Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 40, 2010 - Issue 3
135
Views
9
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Chiral effects in adrenocorticolytic action of o,p′-DDD (mitotane) in human adrenal cells

, , &
Pages 177-183 | Received 26 Aug 2009, Accepted 05 Nov 2009, Published online: 04 Jan 2010

References

  • Ahlman H, Khorram-Manesh A, Jansson S, Wangberg B, Nilsson O, Jacobsson CE, Lindstedt S. (2001). Cytotoxic treatment of adrenocortical carcinoma. World J Surg 25(7):927–33.
  • Allolio B, Fassnacht M. (2006). Clinical Review: Adrenocortical carcinoma: clinical update. J Clin Endocrinol Metab 91(6):2027–37.
  • Asp V, Lindström V, Olsson JA, Bergström U, Brandt I. (2009). Cytotoxicity and decreased corticosterone production in adrenocortical Y-1 cells by 3-methylsulfonyl-DDE and structurally related molecules. Archiv Toxicol 83(4):389–96.
  • Baudin E, Pellegriti G, Bonnay M, Penfornis A, Laplanche A, Vassal G, Schlumberger M. (2001). Impact of monitoring plasma 1,1-dichlorodiphenildichloroethane (o,p′-DDD) levels on the treatment of patients with adrenocortical carcinoma. Cancer 92(6): 1385–92.
  • Bergenstal D, Hertz R, Lipsett M, Moy R. (1960). Chemotherapy of adrenocortical cancer with o,p′-DDD. Ann Intern Med 53:672–82.
  • Cai W, Benitez R, Counsell RE, Djanegara T, Schteingart DE, Sinsheimer JE, Wotring LL. (1995a). Bovine adrenal cortex transformations of mitotane [1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; o,p′-DDD] and its p,p′- and m,p′-isomers. Biochem Pharmacol 49(10):1483–9.
  • Cai W, Djanegara T, Sinsheimer J, Wotring L, Counsell E, Schteingart D. (1995b). Metabolic activation and binding of mitotane in adrenal cortex homogenates. J Pharmaceut Sci 84(2):134–8.
  • Cantillana T, Eriksson L. (2009). (2S)-1,1-dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane. Acta Crystallographica E65:o297.
  • Cantillana T, Lindstrom V, Eriksson L, Brandt I, Bergman A. (2009). Interindividual differences in o,p′-DDD enantiomer kinetics examined in Gottingen minipigs. Chemosphere 76(2):167–72.
  • Eriksson T, Björkman S, Höglund P. (2001). Clinical pharmacology of thalidomide. European J Clin Pharmacol 57(5):365–76.
  • Haak HR, Hermans J, van de Velde CJ, Lentjes EG, Goslings BM, Fleuren GJ, Krans HM. (1994). Optimal treatment of adrenocortical carcinoma with mitotane: results in a consecutive series of 96 patients. Br J Cancer 69(5):947–51.
  • Hahner S, Fassnacht M. (2005). Mitotane for adrenocortical carcinoma treatment. Curr Opin Investig Drugs 6(4):386–94.
  • 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(1):101–13.
  • Hart MM, Straw JA. (1971). Studies on the site of action of o,p′-DDD in the dog adrenal cortex. 1. Inhibition of ACTH-mediated pregnenolone synthesis. Steroids 17(1–5):559–74.
  • 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(1–5):575–86.
  • Hoekstra PF, Burnison BK, Neheli T, Muir DC. (2001). Enantiomer-specific activity of o,p′-DDT with the human estrogen receptor. Toxicol Lett 125(1–3):75–81.
  • Huang H, Fojo T. (2008). Adjuvant mitotane for adrenocortical cancer — a recurring controversy. J Clin Endocrinol Metab 93(10):3730–2.
  • Icard P, Goudet P, Charpenay C, Andreassian B, Carnaille B, Chapuis Y, Cougard P, Henry JF, Proye C. (2001). Adrenocortical carcinomas: surgical trends and results of a 253-patient series from the French Association of Endocrine Surgeons study group. World J Surg 25(7):891–7.
  • Lindholm A, Klasson-Wehler E, Wehler T, Bergman Å. (1987). Synthesis of 14C-labelled DDD isomers of high specific activity. J Labelled Comp Radiopharm 24:1011–9.
  • Lund BO, Ghantous H, Bergman å, Brandt I. (1989). Covalent binding of four DDD isomers in the mouse lung: lack of structure specificity. Pharmacol Toxicol 65(4):282–6.
  • Lund BO, Klasson-Wehler E, Brandt I. (1986). o,p′-DDD in the mouse lung: selective uptake, covalent binding and effect on drug metabolism. Chemico-Biol Interact 60(2):129–41.
  • Martz F, Straw JA. (1977). The in vitro metabolism of 1-(o-chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane (o,p′-DDD) by dog adrenal mitochondria and metabolite covalent binding to mitochondrial macromolecules: a possible mechanism for the adrenocorticolytic effect. Drug Metab Dispos 5(5):482–6.
  • Martz F, Straw JA. (1980). Metabolism and covalent binding of 1-(o-chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane (o,p′-DDD). Correlation between adrenocorticolytic activity and metabolic activation by adrenocortical mitochondria. Drug Metab Dispos 8(3):127–30.
  • Newell-Price J, Bertagna X, Grossman AB, Nieman LK. (2006). Cushing’s syndrome. Lancet 367(9522):1605–17.
  • Shen H, Virtanen HE, Main KM, Kaleva M, Andersson AM, Skakkebaek NE, Toppari J, Schramm KW. (2006). Enantiomeric ratios as an indicator of exposure processes for persistent pollutants in human placentas. Chemosphere 62(3):390–5.
  • Tada H, Shiho O, Kuroshima K, Koyama M, Tsukamoto K. (1986). An improved colorimetric assay for interleukin 2. J Immunol Methods 93(2):157–65.
  • Tauchmanova L, Colao A, Marzano LA, Sparano L, Camera L, Rossi A, Palmieri G, Marzano E, Salvatore M, Pettinato G, Rossi R, (2004). Andrenocortical carcinomas: twelve-year prospective experience. World J Surg 28(9):896–903.
  • Terzolo M, Angeli A, Fassnacht M, Daffara F, Tauchmanova L, Conton PA, Rossetto R, Buci L, Sperone P, Grossrubatscher E, Reimondo G, Bollito E, Papotti M, Saeger W, Hahner S, Koschker A-C, Arvat E, Ambrosi B, Loli P, Lombardi G, Mannelli M, Bruzzi P, Mantero F, Allolio B, Dogliotti L, Berruti A (2007). Adjuvant Mitotane Treatment for Adrenocortical Carcinoma. N Engl J Med 356(23):2372–80.
  • Terzolo M, Berruti A. (2008). Adjunctive treatment of adreno-cortical carcinoma. Curr Opin Endocrinol Diabet Obes 15(3):221–6.
  • van Slooten H, Moolenaar AJ, van Seters AP, Smeenk D. (1984). The treatment of adrenocortical carcinoma with o,p′-DDD: prognostic implications of serum level monitoring. Eur J Cancer Clin Oncol 20(1):47–53.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.