Biomaterial Database

4-Ethenylidene steroids as mechanism-based inactivators of 3 beta-hydroxysteroid dehydrogenases. 1982

V Balasubramanian, and I R McDermott, and C H Robinson

The synthesis of 4-ethenylidene-5 alpha-androstane-3 beta, 17 beta-diol (5) and of 4-ethenylidene-5 alpha-androstane-3, 17-dione (4) is described. Compound 5 is a competitive inhibitor of solubilized bovine microsomal adrenal delta-5-3 beta-hydroxysteroid dehydrogenase, with Ki = 2.7 microM, and is converted by the enzyme to the corresponding 3-ketone. Compound 4 is shown to irreversibly inactivate the enzyme in a time-dependent manner (t 1/2 = 31 min; 55 microM; pH = 7.0). The substrate, dehydroepiandrosterone, protects against inactivation by compound 4. In contrast, compound 5 is not oxidized at the 3-position by the 3 beta-(and 17 beta)-hydroxysteroid dehydrogenase from P. testosteroni, but is oxidized at the 17-position. Nevertheless, the 4-ethenylidene-3,17-diketone (4) causes irreversible time-dependent inactivation (t 1/2 = 28 min; 64 microM; pH = 7.0) when incubated directly with this bacterial enzyme, acting as an affinity label.

UI	MeSH Term	Description	Entries
D011549	Pseudomonas	A genus of gram-negative, aerobic, rod-shaped bacteria widely distributed in nature. Some species are pathogenic for humans, animals, and plants.	Chryseomonas,Pseudomona,Flavimonas
D002417	Cattle	Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor.	Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D002850	Chromatography, Gel	Chromatography on non-ionic gels without regard to the mechanism of solute discrimination.	Chromatography, Exclusion,Chromatography, Gel Permeation,Chromatography, Molecular Sieve,Gel Filtration,Gel Filtration Chromatography,Chromatography, Size Exclusion,Exclusion Chromatography,Gel Chromatography,Gel Permeation Chromatography,Molecular Sieve Chromatography,Chromatography, Gel Filtration,Exclusion Chromatography, Size,Filtration Chromatography, Gel,Filtration, Gel,Sieve Chromatography, Molecular,Size Exclusion Chromatography
D000311	Adrenal Glands	A pair of glands located at the cranial pole of each of the two KIDNEYS. Each adrenal gland is composed of two distinct endocrine tissues with separate embryonic origins, the ADRENAL CORTEX producing STEROIDS and the ADRENAL MEDULLA producing NEUROTRANSMITTERS.	Adrenal Gland,Gland, Adrenal,Glands, Adrenal
D000732	Androstanols	Androstanes and androstane derivatives which are substituted in any position with one or more hydroxyl groups.	Hydroxyandrostanes
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D001667	Binding, Competitive	The interaction of two or more substrates or ligands with the same binding site. The displacement of one by the other is used in quantitative and selective affinity measurements.	Competitive Binding
D015096	3-Hydroxysteroid Dehydrogenases	Catalyze the oxidation of 3-hydroxysteroids to 3-ketosteroids.	3-beta-Hydroxysteroid Dehydrogenase,3 Hydroxysteroid Dehydrogenases,3 beta Hydroxysteroid Dehydrogenase,Dehydrogenase, 3-beta-Hydroxysteroid,Dehydrogenases, 3 Hydroxysteroid,Dehydrogenases, 3-Hydroxysteroid,Hydroxysteroid Dehydrogenases, 3
D015113	Androstane-3,17-diol	The unspecified form of the steroid, normally a major metabolite of TESTOSTERONE with androgenic activity. It has been implicated as a regulator of gonadotropin secretion.	5 Androstane 3,17 diol,5 alpha-Androstane-3 alpha,17 beta-diol,5 alpha-Androstane-3 beta,17 alpha-diol,5 alpha-Androstane-3 beta,17 beta-diol,5 alpha-Androstane-3alpha,17 beta-diol,5 beta-Androstane-3 alpha,17 beta-diol,5-Androstane-3,17-diol,5alpha-Androstane-3beta,17alpha-diol,5 alpha Androstane 3 alpha,17 beta diol,5 alpha Androstane 3 beta,17 alpha diol,5 alpha Androstane 3 beta,17 beta diol,5 alpha Androstane 3alpha,17 beta diol,5 beta Androstane 3 alpha,17 beta diol,5alpha Androstane 3beta,17alpha diol,Androstane 3,17 diol
D066298	In Vitro Techniques	Methods to study reactions or processes taking place in an artificial environment outside the living organism.	In Vitro Test,In Vitro Testing,In Vitro Tests,In Vitro as Topic,In Vitro,In Vitro Technique,In Vitro Testings,Technique, In Vitro,Techniques, In Vitro,Test, In Vitro,Testing, In Vitro,Testings, In Vitro,Tests, In Vitro,Vitro Testing, In