Article  CAS  Google Scholar 

  • Kümmerer K (2001) Drugs in the environment: emission of drugs, diagnostic aids and disinfectants into wastewater by hospitals in relation to other sources—a review. Chemosphere 45:957–969

    Article  Google Scholar 

  • Lee CC, Huffman GL (1996) Medical waste management/incineration. J Hazard Mater 48:1–30

    Article  CAS  Google Scholar 

  • Legrini O, Oliveros E, Braun AM (1993) Photochemical processes for water-treatment. Chem Rev 93:671–698

    Article  CAS  Google Scholar 

  • Li N, Yang X (2005) Promoted electron transfer of mitoxantrone binding with DNA by cytochrome c. Biochem Bioph Res Co 331:947–952

    Article  CAS  Google Scholar 

  • Li N, Maa Y, Yanga C, Guoc L, Yanga X (2005) Interaction of anticancer drug mitoxantrone with DNA analysed by electrochemical and spectroscopic methods. Biophys Chem 116:199–205

    Article  CAS  Google Scholar 

  • Machulek A Jr, Gogritcchiani E, Moraes JEF, Quina FH, Braun AM, Oliveros E (2009a) Kinetic and mechanistic investigation of the ozonolysis of 2,4-xylidine (2,4-dimethyl-aniline) in acid aqueous solution. Sep Purif Technol 67:141–148

    Article  CAS  Google Scholar 

  • Machulek A Jr, Moraes JEF, Okano LT, Silvério CA, Quina FH (2009b) Photolysis of ferric ion in the presence of sulfate or chloride ions: implications for the photo-Fenton process. Photochem Photobiol Sci 8:985–991

    Article  CAS  Google Scholar 

  • Micheletti AC, Honda NK, Lima DP, Beatriz A, Santana MR, Carvalho NCP, Matos MFC, Queiróz LMM, Bogo D, Zorzattto JR (2011) Chemical modifications of a natural xanthone and antimicrobial activity against multidrug resistant Staphylococcus aureus and cytotoxicity against human tumor cell lines. Quim Nova 34:1014–1020

    Article  CAS  Google Scholar 

  • Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Mayo J, Boyd M (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer I 83:757–766

    Article  CAS  Google Scholar 

  • National Cancer Institute (Inca). Brazil: Ministério da Saúde. INC; c1996-2011 Available from: http://www.inca.org.br/. Accessed 20 November 2011 (in Portuguese).

  • Neyens E, Baeyens J (2003) A review of classic Fenton’s peroxidation as an advanced oxidation technique. J Hazard Mater B98:33–50

    Article  Google Scholar 

  • Nogueira RFP, Oliveira MC, Paterlini WC (2005) Simple and fast spectrophotometric determination of H2O2 in photo-Fenton reactions using metavanadate. Talanta 66:86–91

    Article  CAS  Google Scholar 

  • Nussbaumer S, Bonnabry P, Veuthey J-L, Fleury-Souverain S (2011) Analysis of anticancer drugs: a review. Talanta 85:2265–2289

    Article  CAS  Google Scholar 

  • Ocampo-Pérez R, Sanchez-Polo M, Rivera-Utrilla J, Leyva-Ramos R (2010) Degradation of antineoplastic cytarabine in aqueous phase by advanced oxidation processes based on ultraviolet radiation. J Chem Eng 165:581–588

    Article  Google Scholar 

  • Osugi ME, Rajeshwar K, Ferraz ERA, Oliveira DP, Araújo ÂR, Zanoni MVB (2009) Comparison of oxidation efficiency of disperse dyes by chemical and photoelectrocatalytic chlorination and removal of mutagenic activity. Electrochim Acta 54:2086–2093

    Article  CAS  Google Scholar 

  • Pereira AV, Valus N, Beltrame FL, Garrido LH (2011) Determination of iron (III) in pharmaceutical products by photometric titration. Acta Sci Health Sci 33:65–70 (in Portuguese)

    Article  CAS  Google Scholar 

  • Pérez-Moya M, Graells M, Castells G, Amigó J, Ortega E, Buhigas G, Pérez LM, Mansilla HD (2010) Characterization of the degradation performance of the sulfamethazine antibiotic by photo-Fenton process. Water Res 44:2533–2540

    Article  Google Scholar 

  • Pignatello JJ, Oliveros E, Mackay A (2006) Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry. Crit Rev Env Sci Tec 36:1-84. Errata (2007) Crit Rev Env Sci Tec 37:273-275.

    Google Scholar 

  • Rajeshwar K, Osugi ME, Chanmanee W, Chenthamarakshan CR, Zanoni MVB, Kajitvichyanukul P, Krishnan-Ayer R (2008) Heterogeneous photocatalytic treatment of organic dyes in air and aqueous media. J Photoch Photobio C 9:171–192

    Article  CAS  Google Scholar 

  • Safarzadeh-Amiri A, Bolton JR, Cater JR (1997) Ferrioxalate-mediated photodegradation of organic pollutants in contaminated water. Water Res 31:787–798

    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 

  • Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer drug screening. J Nat Cancer Inst 82:1107–1112

    Article  CAS  Google Scholar 

  • Turci R, Sottani C, Schierl R, Minoia C (2006) Validation protocol and analytical quality in biological monitoring of occupational exposure to antineoplastic drugs. Toxicol Lett 162:256–262

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors wish to thank the Brazilian funding agencies CNPq, CAPES, and FUNDECT for their financial support. A.M. Jr. is associated with NAP-PhotoTech, the USP Research Consortium for Photochemical Technology, and INCT-EMA. The authors also wish to thank the Hospital Regional, in Campo Grande, Mato Grosso do Sul (Brazil), for the generous donation of mitoxantrone.

Author information

Authors and Affiliations

  1. Centro de Ciências Exatas e Tecnologia (CCET), Universidade Federal de Mato Grosso do Sul, Av. Senador Filinto Muller, 1555, CP 549, Campo Grande, MS, 79074-460, Brazil

    Rodrigo Pereira Cavalcante, Lucas da Rocha Sandim, Antônio Marcos Jacques Barbosa, Marly Eiko Osugi, Silvio Cesar de Oliveira, Amilcar Machulek Jr & Valdir Souza Ferreira

  2. Centro de Ciências Biológicas e da Saúde (CCBS), Universidade Federal de Mato Grosso do Sul, Cidade Universitária, CP 549, Campo Grande, MS, 79070-900, Brazil

    Danielle Bogo & Maria de Fatima Cepa Matos

  3. Laboratório Central de Saúde Pública do Estado de Mato Grosso do Sul (LACEN-MS), Av. Senador Filinto Muller, 1666, Campo Grande, MS, 79074-460, Brazil

    Antônio Marcos Jacques Barbosa

  4. Universidade Federal de Mato Grosso do Sul, Ant. Estrada para Fazenda Campo Bom, CP 112, Chapadão do Sul, MS, 79560-000, Brazil

    Matildes Blanco

Authors
  1. Rodrigo Pereira Cavalcante
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lucas da Rocha Sandim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Danielle Bogo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Antônio Marcos Jacques Barbosa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Marly Eiko Osugi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Matildes Blanco
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Silvio Cesar de Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Maria de Fatima Cepa Matos
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Amilcar Machulek Jr
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Valdir Souza Ferreira
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marly Eiko Osugi.

Additional information

Responsible editor: Philippe Garrigues

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cavalcante, R.P., da Rocha Sandim, L., Bogo, D. et al. Application of Fenton, photo-Fenton, solar photo-Fenton, and UV/H2O2 to degradation of the antineoplastic agent mitoxantrone and toxicological evaluation. Environ Sci Pollut Res 20, 2352–2361 (2013). https://doi.org/10.1007/s11356-012-1110-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-012-1110-y

Keywords

Search

Navigation