Placenta
Volume 29, Issue 11 , Pages 962-969 , November 2008

Maternal Di-(2-ethylhexyl)-phthalate Exposure Influences Essential Fatty Acid Homeostasis in Rat Placenta

  • Y. Xu

      Affiliations

    • Department of Pharmaceutics, Rutgers University, Piscataway, NJ 08854, USA
    • Current address: Drug Metabolism and Pharmacokinetics, Merck Research Laboratories, West Point, PA, USA.
  • ,
  • S. Agrawal

      Affiliations

    • Department of Pharmaceutics, Rutgers University, Piscataway, NJ 08854, USA
    • Current address: Discovery Medicine and Clinical Pharmacology, Bristol-Myers Squibb Co., Lawrenceville, NJ, USA.
  • ,
  • T.J. Cook

      Affiliations

    • Department of Pharmaceutical and Biomedical Sciences, Touro College of Pharmacy, New York, NY 10027, USA
  • ,
  • G.T. Knipp

      Affiliations

    • Department of Industrial and Physical Pharmacy, Purdue University, School of Pharmacy, 1205 Kent Avenue, West Lafayette, IN 47906, USA
    • Corresponding Author InformationCorresponding author. Tel.: +1 765 463 1989X112; fax: +1 765 497 7290.

,Accepted 11 August 2008.

References 

  1. Knipp G, Audus KL, Soares MJ. Nutrient transport across the placenta. Adv Drug Deliv Rev. 1999;38:41–58
  2. Innis SM. Perinatal biochemistry and physiology of long-chain polyunsaturated fatty acids. J Pediatr. 2003;143:S1–S8
  3. Haggarty P. Effect of placental function on fatty acid requirements during pregnancy. Eur J Clin Nutr. 2004;58:1559–1570
  4. Dutta-Roy AK. Transport mechanisms for long-chain polyunsaturated fatty acids in the human placenta. Am J Clin Nutr. 2000;71:S315–S322
  5. Xu Y, Wang Q, Cook TJ, Knipp GT. Effects of placental fatty acid metabolism and regulation by peroxisome proliferator activated receptor on pregnancy and fetal outcome. J Pharm Sci. 2007;96:2582–2606
  6. Fournier T, Tsatsaris V, Handschuh K, Evain-Brion D. PPARs and the placenta. Placenta. 2007;28:65–76
  7. Kavloc R, Boekelheide K, Chapin R, Cunningham M, Faustman E, Foster P, et al. NTP center for the evaluation of risks to human reproduction: phthalates expert panel report on the reproductive and developmental toxicity of di(2-ethylhexyl)-phthalate. Reprod Toxicol. 2002;16:529–653
  8. Singh AR, Lawrence WH, Autian J. Maternal-fetal transfer of 14C-di-2-ethylhexyl-phthalate and 14C-diethyl phthalate in rats. J Pharm Sci. 1975;64:1347–1350
  9. Kihlstrom I. Placental transfer of diethylhexyl phthalate in the guinea-pig placenta perfused in situ. Acta Pharmacol Toxicol (Copenh). 1983;53:23–27
  10. Silva MJ, Reidy JA, Herbert AR, Preau JL, Needham LL, Calafat AM. Detection of phthalate metabolites in human amniotic fluid. Bull Environ Contam Toxicol. 2004;72:1226–1231
  11. Dzhekova-Stojkova S, Bogdanska J, Stojkova Z. Peroxisome proliferators: their biological and toxicological effects. Clin Chem Lab Med. 2001;39:468–474
  12. Xu Y, Cook TJ, Knipp GT. Effect of di-(2-ethylhexyl)-phthalate and its metabolites on fatty acid homeostasis regulating proteins in HRP-1 cells. Toxicol Sci. 2005;84:287–300
  13. Xu Y, Agrawal S, Cook TJ, Knipp GT. Di-(2-ethylhexyl)-phthalate affects fetal brain lipid profiling in rat upon maternal exposure. Arch Toxicol. 2007;81:57–62
  14. Soares MJ. Molecular mechanisms of placental development. In:  Battaglia FC editors. Placental function and fetal nutrition. Nestlé nutrition workshop series. vol. 39:Philadelphia, PA: Nestec Ltd., Vevey/Lippincott-Raven Publishers; 1997;p. 31–45
  15. Xu Y, Knipp GT, Cook TJ. Expression of CYP4A isoforms in developing rat placenta and trophoblast cell models. Placenta. 2005;26:218–225
  16. Xu Y, Knipp GT, Cook TJ. Expression of COX isoforms in developing rat placenta and trophoblast cell models. Mol Pharm. 2005;2:481–490
  17. Yaghi A, Webb CD, Scott JA, Mehta S, Bend JR, McCormack DG. Cytochrome P450 metabolites of arachidonic acid but not cyclooxygenase-2 metabolites contribute to the pulmonary vascular hyporeactivity in rats with acute pseudomonas pneumonia. J Pharmacol Exp Ther. 2001;297:479–488
  18. Kawai S. Cyclooxygenase selectivity and the risk of gastro-intestinal complications of various non-steroidal anti-inflammatory drugs: a clinical consideration. Inflamm Res. 1998;47(Suppl. 2):S102–S106
  19. Maloney E, Waxman DJ. trans-Activation of PPARalpha and PPARgamma by structurally diverse environmental chemicals. Toxicol Appl Pharmacol. 1999;161:209–218
  20. Latini G, De Felice C, Presta G, Del Vecchio A, Paris I, Ruggieri F, et al. Exposure to di(2-ethylhexyl)-phthalate in humans during pregnancy. A preliminary report. Biol Neonate. 2003;83:22–24
  21. Barak Y, Nelson MC, Ong ES, Jones YZ, Ruiz-Lozano P, Chien KR, et al. PPAR gamma is required for placental, cardiac, and adipose tissue development. Mol Cell. 1999;4:585–595
  22. Hurst CH, Waxman DJ. Activation of PPARalpha and PPARgamma by environmental phthalate monoesters. Toxicol Sci. 2003;74:297–308
  23. Barak Y, Liao D, He W, Ong ES, Nelson MC, Olefsky JM, et al. Effects of peroxisome proliferator-activated receptor delta on placentation, adiposity, and colorectal cancer. Proc Natl Acad Sci U S A. 2006;99:303–308
  24. Michalik L, Desvergne B, Dreyer C, Gavillet M, Laurini RN, Wahli W. PPAR expression and function during vertebrate development. Int J Dev Biol. 2002;46:105–114
  25. Motojima K, Passilly P, Peters JM, Gonzalez FJ, Latruffe N. Expression of putative fatty acid transporter genes are regulated by peroxisome proliferator-activated receptor alpha and gamma activators in a tissue- and inducer-specific manner. J Biol Chem. 1998;273:16710–16714
  26. Kretschmer XC, Baldwin WS. CAR and PXR: xenosensors of endocrine disrupters?. Chem Biol Interact. 2005;155:111–128
  27. Tapiero H, Ba GN, Couvreur P, Tew KD. Polyunsaturated fatty acids (PUFAs) and eicosanoids in human health and pathologies. Biomed Pharmacother. 2002;56:215–222
  28. Wong JS, Gill SS. Gene expression changes induced in mouse liver by di(2-ethylhexyl)-phthalate. Toxicol Appl Pharmacol. 2002;185:180–196
  29. Kim HS, Ishizuka M, Kazusaka A, Fujita S. Alterations of activities of cytosolic phospholipase A2 and arachidonic acid-metabolizing enzymes in di-(2-ethylhexyl)-phthalate-induced testicular atrophy. J Vet Med Sci. 2004;66:1119–1124
  30. Johnson EF, Hsu MH, Savas U, Griffin KJ. Regulation of P450 4A expression by peroxisome proliferator activated receptors. Toxicology. 2002;181-182:203–206
  31. Kniss DA. Cyclooxygenases in reproductive medicine and biology. J Soc Gynecol Investig. 1999;6:285–292
  32. Narotsky MG, Weller EA, Chinchilli VM, Kavlock RJ. Nonadditive developmental toxicity in mixtures of trichloroethylene, di(2-ethylhexyl)-phthalate, and heptachlor in a 5×5×5 design. Fundam Appl Toxicol. 1995;27:203–216
  33. Staels B, Koenig W, Habib A, Merval R, Lebret M, Torra IP, et al. Activation of human aortic smooth-muscle cells is inhibited by PPARalpha but not by PPARgamma activators. Nature. 1998;393:790–793
  34. Inoue H, Tanabe T, Umesono K. Feedback control of cyclooxygenase-2 expression through PPARgamma. J Biol Chem. 2000;275:28028–28032
  35. Subbaramaiah K, Lin DT, Hart JC, Dannenberg AJ. Peroxisome proliferator-activated receptor gamma ligands suppress the transcriptional activation of cyclooxygenase-2. Evidence for involvement of activator protein-1 and CREB-binding protein/p300. J Biol Chem. 2001;276:12440–12448
  36. Bell FP. Effects of phthalate esters on lipid metabolism in various tissues, cells and organelles in mammals. Environ Health Perspect. 1982;45:41–50
  37. Uauy R, Hoffman DR, Peirano P, Birch DG, Birch EE. Essential fatty acids in visual and brain development. Lipids. 2001;36:885–895
  38. Amusquivar E, Ruperez FJ, Barbas C, Herrera E. Low arachidonic acid rather than alpha-tocopherol is responsible for the delayed postnatal development in offspring of rats fed fish oil instead of olive oil during pregnancy and lactation. J Nutr. 2000;130:2855–2865

PII: S0143-4004(08)00248-8

doi: 10.1016/j.placenta.2008.08.011

Placenta
Volume 29, Issue 11 , Pages 962-969 , November 2008