Perspectives on ecological risk assessment of chiral compounds

Integrated Environmental Assessment and Management

Volumn 5, Issue 3, 2009, Pages 364-373

  Stanley, Jacob K ^a,b   Brooks, Bryan W ^a  

^a BAYLOR UNIVERSITY   (United States)

^b US ARMY ENGINEER RESEARCH AND DEVELOPMENT CENTER   (United States)

Author keywords

Chiral; Enantiomer hazard ratio; Enantiomers; Risk assessment; Stereoisomers

Indexed keywords

PESTICIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL MONITORING; RISK ASSESSMENT; RISK FACTOR;

ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL MONITORING; MOLECULAR STRUCTURE; PESTICIDES; RISK ASSESSMENT; RISK FACTORS;

EID: 73949093060     PISSN: 15513793     EISSN: None     Source Type: Journal    
DOI: 10.1897/IEAM_2008-076.1     Document Type: Review

References (49)

1. Ali I, Aboul-Enein HY, Ghanem A. 2005. Enantioselective toxicity and carcinogenesis. Curr Pharm Anal 1:109-125.
2. Ankley GT, Black MC, Garric J, Hutchinson TH, Iguchi T. 2005. A framework for assessing the hazard of pharmaceutical materials to aquatic species. In: Williams RT, editor. Human pharmaceuticals: Assessing the impacts on aquatic ecosystems. Pensacola (FL): SETAC. p 183-237.
3. Ankley GT, Brooks BW, Huggett DB, Sumpter JP. 2007. Repeating history: Pharmaceuticals in the environment. Environ Sci Technol 41:8211-8217.
4. Barrett AM, Cullum VA. 1968. The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias. Br J Pharmacol 34:43-55.
5. Belden JB, Maul JD, Lydy MJ. 2007. Partitioning and photodegradation of ciprofloxacin in aqueous systems in the presence of organic matter. Chemosphere 66:1390-1395.
6. Brain RA, Ramirez AJ, Fulton BA, Chambliss CK, Brooks BW. 2008. Herbicidal effects of sulfamethoxazole in Lemna gibba: Using p-aminobenzoic acid as a biomarker of effect. Environ Sci Technol 42:8965-8970.
7. Brooks BW, Huggett DB, Brain RA, Ankley GT. 2009. Risk assessment considerations for veterinary medicines in aquatic systems. In: Henderson K, Coats J, editors. Veterinary pharmaceuticals in the environment. Washington DC: American Chemical Society. (forthcoming)
8. Buerge IJ, Poiger T, Müller MD, Buser HR. 2003. Enantioselective degradation of metalaxyl in soils: Chiral preference changes with soil pH. Environ Sci Technol 37:2668-2674.
9. Buser HR, Müller MD. 1998. Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland. Environ Sci Technol 32:626-633.
10. Cleuvers M. 2003. Aquatic ecotoxicity of pharmaceuticals including the assessment of combination effects. Toxicol Lett 142:185-194.
11. Dourson ML, Stara JF. 1983. Regulatory history and experimental support of uncertainty (safety) factors. Reg Toxicol Pharmacol 3:224-238.
12. Fono L, Sedlak DL. 2004. Use of the chiral pharmaceutical propranolol to identify sewage discharges into surface waters. Environ Sci Technol 39:9244-9252.
13. Garrison AW. 2006. Probing the enantioselectivity of chiral pesticides. Environ Sci Technol 40:16-23.
14. Guo X, Fukushima T, Li F, Imai K. 2002. Determination of fluoxetine enantiomers in rat plasma by pre-column fluorescence derivitization and column-switching high-performance liquid chromatography. Analyst 127:480-484.
15. Howe R, Shanks RG. 1966. Optical isomers of propranolol. Nature 210:1336-1338.
16. Jones WJ, Mazur CS, Kenneke JF, Garrison AW. 2007. Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments. Environ Sci Technol 41:8301-8307.
17. Kallenborn R, Hühnerfuss H. 2001. Chiral environmental pollutants, trace analysis and ecotoxicology. Berlin (DE): Springer-Verlag. 209 p.
18. Kim H, Jeong K, Lee S, Jung S. 2003. Molecular modeling of the chiral recognition of propranolol enantiomers by a b-cyclodextrin. Bull Korean Chem Soc 24:95-98.
19. Konwick BJ, Fisk AT, Garrison AW, Avants JK, Black MC. 2005. Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia. Environ Toxicol Chem 24:2350-2355.
20. Kovatcheva A, Golbraith A, Oloff S, Feng J, Zheng W, Tropsha A. 2005. QSAR modeling of datasets with enantioselective compounds using chirality sensitive molecular descriptors. SAR QSAR Environ Res 16:93-102.
21. Kurt-Karakus PB, Stroud JL, Bidleman T, Semple KT, Jantunen L, Jones KC. 2007. Enantioselective degradation of organochlorine pesticides in background soils: Variability in field and laboratory studies. Environ Sci Technol 41:4965-4971.
22. Levin W, Buening MK, Wood AW, Chang RL, Kedzierski B, Thakker DR, Boyd DR, Gadaginamath GS, Armstrong RN, Yagi H, Karle JM, Slagal TJ, Jerina DM, Conney AH. 1980. An enantiomeric interaction in the metabolism and tumorigenicity of (+)- and (-s)-benzo[a]pyrene 7, 8-oxide. J Biol Chem 255:9067-9074.
23. Lewis DL, Garrison AW, Wommack KE, Whittemore A, Steudler P, Melillo J. 1999. Influence of environmental changes on degradation of chiral pollutants in soils. Nature 401:898-901. (Pubitemid 29518954)
24. Liu W, Gan J, Schlenk D, Jury WA. 2005. Enantioselectivity in environmental safety of current chiral insecticides. Proc Natl Acad Sci U S A 102:701-706.
25. Lydy M, Belden J, Wheelock C, Hammock B, Denton D. 2004. Challenges in regulating pesticide mixtures. Ecol Soc 9:1. http://www.ecologyandsociety.org/ vol9/iss6/art1/.
26. Maruya KA, Smalling KL, Vetter W. 2005. Temperature and congener structure affect the enantioselectivity of toxaphene elimination by fish. Environ Sci Technol 39:3999-4004.
27. McConathy J, Owens MJ. 2003. Stereochemistry in drug action. Primary Care Companion J Clin Psychiatry 5:70-73.
28. Meek B, Ohanian E, Renwick A, Naumann B, Lake B, Vu V, Dourson M. 2001. Guidelines for application of chemical-specific adjustment factors in dose/concentration assessment. Comments Toxicol 7:575-590.
29. Mehvar R, Brocks DR. 2001. Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans. J Pharm Pharm Sci 4:185-200.
30. Nikolai LN, McCLure EL, MacLeod SL, Wong CS. 2006. Stereoisomer quantification of the b-blocker drugs atenolol, metoprolol, and propranolol in wastewaters by chiral high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr A 1131:103-109.
31. Padma TV, Dickhut RM, Ducklow H. 2003. Variations in a- hexachlorocyclohexane enantiomer ratios in relation to microbial activity in a temperate estuary. Environ Toxicol Chem 22:1421-1427.
32. Parkhurst BR, Warren-Hicks W, Cardwell RD, Volison J, Etchison T, Butcher JB, Covington SM. 1996. Aquatic ecological risk assessment: A multi-tiered approach, Project 91-AER-1. Alexandria (VA): Water Environment Research Foundation. 228 p.
33. Rand GM. 1995. Fundamentals of aquatic toxicology: Effects, environmental fate and risk assessment. 2nd ed. Philadelphia (PA): Taylor and Francis. 1125 p.
34. Sanderson H, Johnson DJ, Wilson CJ, Brain RA, Solomon KR. 2003. Probabilistic hazard assessment of environmentally occurring pharmaceuticals toxicity to fish, daphnids and algae by ECOSAR screening. Toxicol Lett 144:383-395.
35. Silverman KC, Naumann BD, Holder DJ, Dixit R, Faria EC, Sargent EV, Gallo MA. 1999. Establishing data-driven uncertain factors from published pharmaceutical clinical trial data. Hum Ecol Risk Assess 5:1059-1089. (Pubitemid 129725210)
36. Stanley JK, Ramirez AJ, Chambliss CK, Brooks BW. 2007. Enantiospecific sublethal effects of the antidepressant fluoxetine to a model aquatic vertebrate and invertebrate. Chemosphere 69:9-16.
37. Stanley JK, Ramirez AJ, Mottaleb M, Chambliss CK, Brooks BW. 2006. Enantiospecific toxicity of the b-blocker propranolol to Daphnia magna and Pimephales promelas. Environ Toxicol Chem 25:1780-1786.
38. Suter GW, Efroymson RA, Sample BE, Jones DS. 2000. Ecological risk assessment for contaminated sites. Boca Raton (FL): Lewis. 438 p.
39. Suter II GW. 2007. Ecological risk assessment. 2nd ed. Boca Raton (FL): CRC. 643 p.
40. [USEPA] US Environmental Protection Agency, Environmental Fate and Effects Division. 2000. Interim policy for stereoisomeric pesticides. Washington DC: USEPA. www.epa.gov/oppefed1/ecorisk-ders/stereoisomer-policy.htm. Accessed 12 May 2008.
41. [USFDA] US Food and Drug Administration. 1992. FDA's policy statement for the development of new stereoisomeric drugs. Washington DC: USFDA. http://www.fda.gov/cder/guidance/stereo.htm. Accessed 24 April 2008 .
42. [USFDA] US Food and Drug Administration, Center for Drug Evaluation and Research, Center for Biologics Evaluation and Research. 1998. Guidance for industry, environmental assessment of human drug and biologics applications. Rockville (MD): US Department of Health and Human Services. CMC 6, Revision 1.
43. [VICH] International Cooperation on Harmonisation of Technical Requirements for Registration of Veterinary Medical Products. 2004. Environmental impact assessment for veterinary medicinal products phase II guidance. VICH-GL38. Brussels (BE): VICH. 38 p. .
44. Wang YS, Tai K-T, Yen J-H. 2004. Separation, bioactivity, and dissipation of enantiomers of the organophosphorus insecticide fenamiphos. Ecotox Environ Safe 57:346-353.
45. Wedyan M, Preston MR. 2005. Isomer-selective adsorption of amino acids by components of natural sediment. Environ Sci Technol 39:2115-2119.
46. Wilson WA, Konwick BJ, Garrison AW, Avants JK, Black MC. 2008. Enantioselective chronic toxicity of fipronil to Ceriodaphnia dubia. Arch Environ Contam Toxicol 54:36-43.
47. Wong CS. 2006. Environmental fate processes and biochemical transformations of chiral emerging organic pollutants. Anal Bioanal Chem 386:544-558.
48. Xu C, Wang J, Liu W, Sheng D, Tu Y, Ma Y. 2008. Separation and aquatic toxicity of enantiomers of the pyrethroid insecticide lambda-cyhalothrin. Environ Toxicol Chem 27:174-181.
49. Yen J-H, Tsai C-C, Wang Y-S. 2003. Separation and toxicity of enantiomers of organophosphorus insecticide leptophos. Ecotox Environ Saf 55:236-242.