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Structural basis for inhibition of 17[beta]-hydroxysteroid dehydrogenases by phytoestrogens : the case of fungal 17[beta]-HSDclCassetta, Alberto ...Phytoestrogens are plant-derived compounds that functionally and structurally mimic mammalian estrogens. Phytoestrogens have broad inhibitory activities toward several steroidogenic enzymes, such as ... the 17[beta]-hydroxysteroid dehydrogenases (17[beta]-HSDs), which modulate the biological potency of androgens and estrogens in mammals. However, to date, no crystallographic data are available to explain phytoestrogens binding to mammalian 17[beta]-HSDs. NADP(H)-dependent 17[beta]-HSD from the filamentous fungus Cochliobolus lunatus (17[beta]-HSDcl) has been the subject of extensive biochemical, kinetic and quantitative structure-activity relationship studies that have shown that the flavonols are the most potent inhibitors. In the present study, we investigated the structure-activity relationships of the ternary complexes between the holo form of 17[beta]-HSDcl and the flavonols kaempferol and 3,7-dihydroxyflavone, in comparison with the isoflavones genistein and biochanin A. Crystallographic data are accompanied by kinetic analysis of the inhibition mechanisms for six flavonols (3-hydroxyflavone, 3,7-dihydroxyflavone, kaempferol, quercetin, fisetin, myricetin), one flavanone (naringenin), one flavone (luteolin), and two isoflavones (genistein, biochanin A). The kinetics analysis shows that the degree of hydroxylation of ring B significantly influences the overall inhibitory efficacy of the flavonols. A distinct binding mode defines the interactions between 17[beta]-HSDcl and the flavones and isoflavones. Moreover, the complex with biochanin A reveals an unusual binding mode that appears to account for its greater inhibition of 17[beta]-HSDcl with respect to genistein. Overall, these data provide a blueprint for identification of the distinct molecular determinants that underpin 17[beta]-HSD inhibition by phytoestrogens.Source: Journal of Steroid Biochemistry and Molecular Biology. - ISSN 0960-0760 (Vol. 171, Jul. 2017, str. 80-93)Type of material - article, component part ; adult, seriousPublish date - 2017Language - englishCOBISS.SI-ID - 33183449
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source: Journal of Steroid Biochemistry and Molecular Biology. - ISSN 0960-0760 (Vol. 171, Jul. 2017, str. 80-93)
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Cassetta, Alberto | ![]() |
Stojan, Jure, 1956- | 03723 |
Krastanova, Ivet | ![]() |
Kristan, Katja, 1975- | 24392 |
Brunskole Švegelj, Mojca | 28343 |
Lamba, Doriano | ![]() |
Lanišnik-Rižner, Tea | 11699 |
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