Toxicity, dioxin-like activities, and endocrine effects of DDT metabolites-DDA, DDMU, DDMS, and DDCN

Environmental Science and Pollution Research

Volumn 19, Issue 2, 2012, Pages 403-415

  Wetterauer, Bernhard ^a   Ricking, Mathias ^c   Otte, Jens C ^a,b   Hallare, Arnold V ^d,e   Rastall, Andrew ^a   Erdinger, Lothar ^a   Schwarzbauer, Jan ^d   Braunbeck, Thomas ^a   Hollert, Henner ^a,d  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d RWTH AACHEN UNIVERSITY   (Germany)

^e UNIVERSITY OF THE PHILIPPINES MANILA   (Philippines)

Author keywords

Cytotoxicity; DDA; DDCN; DDMS; DDMU; DDT metabolites; Dioxin like activity; Dot blot RNAse protection assay; EROD; Estrogenic activity; Yeast estrogen screen

Indexed keywords

1,1 BIS(4 CHLOROPHENYL)ETHYLENE; 1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHANE; 1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHYLENE; ACETONITRILE DERIVATIVE; AMIDE; BIS(P CHLOROPHENYL)ACETIC ACID; BIS(P-CHLOROPHENYL)ACETIC ACID; CHLORPHENOTANE; DDMS; DRUG DERIVATIVE; ENDOCRINE DISRUPTOR; ESTROGEN; HEAVY METAL; P,P' DDCN; P,P'-DDCN; SULFONE; VITELLOGENIN;

BASELINE CONDITIONS; BIOACTIVITY; BIOASSAY; CONCENTRATION (COMPOSITION); DDE; DDT; DOSE-RESPONSE RELATIONSHIP; ECOTOXICOLOGY; ENDOCRINE DISRUPTOR; ESTROGENIC COMPOUND; METABOLITE; RISK ASSESSMENT; SALMONID; SEDIMENT POLLUTION; SURFACE WATER;

ANIMAL; ARTICLE; CHEMISTRY; ENVIRONMENTAL MONITORING; GERMANY; GROWTH, DEVELOPMENT AND AGING; MALE; METABOLISM; METHODOLOGY; PHYSIOLOGY; RAINBOW TROUT; RIVER; SEDIMENT; TOXICITY TESTING; WATER POLLUTANT;

ACETONITRILES; AMIDES; ANIMALS; BERLIN; DDT; DICHLORODIPHENYL DICHLOROETHYLENE; DICHLORODIPHENYLDICHLOROETHANE; ENDOCRINE DISRUPTORS; ENVIRONMENTAL MONITORING; ESTROGENS; GEOLOGIC SEDIMENTS; MALE; METALS, HEAVY; ONCORHYNCHUS MYKISS; RIVERS; SULFONES; TOXICITY TESTS, ACUTE; VITELLOGENINS; WATER POLLUTANTS, CHEMICAL;

BERLIN; ELBE BASIN; GERMANY; MULDE RIVER; SAXONY-ANHALT; TELTOW CANAL;

ONCORHYNCHUS MYKISS;

EID: 84855995145     PISSN: 09441344     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11356-011-0570-9     Document Type: Article

References (82)

1. ATSDR, Agency for Toxic Substances and Disease Registry, Public Health Service, U. S. Department of Health and Human Services (2002) Toxicological profile for DDT, DDE and DDD. http://www.atsdr.cdc.gov/toxprofiles/tp35.pdf.
2. Beck I-C, Bruhn R, Gandrass J (2006) Analysis of estrogenic activity in coastal surface waters of the Baltic Sea using the yeast estrogen screen. Chemosphere 63: 1870-1878.
3. Behrens A, Schirmer K, Bols NC, Segner H (1998) Microassay for rapid measurement of 7-ethoxyresorufin-O-deethylase activity in intact fish hepatocytes. Mar Environ Res 46: 369-373.
4. Binelli A, Ricciardi F, Riva C, Provini A (2006) New evidences for old biomarkers: effects of several xenobiotics on EROD and AChE activities in zebra mussel (Dreissena polymorpha). Chemosphere 62: 510-519.
5. Binelli A, Riva C, Cogni D, Provini A (2008) Genotoxic effects of p, p′-DDT (1, 1, 1-trichloro-2, 2-bis-(chlorophenyl)ethane) and its metabolites in zebra mussel (D. polymorpha) by SCGE assay and micronucleus test. Environ Mol Mutagen 49: 406-415.
6. Bitman J, Cecil HC, Harris SJ, Fries GF (1968) Estrogenic activity of o, p'-DDT in the mammalian uterus and avian oviduct. Science 162: 371-372.
7. Borenfreund E, Puerner JA (1984) A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR-90). J Tissue Cult Meth 9: 7-9.
8. Braunbeck T, Storch V (1992) Senescence of hepatocytes isolated from rainbow trout (Oncorhynchus mykiss) in primary culture-an ultrastructural study. Protoplasma 170: 138-159.
9. Chen CW, Hurd C, Vorojeikina DP, Arnold SF, Notides AC (1997) Transcriptional activation of the human estrogen receptor by DDT isomers and metabolites in yeast and MCF-7 cells. Biochem Pharmacol 53: 1161-1172.
10. Dietz R, Riget F, Cleemann M, Aarkrog A, Johansen P, Hansen JC (2000) Comparison of contaminants from different trophic levels of ecosystems. Sci Total Environ 245: 221-231.
11. Donohoe RM, Curtis LR (1996) Estrogenic activity of chlordecone, o, p′-DDT and o, p′-DDE in juvenile rainbow trout: induction of vitellogenesis and interaction with hepatic estrogen binding sites. Aquat Toxicol 36: 31-52.
12. Dünnbier U, Heberer T, Reilich C (1997) Occurrence of bis (chlorophenyl)acetic acid (DDA) in surface and ground water in Berlin. Fresen Environ Bull 6: 753-759.
13. Eganhouse RP, Pontolillo J (2000) Depositional history of organic contaminants on the Palos Verdes Shelf, California. Mar Chem 70: 317-338.
14. Eganhouse RP, Pontolillo J (2008) DDE in sediments of the Palos Verdes Shelf, California: in situ transformation rates and geochemical fate. Environ Sci Technol 42: 6392-6398.
15. Eganhouse RP, Pontolillo J, Leiker TJ (2000) Diagenetic fate of organic contaminants on the Palos Verdes Shelf, California. Mar Chem 70: 289-315.
16. Falandysz J, Strandberg L, Puzyn T, Gucia M, Rappe C (2001) Chlorinated cyclodiene pesticide residues in blue mussel, crab and fish in the Gulf of Gdańsk, Baltic Sea. Environ Sci Technol 35: 4163-4169.
17. Falandysz J, Wyrzkowska B, Warzocha J, Barska I, Garbacik-Wesowska SP (2004) Organochlorine pesticides and PCBs in perch Perca fluviatilis from the Odra/Oder river estuary, Baltic Sea. Food Chem 87: 17-23.
18. Feng J, Turnbull M (2009) 1, 1, 1-Trichloro-2, 2-bis-(4′-chlorophenyl)-ethane (DDT) anaerobic graphic pathway map. In: Biocatalysis/Biodegradation Database. University of Minnesota. http://umbbd.msi.umn.edu/ddt2/ddt2_image_map.html. Accessed 03 March 2009.
19. Franke S, Heinzel N, Specht M, Francke W (2005) Identfication of organic pollutants in waters and sediments from the lower Mulde river area. Acta Hydrochim Hydrobiol 33: 519-542.
20. Frische K, Schwarzbauer J, Ricking M (2010) Structural diversity of organochlorine compounds in groundwater affected by an industrial point source. Chemosphere 81: 500-508.
21. Fry DM, Toone CK (1981) DDT-induced feminization of gull embryos. Science 213: 922-924.
22. Garrison AW, Nzengung VA, Avants JK, Ellington JJ, Jones WJ, Rennels D, Wolfe NL (2000) Phytodegradation of p, p′-DDT and the enantiomers of o, p′-DDT. Environ Sci Technol 34: 1663-1670.
23. Gaw SK, Palmer G, Kim ND, Wilkins AL (2003) Preliminary evidence that copper inhibits the degradation of DDT to DDE in pip and stonefruit orchard soils in the Auckland region, New Zealand. Environ Pollut 122: 1-5.
24. Guo Y, Zhang BZ, Meng XZ, Yu HY, Ran Y, Li SM, Zeng EY (2009) Occurrence and fate of 1-chloro-2, 2-bis(4-chlorophenyl)ethene in the environment of the Pearl river delta, South China. Environ Sci Technol 43: 3073-3079.
25. Heberer T, Dünnbier U (1999) DDT metabolite bis(chlorophenyl)acetic acid: the neglected environmental contaminant. Environ Sci Technol 33: 2346-2351.
26. Heim S, Ricking M, Schwarzbauer J, Littke R (2005) Halogenated compounds in a dated sediment core of the Teltow Canal, Berlin: time related sediment contamination. Chemosphere 61: 1427-1438.
27. Hilscherova K, Machala M, Kannan K, Blankenship AL, Giesy JP (2000) Cell bioassays for detection of aryl hydrocarbon (AhR) and estrogen receptor (ER) mediated activity in environmental samples. Environ Sci Pollut Res 7: 159-171.
28. Hollert H, Dürr M, Erdinger L, Braunbeck T (2000) Cytotoxicity of settling particulate matter and sediments of the Neckar River (Germany) during a winter flood. Environ Toxicol Chem 19: 528-534.
29. Hollert H, Dürr M, Olsman H, Halldin K, van Bavel B, Brack W, Tysklind M, Engwall M, Braunbeck T (2002) Biological and chemical determination of dioxin-like compounds in sediments by means of a sediment triad approach in the catchment area of the River Neckar. Ecotoxicology 11: 323-336.
30. Hollert H, Dürr M, Holtey-Weber R, Islinger M, Brack W, Färber H, Erdinger L, Braunbeck T (2005) Endocrine disruption of water and sediment extracts in a non-radioactive dot blot/RNAse protection-assay using isolated hepatocytes of rainbow trout - deficiencies between bioanalytical effectiveness and chemically determined concentrations and how to explain them. Environ Sci Pollut Res 12: 347-360.
31. Islinger M, Pawlowski S, Hollert H, Völkl A, Braunbeck T (1999) Measurement of vitellogenin-mRNA expression in primary cultures of rainbow trout hepatocytes in a non-radioactive RNAse protection assay/RNAse protection-assay. Sci Total Environ 233: 109-122.
32. Jafvert CT (1990) Environmental research brief: assessing the environmental partitioning of organic acid compounds. EPA/600/M-89/016.
33. Jensen S, Göthe R, Kindstedt MO (1972) Bis-(p-chlorophenyl)-acetonitrile (DDCN), a new DDT derivative formed in anaerobic digested sewage sludge and lake sediment. Nature 240: 421-422.
34. Jeong HG, Kim JY (2002) Effects of o, p′-DDT on the 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin-inducible CYP1A1 expression in murine Hepa-1c1c7 cells. Food Chem Toxicol 40: 1685-1692.
35. Kale SP, Murthy NBK, Raghu K, Sherkhane PD, Carvalho FP (1999) Studies on degradation of 14C-DDT in the marine environment. Chemosphere 39: 959-968.
36. Keith LH, Telliard WA (1979) Priority pollutants: I-a perspective view. Environ Sci Technol 13: 416-423.
37. Kelce WR, Stone CR, Laws SC, Gray LE, Kemppainen JA, Wilson EM (1995) Persistent DDT metabolite p, p′-DDE is a potent androgen receptor antagonist. Nature 375: 581-585.
38. Kennedy SW, Lones SP (1994) Simultaneous measurement of cytochrome P4501A catalytic activity and total protein concentration with a fluorescence plate reader. Anal Biochem 222: 217-223.
39. Kosmehl T, Krebs F, Manz W, Erdinger L, Braunbeck T, Hollert H (2004) Comparative genotoxicity testing of Rhine river sediment extracts using the comet assay with permanent fish cell lines (RTG-2 and RTL-W1) and the Ames test. JSS - J Soils Sediments 4: 84-94.
40. Kronimus A, Schwarzbauer J (2007) Non-target screening of extractable and non-extractable organic xenobiotics in riverine sediments of Ems and Mulde rivers, Germany. Environ Pollut 147: 176-186.
41. Kronimus A, Schwarzbauer J, Ricking M (2006) Analysis of non-extractable DDT-related compounds in riverine sediments of the Teltow Canal, Berlin, by pyrolysis and thermochemolysis. Environ Sci Technol 40: 5882-5890.
42. Leaños-Castañeda O, van der Kraak G (2007) Functional characterization of estrogen receptor subtypes, ERα and ERβ, mediating vitellogenin production in the liver of rainbow trout. Toxicol Appl Pharm 224: 116-125.
43. Leaños-Castañeda O, van der Kraak G, Rodríguez-Canul R, Gold G (2007) Endocrine disruption mechanism of o, p′-DDT in mature tilapia (Oreochromis niloticus). Toxicol Appl Pharm 221: 158-167.
44. Lee LEJ, Clemons JH, Bechtel DG, Caldwell SJ, Han KB, Pasitschniak-Arts M, Mosser DD, Bols NC (1993) Development and characterization of a rainbow trout liver cell line expressing cytochrome P450-dependent monooxygenase activity. Cell Biol Toxicol 9: 279-294.
45. Llompart M, Lores M, Lourido M, Sánchez-Prado L, Cela R (2003) On-fiber photodegradation after solid-phase microextraction of p, p′-DDT and two of its major photoproducts, p, p′-DDE and p, p′-DDD. J Chrom A 985: 175-183.
46. Lotufo GR, Landrum PF, Gedeon ML, Tigue EA, Herche LR (2000) Comparative toxicity and toxicokinetics of DDT and its major metabolites in freshwater amphipods. Environ Toxicol Chem 19: 368-379.
47. Lotufo GR, Landrum PF, Gedeon ML (2001) Toxicity and bioaccumulation of DDT in freshwater amphipods in exposures to spiked sediments. Environ Toxicol Chem 20: 810-825.
48. Lubet RA, Dragnev KH, Chauhan DP, Nims RW, Diwan BA, Ward JM, Jones CR, Rice JM, Miller MS (1992) A pleiotropic response to phenobarbital-type enzyme inducers in the F344/NCr rat-effects of chemicals of varied structure. Biochem Pharmacol 43: 1067-1078.
49. Megharaj M, Kantachote D, Singleton I, Naidu R (2000) Effects of long-term contamination of DDT on soil microflora with special reference to soil algae and algal transformation of DDT. Environ Pollut 109: 35-42.
50. Metcalf RL (1973) A century of DDT. J Agr Food Chem 21: 511-519.
51. Nims RW, Lubet RA, Fox SD, Jones CR, Thomas PE, Reddy AB, Kocarek TA (1998) Comparative pharmacodynmics of CYP2B induction by DDT, DDE and DDD in male rat liver and cultured rat hepatocytes. J Toxicol Environ Health A 53: 455-477.
52. Pawlowski S, Ternes TA, Bonerz M, Rastall AC, Erdinger L, Braunbeck T (2004) Estrogenicity of solid phase-extracted water samples from two municipal sewage treatment plant effluents and river Rhine water using the yeast estrogen screen. Toxicol in Vitro 18: 129-138.
53. Petit F, Goff PL, Cravédi JP, Valotaire Y, Pakdel F (1997) Two complementary bioassays for screening the estrogenic potency of xenobiotics: recombinant yeast for trout estrogen receptor and trout hepatocyte cultures. J Mol Endocrinol 19: 321-335.
54. Petit F, Goff PL, Cravédi JP, Kah O, Valotaire Y, Pakdel F (1999) Trout oestrogen receptor sensitivity to xenobiotics as tested by different bioassays. Aquaculture 177: 353-365.
55. Petrulis JR, Chen G, Benn S, LaMarre J, Bunce NJ (2001) Application of the ethoxyresorufin-O-deethylase (EROD) assay to mixtures of halogenated aromatic compounds. Environ Toxicol 16: 177-184.
56. Phuong PK, Son CPN, Sauvain JJ, Tarradellas J (1998) Contamination by PCB′s, DDT's, and heavy metals in sediments of Ho Chi Minh City's Canals, Viet Nam. Bull Environ Contam Toxicol 60: 347-354.
57. Planche G, Croisy A, Malaveille C, Tomatis L, Bartsch H (1979) Metabolic and mutagenicity studies on DDT and 15 derivatives. Detection of 1, 1-bis(p-chlorophenyl)-2, 2-dichloroethane and 1, 1-bis(p-chlorophenyl)-2, 2, 2-trichloroethyl acetate (kelthane acetate) as mutagens in Salmonella typhimurium and of 1, 1-bis(p-chlorophenyl) ethylene oxide, a likely metabolite, as an alkylating agent. Chem-Biol Interactions 25: 157-175.
58. Preuss TG, Gehrhardt J, Schirmer K, Coors A, Rubach M, Russ A, Jones PD, Giesy JP, Ratte HT (2006) Nonylphenol isomers differ in estrogenic activity. Environ Sci Technol 40: 5147-5153.
59. Preuss TG, Gurer-Orhan H, Meerman J, Ratte HT (2010) Some nonylphenol isomers show antiestrogenic potency in the MVLN cell assay. Toxicol Vitr 24: 129-134.
60. Quensen JF, Tiedje JM, Jain MK, Mueller SA (2001) Factors controlling the rate of DDE dechlorination to DDMU in Palos Verdes margin sediments under anaerobic conditions. Environ Sci Technol 35: 286-291.
61. Rastall AC, Neziri A, Vukovic Z, Jung C, Mijovic S, Hollert H, Nikcevic S, Erdinger L (2004) The identification of readily bioavailable pollutants in Lake Shkodra/Skadar using semipermeable membrane devices (SPMDs), bioassays and chemical analysis. Environ Sci Pollut Res 11: 240-253.
62. Reich AR, Perkins JL, Cutter G (1986) DDT contamination of a north Alabama aquatic ecosystem. Environ Toxicol Chem 5: 725-736.
63. Ren L, Lattier D, Lech JJ (1996) Estrogenic activity in rainbow trout determined with a new cDNA probe for vitellogenesis, pSG5Vg1. 1. Bull Environ Contam Toxicol 56: 287-294.
64. Renner R (1998) 'Natural' remediation of DDT, PCBs debated. Environ Sci Technol/News 32: 360 A-363 A.
65. Routledge EJ, Sumpter JP (1996) Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environ Toxicol Chem 15: 241-248.
66. Sayles GD, You G, Wang M, Kupferle MJ (1997) DDT, DDD and DDE dechlorination by zero-valent iron. Environ Sci Technol 31: 3448-3454.
67. Schwarzbauer J (1997) Screening, Identifizierung und quantitative Analyse organischer Substanzen in Sediment und Schwebstoff des Elbesystems. PhD Thesis University Hamburg, Department of Chemistry, 1-282.
68. Schwarzbauer J, Ricking M, Franke S, Francke W (2001) Halogenated organic contaminants in sediments of the Havel and Spree rivers (Germany). Part 5 of organic compounds as contaminants of the Elbe River and its tributaries. Environ Sci Technol 35: 4015-4025.
69. Schwarzbauer J, Ricking M, Littke R (2003) DDT-related compounds bound to the nonextractable particulate matter in sediments of the Teltow Canal, Germany. Environ Sci Technol 37: 488-495.
70. Sharpe RM (1995) Another DDT connection. Nature 375: 538-539.
71. Smeets JMW, van Holsteijn I, Giesy JP, Seinen W, van den Berg M (1999) Estrogenic potencies of several environmental pollutants, as determined by vitellogenin induction in a carp hepatocyte assay. Toxicol Sci 50: 206-213.
72. Sohoni P, Sumpter JP (1998) Several environmental oestrogens are also anti-androgens. J Endocrin 158: 327-339.
73. van Zwieten L, Ayres MR, Morris SG (2003) Influence of arsenic co-contamination on DDT breakdown and microbial activity. Environ Pollut 124: 331-339.
74. Voldner EC, Li YF (1995) Global usage of selected persistent organochlorines. Sci Total Environ 160(161): 201-210.
75. Vos JG, Dybing E, Greim HA, Ladefoged O, Lambré C, Tarazona JV, Brandt I, Vethaak AD (2000) Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Crit Rev Toxicol 30: 71-133.
76. Wan Y, Hu J, Liu J, An W, Tao S, Jia Z (2005) Fate of DDT-related compounds in Bohai Bay and its adjacent Haihe Bay, North China. Mar Pollut Bull 50: 439-445.
77. West CW, Phipps GL, Hoke RA, Goldenstein TA, van der Meiden FM, Kosian PA, Ankley GT (1994) Sediment core versus grab samples: evaluation of contamination and toxicity at a DDT-contaminated site. Ecotoxicol Environ Safety 28: 208-220.
78. Wolf K, Quimby MC (1962) Established eurythermic line of fish cells in vitro. Science 135: 1065-1066.
79. Wölz J, Engwall M, Maletz S, Takner HO, van Bavel B, Kammann U, Klempt M, Weber R, Braunbeck T, Hollert H (2008) Changes in toxicity and Ah receptor agonist activity of suspended particulate matter during flood events at the rivers Neckar and Rhine-a mass balance approach using in vitro methods and chemical analysis. Environ Sci Pollut Res 15: 536-553.
80. Yn X, Guo Y, Xie M, Shen RL, Zeng EY (2009) Detection of DDT and its metabolites in two estuaries of South China using a SPME-based device: first report of p, p′-DDMU in water column. Environ Pollut 157: 1382-1387.
81. Zahn J, Fahimi HD, Vöelkl A (1997) Sensitive nonradioactive dot blot/ribonuclease protection-assay for quantitative determination of mRNA. Biotechniques 22: 500-505.
82. Zeng EY, Venkatesan MI (1999) Dispersion of sediment DDTs in the coastal ocean of Southern California. Sci Total Environ 229: 195-208.