Anticipating the fate and impact of organic environmental contaminants: A new approach applied to the pharmaceutical furosemide

Chemosphere

Volumn 113, Issue , 2014, Pages 193-199

  Laurencé, Céline ^a   Rivard, Michael ^a   Martens, Thierry ^a   Morin, Christophe ^b   Buisson, Didier ^c   Bourcier, Sophie ^d   Sablier, Michel ^c,d   Oturan, Mehmet A ^e  

^a UNIVERSITÉ PARIS EST   (France)

^b UNIVERSITÉ PARIS EST CRÉTEIL   (France)

^c MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^d LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^e Université Paris Est UPEM   (France)

Author keywords

Bioconversion; Electro Fenton; Furosemide; Toxicity

Indexed keywords

BIOCONVERSION; CONTAMINATION; MOLECULES; TOXICITY;

ELECTRO-FENTON; ENVIRONMENTAL CONTAMINANT; ENVIRONMENTAL DETECTION; FUROSEMIDES; INFORMATION CONCERNING; MULTI-DISCIPLINARY APPROACH; TOXICOLOGICAL EVALUATION; TRANSFORMATION PRODUCTS;

ENVIRONMENTAL IMPACT;

FUROSEMIDE; PYRIDINIUM DERIVATIVE;

BIOTRANSFORMATION; DRUG; ECOTOXICOLOGY; ENVIRONMENTAL FATE; IDENTIFICATION METHOD; ORGANIC POLLUTANT; TOXICITY;

AGROBACTERIUM TUMEFACIENS; ARTHROBACTER; ARTICLE; ASPERGILLUS CANDIDUS; BIOTRANSFORMATION; CELL DEATH; CELL SURVIVAL; CELL VIABILITY; COLLISIONALLY ACTIVATED DISSOCIATION; COMPARATIVE STUDY; CONTROLLED STUDY; CUNNINGHAMELLA ECHINULATA; ELECTROLYSIS; ENVIRONMENTAL IMPACT; FENTON REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MINERALIZATION; MOLECULE; NONHUMAN; OXIDATION; OXIDATION KINETICS; POLLUTANT; POLLUTION; PROTON NUCLEAR MAGNETIC RESONANCE; TOXICOLOGY;

BIOCONVERSION; ELECTRO-FENTON; FUROSEMIDE; TOXICITY;

ANALYSIS OF VARIANCE; BACTERIA; BIOTRANSFORMATION; CASPASE 3; ECOTOXICOLOGY; ENVIRONMENTAL MONITORING; ENVIRONMENTAL POLLUTANTS; FUNGI; FUROSEMIDE; INTERDISCIPLINARY COMMUNICATION; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; SPECIES SPECIFICITY; TANDEM MASS SPECTROMETRY; TOXICITY TESTS;

EID: 84904638277     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2014.05.036     Document Type: Article

References (44)

1. Asha S., Vidyavathi M. Cunninghamella - a microbial model for drug metabolism studies - a review. Biotechnol. Adv. 2009, 27:16-29.
2. Azerad R. Microbial models for drug metabolism. Adv. Biochem. Eng. Biot. 1999, 63:169-218.
3. Besse J.-P., Garric J. Human pharmaceuticals in surface waters. Toxicol. Lett. 2008, 176:104-123.
4. Brillas E., Sires I., Oturan M.A. Electro-Fenton process and related electrochemical technologies based on Fenton's reaction chemistry. Chem. Rev. 2009, 109:6570-6631.
5. Buchberger W.W. Current approaches to trace analysis of pharmaceuticals and personal care products in the environment. J. Chromatogr. A 2011, 1218:603-618.
6. Castiglioni S., Bagnati R., Fanelli R., Pomati F., Calamari D., Zuccato E. Removal of pharmaceuticals in sewage treatment plants in Italy. Environ. Sci. Technol. 2006, 40:357-363.
7. Chen L.-J., Burka L.T. Chemical and enzymatic oxidation of furosemide: formation of pyridinium salts. Chem. Res. Toxicol. 2007, 20:1741-1744.
8. Daughton C.G. Environmental stewardship and drugs as pollutants. Lancet 2002, 360:1035-1036.
9. Daughton C.G., Ternes T.A. Pharmaceuticals and personal care products in the environment: agents of subtle change?. Environ. Health Perspect. Suppl. 1999, 107:907-938.
10. Deblonde T., Cossu-Leguille C., Hartemann P. Emerging pollutants in wastewater: a review of the literature. Int. J. Hyg. Environ. Health 2011, 214:442-448.
11. Dirany A., Sires I., Oturan N., Oturan M.A. Electrochemical abatement of the antibiotic sulfamethoxazole from water. Chemosphere 2010, 81:594-602.
12. Dirany A., Efremova-Aaron S., Oturan N., Sires I., Oturan M.A., Aaron J.J. Study of the toxicity of sulfamethoxazole and its degradation products in water by a bioluminescence method during application of the electro-Fenton treatment. Anal. Bioanal. Chem. 2011, 400:353-360.
13. Dirany A., Sires I., Oturan N., Ozcan A., Oturan M.A. Electrochemical wastewater treatment for antibiotic sulfachloropyridazine degradation: kinetics, reaction pathways, and toxicity evolution. Environ. Sci. Technol. 2012, 46:4074-4082.
14. Fatta-Kassinos D., Meric S., Nikolaou A. Pharmaceutical residues in environmental waters and wastewater: current state of knowledge and future research. Anal. Bioanal. Chem. 2011, 399:251-275.
15. Fatta-Kassinos D., Vasquez M.I., Kuemmerer K. 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 2011, 85:693-709.
16. Fromentin Y., Grellier P., Wansi J.D., Lallemand M.-C., Buisson D. Yeast-mediated xanthone synthesis through oxidative intramolecular cyclization. Org. Lett. 2012, 14:5054-5057.
17. Galluzzi L., Aaronson S.A., Abrams J., Alnemri E.S., Andrews D.W., Baehrecke E.H., Bazan N.G., Blagosklonny M.V., Blomgren K., Borner C., Bredesen D.E., Brenner C., Castedo M., Cidlowski J.A., Ciechanover A., Cohen G.M., De Laurenzi V., De Maria R., Deshmukh M., Dynlacht B.D., El-Deiry W.S., Flavell R.A., Fulda S., Garrido C., Golstein P., Gougeon M.L., Green D.R., Gronemeyer H., Hajnoczky G., Hardwick J.M., Hengartner M.O., Ichijo H., Jaattela M., Kepp O., Kimchi A., Klionsky D.J., Knight R.A., Kornbluth S., Kumar S., Levine B., Lipton S.A., Lugli E., Madeo F., Malorni W., Marine J.C.W., Martin S.J., Medema J.P., Mehlen P., Melino G., Moll U.M., Morselli E., Nagata S., Nicholson D.W., Nicotera P., Nunez G., Oren M., Penninger J., Pervaiz S., Peter M.E., Piacentini M., Prehn J.H.M., Puthalakath H., Rabinovich G.A., Rizzuto R., Rodrigues C.M.P., Rubinsztein D.C., Rudel T., Scorrano L., Simon H.U., Steller H., Tschopp J., Tsujimoto Y., Vandenabeele P., Vitale I., Vousden K.H., Youle R.J., Yuan J., Zhivotovsky B., Kroemer G. Guidelines for the use and interpretation of assays for monitoring cell death in higher eukaryotes. Cell Death Differ. 2009, 16:1093-1107.
18. Heberer T. Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. Toxicol. Lett. 2002, 131:5-17.
19. Henschel K.P., Wenzel A., Diedrich M., Fliedner A. Environmental hazard assessment of pharmaceuticals. Regul. Toxicol. Pharmacol. 1997, 25:220-225.
20. Hezari M., Davis P.J. Microbial models of mammalian metabolism. N-dealkylation of furosemide to yield the mammalian metabolite CSA using Cunninghamella elegans. Drug Metab. Dispos. 1992, 20:882-888.
21. Ibanez M., Sancho J.V., Pozo O.J., Hernandez F. Use of quadrupole time-of-flight mass spectrometry in environmental analysis: elucidation of transformation products of triazine herbicides in water after UV exposure. Anal. Chem. 2004, 76:1328-1335.
22. Joyeau R., Planchon M., Abessolo J., Aissa K., Bance C., Buisson D. Combinatorial approach to the selection of active microorganisms in biotransformation: application to sinomenine. J. Mol. Catal. B: Enzym. 2013, 85-86:65-70.
23. Jurado A., Vazquez-Sune E., Carrera J., Lopez de Alda M., Pujades E., Barcelo D. Emerging organic contaminants in groundwater in Spain: a review of sources, recent occurrence and fate in a European context. Sci. Total Environ. 2012, 440:82-94.
24. Khalaf H., Salste L., Karlsson P., Ivarsson P., Jass J., Olsson P.-E. In vitro analysis of inflammatory responses following environmental exposure to pharmaceuticals and inland waters. Sci. Total Environ. 2009, 407:1452-1460.
25. Khetan S.K., Collins T.J. Human pharmaceuticals in the aquatic environment: a challenge to green chemistry. Chem. Rev. 2007, 107:2319-2364.
26. Koopman F., Wierckx N., de Winde J.H., Ruijssenaars H.J. Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14. Proc. Natl. Acad. Sci. 2010, 107:4919-4924.
27. Kuemmerer K.E. Pharmaceuticals in the environment: sources, fate, effects and risks 2004, Springer GmbH, Berlin. second ed.
28. Laurence C., Rivard M., Lachaise I., Bensemhoun J., Martens T. Preparative access to transformation products (TPs) of furosemide: a versatile application of anodic oxidation. Tetrahedron 2011, 67:9518-9521.
29. Lee W.I., Yoon W.H., Shin W.G., Song I.S., Lee M.G. Pharmacokinetics and pharmacodynamics of furosemide after direct administration into the stomach or duodenum. Biopharm. Drug Dispos. 1997, 18:753-767.
30. Levi Y. Challenges in the assessment and management of health risks associated with emerging water micropollutants. Bull. Acad. Natl. Med. 2009, 193:1331-1344.
31. Li W., Josephs J.L., Skiles G.L., Humphreys W.G. Metabolite generation via microbial biotransformations with actinomycetes: rapid screening for active strains and biosynthesis of important human metabolites of two development-stage compounds, 5-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non7-yl-methyl]-3-thiophenecarboxylic acid (BMS-587101) and dasatinib. Drug Metab. Dispos. 2008, 36:721-730.
32. Marvalin C., Azerad R. Microbial production of phase I and phase II metabolites of propranolol. Xenobiotica 2011, 41:175-186.
33. Mondal S.C., Tripathi D.N., Vikram A., Ramarao P., Jena G.B. Furosemide-induced genotoxicity and cytotoxicity in the hepatocytes, but weak genotoxicity in the bone marrow cells of mice. Fundam. Clin. Pharmacol. 2012, 26:383-392.
34. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65:55-63.
35. Oturan M.A., Peiroten J., Chartrin P., Acher A.J. Complete destruction of p-nitrophenol in aqueous medium by electro-Fenton method. Environ. Sci. Technol. 2000, 34:3474-3479.
36. Özcan A., Sahin Y., Koparal A.S., Oturan M.A. Degradation of picloram by the electro-Fenton process. J. Hazard. Mater. 2008, 153:18-727.
37. Rakonczay Z., Hegyi P., Hasegawa M., Inoue M., You J., Iida A., Ignath I., Alton E.W.F.W., Griesenbach U., Ovari G., Vag J., Da Paula A.C., Crawford R.M., Varga G., Amaral M.D., Mehta A., Lonovics J., Argent B.E., Gray M.A. CFTR gene transfer to human cystic fibrosis pancreatic duct cells using a Sendai virus vector. J. Cell Physiol. 2008, 214:442-455.
38. Richardson S.D. Environmental mass spectrometry: emerging contaminants and current issues. Anal. Chem. 2010, 82:4742-4774.
39. Rocco L., Frenzilli G., Fusco D., Peluso C., Stingo V. Evaluation of zebrafish DNA integrity after exposure to pharmacological agents present in aquatic environments. Ecotoxicol. Environ. Saf. 2010, 73:1530-1536.
40. Rodil R., Quintana J.B., Concha-Grana E., Lopez-Mahia P., Muniategui-Lorenzo S., Prada-Rodriguez D. Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain). Chemosphere 2012, 86:1040-1049.
41. 2+ system in the electro-Fenton degradation of the antimicrobial chlorophene. Appl. Catal. B - Environ. 2007, 72:382-394.
42. 2-blockers. Studies on single and multicomponent synthetic aqueous solutions. Water Res. 2010, 44:109-3120.
43. Smith R.V., Rosazza J.P. Microbial models of mammalian metabolism. J. Pharm. Sci. 1975, 64:1737-1759.
44. Williams D.P., Antoine D.J., Butler P.J., Jones R., Randle L., Payne A., Howard M., Gardner I., Blagg J., Park B.K. The metabolism and toxicity of furosemide in the Wistar rat and CD-1 mouse: a chemical and biochemical definition of the toxicophore. J. Pharmacol. Exp. Ther. 2007, 322:1208-1220.