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Document Page 193 The enzyme 11β-HSD interconverts the active glucocorticoid cortisol and cortisone, an inactive metabolite (Figure 1a). By the oxidation of cortisol to cortisone, 11β-HSD prevents glucocorticoids from deleterious actions in certain cell types. For example, excess glucocorticoids in Leydig cells inhibit testosterone synthesis [3,11]. Expression of 11β-HSD in Leydig cells prevents this effect of glucocorticoids. In this way, 11β-HSD is important in androgen action. The enzyme 11β-HSD is also important in aldosterone action in the distal tubule of the kidney. Glucocorticoids have high affinity for the mineralocorticoid receptor [12] and can stimulate the mineralocorticoid response—uptake of sodium from urine—one effect of which is to increase blood pressure. Local expression of 11β-HSD in the distal tubule prevents this effect of glucocorticoids. The steroid aldosterone, which is not metabolized by 11β-HSD, can bind to the mineralocorticoid receptor and regulate sodium and potassium balance. Thus, 11β-HSD has an important role in regulating the biological actions of both glucocorticoids and mineralocorticoids. As would be expected, interference with 11β-HSD activity due to a mutation [13,14] or by an inhibitor such as licorice (Figure 2) [1–3,15] has a variety of physiological effects including high blood pressure due to mineralocorticoid actions of glucocorticoids in the kidney's distal tubule. Thus, studies to unravel genetic hypertension in children and the actions of aldosterone in the kidney yielded the general insight that, at specific times, altered expression of 11β-HSD in specific tissues is an important mechanism for regulating glucocorticoid, mineralocorticoid, and androgen action. A similar mechanism has been found for 17β-hydroxysteroid dehydrogenase (17β-HSD), the enzyme that regulates the concentrations of estradiol and testosterone in human [5,16,17] (Figure 1b). Genetics diseases associated with mutations in this enzyme lead to developmental abnormalities [18]. Enzymes that regulate the concentrations of retinoids [19] and prostaglandins [20] may also have a similar role [6]. B. Multiple Divergent 11β-Hydroxysteroid and 17β-Hydroxysteroid Dehydrogenases The cloning and sequencing of 11β-HSD [21–25] and 17β-HSD [16–18,26] revealed two 11β-HSDs and four 17β-HSDs with very different sequences http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_193.html [4/5/2004 5:05:01 PM]
Document Figure 2 Structure of licorice and carbenoxolone. Glycyrrhizic acid, a constituent of licorice extract, is found in the root of Glycyrrhiza glabra. The glycosidic group at C3 is cleaved by bacteria in the small intestine to form glycyrrhetinic acid, the compound that inhibits 11β-hydroxysteroid dehydrogenase. Carbenoxolone, a water soluble synthetic analog of glycyrrhetinic acid, is widely used to regulate 11β-HSD in vitro and in vivo. Page 194 (Figure 3, Table 1). This was surprising, as one would expect the two 11β-HSDs to be similar because they recognize the same substrates. Instead, the two 11β-HSDs have less than 20% sequence identity, after including gaps in the alignment (Table 1). The same degree of sequence divergence is found in the four 17β-HSDs [6]. This sequence divergence is reflected in differences in their catalytic properties. For example 11β-hydroxysteroid dehydrogenase-type 1 (11β-HSD-1) is an NADPH-dependent enzyme that converts cortisone to cortisol, and 11β-hydroxysteroid dehydrogenase-type 2 is an NAD +-dependent enzyme that oxidizes cortisol to cortisone. The enzyme 17βHSD-1 is an NADPH-dependent enzyme that converts estrone to estradiol, and 17βHSD-2 is an NAD +-dependent enzyme that oxidizes estradiol to estrone and testosterone to androstenedione. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_194.html (1 of 2) [4/5/2004 5:05:06 PM]
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Document 106. Cirino NM, Cameron CE
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Page 197 and 198: Document IV. Drug Design Progressio
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Page 201 and 202: Document Table 1 Inhibition Data fo
Page 203 and 204: Document Page 166 As predicated, th
Page 205 and 206: Document References 1. Parks RE Jr.
Page 207 and 208: Document 17. Ealick SE, Rule SA, Ca
Page 209 and 210: Document 6 Structural Implications
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Page 221 and 222: Document Page 182 (SAR) model. The
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Page 227 and 228: Document 5. Willenbrock F, Murphy G
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Page 233 and 234: Document 7 Structure—Function Rel
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Page 251 and 252: Document Page 205 enzyme and of phe
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Page 255 and 256: Document 13. Wilson RC, Krozowski Z
Page 257 and 258: Document 29. Baker ME. Genealogy of
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Document Page 438 proteins. One pot
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Document Page 476 nM, respectively.
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Document A. The Canyon Page 491 The
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Document D ddI, 152 tumour necrosis
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