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Neurosteroids: Can a 2alpha,3alpha-epoxy ring make up for the 3alpha-hydroxyl group?
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SYSNO ASEP 0458613 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Neurosteroids: Can a 2alpha,3alpha-epoxy ring make up for the 3alpha-hydroxyl group? Tvůrce(i) Kasal, Alexander (UOCHB-X)
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Mareš, Pavel (FGU-C) RID, ORCID
Krištofíková, Z. (CZ)
Leitao, A. J. (PT)
Sá e Melo, M. L. (PT)
Silva, M. M. C. (PT)Zdroj.dok. Steroids. - : Elsevier - ISSN 0039-128X
Roč. 105, Jan (2016), s. 12-18Poč.str. 7 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova neurosteroids ; NMR spectrometry ; GABA(A) receptor ; TBPS-test Vědní obor RIV CC - Organická chemie Vědní obor RIV – spolupráce Fyziologický ústav - Neurologie, neurochirurgie, neurovědy CEP GA305/09/0846 GA ČR - Grantová agentura ČR GBP304/12/G069 GA ČR - Grantová agentura ČR Institucionální podpora UOCHB-X - RVO:61388963 ; FGU-C - RVO:67985823 UT WOS 000368219900002 EID SCOPUS 84949519080 DOI 10.1016/j.steroids.2015.11.007 Anotace Seven steroid epoxides were prepared from 5 alpha-pregn-2-en-20-one and 5 alpha-pregn-3-en-20-one and their side-chain derivatives. All compounds were tested in vitro for binding to gamma-aminobutyric acid (GABA(A)) receptor, some of them also in vivo for anticonvulsant action. 2 alpha,3 alpha-Epoxy-5 alpha-pregnan-20-one inhibited the TBPS binding to the GABA(A) receptor and showed a moderate anticonvulsant action in immature rats. In contrast, its 3 alpha,4 alpha-isomer was inactive. More polar epoxide derivatives, modified at the side chain were less active or inactive. Noteworthy, diol 20, the product of trans-diaxial opening of the 2 alpha,3 alpha-epoxide 4, was not able to inhibit the TBPS binding, showing that the activity of the epoxide is due to the compound itself and not to its hydrolytic product. The 3 alpha-hydroxyl group is known to be essential for the GABA(A) receptor binding. Despite the shortness of in vivo effects which are probably due to metabolic inactivation of the products prepared, our results show that the 2 alpha,3 alpha-epoxy ring is another structural pattern with ability to bind the GABA(A)R. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2017
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