TiO2 photocatalytic degradation and transformation of oxazaphosphorine drugs in an aqueous environment

Journal of Hazardous Materials

Volumn 287, Issue , 2015, Pages 133-141

  Lai, Webber Wei Po ^a   Lin, Hank Hui Hsiang ^a   Lin, Angela Yu Chen ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Oxazaphosphorine drugs; Photocatalytic degradation; Titanium dioxide; Toxicity

Indexed keywords

CHEMICAL BONDS; CHLORINE COMPOUNDS; TITANIUM DIOXIDE; TOXICITY;

BOND BREAKING PROCESS; CHLORINATED BYPRODUCTS; DECOMPOSITION PROCESS; INITIAL CONCENTRATION; OXAZAPHOSPHORINE DRUGS; PHOTO CATALYTIC DEGRADATION; PHOTOCATALYTIC DEGRADATION PATHWAYS; PHOTOCATALYTIC OXIDATIONS;

BYPRODUCTS;

CYCLOPHOSPHAMIDE; IFOSFAMIDE; OXAZAPHOSPHORINE; TITANIUM DIOXIDE; TROFOSFAMIDE; TITANIUM; WASTE WATER; WATER POLLUTANT;

AQUEOUS SOLUTION; CATALYSIS; DECOMPOSITION; DRUG; ORGANIC COMPOUND; OXIDE; PHOTODEGRADATION; TOXICITY; TRANSFORMATION;

ACUTE TOXICITY; AQUATIC ENVIRONMENT; ARTICLE; DEAMINATION; DECHLORINATION; DRUG TRANSFORMATION; METABOLISM; OXIDATION; PH; PHOTOCATALYSIS; PHOTODEGRADATION; REACTION TIME; STATIC ELECTRICITY; SURFACE CHARGE; CHEMISTRY; EVALUATION STUDY; KINETICS; OXIDATION REDUCTION REACTION; PHOTOLYSIS; RADIATION RESPONSE; TOXICITY; TOXICITY TESTING; ULTRAVIOLET RADIATION; VIBRIO; WASTE WATER; WATER POLLUTANT;

CYCLOPHOSPHAMIDE; KINETICS; OXIDATION-REDUCTION; PHOTOLYSIS; TITANIUM; TOXICITY TESTS; ULTRAVIOLET RAYS; VIBRIO; WASTE WATER; WATER POLLUTANTS, CHEMICAL;

EID: 84922262071     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2015.01.045     Document Type: Article

References (62)

1. Carballa M., Omil F., Lema J.M. Comparison of predicted and measured concentrations of selected pharmaceuticals, fragrances and hormones in Spanish sewage. Chemosphere 2008, 72:1118-1123.
2. Halling-Sorensen B., Nielsen S.N., Lanzky P.F., Ingerslev F., Lutzhoft H.C.H., Jorgensen S.E. Occurrence, fate and effects of pharmaceutical substances in the environment - a review. Chemosphere 1998, 36:357-394.
3. Joss A., Andersen H., Ternes T., Richle P.R., Siegrist H. Removal of estrogens in municipal wastewater treatment under aerobic and anaerobic conditions: consequences for plant optimization. Environ. Sci. Technol. 2004, 38:3047-3055.
4. DeMeo M.P., Merono S., DeBaille A.D., Botta A., Laget M., Guiraud H., Dumenil G. Monitoring exposure of hospital personnel handling cytostatic drugs and contaminated materials. Int. Arch. Occup. Environ. Health 1995, 66:363-368.
5. Jackson M.A., Stack H.F., Waters M.D. Genetic activity profiles of anticancer drugs. Mutat. Res. 1996, 355:171-208.
6. Zounkova R., Odraska P., Dolezalova L., Hilscherova K., Marsalek B., Blaha L. Ecotoxicity and genotoxicity assessment of cytostatic pharmaceuticals. Environ. Toxicol. Chem. 2007, 26:2208-2214.
7. Boos J., Welslau U., Ritter J., Blaschke G., Schellong G. Urinary-excretion of the enantiomers of ifosfamide and its inactive metabolites in children. Cancer Chemother. Pharmcol. 1991, 28:455-460.
8. Kummerer K., StegerHartmann T., Meyer M. Biodegradability of the anti-tumour agent ifosfamide and its occurrence in hospital effluents and communal sewage. Water Res. 1997, 31:2705-2710.
9. Yin J., Shao B., Zhang J., Li K. A preliminary study on the occurrence of cytostatic drugs in hospital effluents in Beijing, China. Bull. Environ. Contam. Toxicol. 2010, 84:39-45.
10. Lin A.Y.C., Lin Y.C., Lee W.N. Prevalence and sunlight photolysis of controlled and chemotherapeutic drugs in aqueous environments. Environ. Pollut. 2014, 187:170-181.
11. Buerge I.J., Buser H.R., Poiger T., Muller M.D. Occurrence and fate of the cytostatic drugs cyclophosphamide and ifosfamide in wastewater and surface waters. Environ. Sci. Technol. 2006, 40:7242-7250.
12. Ternes T.A. Occurrence of drugs in German sewage treatment plants and rivers. Water Res. 1998, 32:3245-3260.
13. Busetti F., Linge K.L., Heitz A. Analysis of pharmaceuticals in indirect potable reuse systems using solid-phase extraction liquid chromatography-tandem mass spectrometry. J. Chromatogr. 2009, 1216:5807-5818.
14. J.F.Zhang V.W.C., Chang A., Giannis J.Y.Wang Removal of cytostatic drugs from aquatic environment: a review. Sci. Total Environ. 2013, 445:281-298.
15. StegerHartmann T., Kummerer K., Hartmann A. Biological degradation of cyclophosphamide and its occurrence in sewage water. Ecotoxicol. Environ. Saf. 1997, 36:174-179.
16. Gomez-Canela C., Cortes-Francisco N., Oliva X., Pujol C., Ventura F., Lacorte S., Caixach J. Occurrence of cyclophosphamide and epirubicin in wastewaters by direct injection analysis-liquid chromatography-high-resolution mass spectrometry. Environ. Sci. Pollut. R 2012, 19:3210-3218.
17. Moldovan Z. Occurrences of pharmaceutical and personal care products as micropollutants in rivers from Romania. Chemosphere 2006, 64:1808-1817.
18. Martin J., Camacho-Munoz D., Santos J.L., Aparicio I., Alonso E. Simultaneous determination of a selected group of cytostatic drugs in water using high-performance liquid chromatography-triple-quadrupole mass spectrometry. J. Sep. Sci. 2011, 34:3166-3177.
19. Kerbusch T., de Kraker J., Keizer H.J., van Putten J.W.G., Groen H.J.M., Jansen R.L.H., Schellens J.H.M., Beijnen J.H. Clinical pharmacokinetics and pharmacodynamics of ifosfamide and its metabolites. Clin. Pharmacokinet. 2001, 40:41-62.
20. Fleming R.A. An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy 1997, 17:S146-S154.
21. Mohrmann M., Ansorge S., Schmich U., Schonfeld B., Brandis M. Toxicity of ifosfamide, cyclophosphamide and their metabolites in renal tubular cells in culture. Pediatr. Nephrol. 1994, 8:157-163.
22. Bus J.S., Gibson J.E. Teratogenicity and neonatal toxicity of ifosfamide in mice. Proc. Soc. Exp. Biol. Med. 1973, 143:965-970.
23. Murthy V.V., Becker B.A., Steele W.J. Effects of dosage, phenobarbital, and 2-diethylaminoethyl-2 2-diphenylvalerate on binding of cyclophosphamide and-or its metabolites to DNA RNA and protein of embryo and liver in pregnant mice. Cancer Res. 1973, 33:664-670.
24. Mohn G.R., Ellenberger J. Genetic effects of cyclophosphamide, ifosfamide and trofosfamide. Mutat. Res. 1976, 32:331-360.
25. Reichardt P., Pink D., Tilgner J., Kretzschmar A., Thuss-Patience P.C., Dorken B. Oral trofosfamide: an active and well-tolerated maintenance therapy for adult patients with advanced bone and soft tissue sarcomas. Results of a retrospective analysis. Onkologie 2002, 25:541-546.
26. Horvath V., Hartlapp J.H., Hegewisch-Becker S., Feyerabend T., von Weikersthal L.F., Illiger H.J., Jager E., Peters S.O., Reichardt P., Uthgenannt D., Weber K., Wagner T., Wiedemann G.J., Zschaber R. Oral trofosfamide in elderly and/or heavily pretreated patients with metastatic lung cancer. Onkologie 2000, 23:341-344.
27. StegerHartmann T., Kummerer K., Schecker J. Trace analysis of the antineoplastics ifosfamide and cyclophosphamide in sewage water by two-step solid-phase extraction and gas chromatography mass spectrometry. J. Chromatogr. A 1996, 726:179-184.
28. Ternes T.A., Bonerz M., Herrmann N., Loffler D., Keller E., Lacida B.B., Alder A.C. Determination of pharmaceuticals, iodinated contrast media and musk fragrances in sludge by LC/tandem MS and GC/MS. J. Chromatogr. A 2005, 1067:213-223.
29. 2 suspensions: identification of intermediates and reaction pathways. J. Hazard. Mater. 2009, 168:94-101.
30. 2 and ZnO suspensions. Catal. Today 2009, 144:100-105.
31. Yang H., Li G.Y., An T.C., Gao Y.P., Fu J.M. Photocatalytic degradation kinetics and mechanism of environmental pharmaceuticals in aqueous suspension of TiO(2): a case of sulfa drugs. Catal. Today 2010, 153:200-207.
32. Moctezuma E., Leyva E., Aguilar C.A., Luna R.A., Montalvo C. Photocatalytic degradation of paracetamol: intermediates and total reaction mechanism. J. Hazard. Mater. 2012, 243:130-138.
33. Postigo C., Sirtori C., Oller I., Malato S., Maldonado M.I., de Alda M.L., Barcelo D. Photolytic and photocatalytic transformation of methadone in aqueous solutions under solar irradiation: kinetics, characterization of major intermediate products and toxicity evaluation. Water Res. 2011, 45:4815-4826.
34. Postigo C., Sirtori C., Oller I., Malato S., Maldonado M.I., de Alda M.L., Barcelo D. Solar transformation and photocatalytic treatment of cocaine in water: kinetics, characterization of major intermediate products and toxicity evaluation. Appl. Catal. B: Environ. 2011, 104:37-48.
35. 2 in an aqueous environment. Water Res. 2014, 48:559-568.
36. Herrmann J.M. Heterogeneous photocatalysis: fundamentals and applications to the removal of various types of aqueous pollutants. Catal. Today 1999, 53:115-129.
37. Gad-Allah T.A., Ali M.E.M., Badawy M.I. Photocatalytic oxidation of ciprofloxacin under simulated sunlight. J. Hazard. Mater. 2011, 186:751-755.
38. Ahmed S., Rasul M.G., Martens W.N., Brown R., Hashib M.A. Advances in heterogeneous photocatalytic degradation of phenols and dyes in wastewater: a review. Water Air Soil Pollut. 2011, 215:3-29.
39. So C.M., Cheng M.Y., Yu J.C., Wong P.K. Degradation of azo dye procion red MX-5B by photocatalytic oxidation. Chemosphere 2002, 46:905-912.
40. Chong M.N., Jin B., Chow C.W.K., Saint C. Recent developments in photocatalytic water treatment technology: a review. Water Res. 2010, 44:2997-3027.
41. 2 materials - determination of intermediates and reaction pathways. Water Res. 2004, 38:955-964.
42. Dalrymple O.K., Yeh D.H., Trotz M.A. Removing pharmaceuticals and endocrine-disrupting compounds from wastewater by photocatalysis. J. Chem. Technol. Biotechnol. 2007, 82:121-134.
43. Mahoney B.P., Raghunand N., Baggett B., Gillies R.J. Tumor acidity, ion trapping and chemotherapeutics I. Acid pH affects the distribution of chemotherapeutic agents in vitro. Biochem. Pharmacol. 2003, 66:1207-1218.
44. Tizaoui C., Mezughi K., Bickley R. Heterogeneous photocatalytic removal of the herbicide clopyralid and its comparison with UV/H(2)O(2) and ozone oxidation techniques. Desalination 2011, 273:197-204.
45. Rao A.N., Sivasankar B., Sadasivam V. Kinetic study on the photocatalytic degradation of salicylic acid using ZnO catalyst. J. Hazard. Mater. 2009, 166:1357-1361.
46. 2 photocatalysis. Water Res. 2008, 42:3480-3488.
47. Buxton G.V., Greenstock C.L., Helman W.P., Ross A.B. Critical-review of rate constants for reactions of hydrated electrons, hydrogen-atoms and hydroxyl radicals (Oh/O) in aqueous-solution. J. Phys. Chem. Ref. Data 1988, 17:513-886.
48. 2-assisted photocatalytic process. Appl. Catal. A-Gen. 2006, 301:152-157.
49. 2 surface characteristic in UV-illuminated photodegradation of Acid Orange 7. J. Photochem Photobiol. A 2005, 172:47-54.
50. Minero C., Mariella G., Maurino V., Vione D., Pelizzetti E. Photocatalytic transformation of organic compounds in the presence of inorganic ions. 2. Competitive reactions of phenol and alcohols an a titanium dioxide-fluoride system. Langmuir 2000, 16:8964-8972.
51. Carraway E.R., Hoffman A.J., Hoffmann M.R. Photocatalytic oxidation of organic-acids on quantum-Sized semiconductor colloids. Environ. Sci. Technol. 1994, 28:786-793.
52. Boos J., Kupker F., Blaschke G., Jurgens H. Trofosfamide metabolism in different species-ifosfamide is the predominant metabolite. Cancer Chemother. Pharmacol. 1993, 33:71-76.
53. Yule S.M., Boddy A.V., Cole M., Price L., Wyllie R., Tasso M.J., Pearson A.D.J., Idle J.R. Cyclophosphamide metabolism in children. Cancer Res. 1995, 55:803-809.
54. Hadidi A.H.F.A., Coulter C.E.A., Idle J.R. Phenotypically deficient urinary elimination of carboxyphosphamide after cyclophosphamide administration to cancer-patients. Cancer Res. 1988, 48:5167-5171.
55. Struck R.F., Kirk M.C., Mellett L.B., el Dareer S., Hill D.L. Urinary metabolites of the antitumor agent cyclophosphamide. Mol. Pharmacol. 1971, 7:519-529.
56. Voelcker G., Wagner T., Hohorst H.J. Identification and pharmacokinetics of cyclophosphamide (nsc-26271) metabolites invivo. Cancer Treat Rep. 1976, 60:415-422.
57. 2 suspensions. Appl. Catal. B-Environ. 2006, 67:197-205.
58. 2. Water Res. 2013, 47:2041-2049.
59. Choi J., Lee H., Choi Y., Kim S., Lee S., Lee S., Choi W., Lee J. Heterogeneous photocatalytic treatment of pharmaceutical micropollutants: effects of wastewater effluent matrix and catalyst modifications. Appl. Catal. B-Environ. 2014, 147:8-16.
60. Doll T.E., Frimmel F.H. Photocatalytic degradation of carbamazepine, clofibric acid and iomeprol with P25 and Hombikat UV100 in the presence of natural organic matter (NOM) and other organic water constituents. Water Res. 2005, 39:403-411.
61. Epling G.A., Lin C. Investigation of retardation effects on the titanium dioxide photodegradation system. Chemosphere 2002, 46:937-944.
62. 2 photocatalyst. Water Res. 2011, 45:3787-3796.