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Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis
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SYSNO ASEP 0539592 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis Author(s) Šolínová, Veronika (UOCHB-X) RID, ORCID
Brynda, Jiří (UMG-J) RID
Šícha, Václav (UACH-T) RID, ORCID, SAI
Holub, Josef (UACH-T) SAI, RID, ORCID
Grüner, Bohumír (UACH-T) RID, SAI, ORCID
Kašička, Václav (UOCHB-X) RID, ORCIDSource Title Electrophoresis. - : Wiley - ISSN 0173-0835
Roč. 42, 7/8 (2021), s. 910-919Number of pages 10 s. Language eng - English Country DE - Germany Keywords acid dissociation constant ; capillary electrophoresis ; carboranes ; limiting ionic mobilities ; stokes hydrodynamic radii OECD category Analytical chemistry R&D Projects GA20-03899S GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 ; UMG-J - RVO:68378050 ; UACH-T - RVO:61388980 UT WOS 000609306700001 EID SCOPUS 85100141579 DOI 10.1002/elps.202000298 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2022 Electronic address https://doi.org/10.1002/elps.202000298
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