Recent progress in 11-β-hydroxysteroid dehydrogenase type 1 (11-β-HSD1) inhibitor development

Drugs of the Future

Volumn 31, Issue 3, 2006, Pages 231-243

  Barf, Tjeerd ^a   Williams, Meredith ^a  

^a Box 6443 ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE INHIBITOR; 2' HYDROXYFLAVANONE; 3 CHLORO 2 METHYL N [4 [2 (4 METHYL 1 PIPERAZINYL) 2 OXOETHYL] 2 THIAZOLYL]BENZENESULFONAMIDE; ADAMANTYLACETAMIDE; BUDESONIDE; BVT 14225; CARBENOXOLONE; CHENODEOXYCHOLIC ACID; DEFLAZACORT; DEXAMETHASONE; ESTRADIOL; FLAVANONE; FLAVANONE DERIVATIVE; FUROSEMIDE; GLYCYRRHETINIC ACID DERIVATIVE; MENTHONE; NARINGENIN; NEOMENTHOL; OXIDOREDUCTASE INHIBITOR; PREDNISOLONE; PREDNISONE; STANOZOLOL; STEROID; STZ 976; SULFONAMIDE; SULFONAMIDOTHIAZOLE DERIVATIVE; THIADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

CRYSTAL STRUCTURE; DNA MODIFICATION; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG STRUCTURE; DYSLIPIDEMIA; ENZYME ACTIVITY; FATTY LIVER; GLUCOSE BLOOD LEVEL; HUMAN; HYPERTENSION; IC 50; INSULIN RESISTANCE; METABOLIC SYNDROME X; NONHUMAN; OBESITY; REVIEW; TRIACYLGLYCEROL BLOOD LEVEL;

EID: 33744935789     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2006.031.03.884977     Document Type: Review

References (98)

1. Nyirenda, M.J., Lindsay, R.S., Kenyon, C.J., Burchell, A., Seckl, J.R. Glucocorticoid exposure in late gestation permanently programs rat hepatic phosphoenolpyruvate carboxykinase and glucocorticoid receptor expression and causes glucose intolerance in adult offspring. J Clin Invest 1998, 101: 2174-81.
2. Friedman, J.E., Yun, J.S., Patel, Y.M., McGrane, M.M., Hanson, R.W. Glucocorticoids regulate the induction of phosphoenolpyruvate carboxykinase (GTP) gene transcription during diabetes. J Biol Chem 1993, 268: 12952-7.
3. Von Geldern, T.W., Tu, N., Kym, P.R. et al. Liver-selective glucocorticoid antagonists: A novel treatment for type 2 diabetes. J Med Chem 2004, 47: 4213-30.
4. Hasselgren, P.O. Glucocorticoids and muscle catabolism. Curr Opin Clin Nutr Met Care 1999, 2: 201-5.
5. Holmäng, A., Björntorp, P. The effects of cortisol on insulin sensitivity in muscle. Acta Physiol Scand 1992, 144: 425-31.
6. Reynolds, R.M., Chapman, K.E., Seckl, J.R., Walker, B.R., McKeigue, P.M., Lithell, H. Skeletal muscle glucocorticoid receptor density and insulin resistance. JAMA - J Am Med Assoc 2002, 287: 2505-6.
7. Whorwood, C.B., Donovan, S.J., Flanagan, D., Phillips, D.I.W., Byrne, C.D. Increased glucocorticoid receptor expression in human skeletal muscle cells may contribute to the pathogenesis of the metabolic syndrome. Diabetes 2002, 51: 1066-75.
8. Bujalska, I.J., Kumar, S., Hewison, M., Stewart, P.M. Differentiation of adipose stromal cells: The roles of glucocorticoids and 11β-hydroxysteroid dehydrogenase. Endocrinology 1999, 140: 3188-96.
9. Arvaniti, K., Richard, D., Picard, F., Deshaies, Y. Lipid deposition in rats centrally infused with leptin in the presence or absence of corticosterone. Am J Physiol Endocrinol Metab 2001, 281: E809-16.
10. Lambillotte, C., Gilon, P., Henquin, J.-C. Direct glucocorticoid inhibition of insulin secretion. An in vitro study of dexamethasone effects in mouse islets. J Clin Invest 1997, 99: 414-23.
11. Ross, E.J., Linch, D.C. Cushing's syndrome - Killing disease: Discriminatory value of signs and symptoms aiding early diagnosis. Lancet 1982, 2: 646-9.
12. Stewart, P.M., Whorwood, C.B. 11β-Hydroxysteroid dehydrogenase activity and corticosteroid hormone action. Steroids 1994. 59: 90-5.
13. Tomlinson, J.W., Walker, E.A., Bujalska, I.J. et al. 11β- Hydroxysteroid dehydrogenase type 1: A tissue-specific regulator of glucocorticoid response. Endocrine Rev 2004, 25: 831-66.
14. Seckl, J.R., Mortron, N.M., Chapman, K.E., Walker, B.R. Glucocorticoids and 11β-hydroxysteroid dehydrogenase in adipose tissue. Rec Prog Horm Res 2004, 59: 359-93.
15. Stulnig, T., Waldhäusl, W. 11β-Hydroxysteroid dehydrogenase type 1 in obesity and type 2 diabetes. Diabetologia 2004, 47: 1-11.
16. Whorwood, C.B., Mason, J.I., Ricketts, M.L., Howie, A.J., Stewart, P.M. Detection of human 11β-hydroxysteroid dehydrogenase isoforms using reverse-transcriptase-polymerase chain reaction and localisation of the type 2 isoform to renal collecting ducts. Mol Cell Endocrinol 1995, 110: R7-12.
17. Ricketts, J.L., Verhaeg, J.M., Bujalska, I., Howie A.J., Rainey, W.E., Stewart, P.M. Immunohistochemical localization of type 1 11β-hydroxysteroid dehydrogenase in human tissues. J Clin Endocrinol Metab 1998, 83: 1325-35.
18. Tannin, G.M., Agarwal, A.K., Monder, C., New, M.I., White, P.C. The human gene for 11β-hydroxysteroid dehydrogenase. Structure, tissue distribution, and chromosomal localization. J Biol Chem 1991, 266: 16653-8.
19. Bujalska, I.J., Kumar, S., Stewart, P.M. Does central obesity reflect "Cushing's disease of the omentum"? Lancet 1997, 349: 1210-3.
20. Davani, B., Khan, A., Hult, M. et al. Type 1 11β-hydroxysteroid dehydrogenase mediates glucocorticoid activation and insulin release in pancreatic islets. J Biol Chem 2000, 275: 34841-4.
21. Oppermann, U.C.T., Persson, B., Jörnvall, H. Function, gene organization and protein structure of 11β-hydroxysteroid dehydrogenase isoforms. Eur J Biochem 1997, 249: 355-60.
22. Agarwal, A.K. Cortisol metabolism and visceral obesity: Role of 11β-hydroxysteroid dehydrogenase type I enzyme and reduced co-factor NADPH. Endocrine Res 2003, 29: 411-8.
23. Stewart, P., Murry, B., Mason, J. Human kidney 11-hydroxysteroid dehydrogenase is a high affinity nicotinamide adenine dinucleotide-dependent enzyme and differs from the cloned type 1 isoform. J Clin Endocrinol Metab 1994, 79: 480-4.
24. Stewart, P.M., Wallace, A.M., Valentino, R., Burt, D., Shackleton, C.H.L., Edwards, C.R.W. Mineralocorticoid activity of liquorice: 11β-Hydroxysteroid dehydrogenase deficiency comes with age. Lancet 1987, 2: 821-4.
25. Kotelevtsev, Y., Holmes, M.C., Burchell, A. et al. 11β- Hydroxysteroid dehydrogenase type 1 knockout mice show attenuated glucocorticoid-inducible responses and resist hyperglycemia on obesity or stress. Proc Natl Acad Sci USA 1997, 94: 14924-9.
26. Morton, N.M., Holmes, M.C., Fievet, C. et al. Improved lipid and lipoprotein profile, hepatic insulin sensitivity, and glucose tolerance in 11β-hydroxysteroid dehydrogenase type 1 null mice. J Biol Chem 2001, 276: 41293-300.
27. Morton, N.M., Paterson, J.M., Masuzaki, H. et al. Novel adipose tissue-mediated resistance to diet-induced visceral obesity in 11β-hydroxysteroid dehydrogenase type 1-deficient mice. Diabetes 2004, 53: 931-8.
28. Morton, N.M., Ramage, L., Seckl, J.R. Down-regulation of adipose 11β-hydroxysteroid dehydrogenase type 1 by high-fat feeding in mice: A potential adaptive mechanism counteracting metabolic disease. Endocrinology 2004, 145: 2707-12.
29. Paterson, J.M., Morton, N.M., Fievet, C. et al. Metabolic syndrome without obesity: Hepatic overexpression of 11β-hydroxysteroid dehydrogenase type 1 in transgenic mice. Proc Natl Acad Sci USA 2004, 101: 7088-93.
30. Masuzaki, H., Paterson, J., Shinyama, H. et al. A transgenic model of visceral obesity and the metabolic syndrome. Science 2001, 294: 2166-70.
31. Masuzaki, H., Yamamoto, H., Kenyon, C.J. et al. Transgenic amplification of glucocorticoid action in adipose tissue causes high blood pressure in mice. J Clin Invest 2003, 112: 83-90.
32. Berger, J., Tanen, M., Eibrecht, A. et al. Peroxisome proliferator-activated receptor-gamma ligands inhibit adipocyte 11β-hydroxysteroid dehydrogenase type 1 expression and activity. J Biol Chem 2001, 276: 12629-35.
33. Stulnig, T.M., Oppermann, U., Steffensen, K.R., Schuster, G.U. Gustafsson, J.-A. Liver X receptors downregulate 11β-hydroxysteroid dehydrogenase type 1 expression and activity. Diabetes 2002, 51: 2426-33.
34. Walker, B.R., Connacher, A.A., Lindsay, P.M., Webb, D.J., Edwards, C.R.W. Carbenoxolone increases hepatic insulin sensitivity in man: A novel role for 11-oxosteroid reductase in enhancing glucocorticoid receptor activation. J Clin Endocrinol Metab 1995, 80: 3155-9.
35. Andrews, R.C., Rooyackers, O., Walker, B.R. Effects of the 11β-hydroxysteroid dehydrogenase inhibitor carbenoxolone on insulin sensitivity in men with type 2 diabetes. J Clin Endocrinol Metab 2003, 88: 285-91.
36. Rask, E., Olsson, T., Söderberg, S. et al. Tissue-specific dysregulation of cortisol metabolism in human obesity. J Clin Endocrinol Metab 2001, 86: 1418-21.
37. Rask, E., Walker, B.R., Söderberg, S. et al. Tissue-specific changes in peripheral cortisol metabolism in obese women: Increased adipose 11β-hydroxysteroid dehydrogenase type 1 activity. J Clin Endocrinol Metab 2002, 87: 3330-6.
38. Paulmyer-Lacroix, O., Boullu, S., Oliver, C., Alessi, M.C., Grino, M. Expression of the mRNA coding for 11β-hydroxysteroid dehydrogenase type 1 in adipose tissue from obese patients: An in situ hybridization study. J Clin Endocrinol Metab 2002, 87: 2701-5.
39. Engeli, S., Böhnke, J., Feldpausch, M. et al. Regulation of 11β-HDS genes in human adipose tissue: Influence of central obesity and weight loss. Obes Res 2004, 1: 9-17.
40. Kannisto, K., Pietiläinen, K.H., Ehrenborg, E. et al. Overexpressoin of 11β-hydroxysteroid dehydrogenase type 1 in adipose tissue is associated with acquired obesity and features of insulin resistance: Studies in young adult monozygotic twins. J Clin Endocrinol Metab 2004, 89: 4414-21.
41. Tomlinson, J.W., Sinha, B., Bujalska, I., Stewart, P.M. Expression of 11β-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity. J Clin Endocrinol Metab 2002, 87: 5630-5.
42. Valsamakis, G., Anwar, A., Tomlinson, J.W. et al. 11β-Hydroxysteroid dehydrogenase type 1 activity in lean and obese males with type 2 diabetes mellitus. J Clin Endocrinol Metab 2004, 89: 4755-61.
43. Stewart, P.M., Tomlinson, J.W. Cortisol, 11β-hydroxysteroid dehydrogenase type 1 and central obesity. Trends Endocrinol Metab 2002, 13: 94-6.
44. Hult, M., Jörnvall, H., Oppermann, U.C.T. Selective inhibition of human type 1 11β-hydroxysteroid dehydrogenase by synthetic steroids and xenobiotics. FEBS Lett 1998, 441: 25-8.
45. Voice, M., Seckl, J.R., Edwards, C.R.W., Chapman, K.E. 11β-Hydroxysteroid dehydrogenase type 1 expression in 2S FAZA hepatoma cells is hormonally regulated: A model system for the study of hepatic glucocorticoid metabolism. Biochem J 1996, 317: 621-5.
46. Low, S.C., Chapman, K.E., Edwards, C.R.W., Seckl, J.R. 'Liver-type' 11β-hydroxysteroid dehydrogenase cDNA encodes reductase but not dehydrogenase activity in intact mammalian COS-7 cells. J Mol Endocrinol 1994, 13: 167-74.
47. Diederich, S., Grossmann, C., Hanke, B. et al. In the search for specific inhibitors of human 11β-hydroxysteroid-dehydrogenases (11β-HDSs): Chenodeoxycholic acid selectively inhibits 11β-HSD-1. Eur J Endocrinol 2000, 142: 200-7.
48. Schweizer, R.A.S., Atanasov, A.G., Frey, B.M., Odermatt, A. A rapid screening assay for inhibitors of 11β-hydroxysteroid dehydrogenases (11β-HSD): Flavanone selectively inhibits 11β-HSD1 reductase activity. Mol Cell Endocrinol 2003, 212: 41-9.
49. Vicker, N., Su, X., Lawrence, H. et al. A novel 18β-glycyrrhetinic acid analogue as a potent and selective inhibitor of 11β-hydroxysteroid dehydrogenase 2. Bioorg Med Chem Lett 2004, 14: 3263-7.
50. Su, X., Lawrence, H., Ganeshapillai, D. et al. Novel 18β- glycyrrhetinic acid analogues as potent and selective inhibitors of 11β-hydroxysteroid dehydrogenase 2. Bioorg Med Chem 2004, 12: 4439-57.
51. Li, R.-S., Nakagawa, Y., Nakanishi, T., Fujisawa, Y., Ohzeki, T. Different responsiveness in body weight and hepatic 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 mRNA to 11β-HSD inhibition by glycyrrhetinic acid treatment in obese and lean Zucker rats. Metabolism 2004, 53: 600-6.
52. Livingstone, D.E.W., Jones, G.G., Smith, K. et al. Understanding the role of glucocorticoids in obesity: Tissue-specific alterations of corticosterone metabolism in obese Zucker rats. Endocrinology 2000, 141: 560-3.
53. Jamieson, P.M., Nyirenda, M.J., Walker, B.R., Chapman, K.E., Seckl, J.R. Interactions between oestradiol and glucocorticoid regulatory effects on liver-specific glucocorticoid-inducible genes: Possible evidence for a role of hepatic 11β-hydroxysteroid dehydrogenase type 1. J Endocrinol 1999, 160: 103-9.
54. Barf, T., Vallgårda, J., Emond, R. et al. Arylsulfonamidothiazoles as a new class of potential antidiabetic drugs. Discovery of potent and selective inhibitors of the 11β-hydroxysteroid dehydrogenase type 1. J Med Chem 2002, 45: 3813-5.
55. Alberts, P., Engblom, L., Edling, N. et al. Selective inhibition of 11β-hydroxysteroid dehydrogenase type 1 decreases blood glucose concentrations in hyperglycaemic mice. Diabetologia 2002, 45: 1528-32.
56. Alberts, P., Nilsson, C., Selen, G. et al. Selective inhibition of 11β-hydroxysteroid dehydrogenase type 1 improves hepatic insulin sensitivity in hyperglycaemic mice strains. Endocrinology 2003, 144: 4755-62.
57. Olson, S., Balkovec, J., Gao, Y.-D. et al. Selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1. Adamantyl triazoles as pharmacological agents for the treatment of metabolic syndrome. Keystone Symp 2004, Abst X2-239.
58. Hermanowski-Vosatkal, A., Mundtl, S., Nunes, C. et al. 11β-HSD1 inhibition ameliorates metabolic syndrome in mice. Keystone Symp 2004, Abst X2-215.
59. Berwaer, M. Promising new targets. The therapeutic potential of 11β-HSD1 inhibition. 6th Annu Conf Diabetes (Oct 18-19, London) 2004.
60. Barton, P.J., Clarke, D.S., Davies, C.D., Hargreaves, R.B., Pease, J.R., Rankine, M.T. Preparation of (hetero)aryl ketones as 11βHSD1 inhibitors. WO 2004011410.
61. Barton, P.J., Clarke, D.S., Donald, C.S., Pease, J.E. Preparation of 2-oxo-ethanesulfonamidse derivatives useful as inhibitors of 11βHSD1. WO 2004041264.
62. Barton, P.J., Jewsbury, P.J., Pease, J.E. Preparation of 1.4-disubstituted piperidine derivatives and their use as 11-βHSD1 inhibitors. WO 2004033427.
63. Williams, M., Pyring, D., Vagberg, J. et al. Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1. WO 2004103980.
64. Williams, M., Kurz, G., Nilsson, M., Vallgarda, J. Preparation of N-thienyl arene- and heteroarenesulfonamides as inhibitors of 11-β-hydroxy steroid dehydrogenase type 1. WO 03044009.
65. Williams, M., Kurz, G., Nilsson, M., Vallgarda, J. N-Thiadiazolyl arene- and heteroarenesulfonamides as inhibitors of 11-β-hydroxy steroid dehydrogenase type 1. WO 03044000.
66. Barf, T., Emond, R., Kurz, G., Vallgarda, J., Nilsson, M., Zhang, L. Preparation of N-thiazolyl arene- and heteroarenesulfonamides as inhibitors of 11β-hydroxy steroid dehydrogenase type 1. WO 03043999.
67. Barf, T., Nilsson, M., Vallgarda, J. Preparation of thiazolylbenzenesulfonamides and analogs as 11-β-hydroxysteroid dehydrogenase type 1 inhibitors for treatment of diabetes and related diseases. WO 0190094.
68. Nilsson, M. Preparation of N-(5-nitrothiazol-2-yl)benzenesulfonamides as 11-β-hydroxysteroid dehydrogenase type 1 inhibitors for treatment of diabetes and related diseases. WO 0190093
69. Kurz, G., Nilsson, M. Preparation of N-thiazol-2-ylbenzenesulfonamides as 11-β-hydroxysteroid dehydrogenase type 1 inhibitors for treatment of diabetes and related diseases. WO 0190092.
70. Barf, T., Nilsson, M., Kurz, G., Vallgarda, J. Preparation of N-thiazol-2-ylbenzenesulfonamides as 11-β-hydroxysteroid dehydrogenase type 1 inhibitors for treatment of diabetes and related diseases. WO 0190091.
71. Barf, T., Emond, R., Kurz, G., Vallgarda, J., Nilsson, M. Preparation of N-thiazol-2-ylbenzenesulfonamides as 11-β-hydroxysteroid dehydrogenase type 1 inhibitors for the treatment of diabetes and related diseases. WO 0190090.
72. Hanauske-Abel, H.M. Inhibitors of 11β-hydroxystyeroid dehydrogenase and their therapeutic uses as antiinflammatories, allergy inhibitors, and antitumor agents. WO 2004027047.
73. Linders, J.T.M., Willemsens, G.H.M., Gilissen, R.A.H.J. et al. Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors. WO 2004056744.
74. Linders, J.T.M., Willemsens, G.H.M., Gilissen, R.A.H.J. et al. Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors. WO 2004056745.
75. Waddell, S.T., Santorelli, G.M., Maletic, M.M. et al. Preparation of 2-(bicyclo[2.2.2]octan-1-yl)-1,2,4-triazole derivatives as inhibitors of 11-β-hydroxysteroid dehydrogenase-1. US 2004133011.
76. Olson, S.H., Balkovec, J.M., Zhu, Y. Preparation of triazolyl 11β-hydroxysteroid dehydrogenase-1 inhibitors for the treatment of diabetes, obesity and dyslipidemia. WO 03104208.
77. Olson, S.H., Balkovec, J.M., Zhu, Y. Preparation of triazolyl 11β-hydroxysteroid dehydrogenase-1 inhibitors for the treatment of diabetes, obesity and dyslipidemia. WO 03104207.
78. Balkovec, J.M., Thieringer, R., Mundt, S.S. et al. Preparation of 1,2,4-triazole derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia. WO 03065983.
79. Fong, T.M., Von der Ploeg, L.H.T. Method using CB1 receptor antagonists and 11β-hydroxysteroid dehydrogenase 1 (11βHSD1) inhibitors for the treatment or prevention of obesity. WO 03075660.
80. Coppola, G.M., Damon, R.E., Kukkola, P.J., Stanton, J.L. Amide derivatives and their use as inhibitors of 11-β-hydroxysteroid dehydrogenase type I. WO 2004065351.
81. Gundertofte, A., Jorgensen, A.S., Kampen, G.C.T. et al. Preparation of azabicyclooctane and azatricycloundecane aryl amides as 11β-hydroxysteroid dehydrogenase type 1 modulators. WO 2004089896.
82. Andersen, H.S., Kampen, G.C.T., Christensen, I.T., Mogensen, J.P., Larsen, A.R. Pharmaceutical use of substituted pyrazolo[1.5-a]pyrimidines as 11β-hydroxysteroid dehydrogenase type I modulators, especially inhibitors, for treating metabolic disorders, type II diabetes and related diseases, and their preparation. WO 2004089471.
83. Ansdersen, H.S., Kampen, G.C.T., Christensen, I.T., Mogensen, J.P., Larsen, A.R., Kilburn, J.P. Pharmaceutical use of substituted amides as 11-β-hydroxysteroid dehydrogenase type 1 modulators, especially inhibitors, for treating metabolic disorders. WO 2004089470.
84. Andersen, H.S., Kampen, G.C.T., Christensen, I.T., Mogensen, J.P., Larsen, A.R. Preparation and use of fused 1,2,4-triazoles for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1). WO 2004089380.
85. Andersen, H.S., Kampen, G.C.T., Christensen, I.T., Mogensen, J.P., Larsen, A.R. Pharmaceutical use of substituted 1,2,4-triazoles for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1). WO 2004089367.
86. Vicker, N., Su, X., Ganeshapillai, D., Purohit, A., Reed, M.J., Potter, B.V.L. Preparation of arylsulfonylbenzazoles as inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 and type 2. WO 2004037251.
87. Potter, B.V.L., Purohit, A., Reed, M.J., Vicker, N. Use of glycyrrhetinic acid and progesterone derivatives which inhibit 11β-hydroxysteroid dehydrogenase as medicaments. WO 02072084.
88. Oppermann, U., Filling, C., Hult, M. et al. Short-chain dehydrogenases/reductases (SDR): The 2002 update. Chem Biol Interact 2003, 143-144: 247-53.
89. Oppermann, U., Filling, C., Jörnvall, H. Forms and functions of human SDR enzymes. Chem Biol Interact 2001, 130-132: 699-705.
90. Filling, C., Nordling, E., Benach, J. et al. Structural role of conserved Asn179 in the short-chain dehydrogenase/reductase scaffold. Biochem Biophys Res Commun 2001, 289: 712-7.
91. Ogg, D., Elleby, B., Norström, C., Stefansson, K., Abrahmśn, L., Oppermann, U., Svensson, S. The crystal structure of guinea pig 11β-hydroxysteroid dehydrogenase type 1 provides a model for enzyme-lipid bilayer interactions. J Biol Chem 2005, 280: 3789-94.
92. Jörnvall, H., Woenckhaus, C., Schattle, E., Jeck, R. Modification of alcohol dehydrogenases with two NAD+ analogs containing reactive substituents on the functional side of the molecule. FEBS Lett 1975, 54: 297-301.
93. Hosfield, D.J., Wu, Y., Skene, R.J., Hilgers, M., Jennings, A., Snell, G.P., Aergeerts, K. Conformational flexibility in crystal structures of human 11β-HSD1 provide insights into glucocorticoid interconversion and enzyme regulation. J Biol Chem 2005, 280: 4639-48.
94. Structural Genomics: http://www.sgc.ox.ac.uk/structures/2bel.html.
95. Harris, H.J., Kotelevtsev, Y., Mullins, J.J., Seckl, J.R., Holmes, M.C. Intracellular regeneration of glucocorticoids by 11β-hydroxysteroid dehydrogenase (11β-HSD-1) plays a key role in regulation of the hypothalamic-pituitary-adrenal axis: Analysis of 11β-HSD-1-deficient mice. Endocrinology 2001, 142: 114-20.
96. Chrousos, G.P. Is 11β-hydroxysteroid dehydrogenase type 1 a good therapeutic target for blockade of glucocorticoid actions? Proc Natl Acad Sci USA 2004, 101: 6329-30.
97. Hult, M., Shafqat, N., Svensson, S. et al. Human and rodent typel 11β-hydroxysteroid dehydrogenases are 7β-hydroxycholesterol dehydrogenases involved in oxysterol metabolism. Cell Mol Life Sci 2004, 61: 992-9.
98. Schweizer, R.A.S., Zürcher, M., Balaza, Z., Dick, B., Odermatt, A. Rapid hepatic metabolism of 7-ketocholesterol by 11β-hydroxysteroid dehydrogenase type 1. J Biol Chem 2004, 279: 18415-24.