Extreme Basicity of Biguanide Drugs in Aqueous Solutions: Ion Transfer Voltammetry and DFT Calculations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F16%3A43902556" target="_blank" >RIV/60461373:22310/16:43902556 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388955:_____/16:00463225

Výsledek na webu

<a href="http://pubs.acs.org/doi/pdfplus/10.1021/acs.jpca.6b04786" target="_blank" >http://pubs.acs.org/doi/pdfplus/10.1021/acs.jpca.6b04786</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jpca.6b04786" target="_blank" >10.1021/acs.jpca.6b04786</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Extreme Basicity of Biguanide Drugs in Aqueous Solutions: Ion Transfer Voltammetry and DFT Calculations

Popis výsledku v původním jazyce

Ion transfer voltammetry is used to estimate the acid dissociation constants K-a1 and K-a2 of the mono- and diprotonated forms of the biguanide drugs metformin (MF), phenformin (PF), and 1-phenylbiguanide (PB) in an aqueous solution. Measurements gave the pK(a1), values for MFH+, PFH+, and PBH+ characterizing the basicity of MF, PF, and PB, which are significantly higher than those reported in the literature. As a result, the monoprotonated forms of these biguanides should prevail in a considerably broader range of pH 1-15 (MFH+, PFH+) and 2-13 (PBH+). DFT calculations with solvent correction were performed for possible tautomeric forms of neutral, monoprotonated, and diprotonated species. Extreme basicity of all drugs is confirmed by DFT calculations of plc, for the most stable tautomers of the neutral and protonated forms with explicit water molecules in the first solvation sphere included.

Název v anglickém jazyce

Extreme Basicity of Biguanide Drugs in Aqueous Solutions: Ion Transfer Voltammetry and DFT Calculations

Popis výsledku anglicky

Ion transfer voltammetry is used to estimate the acid dissociation constants K-a1 and K-a2 of the mono- and diprotonated forms of the biguanide drugs metformin (MF), phenformin (PF), and 1-phenylbiguanide (PB) in an aqueous solution. Measurements gave the pK(a1), values for MFH+, PFH+, and PBH+ characterizing the basicity of MF, PF, and PB, which are significantly higher than those reported in the literature. As a result, the monoprotonated forms of these biguanides should prevail in a considerably broader range of pH 1-15 (MFH+, PFH+) and 2-13 (PBH+). DFT calculations with solvent correction were performed for possible tautomeric forms of neutral, monoprotonated, and diprotonated species. Extreme basicity of all drugs is confirmed by DFT calculations of plc, for the most stable tautomers of the neutral and protonated forms with explicit water molecules in the first solvation sphere included.

Druh

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

CEP obor

CA - Anorganická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA15-03139S" target="_blank" >GA15-03139S: Nové elektroforetické přístupy pro studium obezity a diabetu</a><br>

Návaznosti

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

Journal of Physical Chemistry A

ISSN

1089-5639

e-ISSN

—

Svazek periodika

120

Číslo periodika v rámci svazku

37

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

7344-7350

Kód UT WoS článku

000384034300013

EID výsledku v databázi Scopus

2-s2.0-84988708744