Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p′-DDD in Y-1 adrenal cells

Archives of Toxicology

Volumn 81, Issue 11, 2007, Pages 793-801

  Hermansson, Veronica ^a   Asp, Vendela ^a   Bergman, Åke ^b   Bergström, Ulrika ^a   Brandt, Ingvar ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Adrenal cortex; Cytochrome P450; Metabolic activation; Toxicity; Y 1

Indexed keywords

1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHANE; 1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHYLENE; 2 (3 METHYLSULFONYL 4 CHLOROPHENYL) 2 (4 CHLOROPHENYL) 1,1 DICHLOROETHENE; CYTOCHROME P450; CYTOCHROME P450 CYP11B1; DEOXYCORTICOSTERONE; ETOMIDATE; KETOCONAZOLE; METYRAPONE; UNCLASSIFIED DRUG;

ADRENAL CORTEX; ADRENAL CORTEX CELL; ADRENAL CORTEX DISEASE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL LINE; CONTROLLED STUDY; DETOXIFICATION; FEMALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; STEROIDOGENESIS;

ADRENAL GLANDS; ANIMALS; CELL LINE; CYTOCHROME P-450 ENZYME SYSTEM; DICHLORODIPHENYL DICHLOROETHYLENE; FEMALE; GLUTATHIONE; MICE; MICE, INBRED C57BL; MITOTANE; PROTEIN BINDING; SULFHYDRYL COMPOUNDS;

MURINAE; MUS;

EID: 35748934768     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-007-0206-5     Document Type: Article

References (43)

1. Bahrami F, Brittebo EB, Bergman A, Larsson C, Brandt I (1999) Localization and comparative toxicity of methylsulfonyl-2,5-and 2,6-dichlorobenzene in the olfactory mucosa of mice. Toxicol Sci 49:116-123
2. Bergman A, Wachtmeister CA (1977) Synthesis of methanesulfonyl derivatives of 2,2-bis(4-chlorophenyl)-1,1-dichloroethylene (p,p′-DDE), present in seal from the Baltic. Acta Chem Scand B 31:90-91
3. Black SM, Szklarz GD, Harikrishna JA, Lin D, Wolf CR, Miller WL (1993) Regulation of proteins in the cholesterol side-chain cleavage system in JEG-3 and Y-1 cells. Endocrinology 132:539-545
4. Brandt I, Jönsson CJ, Lund BO (1992) Comparative studies on adrenocorticolytic DDT-metabolites. Ambio 21:602-605
5. Cai W, Counsell RE, Djanegara T, Schteingart DE, Sinsheimer JE, Wotring LL (1995) Metabolic activation and binding of mitotane in adrenal cortex homogenates. J Pharm Sci 84:134-138
6. Cohen SD, Pumford NR, Khairallah EA, Boekelheide K, Pohl LR, Amouzadeh HR, Hinson JA (1997) Selective protein covalent binding and target organ toxicity. Toxicol Appl Pharmacol 143:1-12
7. Couch RM, Muller J, Perry YS, Winter JS (1987) Kinetic analysis of inhibition of human adrenal steroidogenesis by ketoconazole. J Clin Endocrinol Metab 65:551-554
8. Domalik LJ, Chaplin DD, Kirkman MS, Wu RC, Liu WW, Howard TA, Seldin MF, Parker KL (1991) Different isozymes of mouse 11 beta-hydroxylase produce mineralocorticoids and glucocorticoids. Mol Endocrinol 5:1853-1861
9. Dörr HG, Kuhnle U, Holthausen H, Bidlingmaier F, Knorr D (1984) Etomidate: a selective adrenocortical 11 beta-hydroxylase inhibitor. Klin Wochenschr 62:1011-1013
10. Gold B, Brunk G (1982) Metabolism of 1,1,1-trichloro-2,2-bis(p- chlorophenyl)ethane and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane in the mouse. Chem Biol Interact 41:327-339
11. Gonzalez FJ (2005) Role of cytochromes P450 in chemical toxicity and oxidative stress: studies with CYP2E1. Mutat Res 569:101-110
12. Guo IC, Huang C, Chung BC (1993) Differential regulation of the CYP11A1 (P450scc) and ferredoxin genes in adrenal and placental cells. DNA Cell Biol 12:849-860
13. Hart MM, Straw JA (1971) Effect of 1-(o-chlorophenyl)-1-/(p-chlorophenyl) -2,2-dichloroethane in vivo on baselines and adrenocorticotropic hormone-induced steroid production in dog adrenal slices. Biochem Pharmacol 20:1689-1691
14. Hart MM, Swackhamer ES, Straw JA (1971) Studies on the site of action of o,p′-DDD in the dog adrenal cortex. II. TPNH- and corticosteroid precursor-stimulation of o,p′-DDD inhibited steroidogenesis. Steroids 17:575-586
15. Hart MM, Reagan RL, Adamson RH (1973) The effect of isomers of DDD on the ACTH-induced steroid output, histology and ultrastructure of the dog adrenal cortex. Toxicol Appl Pharmacol 24:101-113
16. 2-DDE and o,p-DDD (mitotane) in minipigs. Cancer Chemother Pharmacol (in press). doi:10-1007/s00280-007-0468-x
17. Ikediobi CO, Badisa VL, Ayuk-Takem LT, Latinwo LM, West J (2004) Response of antioxidant enzymes and redox metabolites to cadmium-induced oxidative stress in CRL-1439 normal rat liver cells. Int J Mol Med 14:87-92
18. Johansson M, Larsson C, Bergman A, Lund BO (1998) Structure-activity relationship for inhibition of CYP11B1-dependent glucocorticoid synthesis in Y1 cells by aryl methyl sulfones. Pharmacol Toxicol 83:225-230
19. 2-DDE and some CYP inhibitors on glucocorticoid steroidogenesis in the H295R human adrenocortical carcinoma cell line. Toxicol In Vitro 16:91-99
20. Jönsson C-J, Rodriguez Martinez H, Lund BO, Bergman Å, Brandt I (1991) Adrenocortical toxicity of 3-methylsulfonyl-DDE in mice. II. Mitochondrial changes following ecologically relevant doses. Fundam Appl Toxicol 16:365-374
21. Jönsson C-J, Lund B-O, Bergman Å, Brandt I (1993) Adrenocorticolytic DDT-metabolites: studies in mink, Mustela vison and otter, Lutra lutra. Ecotoxicology 2:41-53
22. Lamberts SW, Bons EG, Bruining HA, de Jong FH (1987) Differential effects of the imidazole derivatives etomidate, ketoconazole and miconazole and of metyrapone on the secretion of cortisol and its precursors by human adrenocortical cells. J Pharmacol Exp Ther 240:259-264
23. Lindhe Ö, Lund B-O, Bergman Å, Brandt I (2001) Irreversible binding and adrenocorticolytic activity of the DDT metabolite 3-methylsulphonyl-DDE examined in tissue slice culture. Environ Health Perspect 109:105-110
24. Lindhe Ö, Skogseid B, Brandt I (2002) Cytochrome P450-catalysed binding of 3-methylsulfonyl-DDE and o,p′-DDD in human adrenal zona fasciculata/reticularis. J Clin Endocrinol Metabol 87:1319-1326
25. 14C-labelled DDD isomers of high specific activity. J Labelled Comp Radiopharm 24:1011-1019
26. Lund BO, Lund J (1995) Novel involvement of a mitochondrial steroid hydroxylase (P450c11) in xenobiotic metabolism. J Biol Chem 270:20895-20897
27. Lund BO, Klasson Wehler E, Brandt I (1986) o,p′-DDD in the mouse lung: selective uptake, covalent binding and effect on drug metabolism. Chem Biol Interact 60:129-141
28. Lund BO, Bergman Å, Brandt I (1988) Metabolic activation and toxicity of a DDT-metabolite, 3-methylsulphonyl-DDE, in the adrenal zona fasciculata in mice. Chem Biol Interact 65:25-40
29. Martz F, Straw JA (1980) Metabolism and covalent binding of o,p′-DDD: correlation between adrenocorticolytic activity and metabolic activation by adrenocortical mitochondria. Drug Metab Dispos 8:127-130
30. Mukai K, Mitani F, Agake R, Ishimura Y (1998) Adrenocorticotropic hormone stimulates CYP11B1 gene transcription through a mechanism involving AP-1 factors. Eur J Biochem 256:190-200
31. Ogishima T, Suzuki H, Hata J, Mitani F, Ishimura Y (1992) Zone-specific expression of aldosterone synthase cytochrome P-450 and cytochrome P-45011 beta in rat adrenal cortex: histochemical basis for the functional zonation. Endocrinology 130:2971-2977
32. Parker KL, Chaplin DD, Wong M, Seidman JG, Smith JA, Schimmer BP (1985) Expression of murine 21-hydroxylase in mouse adrenal glands and in transfected Y1 adrenocortical tumor cells. Proc Natl Acad Sci USA 82:7860-7864
33. Pelletier G, Li S, Luu-The V, Tremblay Y, Belanger A, Labrie F (2001) Immunoelectron microscopic localization of three key steroidogenic enzymes (cytochrome P450(scc), 3 beta-hydroxysteroid dehydrogenase and cytochrome P450(c17)) in rat adrenal cortex and gonads. J Endocrinol 171:373-383
34. Rainey WE, Saner K, Schimmer BP (2004) Adrenocortical cell lines. Mol Cell Endocrinol 228:23-38
35. Rice DA, Aitken LD, Vandenbark GR, Mouw AR, Franklin A, Schimmer BP, Parker KL (1989) A cAMP-responsive element regulates expression of the mouse steroid 11 beta-hydroxylase gene. J Biol Chem 264:14011-14015, issn:10021-19258
36. Seamon KB, Padgett W, Daly JW (1981) Forskolin: unique diterpene activator of adenylate cyclase in membranes and in intact cells. Proc Natl Acad Sci USA 78:3363-3367
37. Sedlak J, Hanus L (1982) Changes of glutathione and protein bound SH-groups concentration in rat adrenals under acute and repeated stress. Endocrinol Exp 16:103-109
38. Sedlak J, Lindsay RH (1968) Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal Biochem 25:192-205
39. Tada H, Shiho O, Kuroshima K, Koyama M, Tsukamoto K (1986) An improved colorimetric assay for interleukin 2. J Immunol Methods 93:157-165
40. Varga I, Racz K, Kiss R, Futo L, Toth M, Sergev O, Glaz E (1993) Direct inhibitory effect of etomidate on corticosteroid secretion in human pathologic adrenocortical cells. Steroids 58:64-68
41. Wallin H, Schelin C, Tunek A, Jergil B (1981) A rapid and sensitive method for determination of covalent binding of benzo[a]pyrene to proteins. Chem Biol Interact 38:109-118
42. Wong M, Rice DA, Parker KL, Schimmer BP (1989) The roles of cAMP and cAMP-dependent protein kinase in the expression of cholesterol side chain cleavage and steroid 11 beta-hydroxylase genes in mouse adrenocortical tumor cells. J Biol Chem 264:12867-12871
43. Yasumura Y, Buonassisi V, Sato G (1966) Clonal analysis of differentiated function in animal cell cultures. I. Possible correlated maintenance of differentiated function and the diploid karyotype. Cancer Res 26:529-535