Structure-dependent inhibition of human and rat 11β-hydroxysteroid dehydrogenase 2 activities by phthalates

Chemico-Biological Interactions

Volumn 183, Issue 1, 2010, Pages 79-84

  Zhao, Binghai ^a,b,c   Chu, Yanhui ^c   Huang, Yadong ^d   Hardy, Dianne O ^b   Lin, Shaoqiang ^e   Ge, Ren Shan ^b,e  

^a JILIN UNIVERSITY   (China)

^b POPULATION COUNCIL   (United States)

^c Mu Dan Jiang Medical College   (China)

^d JINAN UNIVERSITY   (China)

^e WENZHOU MEDICAL UNIVERSITY   (China)

Author keywords

11 HSD2; Enzyme inhibition; Kidney microsome; Phthalates

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE 2; ALCOHOL DERIVATIVE; CARBON; ESTER DERIVATIVE; PHTHALATE DIESTER DERIVATIVE; PHTHALATE MONOESTER DERIVATIVE; PHTHALIC ACID 2 ETHYLHEXYL MONOESTER; PHTHALIC ACID BIS(2 ETHYLHEXYL) ESTER; PHTHALIC ACID DERIVATIVE; PHTHALIC ACID DIBUTYL ESTER; PHTHALIC ACID DICYCLOHEXYL ESTER; PHTHALIC ACID DIPROPYL ESTER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; METABOLITE; NONHUMAN; POLLUTION; RAT;

11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 2; ANIMALS; ENDOCRINE DISRUPTORS; ENVIRONMENTAL POLLUTANTS; GLUCOCORTICOIDS; HUMANS; MICROSOMES; PHTHALIC ACIDS; RATS;

RATTUS;

EID: 71349087068     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2009.09.014     Document Type: Article

References (38)

1. Marsee K., Woodruff T.J., Axelrad D.A., Calafat A.M., and Swan S.H. Estimated daily phthalate exposures in a population of mothers of male infants exhibiting reduced anogenital distance. Environ. Health Perspect. 114 6 (2006) 805-809
2. Akingbemi B.T., and Hardy M.P. Oestrogenic and antiandrogenic chemicals in the environment: effects on male reproductive health. Ann. Med. 33 6 (2001) 391-403
3. Stahlhut R.W., van Wijngaarden E., Dye T.D., Cook S., and Swan S.H. Concentrations of urinary phthalate metabolites are associated with increased waist circumference and insulin resistance in adult U.S. males. Environ. Health Perspect. 115 6 (2007) 876-882
4. Albro P.W., Chapin R.E., Corbett J.T., Schroeder J., and Phelps J.L. Mono-2-ethylhexyl phthalate, a metabolite of di-(2-ethylhexyl) phthalate, causally linked to testicular atrophy in rats. Toxicol. Appl. Pharmacol. 100 2 (1989) 193-200
5. Kavlock R., Boekelheide K., Chapin R., Cunningham M., Faustman E., Foster P., Golub M., Henderson R., Hinberg I., Little R., Seed J., Shea K., Tabacova S., Tyl R., Williams P., and Zacharewski T. NTP Center for the Evaluation of Risks to Human Reproduction: phthalates expert panel report on the reproductive and developmental toxicity of di-n-octyl phthalate. Reprod. Toxicol. 16 5 (2002) 721-734
6. Storr H.L., Chan L.F., Grossman A.B., and Savage M.O. Paediatric Cushing's syndrome: epidemiology, investigation and therapeutic advances. Trends Endocrinol. Metab. 18 4 (2007) 167-174
7. Lakshmi V., and Monder C. Purification and characterization of the corticosteroid 11 beta-dehydrogenase component of the rat liver 11 beta-hydroxysteroid dehydrogenase complex. Endocrinology 123 5 (1988) 2390-2398
8. Agarwal A.K., Monder C., Eckstein B., and White P.C. Cloning and expression of rat cDNA encoding corticosteroid 11 beta-dehydrogenase. J. Biol. Chem. 264 32 (1989) 18939-18943
9. Monder C., and Shackleton C.H. 11 beta-Hydroxysteroid dehydrogenase: fact or fancy?. Steroids 44 5 (1984) 383-417
10. Agarwal A.K., Mune T., Monder C., and White P.C. Cloning of cDNA encoding an NAD(+)-dependent isoform of 11 beta-hydroxysteroid dehydrogenase in sheep kidney. Endocr. Res. 21 1-2 (1995) 389-397
11. Albiston A.L., Smith R.E., Obeyesekere V.R., and Krozowski Z.S. Cloning of the 11 beta HSD type II enzyme from human kidney. Endocr. Res. 21 1-2 (1995) 399-409
12. White P.C., Mune T., and Agarwal A.K. 11 beta-hydroxysteroid dehydrogenase and the syndrome of apparent mineralocorticoid excess. Endocr. Rev. 18 1 (1997) 135-156
13. Wyrwoll C.S., Mark P.J., and Waddell B.J. Developmental programming of renal glucocorticoid sensitivity and the renin-angiotensin system. Hypertension 50 3 (2007) 579-584
14. Aufdenblatten M., Baumann M., Raio L., Dick B., Frey B.M., Schneider H., Surbek D., Hocher B., and Mohaupt M.G. Prematurity is related to high placental cortisol in preeclampsia. Pediatr. Res. 65 2 (2009) 198-202
15. Ohshima M., Ohno S., and Nakajin S. Inhibitory effects of some possible endocrine-disrupting chemicals on the isozymes of human 11beta-hydroxysteroid dehydrogenase and expression of their mRNA in gonads and adrenal glands. Environ. Sci. 12 4 (2005) 219-230
16. Lakshmi V., and Monder C. Extraction of 11 beta-hydroxysteroid dehydrogenase from rat liver microsomes by detergents. J. Steroid Biochem. 22 3 (1985) 331-340
17. Ge R.S., Hardy D.O., Catterall J.F., and Hardy M.P. Opposing changes in 3alpha-hydroxysteroid dehydrogenase oxidative and reductive activities in rat leydig cells during pubertal development. Biol. Reprod. 60 4 (1999) 855-860
18. Shneider B., Schena J., Truog R., Jacobson M., and Kevy S. Exposure to di(2-ethylhexyl)phthalate in infants receiving extracorporeal membrane oxygenation. N. Engl. J. Med. 320 23 (1989) 1563
19. Saillenfait A.M., Gallissot F., and Sabate J.P. Differential developmental toxicities of di-n-hexyl phthalate and dicyclohexyl phthalate administered orally to rats. J. Appl. Toxicol. (2009)
20. Howdeshell K.L., Wilson V.S., Furr J., Lambright C.R., Rider C.V., Blystone C.R., Hotchkiss A.K., and Gray Jr. L.E. A mixture of five phthalate esters inhibits fetal testicular testosterone production in the Sprague-Dawley rat in a cumulative, dose-additive manner. Toxicol. Sci. 105 1 (2008) 153-165
21. Gray Jr. L.E., Ostby J., Furr J., Price M., Veeramachaneni D.N., and Parks L. Perinatal exposure to the phthalates DEHP, BBP, and DINP, but not DEP, DMP, or DOTP, alters sexual differentiation of the male rat. Toxicol. Sci. 58 2 (2000) 350-365
22. Hines E.P., Calafat A.M., Silva M.J., Mendola P., and Fenton S.E. Concentrations of phthalate metabolites in milk, urine, saliva, and Serum of lactating North Carolina women. Environ. Health Perspect. 117 1 (2009) 86-92
23. Zhang Y., Lin L., Cao Y., Chen B., Zheng L., and Ge R.S. Phthalate levels and low birth weight: a nested case-control study of chinese newborns. J. Pediatr. (2009) 500-504
24. Jaquiery A.L., Oliver M.H., Bloomfield F.H., Connor K.L., Challis J.R., and Harding J.E. Fetal exposure to excess glucocorticoid is unlikely to explain the effects of periconceptional undernutrition in sheep. J. Physiol. 572 Pt 1 (2006) 109-118
25. Seckl J.R., and Meaney M.J. Glucocorticoid programming. Ann. N. Y. Acad. Sci. 1032 (2004) 63-84
26. Dave-Sharma S., Wilson R.C., Harbison M.D., Newfield R., Azar M.R., Krozowski Z.S., Funder J.W., Shackleton C.H., Bradlow H.L., Wei J.Q., Hertecant J., Moran A., Neiberger R.E., Balfe J.W., Fattah A., Daneman D., Akkurt H.I., De Santis C., and New M.I. Examination of genotype and phenotype relationships in 14 patients with apparent mineralocorticoid excess. J. Clin. Endocrinol. Metab. 83 7 (1998) 2244-2254
27. Kajantie E., Dunkel L., Turpeinen U., Stenman U.H., Wood P.J., Nuutila M., and Andersson S. Placental 11 beta-hydroxysteroid dehydrogenase-2 and fetal cortisol/cortisone shuttle in small preterm infants. J. Clin. Endocrinol. Metab. 88 1 (2003) 493-500
28. Thapa L., He C.M., and Chen H.P. Study on the expression of angiotensin II (ANG II) receptor subtype 1 (AT1R) in the placenta of pregnancy-induced hypertension. Placenta 25 7 (2004) 637-641
29. Lanz C.B., Causevic M., Heiniger C., Frey F.J., Frey B.M., and Mohaupt M.G. Fluid shear stress reduces 11ss-hydroxysteroid dehydrogenase type 2. Hypertension 37 1 (2001) 160-169
30. Goland R.S., Tropper P.J., Warren W.B., Stark R.I., Jozak S.M., and Conwell I.M. Concentrations of corticotrophin-releasing hormone in the umbilical-cord blood of pregnancies complicated by pre-eclampsia. Reprod. Fertil. Dev. 7 5 (1995) 1227-1230
31. Benediktsson R., Calder A.A., Edwards C.R., and Seckl J.R. Placental 11 beta-hydroxysteroid dehydrogenase: a key regulator of fetal glucocorticoid exposure. Clin. Endocrinol. (Oxf.) 46 2 (1997) 161-166
32. Schoof E., Girstl M., Frobenius W., Kirschbaum M., Dorr H.G., Rascher W., and Dotsch J. Decreased gene expression of 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase in human placenta of patients with preeclampsia. J. Clin. Endocrinol. Metab. 86 3 (2001) 1313-1317
33. Schoof E., Girstl M., Frobenius W., Kirschbaum M., Repp R., Knerr I., Rascher W., and Dotsch J. Course of placental 11beta-hydroxysteroid dehydrogenase type 2 and 15-hydroxyprostaglandin dehydrogenase mRNA expression during human gestation. Eur. J. Endocrinol. 145 2 (2001) 187-192
34. Ge R.S., Chen G.R., Tanrikut C., and Hardy M.P. Phthalate ester toxicity in Leydig cells: developmental timing and dosage considerations. Reprod. Toxicol. 23 3 (2007) 366-373
35. Sharpe R.M., and Skakkebaek N.E. Testicular dysgenesis syndrome: mechanistic insights and potential new downstream effects. Fertil. Steril. 89 2 Suppl. (2008) e33-e38
36. Honda Y., Ohno S., and Nakajin S. Leydig cells from neonatal pig testis abundantly express 11beta-hydroxysteroid dehydrogenase (11beta-HSD) type 2 and effectively inactivate cortisol to cortisone. J. Steroid Biochem. Mol. Biol. 108 1-2 (2008) 91-101
37. Albiston A.L., Obeyesekere V.R., Smith R.E., and Krozowski Z.S. Cloning and tissue distribution of the human 11 beta-hydroxysteroid dehydrogenase type 2 enzyme. Mol. Cell Endocrinol. 105 2 (1994) R11-R17
38. Ge R.S., Dong Q., Niu E.M., Sottas C.M., Hardy D.O., Catterall J.F., Latif S.A., Morris D.J., and Hardy M.P. 11β-Hydroxysteroid dehydrogenase 2 in rat leydig cells: its role in blunting glucocorticoid action at physiological levels of substrate. Endocrinology 146 6 (2005) 2657-2664