A predictive quantitative structure-activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons to Daphnia magna with the use of factors for photosensitization and photomodification

Environmental Toxicology and Chemistry

Volumn 26, Issue 3, 2007, Pages 406-415

  Lampi, Mark A ^a   Gurska, Jolanta ^a   Huang, Xiao Dong ^a   Dixon, D George ^a   Greenberg, Bruce M ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Daphnia magna; Photoinduced toxicity; Polycyclic aromatic hydrocarbons; Predictive modeling; Quantitative structure activity relationship

Indexed keywords

DAPHNIA MAGNA; PHOTOINDUCED TOXICITY; PREDICTIVE MODELING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

BIODIVERSITY; ENVIRONMENTAL ENGINEERING; LIGHT ABSORPTION; PHOTOSENSITIVITY; POLYCYCLIC AROMATIC HYDROCARBONS; ULTRAVIOLET RADIATION;

TOXICITY;

ANTHRACENE; BENZ[A]ANTHRACENE; BENZO[A]PYRENE; BENZO[B]FLUORENE; BENZO[E]PYRENE; BENZO[GHI]PERYLENE; CHRYSENE; CORONENE; DIBENZ[AH]ANTHRACENE; DIBENZO[AI]PYRENE; FLUORANTHENE; FLUORENE; NAPHTHACENE; PHENANTHRENE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE; TRIPHENYLENE; UNCLASSIFIED DRUG;

AQUATIC ECOSYSTEM; BIOINDICATOR; CRUSTACEAN; MODEL; PAH; TOXICITY; ULTRAVIOLET RADIATION;

AQUATIC ENVIRONMENT; ARACEAE; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DAPHNIA; LEMNA GIBBA; LIGHT; NONHUMAN; PHOTOSENSITIZATION; POLLUTION MONITORING; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STRUCTURE ACTIVITY RELATION; VIBRIO FISCHERI;

ANIMALS; DAPHNIA; ECOSYSTEM; ENVIRONMENTAL MONITORING; PHOTOCHEMISTRY; PHOTOSENSITIVITY DISORDERS; POLYCYCLIC HYDROCARBONS, AROMATIC; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; ULTRAVIOLET RAYS;

CLADOCERA; DAPHNIA MAGNA; LEMNA; LEMNA GIBBA; VIBRIO FISCHERI;

EID: 34047150943     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/06-295R.1     Document Type: Article

References (46)

1. Epstein SS, Falk HL, Mantel N, Small M. 1964. On association between photodynamic and carcinogenic activities in polycyclic compounds. Cancer Res 24:855-862.
2. Morgan DD, Warshawsky D, Atkinson T. 1977. The relationship between carcinogenic activities of polycyclic aromatic hydrocarbons and their singlet, triplet and singlet-triplet splitting energies and phosphorescence lifetimes. Photochem Photobiol 25:31-38.
3. Newsted JL, Giesy JP. 1987. Predictive models for photoinduced acute toxicity of polycyclic aromatic hydrocarbons to Daphnia magna Strauss (Cladocera, Crustacea). Environ Toxicol Chem 6: 445-461.
4. Mekenyan OG, Ankley GT, Veith GD, Call DJ. 1994. QSARs for photoinduced toxicity: I. Acute lethality of polycyclic aromatic hydrocarbons to Daphnia magna. Chemosphere 28:567-582.
5. Mekenyan OG, Ankley GT, Veith GD, Call DJ. 1994. QSAR estimates of excited states and photoinduced acute toxicity of polycyclic aromatic hydrocarbons. SAR QSAR Environ Res 2: 237-247.
6. Betowski LD, Enlow M, Riddick L. 2002. The phototoxicity of polycyclic aromatic hydrocarbons: A theoretical study of excited states and correlation to experiment. Comput Chem 26:371-377.
7. Ribeiro FAD, Ferreira MMC. 2005. QSAR model of the phototoxicity of polycyclic aromatic hydrocarbons. Journal of Molecular Structure (Theochem) 719:191-200.
8. Krylov SN, Huang X-D, Zeiler LF, Dixon DG, Greenberg BM. 1997. Mechanistic quantitative structure-activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons: I. Physical model based on chemical kinetics in a two-compartment system. Environ Toxicol Chem 16:2283-2295.
9. Huang X-D, Krylov SN, Ren L, McConkey BJ, Dixon DG, Greenberg BM. 1997. Mechanistic quantitative structure-activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons: II. An empirical model for the toxicity of 16 polycyclic aromatic hydrocarbons to the duckweed Lemna gibba L. G-3. Environ Toxicol Chem 16:2296-2303.
10. Foote CS. 1968. Mechanisms of photosensitized oxidation. Science 162:963-970.
11. Oris JT, Giesy JP. 1985. The photoenhanced toxicity of anthracene to juvenile Sunfish (Lepomis spp.). Aquat Toxicol 6:133-146.
12. Diamond SA, Mount DR, Burkhard LP, Ankley GT, Makynen EA, Leonard EN. 2000. Effect of irradiance spectra on the photoinduced toxicity of three polycyclic aromatic hydrocarbons. Environ Toxicol Chem 19:1389-1396.
13. Gala WR, Giesy JP. 1992. Photo-induced toxicity of anthracene to the green alga, Selenastrum capricornutum. Arch Environ Contam Toxicol 23:316-323.
14. Marwood CA, Smith REH, Charlton MN, Solomon KR, Greenberg BM. 2003. Photoinduced toxicity to Lake Erie phytoplankton assemblages from intact and photomodified polycyclic aromatic hydrocarbons. J Gt Lakes Res 29:558-565.
15. Grote M, Schüürmann G, Altenburger R. 2005. Modeling photoinduced algal toxicity of polycyclic aromatic hydrocarbons. Environ Sci Technol 39:4141-4149.
16. El-Alawi YS, Dixon DG, Greenberg BM. 2001. Effects of a preincubation period on the photoinduced toxicity of polycyclic aromatic hydrocarbons to the luminescent bacterium Vibrio fischeri. Environ Toxicol 16:277-286.
17. Ankley GT, Collyard SA, Monson PD, Kosian PA. 1994. Influence of ultraviolet light on the toxicity of sediments contaminated with polycyclic aromatic hydrocarbons. Environ Toxicol Chem 13:1791-1796.
18. Weinstein JE, Polk KD. 2001. Phototoxicity of anthracene and pyrene to glochidia of the freshwater mussel Utterbackia imbecillis. Environ Toxicol Chem 20:2021-2028.
19. Ankley GT, Burkhard LP, Cook PM, Diamond SA, Erickson RJ, Mount DR. 2003. Assessing risks from photoactivated toxicity of PAHs to aquatic organisms. In Douben PET, ed, PAHs: An Ecotoxicological Perspective. John Wiley, Etobicoke, ON, Canada, pp 275-296.
20. McConkey BJ, Duxbury CL, Dixon DG, Greenberg BM. 1997. Toxicity of a PAH photooxidation product to the bacteria Photobacterium phosphoreum and the duckweed Lemna gibba: Effects of phenanthrene and its primary photoproduct, phenanthrenequinone. Environ Toxicol Chem 16:892-899.
21. Mallakin A, McConkey BJ, Miao G, McKibben B, Snieckus V, Dixon DG, Greenberg BM. 1999. Impacts of structural photomodification on the toxicity of environmental contaminants: Anthracene photooxidation products. Ecotoxicol Environ Saf 43: 204-212.
22. Brack W, Altenburger R, Kuster E, Meissner B, Wenzel K-D, Schüürmann G. 2003. Identification of toxic products of anthracene photomodification in simulated sunlight. Environ Toxicol Chem 22:2228-2237.
23. Andino JM, Smith JN, Flagan TC, Goddard WA I, Seinfeld JH. 1996. Mechanism of atmospheric photooxidation of aromatics: A theoretical study. J Phys Chem 100:10967-10980.
24. Lampi MA, Huang X-D, El-Alawi YS, McConkey BJ, Dixon DG, Greenberg BM. 2001. Occurrence and toxicity of photomodified polycyclic aromatic hydrocarbon mixtures present in contaminated sediments. In Greenberg BM, Hull RN, Roberts MH, Gensemer RW, eds, Environmental Toxicology and Risk Assessment: Science, Policy, and Standardization-Implications for Environmental Decisions, Vol 10. STP 1403. American Society for Testing and Materials, West Conshohocken, PA, pp 211-220.
25. Machala M, Giganek M, Blaha L, Minksova K, Vondrack J. 2001. Aryl hydrocarbon receptor-mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments. Environ Toxicol Chem 20:2736-2743.
26. Kurihara R, Shiraishi F, Tanaka N, Hashimoto S. 2005. Presence and estrogenicity of anthracene derivatives in coastal Japanese waters. Environ Toxicol Chem 24:1984-1993.
27. Papadoyannis IN, Zotou A, Samanidou VF. 2002. Development of a solid phase extraction protocol for the simultaneous determination of anthracene and its oxidation products in surface waters by reversed-phase HPLC. J Liq Chromatogr Relat Technol 25:2635-2653.
28. Babu TS, Marder JB, Tripuranthakam S, Dixon DG, Greenberg BM. 2001. Synergistic effects of a photooxidized polycyclic aromatic hydrocarbon and copper on photosynthesis and plant growth: Evidence that in vivo formation of reactive oxygen species is a mechanism of copper toxicity. Environ Toxicol Chem 20:1351-1358.
29. Lampi MA, Gurska Y, McDonald KIC, Xie F, Huang X-D, Dixon DG. 2006. Photoinduced toxicity of PAHs to Daphnia magna: UV-mediated effects and the toxicity of PAH photoproducts. Environ Toxicol Chem 25:1079-1087.
30. Choi J, Oris JT. 2003. Assessment of the toxicity of anthracene photo-modification products using the Topminnow (Poeciliopsis lucida) hepatoma cell line (PLHC-1). Aquat Toxicol 65:243-251.
31. Enya T, Suzuki H, Watanabe T, Hirayama T, Hisamatsu Y. 1997. 3-Nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhaust and airborne particulates. Environ Sci Technol 31:2772-2776.
32. Estrada E, Patelwicz G. 2004. On the usefulness of graph-theoretic descriptors in predicting theoretical parameters. Phototoxicity of polycyclic aromatic hydrocarbons (PAHs). Croat Chem Act 77:203-211.
33. El-Alawi YS, Huang X-D, Dixon DG, Greenberg BM. 2002. Quantitative structure-activity relationship for the photoinduced toxicity of polycyclic aromatic hydrocarbons to the luminescent bacteria Vibrio fischeri. Environ Toxicol Chem 21:2225-2232.
34. Walker JD, Jaworska J, Comber MHI, Schultz TW, Dearden JC. 2003. Guidelines for developing and using quantitative structure-activity relationships. Environ Toxicol Chem 22:1653-1665.
35. Environment Canada. 1990. Biological test method: Acute lethality test using Daphnia spp. EPS 1/RM/11. Ottawa, ON, Canada.
36. Guha S, Jaffe PR, Peters CA. 1998. Solubilization of PAH mixtures by a nonionic surfactant. Environ Sci Technol 32:930-935.
37. Allred PM, Giesy JP. 1985. Solar radiation-induced toxicity of anthracene to Daphnia pulex. Environ Toxicol Chem 4:219-226.
38. Cox DR. 1970. The Analysis of Binary Data. Methuen, London, UK.
39. Stephenson GL, Koper N, Atkinson GF, Solomon KR, Scroggins RP. 2000. Use of nonlinear regression techniques for describing concentration-response relationships of plant species exposed to contaminated site soils. Environ Toxicol Chem 19:2968-2981.
40. Schirmer K, Chan AGJ, Greenberg BM, Dixon DG, Bols NC. 1998. Ability of 16 priority PAHs to be photocytotoxic to a cell line from the rainbow trout gill. Toxicology 127:143-155.
41. Xia T, Korge P, Weiss JN, Li N, Venkatesen MI, Sioutas C, Nel A. 2004. Quinones and aromatic chemical compounds in particulate matter induce mitochondrial dysfunction: Implications for ultrafine particle toxicity. Environ Health Perspect 112:1347-1358.
42. Mallakin A, Dixon DG, Greenberg BM. 2000. Pathway of anthracene modificaton under simulated solar radiation. Chemosphere 40:1435-1441.
43. de Maagd PG-J, Ten Hulscher DTEM, Van Den Heuvel H, Opperhuizen A, Sijm DTHM. 1998. Physicochemical properties of polycyclic aromatic hydrocarbons: Aqueous solubilities, n-octanol/water partition coefficients, and Henry's law constants. Environ Toxicol Chem 17:251-257.
44. Mackay D, Shiu WY, Ma KC. 1992. Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, Vol 2. Lewis, Boca Raton, FL, USA.
45. Güsten H, Horvatic D, Sablijic A. 1991. Modeling n-octanol/ water partition coefficients by molecular topology: Polycyclic aromatic hydrocarbons and their alkyl derivatives. Chemosphere 23:199-213.
46. OSPAR. 2002. Benzo[rst]pentaphene. Oslo-Paris Commission for the Protection of the Marine Environment of the North-East Atlantic. London, UK.