Cytochrome P450-catalyzed binding of 3-methylsulfonyl-DDE and o,p′-DDD in human adrenal Zona Fasciculata/Reticularis

Journal of Clinical Endocrinology and Metabolism

Volumn 87, Issue 3, 2002, Pages 1319-1326

  Lindhe, Örjan ^a   Skogseid, Britt ^b   Brandt, Ingvar ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHANE; 1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHYLENE; ALDOSTERONE; ANDROSTENEDIONE; CORTODOXONE; CYTOCHROME P450; CYTOCHROME P450 11B1; DEOXYCORTICOSTERONE; MITOTANE; UNCLASSIFIED DRUG;

ADRENAL CORTEX CARCINOMA; ADRENAL GLAND; ARTICLE; AUTORADIOGRAPHY; BIOACCUMULATION; CATALYSIS; CATALYST; CONTROLLED STUDY; CUSHING SYNDROME; DRUG SELECTIVITY; FEMALE; GENE MUTATION; HISTOLOGY; HUMAN; HUMAN TISSUE; PRIORITY JOURNAL; REDUCTION; SAMPLING; STEROID RELEASE; TUMOR GROWTH; ZONA FASCICULATA;

ADULT; AUTORADIOGRAPHY; CYTOCHROME P-450 ENZYME SYSTEM; DICHLORODIPHENYL DICHLOROETHYLENE; FEMALE; HORMONES; HUMANS; MALE; MIDDLE AGED; MITOTANE; ZONA FASCICULATA; ZONA RETICULARIS;

EID: 0242516082     PISSN: 0021972X     EISSN: None     Source Type: Journal    
DOI: 10.1210/jc.87.3.1319     Document Type: Article

References (39)

1. Nelson AA, Woodard G 1949 Severe adrenal cortical atrophy (cytotoxic) and hepatic damage produced in dogs by feeding 2,2-bis-(parachlorophenyl)-1,1-dichlorethane (DDD or TDE). Arch Pathol 48:387
2. Bergenstal DM, Hertz R, Lipsett MB, Moy RH 1960 Chemotherapy of adrenocortical cancer with o,p′-DDD. Ann Intern Med 53:672
3. 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
4. Jönsson C-J, Brunströn B, Lund B-O, Brandt I 1993 Toxicity and irreversible binding of two DDT-metabolites (3-metylsulfonyl-DDE and o,p′-DDD) in adrenal interrenal cells in birds. Environ Chem Toxicol 13:1303-1310
5. Jönsson C-J, Lund B-O, Bergman Å, Brandt I 1993 Toxicity of o,p′-DDD and p,p′-DDD in the adrenal cortex of mink. Ecotoxicology 2:41-53
6. Benecke R, Keller E, Vetter B, de Zeeuw RA 1991 Plasma level monitoring of mitotane (o,p′-DDD) and its metabolite (o,p′-DDE) during long-term treatment of Cushing's disease with low doses. Eur J Clin Pharmacol 41:259-261
7. Wooten MD, King DK 1993 Adrenal cortical carcinoma: epidemiology and treatment with mitotane and a review of the literature. Cancer 72:3145-3155
8. Kasperlik-Zaluska AA, Migdalska BM, Makowska AM 1998 Incidentally found adrenocortical carcinoma. A study of 21 patients. Eur J Cancer 34:1721-1724
9. Van Slooten H, Moolenar AJ, Van Seters AP, Smeenk D 1984 The treatment of adrenocortical carcinoma with o,p′-DDD: prognostic implications of serum level monitoring. Eur J Clin Oncol 20:47-53
10. Terzolo M, Pia A, Berruti A, Osella G, Ali A, Carbone V, Testa E, Dogliotti L, Angell A 2000 Low-dose monitored mitotane treatment achieves the therapeutic range with manageable side effects in patients with adrenocortical cancer. J Clin Endocrinol Metab 85:2234-2238
11. Danowski TS, Sarver ME, Moses C, Bonessi JV 1964 o,p′-DDD therapy in Cushing's syndrome and in obesity with Cushinoid changes. Am J Med 37:235-250
12. Wajchenberg BL, Albergaria Pereira MA, Medonca BB, Latronico AC, Campos Carneiro P, Ferreira Alves VA, Zerbini MC, Liberman B, Carlos Gomes G, Kirschner MA 2000 Adrenocortical carcinoma: clinical and laboratory observations. Cancer 88:711-736
13. Jensen S, Jansson B 1976 Methyl sulfone metabolites of PCB and DDE. Ambio 5:257-260
14. Bakke JE, Bergman Å, Larsen GL 1982 Metabolism of 2,4′,5-trichiorobiphenyl by the mercapturic acid pathway. Science 217:645-647
15. 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
16. Lund BO, Lund J 1995 Novel involvement of a mitochondrial steroid hydroxylase (P450c11) in xenobiotic metabolism. J Biol Chem 270:20895-20897
17. 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
18. 2-DDE, to the lactating dam. Pharmacol Toxicol 74:58-60
19. Jönsson C-J, Lund BO, Bergman A, Brandt I 1992 Adrenocortical toxicity of 3-methylsulphonyl-DDE: 3. Studies in fetal and suckling mice. Reprod Toxicol 6:233-240
20. Jönsson C-J, Rodriguez Martinez H, Brandt I 1995 Transplacental toxicity of 3-methylsulphonyl-DDE in the developing adrenal cortex in mice. Reprod Toxicol 9:257-264
21. Jönsson CJ, Lund BO 1994 In vitro bioactivation of the environmental pollutant 3-methylsulphonyl- 2, 2-bis(4-chlorophenyl)-1,1-dichloroethene in the human adrenal gland. Toxicol Lett 71:169-175
22. Smith D 1999 Worldwide trends in DDT levels in human breast milk. Int J Epidemiol 28:179-188
23. Waliszewski SM, Pardio VTS, Chantiri JNP, Infanzon RMR, Rivera J 1996 Organochlorine pesticide residues in adipose tissue of Mexicans. Sci Total Environ 181:125-131
24. Albert LA 1996 Persistent pesticides in Mexico. Rev Environ Contam Toxicol 147:1-44
25. Matuo YK, Lopes JNC, Casanova IC, Matuo T, Lopes JLC 1992 Organochlorine pesticide residues in human milk in the Ribeirao Preto region, state of Sao Paulo, Brazil. Arch Environ Contam Toxicol 22:167-175
26. Gladen BC, Monaghan SC, Lukyanova EM, Hulchiy OP, Shkyryak-Nyzhnyk ZA, Sericano JL, Little RE 1999 Organochlorines in breast milk from two cities in Ukraine. Environ Health Perspect 107:459-462
27. Chikuni O, Nhachi CFB, Nyazema NZ, Polder A, Nafstad I, Skaare JU 1997 Assessment of environmental pollution by PCBs, DDT and its metabolites using human milk of mothers in Zimbabwe. Sci Total Environ 199:183-190
28. Weistrand C, Norén K 1997 Methylsulfonyl metabolites of PCBs and DDE in human tissue. Environ Health Perspect 105:644-649
29. Noren K, Lunden A, Pettersson E, Bergman A 1996 Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Environ Health Perspect 104:766-772
30. 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
31. Bergman Å, Wachtmeister CA 1977 Synthesis of methanesulfonyl derivates of 2,2-bis(4-chlorophenyl)-1,1-dichloroethylene (p,p′-DDE) present in seal from the Baltic. Acta Chem Scand B31:90-91
32. 14C-labelled DDD isomers of high specific activity. J Lab Comp Radiopharmaceut 24:1011-1019
33. Krumdieck CL, dos Santos JE, Ho KJ 1980 A new instrument for the rapid preparation of tissue slices. Anal Biochem 104:118-123
34. Mori K, Hamaoka T 1994 IP Autoradiography System (BAS). Tanpakushitsu Kakusan Koso 39:181-191
35. 14C. Eur J Drug Metab Pharmacokinet 20:89-105
36. 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
37. Erdmann B, Denner K, Gerst H, Lenz D, Bernhardt R 1995 Human adrenal CYP11B1: localization by in situ-hybridization and functional expression in cell cultures. Endocr Res 21:425-435
38. Erdmann B, Gerst H, Bulow H, Lenz D, Bahr V, Bernhardt R 1995 Zone-specific localization of cytochrome P45011B1 in human adrenal tissue by PCR-derived riboprobes. Histochem Cell Biol 104:301-307
39. Lindhe Ö, Granberg L, Brandt I, Cytochrome P450-catalysed irreversible binding examined in precision-cut adrenal slice culture. Proc 6th International Symposium on Biological Reactive Intermediates, Paris, France, 2000