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Chemical Compound Review

p,p'-DDE     1-chloro-4-[2,2-dichloro-1- (4...

Synonyms: p,p-Dde, SPECTRUM330072, CCRIS 193, CHEMBL363207, NSC-1153, ...
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Disease relevance of DDE

  • METHODS: We measured plasma levels of DDE and PCBs prospectively among 240 women who gave a blood sample in 1989 or 1990 and who were subsequently given a diagnosis of breast cancer before June 1, 1992 [1].
  • Our aim was to investigate the association between DDE exposure and preterm birth [2].
  • In addition, adrenocortical adenomas, spontaneous to Syrian golden hamsters, were more frequent in DDE- and DDT-treated animals than in control animals [3].
  • In addition, we show that the lack of DDE-type integrase genes from elements of the DIRS1 group is explained by the finding that the previously uncharacterized ORFs of these elements encode proteins related to the site-specific recombinase of bacteriophage lambda [4].
  • Liver cancer mortality increased significantly with adipose DDE levels in both sexes among whites, but not among African Americans [5].

Psychiatry related information on DDE


High impact information on DDE


Chemical compound and disease context of DDE


Biological context of DDE

  • To elucidate the organization of active sites within this tetramer, the subunit providing the essential active site DDE residues for each cleavage and joining reaction was determined [14].
  • The finding that serum DDE levels increase with age suggests that no equilibrium in body burden has been reached or that pharmacokinetics or serum/adipose partition may vary with age [20].
  • After adjustment for first-degree family history of breast cancer, lifetime lactation, and age at first full-term pregnancy, conditional logistic regression analysis showed a fourfold increase in relative risk of breast cancer for an elevation of serum DDE concentrations from 2.0 ng/mL (10th percentile) to 19.1 ng/mL (90th percentile) [21].
  • A mutation in a DDE motif abolishes both endonucleolytic and phosphoryl transfer activities, suggesting that Tc1A carries a catalytic core common to retroviral integrases and IS transposases [22].
  • When one of the hyperactive Tnps is replaced with a catalytically inactive version containing the mutation EA326 (DDE mutant), the predominant reaction product is a linearized plasmid resulting from single end cleavage [23].

Anatomical context of DDE


Associations of DDE with other chemical compounds

  • Laboratory experiments with DDE-containing marine sediments showed that DDE is dechlorinated to DDMU in both methanogenic and sulfidogenic microcosms and that DDD is dehydrochlorinated to DDMU three orders of magnitude more slowly [12].
  • A specific association was observed between a glycine to valine substitution at codon 12 and both p,p'-DDT and p,p'-DDE concentrations (odds ratio 15.9, p=0.044 and odds ratio 24.1, p=0.028; respectively) [29].
  • Nuclear accumulation of CAR, but not PXR, was observed in the liver tissue following DDE and PB treatment [30].
  • This procedure was designed primarily to protect piscivorous birds and mammals from compounds that bioaccumulate in fish and was used in the Great Lakes Water Quality Initiative (GLI) to calculate wildlife values (WV) for mercury, DDT/DDE, total polychlorinated biphenyls (PCBs), and 2,3,7,8-tetrachlorodibenzodioxin (TCDD) [31].
  • In our previous study we have shown that a water-soluble derivatized dextran named DDE, containing 82.2% methyl carboxylic acid groups, 6.1% benzylamide, and 5.6% sulfonate with a specific anticoagulant activity equivalent to heparin of 0.5 IU/mg could potentiate the mitogenic activity of aFGF on CCL39 cells [32].

Gene context of DDE

  • Androgen receptor activities of p,p'-DDE, fenvalerate and phoxim detected by androgen receptor reporter gene assay [33].
  • Linear-regression analysis showed that interleukin-4 (IL-4) plasma levels were associated with plasma levels of DDT 4.4 (p = .0001) and DDE 4.4 (p = .001) [34].
  • These results suggest that p,p'-DDT and o,p'-DDT exerted their effects on neuronal cells by the stimulation of p44/42 MAPK, and p,p'-DDE had less effects than the other two organochlorines [35].
  • Furthermore, the critical DDE catalytic triad of RAG1 is shared with the Transib transposase as part of conserved motifs [36].
  • In this report, p,p'-DDE, a weak androgen receptor (AR) antagonist, has been examined in a Tier I screening battery designed to detect endocrine-active compounds (EACs) [37].

Analytical, diagnostic and therapeutic context of DDE


  1. Plasma organochlorine levels and the risk of breast cancer. Hunter, D.J., Hankinson, S.E., Laden, F., Colditz, G.A., Manson, J.E., Willett, W.C., Speizer, F.E., Wolff, M.S. N. Engl. J. Med. (1997) [Pubmed]
  2. Association between maternal serum concentration of the DDT metabolite DDE and preterm and small-for-gestational-age babies at birth. Longnecker, M.P., Klebanoff, M.A., Zhou, H., Brock, J.W. Lancet (2001) [Pubmed]
  3. Carcinogenicity study with technical-grade dichlorodiphenyltrichloroethane and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene in hamsters. Rossi, L., Barbieri, O., Sanguineti, M., Cabral, J.R., Bruzzi, P., Santi, L. Cancer Res. (1983) [Pubmed]
  4. The DIRS1 group of retrotransposons. Goodwin, T.J., Poulter, R.T. Mol. Biol. Evol. (2001) [Pubmed]
  5. Cancer mortality and environmental exposure to DDE in the United States. Cocco, P., Kazerouni, N., Zahm, S.H. Environ. Health Perspect. (2000) [Pubmed]
  6. Development after exposure to polychlorinated biphenyls and dichlorodiphenyl dichloroethene transplacentally and through human milk. Gladen, B.C., Rogan, W.J., Hardy, P., Thullen, J., Tingelstad, J., Tully, M. J. Pediatr. (1988) [Pubmed]
  7. Motor function in aging Great Lakes fisheaters. Schantz, S.L., Gardiner, J.C., Gasior, D.M., Sweeney, A.M., Humphrey, H.E., McCaffrey, R.J. Environmental research. (1999) [Pubmed]
  8. Starvation-pesticide unteraetions in juvenile brown pelicans. Thompson, N.P., Courtney, C.H., Forrester, D.J., White, F.H. Bulletin of environmental contamination and toxicology. (1977) [Pubmed]
  9. DDT (dicophane) and postmenopausal breast cancer in Europe: case-control study. van't Veer, P., Lobbezoo, I.E., Martín-Moreno, J.M., Guallar, E., Gómez-Aracena, J., Kardinaal, A.F., Kohlmeier, L., Martin, B.C., Strain, J.J., Thamm, M., van Zoonen, P., Baumann, B.A., Huttunen, J.K., Kok, F.J. BMJ (1997) [Pubmed]
  10. Dioxin-like activities in serum across European and Inuit populations. Long, M., Andersen, B.S., Lindh, C.H., Hagmar, L., Giwercman, A., Manicardi, G.C., Bizzaro, D., Spanò, M., Toft, G., Pedersen, H.S., Zvyezday, V., Bonde, J.P., Bonefeld-Jorgensen, E.C. Environmental health : a global access science source [electronic resource]. (2006) [Pubmed]
  11. Persistent DDT metabolite p,p'-DDE is a potent androgen receptor antagonist. Kelce, W.R., Stone, C.R., Laws, S.C., Gray, L.E., Kemppainen, J.A., Wilson, E.M. Nature (1995) [Pubmed]
  12. Reductive dechlorination of DDE to DDMU in marine sediment microcosms. Quensen, J.F., Mueller, S.A., Jain, M.K., Tiedje, J.M. Science (1998) [Pubmed]
  13. Ban of DDT and subsequent recovery of Reproduction in bald eagles. Grier, J.W. Science (1982) [Pubmed]
  14. Organization and dynamics of the Mu transpososome: recombination by communication between two active sites. Williams, T.L., Jackson, E.L., Carritte, A., Baker, T.A. Genes Dev. (1999) [Pubmed]
  15. Plasma organochlorine levels and the risk of breast cancer: an extended follow-up in the Nurses' Health Study. Laden, F., Hankinson, S.E., Wolff, M.S., Colditz, G.A., Willett, W.C., Speizer, F.E., Hunter, D.J. Int. J. Cancer (2001) [Pubmed]
  16. Serum concentrations of organochlorine compounds and the subsequent development of breast cancer. Helzlsouer, K.J., Alberg, A.J., Huang, H.Y., Hoffman, S.C., Strickland, P.T., Brock, J.W., Burse, V.W., Needham, L.L., Bell, D.A., Lavigne, J.A., Yager, J.D., Comstock, G.W. Cancer Epidemiol. Biomarkers Prev. (1999) [Pubmed]
  17. Susceptibility to infections and immune status in Inuit infants exposed to organochlorines. Dewailly, E., Ayotte, P., Bruneau, S., Gingras, S., Belles-Isles, M., Roy, R. Environ. Health Perspect. (2000) [Pubmed]
  18. Neurosteroid-induced hyperalgesia through a histamine release is inhibited by progesterone and p,p'-DDE, an endocrine disrupting chemical. Uchida, H., Mizuno, K., Yoshida, A., Ueda, H. Neurochem. Int. (2003) [Pubmed]
  19. Organochlorine pesticides and male genital anomalies in the child health and development studies. Bhatia, R., Shiau, R., Petreas, M., Weintraub, J.M., Farhang, L., Eskenazi, B. Environ. Health Perspect. (2005) [Pubmed]
  20. Cross-sectional study of a community with exceptional exposure to DDT. Kreiss, K., Zack, M.M., Kimbrough, R.D., Needham, L.L., Smrek, A.L., Jones, B.T. JAMA (1981) [Pubmed]
  21. Blood levels of organochlorine residues and risk of breast cancer. Wolff, M.S., Toniolo, P.G., Lee, E.W., Rivera, M., Dubin, N. J. Natl. Cancer Inst. (1993) [Pubmed]
  22. Tc1 transposase of Caenorhabditis elegans is an endonuclease with a bipartite DNA binding domain. Vos, J.C., Plasterk, R.H. EMBO J. (1994) [Pubmed]
  23. Trans catalysis in Tn5 transposition. Naumann, T.A., Reznikoff, W.S. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  24. Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Vos, J.G., Dybing, E., Greim, H.A., Ladefoged, O., Lambré, C., Tarazona, J.V., Brandt, I., Vethaak, A.D. Crit. Rev. Toxicol. (2000) [Pubmed]
  25. The effect of subchronic feeding of 1,1-dichloro-2,2-bis(4'-chlorophenyl)ethene (DDE) on its metabolism in mice. Gold, B., Brunk, G. Carcinogenesis (1986) [Pubmed]
  26. Methylsulfonyl metabolites of PCBs and DDE in human tissues. Weistrand, C., Norén, K. Environ. Health Perspect. (1997) [Pubmed]
  27. Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Norén, K., Lundén, A., Pettersson, E., Bergman, A. Environ. Health Perspect. (1996) [Pubmed]
  28. Polychlorinated biphenyls (PCBs) and dichlorodiphenyl dichloroethene (DDE) in human milk: effects of maternal factors and previous lactation. Rogan, W.J., Gladen, B.C., McKinney, J.D., Carreras, N., Hardy, P., Thullen, J., Tingelstad, J., Tully, M. American journal of public health. (1986) [Pubmed]
  29. Serum concentrations of organochlorine compounds and K-ras mutations in exocrine pancreatic cancer. PANKRAS II Study Group. Porta, M., Malats, N., Jariod, M., Grimalt, J.O., Rifà, J., Carrato, A., Guarner, L., Salas, A., Santiago-Silva, M., Corominas, J.M., Andreu, M., Real, F.X. Lancet (1999) [Pubmed]
  30. The environmental pollutant 1,1-dichloro-2,2-bis (p-chlorophenyl)ethylene induces rat hepatic cytochrome P450 2B and 3A expression through the constitutive androstane receptor and pregnane X receptor. Wyde, M.E., Bartolucci, E., Ueda, A., Zhang, H., Yan, B., Negishi, M., You, L. Mol. Pharmacol. (2003) [Pubmed]
  31. Derivation of wildlife values for mercury. Nichols, J., Bradbury, S., Swartout, J. Journal of toxicology and environmental health. Part B, Critical reviews. (1999) [Pubmed]
  32. Derivatized dextrans mimic heparin as stabilizers, potentiators, and protectors of acidic or basic FGF. Tardieu, M., Gamby, C., Avramoglou, T., Jozefonvicz, J., Barritault, D. J. Cell. Physiol. (1992) [Pubmed]
  33. Androgen receptor activities of p,p'-DDE, fenvalerate and phoxim detected by androgen receptor reporter gene assay. Xu, L.C., Sun, H., Chen, J.F., Bian, Q., Song, L., Wang, X.R. Toxicol. Lett. (2006) [Pubmed]
  34. Associations of dichlorodiphenyltrichloroethane (DDT) 4.4 and dichlorodiphenyldichloroethylene (DDE) 4.4 blood levels with plasma IL-4. Daniel, V., Huber, W., Bauer, K., Suesal, C., Conradt, C., Opelz, G. Arch. Environ. Health (2002) [Pubmed]
  35. Dichlorodiphenyltrichloroethane suppresses neurite outgrowth and induces apoptosis in PC12 pheochromocytoma cells. Shinomiya, N., Shinomiya, M. Toxicol. Lett. (2003) [Pubmed]
  36. RAG1 core and V(D)J recombination signal sequences were derived from Transib transposons. Kapitonov, V.V., Jurka, J. PLoS Biol. (2005) [Pubmed]
  37. Detection of the environmental antiandrogen p,p-DDE in CD and long-evans rats using a tier I screening battery and a Hershberger assay. O'Connor, J.C., Frame, S.R., Davis, L.G., Cook, J.C. Toxicol. Sci. (1999) [Pubmed]
  38. Maternal serum level of 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene and risk of cryptorchidism, hypospadias, and polythelia among male offspring. Longnecker, M.P., Klebanoff, M.A., Brock, J.W., Zhou, H., Gray, K.A., Needham, L.L., Wilcox, A.J. Am. J. Epidemiol. (2002) [Pubmed]
  39. Environmental organochlorine exposure and postmenopausal breast cancer risk. Moysich, K.B., Ambrosone, C.B., Vena, J.E., Shields, P.G., Mendola, P., Kostyniak, P., Greizerstein, H., Graham, S., Marshall, J.R., Schisterman, E.F., Freudenheim, J.L. Cancer Epidemiol. Biomarkers Prev. (1998) [Pubmed]
  40. Risk of breast cancer and organochlorine exposure. Wolff, M.S., Zeleniuch-Jacquotte, A., Dubin, N., Toniolo, P. Cancer Epidemiol. Biomarkers Prev. (2000) [Pubmed]
  41. Semen quality and exposure to persistent organochlorine pollutants. Toft, G., Rignell-Hydbom, A., Tyrkiel, E., Shvets, M., Giwercman, A., Lindh, C.H., Pedersen, H.S., Ludwicki, J.K., Lesovoy, V., Hagmar, L., Spanó, M., Manicardi, G.C., Bonefeld-Jorgensen, E.C., Thulstrup, A.M., Bonde, J.P. Epidemiology (Cambridge, Mass.) (2006) [Pubmed]
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