About: Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol

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About: Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1016/j.etap.2014.10.004
Description	17α-Ethinylestradiol (EE2) is an endocrine disruptor (ED) used as an ingredient of oral contraceptives. Rat hepatic microsomes metabolize EE2 to three products; two of them are hydroxylated EE2 derivatives. Of the hydroxylation reactions, 2-hydroxylation, is the major reaction. Cytochrome P450 (CYP) plays a major role in EE2 hydroxylation. To resolve which rat CYPs are responsible for EE2 oxidation, three approaches were used: induction of specific CYPs, selective inhibition of CYPs, and recombinant rat CYPs. The results demonstrate that EE2 is hydroxylated by several rat CYPs, among them CYP2C6 and 2C11 are most efficient in 2-hydroxy-EE2 formation, while CYP2A and 3A catalyze EE2 hydroxylation to the second product. EE2 is also an inhibitor of CYP2C- and CYP3A-catalyzed hydroxylation of endogenous EDs progesterone and testosterone. EE2 acts as a reversible inhibitor of CYP3A-mediated progesterone 6β-hydroxylation and inactivates CYP3A- and CYP2C-catalyzed testosterone 6β-hydroxylation and progesterone 21- or 16α-hydroxylation, respectively, in a mechanism-based manner. 17α-Ethinylestradiol (EE2) is an endocrine disruptor (ED) used as an ingredient of oral contraceptives. Rat hepatic microsomes metabolize EE2 to three products; two of them are hydroxylated EE2 derivatives. Of the hydroxylation reactions, 2-hydroxylation, is the major reaction. Cytochrome P450 (CYP) plays a major role in EE2 hydroxylation. To resolve which rat CYPs are responsible for EE2 oxidation, three approaches were used: induction of specific CYPs, selective inhibition of CYPs, and recombinant rat CYPs. The results demonstrate that EE2 is hydroxylated by several rat CYPs, among them CYP2C6 and 2C11 are most efficient in 2-hydroxy-EE2 formation, while CYP2A and 3A catalyze EE2 hydroxylation to the second product. EE2 is also an inhibitor of CYP2C- and CYP3A-catalyzed hydroxylation of endogenous EDs progesterone and testosterone. EE2 acts as a reversible inhibitor of CYP3A-mediated progesterone 6β-hydroxylation and inactivates CYP3A- and CYP2C-catalyzed testosterone 6β-hydroxylation and progesterone 21- or 16α-hydroxylation, respectively, in a mechanism-based manner. (en)
Title	Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol (en)
skos:prefLabel	Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol Role of rat cytochromes P450 in the oxidation of 17α-ethinylestradiol (en)
skos:notation	RIV/00216208:11310/14:10283266!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GA14-18344S)
http://linked.open...iv/cisloPeriodika	3
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Valášková, Petra Kotrbová, Věra Stiborová, Marie Bořek Dohalská, Lucie
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	43175
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10283266
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Cytochrome P450; Oxidative metabolism; Endocrine disruptor; 17α-Ethinylestradiol (en)
http://linked.open.../riv/klicoveSlovo	Endocrine disruptor 17α-Ethinylestradiol Oxidative metabolism Cytochrome P450
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[C8E45C9D94AD]
http://linked.open...i/riv/nazevZdroje	Environmental Toxicology and Pharmacology
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Development of nanoparticle-based cytostatics and enzymes for enhanced chemotherapy of human neuroblastomas and study of mechanisms of their action
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	38
http://linked.open...iv/tvurceVysledku	Stiborová, Marie Bořek Dohalská, Lucie Černá, Věra Valášková, Petra
http://linked.open...ain/vavai/riv/wos	000347512400018
issn	1382-6689
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.etap.2014.10.004
http://localhost/t...ganizacniJednotka	11310

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