Synthesis of 3 alpha-deuterated 7 alpha-hydroxy-DHEA and 7-oxo-DHEA and application in LC-MS/MS plasma analysis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F16%3A00463516" target="_blank" >RIV/61389030:_____/16:00463516 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00023761:_____/16:N0000011

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.steroids.2016.05.001" target="_blank" >http://dx.doi.org/10.1016/j.steroids.2016.05.001</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.steroids.2016.05.001" target="_blank" >10.1016/j.steroids.2016.05.001</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of 3 alpha-deuterated 7 alpha-hydroxy-DHEA and 7-oxo-DHEA and application in LC-MS/MS plasma analysis

Popis výsledku v původním jazyce

7-Oxygenated metabolites of dehydroepiandrosterone (DHEA) are known for their neuroprotective and immunomodulatory properties. These neuroactive steroids are currently predominately analysed by mass spectrometry, for which the use of internal deuterated standards is necessary. The aim of this study was to synthesize the deuterated derivatives of 7 alpha-hydroxy-DHEA and 7-oxo-DHEA and test them in liquid chromatography-tandem mass spectrometry (LC-MS/MS) in order to enhance the performance characteristics of this method. Here we report the synthesis of 3 alpha deuterium-labelled 7 alpha-hydroxy-DHEA and 7-oxo-DHEA. Deuterium was introduced into the 3 alpha position by reduction of the corresponding 3-ketone with a protected 17-carbonyl group using NaBD4. Our new procedure allows the easier synthesis of deuterated steroid labelled compounds. The use of these deuterated steroids enabled us to improve the human plasma LC-MS/MS analysis of 7 alpha-hydroxy-DHEA and 7-oxo-DHEA in terms of sensitivity, precision and recovery.

Název v anglickém jazyce

Synthesis of 3 alpha-deuterated 7 alpha-hydroxy-DHEA and 7-oxo-DHEA and application in LC-MS/MS plasma analysis

Popis výsledku anglicky

7-Oxygenated metabolites of dehydroepiandrosterone (DHEA) are known for their neuroprotective and immunomodulatory properties. These neuroactive steroids are currently predominately analysed by mass spectrometry, for which the use of internal deuterated standards is necessary. The aim of this study was to synthesize the deuterated derivatives of 7 alpha-hydroxy-DHEA and 7-oxo-DHEA and test them in liquid chromatography-tandem mass spectrometry (LC-MS/MS) in order to enhance the performance characteristics of this method. Here we report the synthesis of 3 alpha deuterium-labelled 7 alpha-hydroxy-DHEA and 7-oxo-DHEA. Deuterium was introduced into the 3 alpha position by reduction of the corresponding 3-ketone with a protected 17-carbonyl group using NaBD4. Our new procedure allows the easier synthesis of deuterated steroid labelled compounds. The use of these deuterated steroids enabled us to improve the human plasma LC-MS/MS analysis of 7 alpha-hydroxy-DHEA and 7-oxo-DHEA in terms of sensitivity, precision and recovery.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

<a href="/cs/project/NT13369" target="_blank" >NT13369: Vliv vybraných endokrinních disruptorů na lidskou spermatogenezi</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Steroids

ISSN

0039-128X

e-ISSN

—

Svazek periodika

112

Číslo periodika v rámci svazku

AUG

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

88-94

Kód UT WoS článku

000380602100011

EID výsledku v databázi Scopus

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