Electrochemical oxidation of 5-hydroxymethyl tolterodine and identification of its oxidation products using liquid chromatography and mass spectrometry

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F16%3A33161394" target="_blank" >RIV/61989592:15310/16:33161394 - isvavai.cz</a>

Výsledek na webu

<a href="http://www.sciencedirect.com/science/article/pii/S0013468616318722" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0013468616318722</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2016.08.137" target="_blank" >10.1016/j.electacta.2016.08.137</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Electrochemical oxidation of 5-hydroxymethyl tolterodine and identification of its oxidation products using liquid chromatography and mass spectrometry

Popis výsledku v původním jazyce

The electrochemical behavior of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of antimuscarinic drugs tolterodine and fesoterodine used to treat urge incontinence and overactive bladder, was investigated using cyclic and differential pulse voltammetry at glassy carbon electrode. Electrooxidation of 5-HMT proceeds as a complex pH-dependent process. Controlled potential electrolysis of 5-HMT solutions was performed at platinum gauze electrode in aqueous-methanolic media. Electrolyzed solutions were analyzed using ultra performance liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry. Two main oxidation centers of the studied molecule were located: the p-hydroxybenzyl alcohol group and the tertiary amino group. Oxidation of the first center proceeds in several steps leading to the formation of 5-formyl tolterodine, p-benzoquinone derivative and several dimeric, hydroxylated and methoxylated products depending on pH of the solution and electrode potential. The second center is oxidized preferentially in alkaline media at higher potentials under the hydrolytic cleavage of diisopropylamine and formation of corresponding aldehydes. Mechanism of the electrochemical oxidation of 5-HMT has been proposed.

Název v anglickém jazyce

Electrochemical oxidation of 5-hydroxymethyl tolterodine and identification of its oxidation products using liquid chromatography and mass spectrometry

Popis výsledku anglicky

The electrochemical behavior of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of antimuscarinic drugs tolterodine and fesoterodine used to treat urge incontinence and overactive bladder, was investigated using cyclic and differential pulse voltammetry at glassy carbon electrode. Electrooxidation of 5-HMT proceeds as a complex pH-dependent process. Controlled potential electrolysis of 5-HMT solutions was performed at platinum gauze electrode in aqueous-methanolic media. Electrolyzed solutions were analyzed using ultra performance liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry. Two main oxidation centers of the studied molecule were located: the p-hydroxybenzyl alcohol group and the tertiary amino group. Oxidation of the first center proceeds in several steps leading to the formation of 5-formyl tolterodine, p-benzoquinone derivative and several dimeric, hydroxylated and methoxylated products depending on pH of the solution and electrode potential. The second center is oxidized preferentially in alkaline media at higher potentials under the hydrolytic cleavage of diisopropylamine and formation of corresponding aldehydes. Mechanism of the electrochemical oxidation of 5-HMT has been proposed.

Druh

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

CEP obor

CB - Analytická chemie, separace

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Electrochimica Acta

ISSN

0013-4686

e-ISSN

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Svazek periodika

215

Číslo periodika v rámci svazku

OCT

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

617-625

Kód UT WoS článku

000384008900070

EID výsledku v databázi Scopus

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