Many putative endocrine disruptors inhibit prostaglandin synthesis

Environmental Health Perspectives

Volumn 119, Issue 4, 2011, Pages 534-541

  Kristensen, David M ^a   Skalkam, Maria L ^a   Audouze, Karine ^b   Lesné, Laurianne ^c   Desdoits Lethimonier, Christele ^c   Frederiksen, Hanne ^a   Brunak, Soren ^b   Skakkebaek, Niels E ^a   Jégou, Bernard ^c   Hansen, Jacob B ^d   Junker, Steffen ^e   Leffers, Henrik ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c UNIVERSITÉ DE RENNES 1   (France)

^d UNIVERSITY OF COPENHAGEN   (Denmark)

^e AARHUS UNIVERSITY   (Denmark)

Author keywords

Antiandrogens; Benzophenones; Cyclooxygenase; Endocrine disruptors; Parabens; Phthalates; PPARs; Prostaglandins

Indexed keywords

4 HYDROXYBENZOIC ACID ESTER; ACETYLSALICYLIC ACID; ANDROGEN; ANTIANDROGEN; ANTIESTROGEN; ARACHIDONIC ACID; BENZOPHENONE DERIVATIVE; ENDOCRINE DISRUPTOR; ESTROGEN; ESTROGEN DERIVATIVE; IBUPROFEN; INDOMETACIN; PARACETAMOL; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PHTHALIC ACID DERIVATIVE; PROSTAGLANDIN; PROSTAGLANDIN D2; PROSTAGLANDIN E RECEPTOR; PROSTAGLANDIN RECEPTOR; PROSTAGLANDIN SYNTHASE; TESTOSTERONE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOOXYGENASE 1 GENE; CYCLOOXYGENASE 2 GENE; ENZYME ACTIVE SITE; FETUS; GENE; HUMAN; HUMAN CELL; IC 50; JUVENILE ANIMAL; MAST CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROSTAGLANDIN RELEASE; PROSTAGLANDIN SYNTHESIS INHIBITION; SERTOLI CELL; TESTIS; TESTOSTERONE SYNTHESIS;

ANIMALS; CYCLOOXYGENASE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOCRINE DISRUPTORS; FATTY ACID SYNTHESIS INHIBITORS; HUMANS; MALE; MAST CELLS; MICE; PROSTAGLANDINS; RATS; TESTIS;

RATTUS;

EID: 79955553551     PISSN: 00916765     EISSN: 15529924     Source Type: Journal    
DOI: 10.1289/ehp.1002635     Document Type: Article

References (44)

1. Adams IR, McLaren A. 2002. Sexually dimorphic development of mouse primordial germ cells: switching from oogenesis to spermatogenesis. Development 129:1155-1164.
2. Amateau SK, McCarthy MM. 2004. Induction of PGE2 by estradiol mediates developmental masculinization of sex behavior. Nat Neurosci 7:643-650.
3. Beasley R, Clayton T, Crane J, von Mutius E, Lai CK, Montefort S, et al. 2008. Association between paracetamol use in infancy and childhood, and risk of asthma, rhinoconjunctivitis, and eczema in children aged 6-7 years: analysis from phase three of the ISAAC programme. Lancet 372:1039-1048.
4. Boisen KA, Kaleva M, Main KM, Virtanen HE, Haavisto AM, Schmidt IM, et al. 2004. Difference in prevalence of congenital cryptorchidism in infants between two Nordic countries. Lancet 363:1264-1269.
5. Chauvigne F, Menuet A, Lesne L, Chagnon MC, Chevrier C, Regnier JF, et al. 2009. Time-and dose-related effects of di-(2-ethylhexyl) phthalate and its main metabolites on the function of the rat fetal testis in vitro. Environ Health Perspect 117:515-521.
6. Christensen KB, Minet A, Svenstrup H, Grevsen K, Zhang H, Schrader E, et al. 2009. Identification of plant extracts with potential antidiabetic properties: effect on human peroxisome proliferator-activated receptor (PPAR), adipocyte differentiation and insulin-stimulated glucose uptake. Phytother Res 23:1316-1325.
7. Diamanti-Kandarakis E, Bourguignon JP, Giudice LC, Hauser R, Prins GS, Soto AM, et al. 2009. Endocrine-disrupting chemicals: an Endocrine Society scientific statement. Endocr Rev 30:293-342.
8. Eustache F, Mondon F, Canivenc-Lavier MC, Lesaffre C, Fulla Y, Berges R, et al. 2009. Chronic dietary exposure to a low-dose mixture of genistein and vinclozolin modifies the reproductive axis, testis transcriptome, and fertility. Environ Health Perspect 117:1272-1279.
9. FitzGerald GA. 2003. COX-2 and beyond: approaches to prostaglandin inhibition in human disease. Nat Rev Drug Discov 2:879-890.
10. Frederiksen H, Taxvig C, Hass U, Vinggaard AM, Nellemann C. 2008. Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration. Toxicol Sci 106:376-383.
11. Fujimoto Y, Usa K, Sakuma S. 2005. Effects of endocrine disruptors on the formation of prostaglandins and arachidonyl-CoA formed from arachidonic acid in rabbit medulla microsomes. Prostaglandins Leukot Essent Fatty Acids 73:447-452.
12. Graham GG, Robins SA, Bryant KJ, Scott KF. 2001. Inhibition of prostaglandin synthesis in intact cells by paracetamol (acetaminophen). Inflammopharmacology 9:131-142.
13. Gupta C. 1989. The role of prostaglandins in masculine differentiation: modulation of prostaglandin levels in the differentiating genital tract of the fetal mouse. Endocrinology 124:129-133.
14. Gupta C, Bentlejewski CA. 1992. Role of prostaglandins in the testosterone-dependent wolffian duct differentiation of the fetal mouse. Biol Reprod 47:1151-1160.
15. Gupta C, Goldman AS. 1986. The arachidonic acid cascade is involved in the masculinizing action of testosterone on embryonic external genitalia in mice. Proc Natl Acad Sci USA 83:4346-4349.
16. Habert R, Devif I, Gangnerau MN, Lecerf L. 1991. Ontogenesis of the in vitro response of rat testis to gonadotropin-releasing hormone. Mol Cell Endocrinol 82:199-206.
17. Hansen JB, Zhang H, Rasmussen TH, Petersen RK, Flindt EN, Kristiansen K. 2001. Peroxisome proliferator-activated receptor δ (PPARδ)-mediated regulation of preadipocyte proliferation and gene expression is dependent on cAMP signaling. J Biol Chem 276:3175-3182.
18. Hofmann MC, Narisawa S, Hess RA, Millan JL. 1992. Immortalization of germ cells and somatic testicular cells using the SV40 large T antigen. Exp Cell Res 201:417-435.
19. Holm M, Andersen HB, Hetland TE, Dahl C, Hoffmann HJ, Junker S, et al. 2008. Seven week culture of functional human mast cells from buffy coat preparations. J Immunol Methods 336:213-221.
20. Hsuanyu Y, Dunford HB. 1992. Prostaglandin H synthase kinetics. The effect of substituted phenols on cyclooxygenase activity and the substituent effect on phenolic peroxidatic activity. J Biol Chem 267:17649-17657.
21. Ishizaka T, Conrad DH, Schulman ES, Sterk AR, Ishizaka K. 1983. Biochemical analysis of initial triggering events of IgE-mediated histamine release from human lung mast cells. J Immunol 130:2357-2362.
22. Koch HM, Bolt HM, Preuss R, Angerer J. 2005. New metabolites of di(2-ethylhexyl)phthalate (DEHP) in human urine and serum after single oral doses of deuterium-labelled DEHP. Arch Toxicol 79:367-376.
23. Kristensen DM, Hass U, Lesné L, Lottrup G, Jacobsen PR, Desdoits-Lethimonier C, et al. 2010. Intrauterine exposure to mild analgesics is a risk factor for development of male reproductive disorders in human and rat. Hum Reprod 26(1):235-244.
24. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, et al. 1996. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 384:644-648.
25. Lassurguere J, Livera G, Habert R, Jegou B. 2003. Time-and dose-related effects of estradiol and diethylstilbestrol on the morphology and function of the fetal rat testis in culture. Toxicol Sci 73:160-169.
26. Luong C, Miller A, Barnett J, Chow J, Ramesha C, Browner MF. 1996. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 3:927-933.
27. Nielsen R, Pedersen TA, Hagenbeek D, Moulos P, Siersbaek R, Megens E, et al. 2008. Genome-wide profiling of PPARγ:RXR and RNA polymerase II occupancy reveals temporal activation of distinct metabolic pathways and changes in RXR dimer composition during adipogenesis. Genes Dev 22:2953-2967.
28. Perzanowski MS, Miller RL, Tang D, Ali D, Garfinkel RS, Chew GL, et al. 2010. Prenatal acetaminophen exposure and risk of wheeze at age 5 years in an urban low-income cohort. Thorax 65:118-123.
29. Picot D, Loll PJ, Garavito RM. 1994. The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature 367:243-249.
30. Rebordosa C, Kogevinas M, Sorensen HT, Olsen J. 2008. Pre-natal exposure to paracetamol and risk of wheezing and asthma in children: a birth cohort study. Int J Epidemiol 37:583-590.
31. Research Collaboratory for Structural Bioinformatics. 2010. RCSB Protein Data Bank. Available: http://home.rcsb.org/ [accessed 17 February 2011].
32. Rowlinson SW, Kiefer JR, Prusakiewicz JJ, Pawlitz JL, Kozak KR, Kalgutkar AS, et al. 2003. A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. J Biol Chem 278:45763-45769.
33. Scott HM, Mason JI, Sharpe RM. 2009. Steroidogenesis in the fetal testis and its susceptibility to disruption by exogenous compounds. Endocr Rev 30(7):883-925.
34. Shaheen SO, Newson RB, Henderson AJ, Headley JE, Stratton FD, Jones RW, et al. 2005. Prenatal paracetamol exposure and risk of asthma and elevated immunoglobulin E in childhood. Clin Exp Allergy 35:18-25.
35. Shaheen SO, Newson RB, Sherriff A, Henderson AJ, Heron JE, Burney PG, et al. 2002. Paracetamol use in pregnancy and wheezing in early childhood. Thorax 57:958-963.
36. Skakkebaek NE, Rajpert-de Meyts E, Main KM. 2001. Testicular dysgenesis syndrome: an increasingly common developmental disorder with environmental aspects. Hum Reprod 16:972-978.
37. Smith WL, DeWitt DL, Garavito RM. 2000. Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 69:145-182.
38. Soliva R, Almansa C, Kalko SG, Luque FJ, Orozco M. 2003. Theoretical studies on the inhibition mechanism of cyclooxygenase-2. Is there a unique recognition site? J Med Chem 46:1372-1382.
39. Swami S, Krishnan AV, Moreno J, Bhattacharyya RS, Gardner C, Brooks JD, et al. 2009. Inhibition of prostaglandin synthesis and actions by genistein in human prostate cancer cells and by soy isoflavones in prostate cancer patients. Int J Cancer 124:2050-2059.
40. Swami S, Krishnan AV, Moreno J, Bhattacharyya RB, Peehl DM, Feldman D. 2007. Calcitriol and genistein actions to inhibit the prostaglandin pathway: potential combination therapy to treat prostate cancer. J Nutr 137(1 suppl):205S-210S.
41. Tavares IA, Bennett A, Gaffen JD, Morris HR, Taylor GW. 1984. The biological activities of phthalate esters on rat gastric muscle. Eur J Pharmacol 106:449-452.
42. Tavares IA, Vine ND. 1985. Phthalic acid esters inhibit arachidonate metabolism by rat peritoneal leucocytes. J Pharm Pharmacol 37:67-68.
43. Ye F, Wu J, Dunn T, Yi J, Tong X, Zhang D. 2004. Inhibition of cyclooxygenase-2 activity in head and neck cancer cells by genistein. Cancer Lett 211:39-46.
44. Zykova TA, Zhu F, Zhai X, Ma WY, Ermakova SP, Lee KW, et al. 2008. Resveratrol directly targets COX-2 to inhibit carcinogenesis. Mol Carcinog 47:797-805.