Chiral pharmaceuticals in the environment

Environmental Chemistry Letters

Volumn 10, Issue 3, 2012, Pages 239-253

  Ribeiro, Ana R ^a,b,c   Castro, Paula M L ^b   Tiritan, Maria E ^a,c  

^a UNIVERSITY INSTITUTE OF HEALTH SCIENCES IUCS   (Portugal)

^b UNIVERSIDADE CATÓLICA PORTUGUESA   (Portugal)

^c UNIVERSITY OF PORTO   (Portugal)

Author keywords

Biodegradation; Chiral pharmaceuticals; Chiral stationary phases; Ecotoxicity; Enantiomeric fraction; Enantioselectivity

Indexed keywords

AQUATIC ORGANISMS; BIODEGRADATION; ENANTIOSELECTIVITY; STEREOCHEMISTRY; TOXICITY;

ANALYTICAL METHOD; BIODEGRADATION PROCESS; CHIRAL PHARMACEUTICALS; CHIRAL STATIONARY PHASE; ECOTOXICITY; ENANTIOMERIC FRACTIONS; ENVIRONMENTAL MATRIXES; PHYSICAL AND CHEMICAL PROPERTIES; SINGLE ENANTIOMERS; SPATIAL CONFIGURATION;

ENANTIOMERS;

EID: 84865439253     PISSN: 16103653     EISSN: 16103661     Source Type: Journal    
DOI: 10.1007/s10311-011-0352-0     Document Type: Review

References (137)

1. Aboul-Enein HY, Ali I (2004) Analysis of the chiral pollutants by chromatography. Toxicol Environ Chem 86(1): 1-22.
2. Ali I, Singh P, Aboul-Enein HY, Sharma B (2009) Chiral analysis of ibuprofen residues in water and sediment. Anal Lett 42(12): 1747-1760.
3. Andersson ME, Aslan D, Clarke A, Roeraade J, Hagman G (2003) Evaluation of generic chiral liquid chromatography screens for pharmaceutical analysis. J Chromatogr A 1005(1-2): 83-101.
4. Ates H, Mangelings D, Vander Heyden Y (2008) Chiral separations in polar organic solvent chromatography: updating a screening strategy with new chlorine-containing polysaccharide-based selectors. J Chromatogr B 875(1): 57-64.
5. Barclay VKH, Tyrefors NL, Johansson IM, Pettersson CE (2011) Trace analysis of fluoxetine and its metabolite norfluoxetine. Part I: development of a chiral liquid chromatography-tandem mass spectrometry method for wastewater samples. J Chromatogr A 1218(33): 5587-5596.
6. Barreiro JC, Vanzolini KL, Madureira TV, Tiritan ME, Cass QB (2010) A column-switching method for quantification of the enantiomers of omeprazole in native matrices of waste and estuarine water samples. Talanta 82(1): 384-391.
7. Barreiro JC, Vanzolini KL, Cass QB (2011) Direct injection of native aqueous matrices by achiral-chiral chromatography ion trap mass spectrometry for simultaneous quantification of pantoprazole and lansoprazole enantiomers fractions. J Chromatogr A 1218(20): 2865-2870.
8. Bartholow M (2010) Top 200 prescription drugs of 2009. Retrieved 27 May 2010.
9. Benotti MJ, Brownawell BJ (2009) Microbial degradation of pharmaceuticals in estuarine and coastal seawater. Environ Pollut 157(3): 994-1002.
10. Benotti MJ, Trenholm RA, Vanderford BJ, Holady JC, Stanford BD, Snyder SA (2009) Pharmaceuticals and endocrine disrupting compounds in U. S. drinking water. Environ Sci Technol 43(3): 597-603.
11. Bhushan R, Martens J (1997) Direct resolution of enantiomers by impregnated TLC. Biomed Chromatogr 11(5): 280-285.
12. Bojarski J (2002) Stereoselective chromatography of cardiovascular drugs: an update. J Biochem Biophys Methods 54(1-3): 197-220.
13. Brooks BW, Turner PK, Stanley JK, Weston JJ, Glidewell EA, Foran CM, Slattery M, La Point TW, Huggett DB (2003) Waterborne and sediment toxicity of fluoxetine to select organisms. Chemosphere 52(1): 135-142.
14. Brooks BW, Chambliss CK, Stanley JK, Ramirez A, Banks KE, Johnson RD, Lewis RJ (2005) Determination of select antidepressants in fish from an effluent-dominated stream. Environ Toxicol Chem 24(2): 464-469.
15. Buser H-R, Poiger T, Muller MD (1999) Occurrence and environmental behavior of the chiral pharmaceutical drug ibuprofen in surface waters and in wastewater. Environ Sci Technol 33(15): 2529-2535.
16. Calisto V, Esteves VI (2009) Psychiatric pharmaceuticals in the environment. Chemosphere 77(10): 1257-1274.
17. Campo VL, Bernardes LSC, Carvalho I (2009) Stereoselectivity in drug metabolism: molecular mechanisms and analytical methods. Curr Drug Metab 10(2): 188-205.
18. Caner H, Groner E, Levy L, Agranat I (2004) Trends in the development of chiral drugs. Drug Discov Today 9(3): 105-110.
19. Carvalho PO, Cass QB, Calafatti SA, Contesini FJ, Bizaco R (2006) Review-alternatives for the separation of drug enantiomers: ibuprofen as a model compound. Braz J Chem Eng 23(3): 291-300.
20. Cass QB, Batigalhia F (2003) Enantiomeric resolution of a series of chiral sulfoxides by high-performance liquid chromatography on polysaccharide-based columns with multimodal elution. J Chromatogr A 987(1-2): 445-452.
21. Cass QB, Degani ALG, Cassiano NM (2003) Effects on enantioselectivity by the use of polysaccharide-based columns by multimodal elution. J Liq Chromatogr Relat Technol 26(13): 2083-2101.
22. Chen C-Y, Shieh W-R, Chen C-S (1992) Clinical implications of using racemic drugs. Clin Res Regul Aff 9(4): 247-259.
23. Choonara IA, Haynes BP, Cholerton S, Breckenridge AM, Park BK (1986) Enantiomers of warfarin and vitamin K1 metabolism. Br J Clin Pharmacol 22(6): 729-732.
24. Christen V, Hickmannb S, Rechenbergb B, Fent K (2010) Highly active human pharmaceuticals in aquatic systems: a concept for their identification based on their mode of action. Aquat Toxicol 96(3): 167-181.
25. Cleuvers M (2004) Mixture toxicity of the anti-inflammatory drugs diclofenac, ibuprofen, naproxen, and acetylsalicylic acid. Ecotoxicol Environ Saf 59(3): 309-315.
26. Cleuvers M (2005) Initial risk assessment for three β-blockers found in the aquatic environment. Chemosphere 59(2): 199-205.
27. Cooper MJ, Anders MW (1974) Metabolic and pharmacodynamic interactions of enantiomers of propoxyphene and methorphan. Life Sci 15(9): 1665-1672.
28. Cordato DJ, Mather LE, Herkes GK (2003) Stereochemistry in clinical medicine: a neurological perspective. J Clin Neurosci 10(6): 649-654.
29. De Andrés F, Castañeda G, Ríos Á (2009) Use of toxicity assays for enantiomeric discrimination of pharmaceutical substances. Chirality 21(8): 751-759.
30. Díaz-Cruz MS, García-Galán MJ, Barceló D (2008) Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography-quadrupole linear ion trap-mass spectrometry. J Chromatogr A 1193(1-2): 50-59.
31. Eljarrat E, Guerra P, Barceló D (2008) Enantiomeric determination of chiral persistent organic pollutants and their metabolites. TrAC Trends Anal Chem 27(10): 847-861.
32. Farré M, Gros M, Hernández B, Petrovic M, Hancock P, Barceló D (2008) Analysis of biologically active compounds in water by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 22(1): 41-51.
33. Feitosa-Felizzola J, Temime B, Chiron S (2007) Evaluating on-line solid-phase extraction coupled to liquid chromatography-ion trap mass spectrometry for reliable quantification and confirmation of several classes of antibiotics in urban wastewaters. J Chromatogr A 1164(1-2): 95-104.
34. Fent K, Weston AA, Caminada D (2006) Ecotoxicology of human pharmaceuticals. Aquat Toxicol 76(2): 122-159.
35. Fernández C, González-Doncel M, Pro J, Carbonell G, Tarazona JV (2010) Occurrence of pharmaceutically active compounds in surface waters of the henares-jarama-tajo river system (madrid, spain) and a potential risk characterization. Sci Total Environ 408(3): 543-551.
36. Flaherty CM, Dodson SI (2005) Effects of pharmaceuticals on Daphnia survival, growth, and reproduction. Chemosphere 61(2): 200-207.
37. Flippin JL, Huggett D, Foran CM (2007) Changes in the timing of reproduction following chronic exposure to ibuprofen in Japanese medaka, Oryzias latipes. Aquat Toxicol 81(1): 73-78.
38. Fong PP (1998) Zebra mussel spawning is induced in low concentrations of putative serotonin reuptake inhibitors. Biol Bull 194: 143-149.
39. Fong PP, Molnar N (2008) Norfluoxetine induces spawning and parturition in estuarine and freshwater bivalves. Bull Environ Contam Toxicol 81(6): 535-538.
40. Fono LJ, Sedlak DL (2005) Use of the chiral pharmaceutical propranolol to identify sewage discharges into surface waters. Environ Sci Technol 39(23): 9244-9252.
41. Fono LJ, Kolodziej EP, Sedlak DL (2006) Attenuation of wastewater-derived contaminants in an effluent-dominated river. Environ Sci Technol 40(23): 7257-7262.
42. Foran CM, Weston J, Slattery M, Brooks BW, Huggett DB (2004) Reproductive assessment of Japanese medaka (Oryzias latipes) following a four-week fluoxetine (SSRI) exposure. Arch Environ Contam Toxicol 46(4): 511-517.
43. Francotte E (2009) Enantioselective chromatography: from its emergence to its successful implementation in the pharmaceutical environment. CHIMIA Int J Chem 63: 867-871.
44. Franz PM, Anliker SL, Callaghan JT, DeSante KA, Dhahir PH, Nelson RL, Rubin A (1990) Disposition in humans of racemic picenadol, an opioid analgesic. Drug Metab Dispos 18(6): 968-973.
45. Giltrow E, Eccles PD, Hutchinson TH, Sumpter JP, Rand-Weaver M (2011) Characterisation and expression of β1-, β2- and β3-adrenergic receptors in the fathead minnow (Pimephales promelas). Gen Comp Endocrinol 173(3): 483-490.
46. Gonçalves RF, Lauretti GR, Mattos AL (2003) Comparative study between 0. 5% bupivacaine and 0. 5% enantiomeric mixture of bupivacaine (S75-R25) in epidural anesthesia. Rev Bras Anestesiol 53(2): 169-176.
47. González S, Petrovic M, Barceló D (2007) Advanced liquid chromatography-mass spectrometry (LC-MS) methods applied to wastewater removal and the fate of surfactants in the environment. TrAC Trends Anal Chem 26(2): 116-124.
48. Görög S (2007) The changing face of pharmaceutical analysis. TrAC Trends Anal Chem 26(1): 12-17.
49. Gros M, Petrovic M, Barceló D (2006) Development of a multi-residue analytical methodology based on liquid chromatography-tandem mass spectrometry (LC-MS/MS) for screening and trace level determination of pharmaceuticals in surface and wastewaters. Talanta 70(4): 678-690.
50. Ha PTT, Hoogmartens J, van Schepdael A (2006) Recent advances in pharmaceutical applications of chiral capillary electrophoresis. J Pharm Biomed Anal 41(1): 1-11.
51. Haginaka J (2008) Recent progresses in protein-based chiral stationary phases for enantioseparations in liquid chromatography. J Chromatogr B 875(1): 12-19.
52. Hansen LK, Frost PC, Larson JH, Metcalfe CD (2008) Poor elemental food quality reduces the toxicity of fluoxetine on Daphniamagna. Aquat Toxicol 86(1): 99-103.
53. Hashem H, Tründelberg C, Attef O, Jira T (2011) Effect of chromatographic conditions on liquid chromatographic chiral separation of terbutaline and salbutamol on Chirobiotic V column. J Chromatogr A 1218(38): 6727-6731.
54. Hashim NH, Nghiem LD, Stuetz RM, Khan SJ (2011) Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor. Water Res 45(18): 6249-6258.
55. Heckmann L-H, Callaghan A, Hooper HL, Connon R, Hutchinson TH, Maund SJ, Sibly RM (2007) Chronic toxicity of ibuprofen to Daphnia magna: effects on life history traits and population dynamics. Toxicol Lett 172(3): 137-145.
56. Hernández-Borges J, Rodríguez-Delgado MÁ, García-Montelongo FJ, Cifuentes A (2005) Chiral analysis of pollutants and their metabolites by capillary electromigration methods. Electrophoresis 26(20): 3799-3813.
57. Hijosa-Valsero M, Matamoros V, Martín-Villacorta J, Bécares E, Bayona JM (2010) Assessment of full-scale natural systems for the removal of PPCPs from wastewater in small communities. Water Res 44(5): 1429-1439.
58. Huang YF, Pryor ME, Mather LE, Veering BT (1998) Cardiovascular and central nervous system effects of intravenous levobupivacaine and bupivacaine in sheep. Anesth Analg 86(4): 797-804.
59. Huggett DB, Brooks BW, Peterson B, Foran CM, Schlenk D (2002) Toxicity of select beta adrenergic receptor-blocking pharmaceuticals (B-blockers) on aquatic organisms. Arch Environ Contam Toxicol 43(2): 229-235.
60. Huggett DB, Khan IA, Foran CM, Schlenk D (2003) Determination of beta-adrenergic receptor blocking pharmaceuticals in United States wastewater effluent. Environ Pollut 121(2): 199-205.
61. Hühnerfuss H, Shah MR (2009) Enantioselective chromatography-A powerful tool for the discrimination of biotic and abiotic transformation processes of chiral environmental pollutants. J Chromatogr A 1216(3): 481-502.
62. Huq F (2007) Molecular modelling analysis of the metabolism of methadone. Asian J Biochem 2(1): 19-30.
63. Hutt AJ (1998) Drug chirality and its pharmacological consequences. In: Smith H, John Williams H (eds) Introduction to the principles of drug design and action, 3rd edn. Elsevier, Amesterdam.
64. Hutt AJ, Valentová J (2003) The chiral switch: the development of single enantiomer drugs from racemates. Acta Fac Pharm Univ Comen 50: 7-23.
65. Isidori M, Lavorgna M, Nardelli A, Parrella A, Previtera L, Rubino M (2005) Ecotoxicity of naproxen and its phototransformation products. Sci Total Environ 348(1-3): 93-101.
66. Izake EL (2007) Chiral discrimination and enantioselective analysis of drugs: an overview. J Pharm Sci 96(7): 1659-1676.
67. Jain AK, Michael R, Ryan JR, McMahon FG (1984) Antihypertensive and biochemical effects of indacrinone enantiomers. Pharmacotherapy 4(5): 278-283.
68. Jiang Z, Schurig V (2008) Existence of a low isoenantioselective temperature in complexation gas chromatography: profound change of enantioselectivity of a nickel(II) chiral selector either bonded to, or dissolved in, poly(dimethylsiloxane). J Chromatogr A 1186(1-2): 262-270.
69. Johnson DJ, Sanderson H, Brain RA, Wilson CJ, Bestari KT, Solomon KR (2005) Exposure assessment and microcosm fate of selected selective serotonin reuptake inhibitors. Regul Toxicol Pharmacol 42(3): 313-323.
70. Jones OAH, Voulvoulis N, Lester JN (2007) The occurrence and removal of selected pharmaceutical compounds in a sewage treatment works utilising activated sludge treatment. Environ Pollut 145(3): 738-744.
71. Kasprzyk-Hordern B, Kondakal VVR, Baker DR (2010) Enantiomeric analysis of drugs of abuse in wastewater by chiral liquid chromatography coupled with tandem mass spectrometry. J Chromatogr A 1217(27): 4575-4586.
72. Khetan SK, Collins TJ (2007) Human pharmaceuticals in the aquatic environment: a challenge to green chemisty. Chem Rev 107(6): 2319-2364.
73. Kim J-W, Ishibashi H, Yamauchi R, Ichikawa N, Takao Y, Hirano M, Koga M, Arizono K (2009) Acute toxicity of pharmaceutical and personal care products on freshwater crustacean (Thamnocephalus platyurus) and fish (Oryzias latipes). J Toxicol Sci 34(2): 227-232.
74. Kot-Wasik A, Debska J, Namiesnik J (2007) Analytical techniques in studies of the environmental fate of pharmaceuticals and personal-care products. TrAC Trends Anal Chem 26(6): 557-568.
75. Lamas JP, Salgado-Petinal C, García-Jares C, Llompart M, Cela R, Gómez M (2004) Solid-phase microextraction-gas chromatography-mass spectrometry for the analysis of selective serotonin reuptake inhibitors in environmental water. J Chromatogr A 1046(1-2): 241-247.
76. Lämmerhofer M (2010) Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. J Chromatogr A 1217(6): 814-856.
77. Li L, Zhou S, Jin L, Zhang C, Liu W (2010) Enantiomeric separation of organophosphorus pesticides by high-performance liquid chromatography, gas chromatography and capillary electrophoresis and their applications to environmental fate and toxicity assays. J Chromatogr B 878(17-18): 1264-1276.
78. Li Y, Dong F, Liu X, Xu J, Li J, Kong Z, Chen X, Song W, Wang Y, Zheng Y (2011) Simultaneous enantioselective determination of fenbuconazole and its main metabolites in soil and water by chiral liquid chromatography/tandem mass spectrometry. J Chromatogr A 1218(38): 6667-6674.
79. Lima VLE (1997) Drugs and chirality: a brief overview. Quim Nova 20(6): 657-663.
80. Lister A, Regan C, van Zwol J, van Der Kraak G (2009) Inhibition of egg production in zebrafish by fluoxetine and municipal effluents: a mechanistic evaluation. Aquat Toxicol 95(4): 320-329.
81. Liu Q-T, Cumming RI, Sharpe AD (2009) Photo-induced environmental depletion processes of β-blockers in river waters. Photochem Photobiol Sci 8(6): 768-777.
82. MacLeod SL, Wong CS (2010) Loadings, trends, comparisons, and fate of achiral and chiral pharmaceuticals in wastewaters from urban tertiary and rural aerated lagoon treatments. Water Res 44(2): 533-544.
83. MacLeod SL, Sudhir P, Wong CS (2007) Stereoisomer analysis of wastewater-derived β-blockers, selective serotonin re-uptake inhibitors, and salbutamol by high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr A 1170(1-2): 23-33.
84. Madureira TV, Barreiro JC, Rocha MJ, Cass QB, Tiritan ME (2009) Pharmaceutical trace analysis in aqueous environmental matrices by liquid chromatography-ion trap tandem mass spectrometry. J Chromatogr A 1216(42): 7033-7042.
85. Maftouh M, Granier-Loyaux C, Chavana E, Marini J, Pradines A, Heyden YV, Picard C (2005) Screening approach for chiral separation of pharmaceuticals: part III. Supercritical fluid chromatography for analysis and purification in drug discovery. J Chromatogr A 1088(1-2): 67-81.
86. Mannschreck A, Kiesswetter R, von Angerer E (2007) Unequal activities of enantiomers via biological receptors: examples of chiral drug, pesticide, and fragrance molecules. J Chem Educ 84(12): 2012-2018.
87. Mascolo G, Balest L, Cassano D, Laera G, Lopez A, Pollice A, Salerno C (2010) Biodegradability of pharmaceutical industrial wastewater and formation of recalcitrant organic compounds during aerobic biological treatment. Bioresour Technol 101(8): 2585-2591.
88. Matamoros V, Hijosa M, Bayona JM (2009) Assessment of the pharmaceutical active compounds removal in wastewater treatment systems at enantiomeric level. Ibuprofen and naproxen. Chemosphere 75(2): 200-205.
89. Mayer JM, Testa B (1997) Pharmacodynamics, pharmacokinetics and toxicity of ibuprofen enantiomers. Drugs Future 22: 1347-1366.
90. Mennigen JA, Harris EA, Chang JP, Moon TW, Trudeau VL (2009) Fluoxetine affects weight gain and expression of feeding peptides in the female goldfish brain. Regul Pept 155(1-3): 99-104.
91. Mennigen JA, Sassine J, Trudeau VL, Moon TW (2010) Waterborne fluoxetine disrupts feeding and energy metabolism in the goldfish Carassius auratus. Aquat Toxicol 100(1): 128-137.
92. Montanari MLC, Cass QB, Leitão A, Andricopulo AD, Montanari CA (2006) The role of molecular interaction fields on enantioselective and nonselective separation of chiral sulfoxides. J Chromatogr A 1121(1): 64-75.
93. Müller TA, Kohler HPE (2004) Chirality of pollutants-effects on metabolism and fate. Appl Microbiol Biotechnol 64(3): 300-316.
94. Munoz-Bellido JL, Munoz-Criado S, Garcìa-Rodrìguez JA (2000) Antimicrobial activity of psychotropic drugs: selective serotonin reuptake inhibitors. Int J Antimicrob Agents 14(3): 177-180.
95. Nakamura Y, Yamamoto H, Sekizawa J, Kondo T, Hirai N, Tatarazako N (2008) The effects of pH on fluoxetine in Japanese medaka (Oryzias latipes): acute toxicity in fish larvae and bioaccumulation in juvenile fish. Chemosphere 70(5): 865-873.
96. Nalecz-Jawecki G (2007) Evaluation of the in vitro biotransformation of fluoxetine with HPLC, mass spectrometry and ecotoxicological tests. Chemosphere 70(1): 29-35.
97. Niessen WMA (2003) Progress in liquid chromatography-mass spectrometry instrumentation and its impact on high-throughput screening. J Chromatogr A 1000(1-2): 413-436.
98. Nikolai LN, McClure EL, MacLeod SL, Wong CS (2006) Stereoisomer quantification of the -blocker drugs atenolol, metoprolol, and propranolol in wastewaters by chiral high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr A 1131(1-2): 103-109.
99. Orlando RM, Cardoso Filho N, Gil ES, Stringhetta JPS (2007) The pharmaceutical importance of chiral drugs. Rev Electrôn Farm IV(1): 8-14.
100. Owen SF, Huggett DB, Hutchinson TH, Hetheridge MJ, Kinter LB, Ericson JF, Sumpter JP (2009) Uptake of propranolol, a cardiovascular pharmaceutical, from water into fish plasma and its effects on growth and organ biometry. Aquat Toxicol 93(4): 217-224.
101. Paterson G, Metcalfe CD (2008) Uptake and depuration of the anti-depressant fluoxetine by the Japanese medaka (Oryzias latipes). Chemosphere 74(1): 125-130.
102. Patrick R, Jan S, Andreas S, Timm K, Burkhard S (2011) First evidence for a stereoselective incorporation of nonylphenol diastereomers in soil-derived organo-clay complexes. Environ Chem Lett 9(2): 293-299.
103. Pavlinov SA, Belolipetskaya VG, Piotrovskii VK, Metelitsa VI, Filatova NP, Bochkareva EV (1990) Enantiomers of propranolol in the blood of patients with cardiovascular diseases during long-term therapy. Pharm Chem J 24(1): 17-19.
104. Pérez S, Barceló D (2007) Application of advanced MS techniques to analysis and identification of human and microbial metabolites of pharmaceuticals in the aquatic environment. TrAC Trends Anal Chem 26(6): 494-514.
105. Pérez S, Barceló D (2008) Applications of LC-MS to quantitation and evaluation of the environmental fate of chiral drugs and their metabolites. TrAC Trends Anal Chem 27(10): 836-846.
106. Perrin C, Matthijs N, Mangelings D, Granier-Loyaux C, Maftouh M, Massart DL, Vander Heyden Y (2002a) Screening approach for chiral separation of pharmaceuticals: part II. Reversed-phase liquid chromatography. J Chromatogr A 966(1-2): 119-134.
107. Perrin C, Vu VA, Matthijs N, Maftouh M, Massart DL, Vander Heyden Y (2002b) Screening approach for chiral separation of pharmaceuticals: part I. Normal-phase liquid chromatography. J Chromatogr A 947(1): 69-83.
108. Pirkle WH, Pochapsky TC (1989) Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers. Chem Rev 89(2): 347-362.
109. Pirzada Z, Personick M, Biba M, Gong X, Zhou L, Schafer W, Roussel C, Welch CJ (2010) Systematic evaluation of new chiral stationary phases for supercritical fluid chromatography using a standard racemate library. J Chromatogr A 1217(7): 1134-1138.
110. Reungoat J, Macova M, Escher BI, Carswell S, Mueller JF, Keller J (2010) Removal of micropollutants and reduction of biological activity in a full scale reclamation plant using ozonation and activated carbon filtration. Water Res 44(2): 625-637.
111. Ribeiro AR, Castro PML, Tiritan ME (2012) Environmental fate of chiral pharmaceuticals: determination, degradation and toxicity. In: Lichtfouse E, Schwarzbauer J, Robert D (eds) Environmental chemistry for a sustainable world, vol 2. Springer, Netherlands, pp 3-45. doi: 10. 1007/978-94-007-2439_1.
112. Rykowska I, Wasiak W (2009) Recent advances in gas chromatography for solid and liquid stationary phases containing metal ions. J Chromatogr A 1216(10): 1713-1722.
113. Sánchez-Argüello P, Fernández C, Tarazona JV (2009) Assessing the effects of fluoxetine on Physa acuta (Gastropoda, Pulmonata) and Chironomus riparius (Insecta, Diptera) using a two-species water-sediment test. Sci Total Environ 407(6): 1937-1946.
114. Sancho R, Minguillón C (2009) The chromatographic separation of enantiomers through nanoscale design. Chem Soc Rev 38(3): 797-805.
115. Santos LHMLM, Araújo 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(1-3): 45-95.
116. Schnell S, Kawano A, Porte C, Lee LEJ, Bols NC (2008) Effects of ibuprofen on the viability and proliferation of rainbow trout liver cell lines and potential problems and interactions in effects assessment. Environ Toxicol 24(2): 157-165.
117. Schurig V (2001) Separation of enantiomers by gas chromatography. J Chromatogr A 906(1-2): 275-299.
118. Scriba GKE (2003) Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: an update. Electrophoresis 24(15): 2409-2421.
119. Sipma J, Osuna B, Collado N, Monclús H, Ferrero G, Comas J, Rodriguez-Roda I (2010) Comparison of removal of pharmaceuticals in MBR and activated sludge systems. Desalination 250(2): 653-659.
120. Smith SW (2009) Chiral toxicology: it's the same thing only different. Toxicol Sci 110(1): 4-30.
121. Sousa EP, Tiritan ME, Oliveira RV, Afonso CMM, Cass QB, Pinto MMM (2004) Enantiomeric resolution of kielcorin derivatives by HPLC on polysaccharide stationary phases using multimodal elution. Chirality 16(5): 279-285.
122. Stanley JK, Ramirez AJ, Chambliss CK, Brooks BW (2007) Enantiospecific sublethal effects of the antidepressant fluoxetine to a model aquatic vertebrate and invertebrate. Chemosphere 69(1): 9-16.
123. Steiner TJ, Ahmed F, Findley LJ, MacGregor EA, Wilkinson M (1998) S-fluoxetine in the prophylaxis of migraine: a phase II double-blind randomized placebo-controlled study. Cephalalgia 18(5): 283-286.
124. Taylor LT (2009) Supercritical fluid chromatography for the 21st century. J Supercrit Fluids 47(3): 566-573.
125. Ternes TA (1998) Occurrence of drugs in German sewage treatment plants and rivers. Water Res 32(11): 3245-3260.
126. Trautwein C, Kümmerer K, Metzger JW (2008) Aerobic biodegradability of the calcium channel antagonist verapamil and identification of a microbial dead-end transformation product studied by LC-MS/MS. Chemosphere 72(3): 442-450.
127. Trenholm RA, Vanderford BJ, Holady JC, Rexing DJ, Snyder SA (2006) Broad range analysis of endocrine disruptors and pharmaceuticals using gas chromatography and liquid chromatography tandem mass spectrometry. Chemosphere 65(11): 1990-1998.
128. Tucker GT (2000) Chiral switches. Lancet 355(9209): 1085-1087.
129. Vanderford BJ, Snyder SA (2006) Analysis of pharmaceuticals in water by isotope dilution liquid chromatography/tandem mass spectrometry. Environ Sci Technol 40(23): 7312-7320.
130. Westerhoff P, Yoon Y, Snyder S, Wert E (2005) Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes. Environ Sci Technol 39(17): 6649-6663.
131. Winder VL, Sapozhnikova Y, Pennington PL, Wirth EF (2009) Effects of fluoxetine exposure on serotonin-related activity in the sheepshead minnow (Cyprinodon variegatus) using LC/MS/MS detection and quantitation. Comp Biochem Physiol C Toxicol Pharmacol 149(4): 559-565.
132. Winkler M, Lawrence JR, Neu TR (2001) Selective degradation of ibuprofen and clofibric acid in two model river biofilm systems. Water Res 35(13): 3197-3205.
133. Winter MJ, Lillicrap AD, Caunter JE, Schaffner C, Alder AC, Ramil M, Ternes TA, Giltrow E, Sumpter JP, Hutchinson TH (2008) Defining the chronic impacts of atenolol on embryo-larval development and reproduction in the fathead minnow (Pimephales promelas). Aquat Toxicol 86(3): 361-369.
134. Wistuba D, Schurig V (2000) Enantiomer separation of chiral pharmaceuticals by capillary electrochromatography. J Chromatogr A 875(1-2): 255-276.
135. Wong CS, Garrison AW (2000) Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns. J Chromatogr A 866(2): 213-220.
136. Zhang H, Spiteller M, Guenther K, Boehmler G, Zuehlke S (2009) Degradation of a chiral nonylphenol isomer in two agricultural soils. Environ Pollut 157(6): 1904-1910.
137. Zhang T, Nguyen D, Franco P (2010) Reversed-phase screening strategies for liquid chromatography on polysaccharide-derived chiral stationary phases. J Chromatogr A 1217(7): 1048-1055.