Probing the primary mechanisms affecting the environmental distribution of estrogen and androgen isomers

Environmental Science and Technology

Volumn 45, Issue 9, 2011, Pages 3989-3995

  Qiao, Xianliang ^a   Carmosini, Nadia ^b   Li, Fei ^c   Lee, Linda S ^d  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

^c YANTAI INSTITUTE OF COASTAL ZONE RESEARCH   (China)

^d PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGRICULTURAL OPERATIONS; ANIMAL MANURE; AQUATIC SPECIES; DESCRIPTORS; DISSOLVED ORGANIC CARBON; ELECTROSTATIC POTENTIALS; ENVIRONMENTAL DISTRIBUTION; ENVIRONMENTAL FATE; ENVIRONMENTAL SORBENTS; H-BONDING; HORMONE CONCENTRATION; LAND APPLICATIONS; PRIMARY MECHANISM; PRIMARY METABOLITE; SOLUTE-SOLVENT INTERACTION; SPECIFIC INTERACTION; STRUCTURAL ISOMERS; TRENBOLONE; WATER PARTITION COEFFICIENTS;

ASSOCIATION REACTIONS; ENDOCRINOLOGY; HEXANE; HORMONES; MAMMALS; MANURES; ORGANIC CARBON; PLANTS (BOTANY); SORPTION; TOLUENE;

ISOMERS;

ANDROGEN; DISSOLVED ORGANIC CARBON; ESTRADIOL; ESTRONE; HEXANE; OCTANOL; ORGANIC CARBON; SOLVENT; TOLUENE; TRENBOLONE; TRENDIONE; UNCLASSIFIED DRUG; WATER;

DISSOLVED ORGANIC CARBON; ENVIRONMENTAL FATE; ESTROGENIC COMPOUND; HORMONE; MANURE; METABOLITE; SORPTION; TOLUENE;

AQUATIC SPECIES; ARTICLE; CHEMICAL INTERACTION; CONTAMINATION; DIALYSIS; ELECTRICITY; ENVIRONMENT; ENVIRONMENTAL DISTRIBUTION; HORMONE SYNTHESIS; HYDROGEN BOND; ISOMER; LIQUID CHROMATOGRAPHY; MANURE; MASS SPECTROMETRY; METABOLITE; NONHUMAN; PARTITION COEFFICIENT; SOLUTE; WASTE AND WASTE RELATED PHENOMENA;

ANDROGENS; ANIMALS; ENVIRONMENTAL POLLUTANTS; ESTRADIOL; ESTROGENS; ISOMERISM; MANURE; TRENBOLONE;

ANIMALIA; MAMMALIA;

EID: 79955535792     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es200073h     Document Type: Article

References (34)

1. Jobling, S.; Nolan, M.; Tyler, C. R.; Brighty, G.; Sumpter, J. P. Widespread sexual disruption in wild fish Environ. Sci. Technol. 1998, 32, 2498-2506 (Pubitemid 28420276)
2. Pettersson, I.; Berg, C. Environmentally relevant concentrations of ethynylestradiol cause female-biased sex ratios in Xenopus tropicalis and Rana temporaria Environ. Toxicol. Chem. 2007, 26, 1005-1009 (Pubitemid 46799759)
3. Brion, F.; Tyler, C. R.; Palazzi, X.; Laillet, B.; Porcher, J. M.; Garric, J.; Flammarion, P. Impacts of 17β-estradiol, including environmentally relevant concentrations, on reproduction after exposure during embryo-larval-, juvenile- and adult-life stages in zebrafish (Danio rerio) Aquat. Toxicol. 2004, 68, 193-217 (Pubitemid 38680883)
4. Lange, I. G.; Daxenberger, A.; Schiffer, B.; Witters, H.; Ibarreta, D.; Meyer, H. H. D. Sex hormones originating from different livestock production systems: fate and potential disrupting activity in the environment Anal. Chim. Acta 2002, 473, 27-37 (Pubitemid 35339428)
5. Lee, L. S.; Strock, T. J.; Sarmah, A. K.; Rao, P. S. C. Sorption and dissipation of testosterone, estrogens, and their primary transformation products in soils and sediments Environ. Sci. Technol. 2003, 37, 4098-4105 (Pubitemid 37108294)
6. Nichols, D. J.; Daniel, T. C.; Moore, P. A.; Edwards, D. R.; Pote, D. H. Runoff of estrogen hormone 17β-estradiol from poultry litter applied to pasture J. Environ. Qual. 1997, 26, 1002-1006 (Pubitemid 27345416)
7. Schiffer, B.; Totsche, K. U.; Jann, S.; Kögel-Knabner, I.; Meyer, K.; Meyer, H. H. D. Mobility of the growth promoters trenbolone and melengestrol acetate in agricultural soil: column studies Sci. Total Environ. 2004, 326, 225-237 (Pubitemid 38622267)
8. Soto, A. M.; Calabro, J. M.; Prechtl, N. V.; Yau, A. Y.; Orlando, E. F.; Daxenberger, A.; Kolok, A. S.; Guillette, L. J.; le Bizec, B.; Lange, I. G.; Sonnenschein, C. Androgenic and estrogenic activity in water bodies receiving cattle feedlot effluent in eastern Nebraska, USA Environ. Health Perspect. 2004, 112, 346-352 (Pubitemid 38351398)
9. Ankley, G. T.; Jensen, K. M.; Makynen, E. A.; Kahl, M. D.; Korte, J. J.; Hornung, M. W.; Henry, T. R.; Denny, J. S.; Leino, R. L.; Wilson, V. S.; Cardon, M. C.; Hartig, P. C.; Gray, L. E. Effects of the androgenic growth promoter 17β-trenbolone on fecundity and reproductive endocrinology of the fathead minnow Environ. Toxicol. Chem. 2003, 40, 3112-3117
10. Jensen, K. M.; Makynen, E. A.; Kahl, M. D.; Ankley, G. T. Effects of the feedlot contaminant 17α-trenbolone on reproductive endocrinology of the fathead minnow Environ. Sci. Technol. 2006, 40, 3112-3117 (Pubitemid 43673319)
11. Huang, C.; Zhang, Z.; Wu, S.; Zhao, Y.; Hu, J. In vitro and in vivo estrogenic effects of 17a-estradiol in medaka (Oryzias latipes) Chemosphere 2010, 80, 608-612
12. Khan, B.; Qiao, X.; Lee, L. S. Stereoselective sorption by agricultural soils and liquid-liquid partitioning of trenbolone (17α and 17β) and trendione Environ. Sci. Technol. 2009, 43, 8827-8833
13. Mashtare, M.; Khan, B.; Lee, L. S. Evaluating stereoselective sorption by soils of 17α-estradiol and 17β-estradiol Chemosphere 2011, 82, 847-852
14. Chiou, C. T.; Malcolm, R. L.; Brinton, T. I.; Klle, D. E. Water solubility enhancement of some organic pollutants and pesticides by dissolved humic and fulvic acids Environ. Sci. Technol. 1986, 20, 502-508 (Pubitemid 16042608)
15. Carmosini, N.; Lee, L. S. Partitioning of fluorotelomer alcohols to octanol and different sources of dissolved organic carbon Environ. Sci. Technol. 2008, 42, 6559-6565
16. nd ed.; Wiley-Interscience, 2003.
17. Yamamoto, H.; Liljestrand, H. M.; Shimizu, Y.; Morita, M. Effects of physical-chemical characteristics on the sorption of selected endocrine disruptors by dissolved organic matter surrogates Environ. Sci. Technol. 2003, 37, 2646-2657 (Pubitemid 36706004)
18. Neale, P. A.; Esher, B. I.; Schäfer, A. I. pH dependence of steroid hormone-organic matter interactions at environmental concentrations Sci. Total Environ. 2009, 407, 1164-1173
19. Hanselman, T. A.; Graetz, D. A.; Wilkie, A. C. Manure-borne estrogens as potential environmental contaminants: a review Environ. Sci. Technol. 2003, 37, 5471-5478 (Pubitemid 37541714)
20. Schiffer, B.; Daxenberger, A; Meyer, K; Meyer, H. The fate of trenbolone acetate and melengesterol acetate after application as growth promoters in cattle: environmental studies Environ Health Perspect. 2001, 109, 1145-1151 (Pubitemid 33130584)
21. Khan, B.; Lee, L. S.; Sassman, S. A. Degradation of synthetic androgens 17α- and 17β-trenbolone and trendione in agricultural soils Environ. Sci. Technol. 2008, 42, 3570-3574 (Pubitemid 351694062)
22. Carmosini, N.; Lee, L. S. Ciprofloxacin sorption by dissolved organic carbon from reference and bio-waste materials Chemosphere 2009, 77, 813-820
23. Karickhoff, S. W.; Brown, D. S. Determination of Octanol/Water Distribution Coefficients, Water Solubilities, and Sediment/Water Partition Coefficients for Hydrophobic Organic Pollutants; EPA-600/4-79-032; Environmental Research Laboratory, Office of Research and Development, U.S. Environmental Protection Agency, 1979.
24. Kamlet, M. J.; Doherty, R. M.; Abraham, M. H.; Marcus, Y.; Taft, R. W. Linear Solvation Energy Relationships. 46. An improved equation for correlation and prediction of octanol/water partition coefficients of organic nonelectrolytes (including strong hydrogen bond donor solutes) J. Phys. Chem. 1988, 92, 5244-5255
25. Kamlet, M. J.; Doherty, R. M.; Carr, P. W.; Mackay, D.; Abraham, M. H.; Taft, R. W. Linear Solvation Energy Relationships. 44. Parameter Estimation Rules That Allow Accurate Prediction of Octanol/Water Partition Coefficients and Other Solubility and Toxicity Properties of Polychlorinated Biphenyls and Polycyclic Aromatic Hydrocarbons Environ. Sci. Technol. 1988, 22, 503-509
26. Headley, A. D.; Starnes, S. D.; Wison, L. Y.; Famini, G. R. Analysis of solute/solvent interactions for the acidity of acetic acids by theoretical descriptors J. Org. Chem. 1994, 59, 8040-8046
27. Wilson, L. Y.; Famini, G. R. Using theoretical descriptors in Quantitative Structure-Activity Relationships: some toxicological indices J. Med. Chem. 1991, 34, 1668-1674
28. Brinck, T.; Murray, J. S.; Politzer, P. Octanol/water partition coefficients expressed in terms of solute molecular surface areas and electrostatic potentials J. Org. Chem. 1993, 58, 7070-7073
29. Politzer, P.; Murray, J. S.; Peralta-Inga, Z. Molecular surface electrostatic potentials in relation to noncovalent interactions in biological systems Int. J. Quantum Chem. 2001, 85, 676-684 (Pubitemid 33105812)
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
31. Neale, P. A.; Escher, B. I.; Schäfer, A. I. Quantification of solute-solute interactions using negligible-depletion solid-phase microextraction: measuring the affinity of estradiol to bulk organic matter Environ. Sci. Technol. 2008, 42, 2886-2892 (Pubitemid 351536927)
32. Danielsen, K. M.; Chin, Y.-P.; Buterbaugh, J. S.; Gustafson, T. L.; Traina, S. J. Solubility enhancement and fluorescence quenching of pyrene by humic substances: the effect of dissolved oxygen on quenching processes Environ. Sci. Technol. 1995, 29, 2162-2165 (Pubitemid 26259088)
33. Mackenzie, K.; Georgi, A.; Kumke, M. U.; Kopinke, F. D. Sorption of pyrene to dissolved humic substances and related model polymers. 2. Solid-phase microextraction (SPME) and fluorescence quenching technique (FQT) as analytical methods Environ. Sci. Technol. 2002, 36, 4403-4409
34. Hunter, C. A.; Sanders, J. K. M. The nature of π-π interactions J. Am. Chem. Soc. 1990, 112, 5525-5534