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Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis

Identifikátory výsledku

  • Kód výsledku v IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00539592" target="_blank" >RIV/61388963:_____/21:00539592 - isvavai.cz</a>

  • Nalezeny alternativní kódy

    RIV/61388980:_____/21:00539592 RIV/68378050:_____/21:00539592

  • Výsledek na webu

    <a href="https://doi.org/10.1002/elps.202000298" target="_blank" >https://doi.org/10.1002/elps.202000298</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/elps.202000298" target="_blank" >10.1002/elps.202000298</a>

Alternativní jazyky

  • Jazyk výsledku

    angličtina

  • Název v původním jazyce

    Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis

  • Popis výsledku v původním jazyce

    Capillary electrophoresis (CE) has been applied for determination of the thermodynamic acidity constants (pKa) of the sulfamidoalkyl and sulfonamidoalkyl groups, the actual and limiting ionic mobilities and hydrodynamic radii of important compounds, eight carborane‐based inhibitors of carbonic anhydrases, which are potential new anticancer drugs. Two types of carboranes were investigated, (i) icosahedral cobalt bis(dicarbollide)(1‐) ion with sulfamidoalkyl moieties, and (ii) 7,8‐nido‐dicarbaundecaborate with sulfonamidoalkyl side chains. First, the mixed acidity constants, pKamix, of the sulfamidoalkyl and sulfonamidoalkyl groups of the above carboranes and their actual ionic mobilities were determined by nonlinear regression analysis of the pH dependences of their effective electrophoretic mobility measured by capillary electrophoresis in the pH range 8.00−12.25, at constant ionic strength (25 mM), and constant temperature (25°C). Second, the pKamix were recalculated to the thermodynamic pKas using the Debye–Hückel theory. The sulfamidoalkyl and sulfonamidoalkyl groups were found to be very weakly acidic with the pKas in the range 10.78−11.45 depending on the type of carborane cluster and on the position and length of the alkyl chain on the carborane scaffold. These pKas were in a good agreement with the pKas (10.67−11.27) obtained by new program AnglerFish (freeware at https://echmet.natur.cuni.cz), which provides thermodynamic pKas and limiting ionic mobilities directly from the raw CE data. The absolute values of the limiting ionic mobilities of univalent and divalent carborane anions were in the range 18.3−27.8 TU (Tiselius unit, 1 × 10−9 m2/Vs), and 36.4−45.9 TU, respectively. The Stokes hydrodynamic radii of univalent and divalent carborane anions varied in the range 0.34−0.52 and 0.42−0.52 nm, respectively.

  • Název v anglickém jazyce

    Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis

  • Popis výsledku anglicky

    Capillary electrophoresis (CE) has been applied for determination of the thermodynamic acidity constants (pKa) of the sulfamidoalkyl and sulfonamidoalkyl groups, the actual and limiting ionic mobilities and hydrodynamic radii of important compounds, eight carborane‐based inhibitors of carbonic anhydrases, which are potential new anticancer drugs. Two types of carboranes were investigated, (i) icosahedral cobalt bis(dicarbollide)(1‐) ion with sulfamidoalkyl moieties, and (ii) 7,8‐nido‐dicarbaundecaborate with sulfonamidoalkyl side chains. First, the mixed acidity constants, pKamix, of the sulfamidoalkyl and sulfonamidoalkyl groups of the above carboranes and their actual ionic mobilities were determined by nonlinear regression analysis of the pH dependences of their effective electrophoretic mobility measured by capillary electrophoresis in the pH range 8.00−12.25, at constant ionic strength (25 mM), and constant temperature (25°C). Second, the pKamix were recalculated to the thermodynamic pKas using the Debye–Hückel theory. The sulfamidoalkyl and sulfonamidoalkyl groups were found to be very weakly acidic with the pKas in the range 10.78−11.45 depending on the type of carborane cluster and on the position and length of the alkyl chain on the carborane scaffold. These pKas were in a good agreement with the pKas (10.67−11.27) obtained by new program AnglerFish (freeware at https://echmet.natur.cuni.cz), which provides thermodynamic pKas and limiting ionic mobilities directly from the raw CE data. The absolute values of the limiting ionic mobilities of univalent and divalent carborane anions were in the range 18.3−27.8 TU (Tiselius unit, 1 × 10−9 m2/Vs), and 36.4−45.9 TU, respectively. The Stokes hydrodynamic radii of univalent and divalent carborane anions varied in the range 0.34−0.52 and 0.42−0.52 nm, respectively.

Klasifikace

  • Druh

    J<sub>imp</sub> - Článek v periodiku v databázi Web of Science

  • CEP obor

  • OECD FORD obor

    10406 - Analytical chemistry

Návaznosti výsledku

  • Projekt

    <a href="/cs/project/GA20-03899S" target="_blank" >GA20-03899S: Afinitní kapilární elektrokinetické metody pro selektivní analýzu biopolymerů a metabolitů a pro studium jejich interakcí</a><br>

  • Návaznosti

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Ostatní

  • Rok uplatnění

    2021

  • Kód důvěrnosti údajů

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

Údaje specifické pro druh výsledku

  • Název periodika

    Electrophoresis

  • ISSN

    0173-0835

  • e-ISSN

    1522-2683

  • Svazek periodika

    42

  • Číslo periodika v rámci svazku

    7/8

  • Stát vydavatele periodika

    DE - Spolková republika Německo

  • Počet stran výsledku

    10

  • Strana od-do

    910-919

  • Kód UT WoS článku

    000609306700001

  • EID výsledku v databázi Scopus

    2-s2.0-85100141579