Determination of acidity constants, ionic mobilities, and hydrodynamic radii of carborane-based inhibitors of carbonic anhydrases by capillary electrophoresis
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
33405254
DOI
10.1002/elps.202000298
Knihovny.cz E-zdroje
- Klíčová slova
- Acid dissociation constant, Capillary electrophoresis, Carboranes, Limiting ionic mobilities, Stokes hydrodynamic radii,
- MeSH
- elektroforéza kapilární MeSH
- hydrodynamika * MeSH
- ionty MeSH
- karboanhydrasy * MeSH
- koncentrace vodíkových iontů MeSH
- kyseliny MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- ionty MeSH
- karboanhydrasy * MeSH
- kyseliny MeSH
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 pKa s using the Debye-Hückel theory. The sulfamidoalkyl and sulfonamidoalkyl groups were found to be very weakly acidic with the pKa s 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 pKa s were in a good agreement with the pKa s (10.67-11.27) obtained by new program AnglerFish (freeware at https://echmet.natur.cuni.cz), which provides thermodynamic pKa s 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.
Institute of Inorganic Chemistry of the Czech Academy of Sciences Husinec Řež Czechia
Institute of Molecular Genetics of the Czech Academy of Sciences Prague 4 Czechia
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Prague 6 Czechia
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Brynda, J., Mader, P., Sicha, V., Fabry, M., Poncova, K., Bakardiev, M., Grüner, B., Cigler, P., Rezacova, P., Angew. Chem., Int. Ed. 2013, 52, 13760-13763.
Mader, P., Pecina, A., Cigler, P., Lepsik, M., Sicha, V., Hobza, P., Grüner, B., Fanfrlik, J., Brynda, J., Rezacova, P., Biomed Res. Int. 2014, 2014, 389869.
Grüner, B., Brynda, J., Das, V., Sicha, V., Stepankova, J., Nekvinda, J., Holub, J., Pospisilova, K., Fabry, M., Pachl, P., Kral, V., Kugler, M., Masek, V., Medvedikova, M., Matejkova, S., Nova, A., Liskova, B., Gurska, S., Dzubak, P., Hajduch, M., Rezacova, P., J. Med. Chem. 2019, 62, 9560-9575.
Dvoranova, J., Kugler, M., Holub, J., Sicha, V., Das, V., Nekvinda, J., El Anwar, S., Havranek, M., Pospisilova, K., Fabry, M., Kral, V., Medvedikova, M., Matejkova, S., Liskova, B., Gurska, S., Dzubak, P., Brynda, J., Hajduch, M., Grüner, B., Rezacova, P., Eur. J. Med. Chem. 2020, 200, 112460.
Nekvinda, J., Kugler, M., Holub, J., El Anwar, S., Brynda, J., Pospisilova, K., Ruzickova, Z., Rezacova, P., Grüner, B., Chem. -Eur. J. 2020, 26, 16541-16553.
Grüner, B., Kugler, M., El Anwar, S., Holub, J., Nekvinda, J., Bavol, D., Ruzickova, Z., Pospisilova, K., Fabry, M., Kral, V., Brynda, J., Rezacova, P., ChemPlusChem 2020, 85.doi.org/10.1002/cplu.202000574.
Krishnamurthy, V. M., Kaufman, G. K., Urbach, A. R., Gitlin, I., Gudiksen, K. L., Weibel, D. B., Whitesides, G. M., Chem. Rev. 2008, 108, 946-1051.
Williams, R. E., Chem. Rev. 1992, 92, 177-207.
Grimes R.N., Carboranes, 3rd edition, Academic Press, London 2016, pp. 1-1041.
McKenna, R., Supuran, C. T., Subcell Biochem. 2014, 75, 291-323.
Slavicek, V., Grüner, B., Vespalec, R., J. Chromatogr. A 2003, 984, 121-134.
Horakova, H., Grüner, B., Vespalec, R., J. Chromatogr. A 2004, 1051, 227-235.
Horakova, H., Vespalec, R., Electrophoresis 2007, 28, 3639-3649.
Horakova, H., Grüner, B., Vespalec, R., Chirality 2011, 23, 307-319.
Valeri, A. L., Kremser, L., Raggi, M. A., Grüner, B., Vespalec, R., Kenndler, E., Electrophoresis 2008, 29, 1658-1666.
Holub, J., El Anwar, S., Jelinek, T., Fojt, L., Ruzickova, Z., Solinova, V., Kasicka, V., Gabel, D., Grüner, B., Eur. J. Inorg. Chem. 2017, 4499-4509.
El Anwar, S., Holub, J., Tok, O., Jelinek, T., Ruzickova, Z., Fojt, L., Solinova, V., Kasicka, V., Grüner, B., J. Organomet. Chem. 2018, 865, 189-199.
Vinas, C., Laromaine, A., Teixidor, F., Horakova, H., Langauf, A., Vespalec, R., Mata, I., Molins, E., Dalton Trans. 2007, 3369-3377.
Vitova, L., Fojt, L., Vespalec, R., J. Chromatogr. A 2014, 1338, 174-183.
Stepanova, S., Kasicka, V., in: Poole, C. F. (Ed.), Capillary Electromigration Separation Methods, Elsevier Inc., Amsterdam 2018, pp. 547-591.
Poole, S. K., Patel, S., Dehring, K., Workman, H., Poole, C. F., J. Chromatogr. A 2004, 1037, 445-454.
Nowak, P., Wozniakiewicz, M., Koscielniak, P., J. Chromatogr. A 2015, 1377, 1-12.
Solinova, V., Kasicka, V., Electrophoresis 2013, 34, 2655-2665.
Cabot, J. M., Fuguet, E., Roses, M., ACS Comb. Sci. 2014, 16, 518-525.
Cabot, J. M., Fuguet, E., Roses, M., Smejkal, P., Breadmore, M. C., Anal. Chem. 2015, 87, 6165-6172.
Konasova, R., Dytrtova, J. J., Kasicka, V., J. Chromatogr. A 2015, 1408, 243-249.
Riesova, M., Svobodova, J., Uselova, K., Tosner, Z., Zuskova, I., Gas, B., J. Chromatogr. A 2014, 1364, 276-288.
Nowak, P. M., Wozniakiewicz, M., Piwowarska, M., Koscielniak, P., J. Chromatogr. A 2016, 1446, 149-157.
Pero-Gascon, R., Benavente, F., Barbosa, J., Sanz-Nebot, V., J. Chromatogr. A 2017, 1508, 148-157.
Geffertova, D., Ali, S. T., Solinova, V., Krecmerova, M., Holy, A., Havlas, Z., Kasicka, V., J. Chromatogr. A 2017, 1479, 185-193.
Nowak, P. M., Olesek, K., Wozniakiewicz, M., Mitoraj, M., Sagan, F., Koscielniak, P., J. Chromatogr. A 2018, 1580, 142-151.
Nowak, P. M., Leszczenko, P., Zarusinska, J., Koscielniak, P., Anal. Bioanal. Chem. 2020, 412, 577-588.
Lebanov, L., Fuguet, E., Melo, J. M., Roses, M., Analyst 2020, 145, 5897-5904.
Barbosa, J., Barron, D., Jimenez-Lozano, E., Sanz-Nebot, V., Anal. Chim. Acta 2001, 437, 309-321.
Porras, S. P., Jyske, P., Riekkola, M. L., Kenndler, E., J. Microcolumn Sep. 2001, 13, 149-155.
Ehala, S., Misek, J., Stara, I. G., Stary, I., Kasicka, V., J. Sep. Sci. 2008, 31, 2686-2693.
Maly, M., Boublik, M., Pocrnic, M., Ansorge, M., Lorincikova, K., Svobodova, J., Hruska, V., Dubsky, P., Gas, B., Electrophoresis 2020, 41, 493-501.
Ansorge, M., Gas, B., Boublik, M., Maly, M., Steflova, J., Hruska, V., Vigh, G., Electrophoresis 2020, 41, 514-522.
Wang, J. L., Xu, X. J., Chen, D. Y., J. Pharm. Biomed. Anal. 2014, 88, 22-26.
Geiser, L., Henchoz, Y., Galland, A., Carrupt, P. A., Veuthey, J. L., J. Sep. Sci. 2005, 28, 2374-2380.
Sanli, S., Altun, Y., Sanli, N., Alsancak, G., Beltran, J. L., J. Chem. Eng. Data 2009, 54, 3014-3021.
Lin, C. E., Lin, W. C., Chen, Y. C., Wang, S. W., J. Chromatogr. A 1997, 792, 37-47.
Lin, C. E., Chang, C. C., Lin, W. C., J. Chromatogr. A 1997, 768, 105-112.
Qiang, Z. M., Adams, C., Water Res. 2004, 38, 2874-2890.
Maslankiewicz, M. J., Marciniec, K., Maslankiewicz, A., Jaworska, M., J. Mol. Struct. 2013, 1033, 284-288.
Sanli, N., Sanli, S., Ozkan, G., Denizli, A., J. Braz. Chem. Soc. 2010, 21, 1952-1960.
Duarte-Hernandez, A. M., Contreras, R., Suarez-Moreno, G. V., Montes-Tolentino, P., Ramos-Garcia, I., Gonzalez, F. J., Flores-Parra, A., J. Mol. Struct. 2015, 1084, 135-147.
Pecina, A., Lepsik, M., Rezac, J., Brynda, J., Mader, P., Rezacova, P., Hobza, P., Fanfrlik, J., J. Phys. Chem. B 2013, 117, 16096-16104.
Koval, D., Kasicka, V., Jiracek, J., Collinsova, M., Electrophoresis 2003, 24, 774-781.
Vcelakova, K., Zuskova, I., Kenndler, E., Gas, B., Electrophoresis 2004, 25, 309-317.
Solinova, V., Kasicka, V., Koval, D., Cesnek, M., Holy, A., Electrophoresis 2006, 27, 1006-1019.
Survay, M. A., Goodall, D. M., Wren, S. A. C., Rowe, R. C., J. Chromatogr. A 1996, 741, 99-113.
