Abstract
The present review describes the recent results on the electrochemical activity of bio-guanidino compounds, such as famotidine, metformin, acyclovir, ganciclovir, zanamivir, moroxydine as well as guanidino compounds, such as S-[(2-guanidino-thiazol-4-yl)methyl]isothiourea hydrochloride, 2-guanidino-1,3-thiazole, 2-guanidinobenzimidazole. The focus is on analyzing the electrode mechanism of the guanidino compounds at the hanging mercury drop electrode and at the silver amalgam film electrode, as well as on the character of the square wave (SW) voltammetric signals. It has been stated, that the compounds can act as electrocatalysts — they are protonated and adsorbed at the surface of the electrode, after which the protonated forms of the compounds are irreversibly reduced, yielding their initial form and hydrogen. The experimental adsorption data obtained by measuring the differential capacity of the double layer, the zero charge potential, and the surface tension at the zero charge potential have established the adsorption processes underlying their electrochemical activity. The analytical application of the obtained voltammetric signals in the determination of these compounds in biological samples is also presented. This review concentrates on our own results in the context of general developments in the field.
[1] M. Hiramatsu, Mol. Cell. Biochem. 244, 57 (2003) http://dx.doi.org/10.1023/A:102249141981310.1023/A:1022491419813Search in Google Scholar
[2] K. Aoyagi, Mol. Cell. Biochem. 244, 11 (2003) http://dx.doi.org/10.1023/A:102247901708710.1023/A:1022479017087Search in Google Scholar
[3] B.D. Cohen, Mol. Cell. Biochem. 244, 31 (2003) http://dx.doi.org/10.1023/A:102248311799610.1023/A:1022483117996Search in Google Scholar
[4] T.J. de Gruaw, K.M. Cecil, A.W. Byars, G.S. Salomons, W.S. Ball, C. Jakobs, Mol. Cell. Biochem. 244, 45 (2003) http://dx.doi.org/10.1023/A:102248721890410.1023/A:1022487218904Search in Google Scholar
[5] S. Skrzypek, V. Mirceski, W. Ciesielski, A. Sokołowski, R. Zakrzewski, J. Pharm. Biomed. Anal. 45, 275 (2007) http://dx.doi.org/10.1016/j.jpba.2007.07.01010.1016/j.jpba.2007.07.010Search in Google Scholar PubMed
[6] S. Skrzypek, W. Ciesielski, A. Sokołowski, S. Yilmaz, D. Kaźmierczak, Talanta 66, 1146 (2005) http://dx.doi.org/10.1016/j.talanta.2005.01.01710.1016/j.talanta.2005.01.017Search in Google Scholar PubMed
[7] S. Skrzypek, W. Ciesielski, S. Yilmaz, Chem. Anal. (Warsaw) 52, 1071 (2007) Search in Google Scholar
[8] S. Skrzypek, A. Nosal-Wiercińska, W. Ciesielski, Collect. Czech. Chem. Commun. 74, 1455 (2009) http://dx.doi.org/10.1135/cccc200904510.1135/cccc2009045Search in Google Scholar
[9] S. Skrzypek, Electroanalysis 22, 2239 (2010) http://dx.doi.org/10.1002/elan.20100016310.1002/elan.201000163Search in Google Scholar
[10] N. Lindegardh, J. Chromatogr. B 1215, 145 (2008) 10.1016/j.chroma.2008.11.009Search in Google Scholar PubMed
[11] D. Guziejewski, S. Skrzypek, A. Łuczak, W. Ciesielski, Collect. Czech. Chem. Commun. 76(2), 131 (2011) http://dx.doi.org/10.1135/cccc201011610.1135/cccc2010116Search in Google Scholar
[12] B. Dogan, B. Uslu, S.A. Ozkan, P. Zuman, Anal. Chem. 80, 209 (2008) http://dx.doi.org/10.1021/ac071315110.1021/ac0713151Search in Google Scholar
[13] Y. Altun, B. Uslu, S.A. Ozkan, Analytical Letters 43(12), 1958 (2010) http://dx.doi.org/10.1080/0003271100368704710.1080/00032711003687047Search in Google Scholar
[14] D. Kul, M. Gumustas, B. Uslu, S.A. Ozkan, Talanta 82(1), 286 (2010) http://dx.doi.org/10.1016/j.talanta.2010.04.03610.1016/j.talanta.2010.04.036Search in Google Scholar
[15] M. Gumustas, S.A. Ozkan, Anal. Bioanal. Chem. 397(1), 189 (2010) http://dx.doi.org/10.1007/s00216-009-3334-310.1007/s00216-009-3334-3Search in Google Scholar
[16] S.A. Ozkan, B. Uslu, Anal. Bioanal. Chem. 372, 582 (2002) http://dx.doi.org/10.1007/s00216-001-1223-510.1007/s00216-001-1223-5Search in Google Scholar
[17] A. Bobrowski, J. Zarębski, Electroanalysis 12, 1177 (2000) http://dx.doi.org/10.1002/1521-4109(200010)12:15<1177::AID-ELAN1177>3.0.CO;2-U10.1002/1521-4109(200010)12:15<1177::AID-ELAN1177>3.0.CO;2-USearch in Google Scholar
[18] B. Raspor, J. Pavicic, Fresenius J. Anal. Chem. 354, 529 (1996) 10.1007/s0021663540529Search in Google Scholar
[19] M. Kuik, K. Krassowski, Collect. Czech. Chem. Commun. 56, 157 (1991) http://dx.doi.org/10.1135/cccc1991015710.1135/cccc19910157Search in Google Scholar
[20] F.G. Banica, N. Spataru, T. Spataru, Electroanalysis 9, 1341 (1997) http://dx.doi.org/10.1002/elan.114009170810.1002/elan.1140091708Search in Google Scholar
[21] F.G. Banica, N. Spataru, Talanta 48, 491 (1999) http://dx.doi.org/10.1016/S0039-9140(98)00259-810.1016/S0039-9140(98)00259-8Search in Google Scholar
[22] N. Spataru, F. G. Banica, Analyst 126, 1907 (2001) http://dx.doi.org/10.1039/b104606n10.1039/b104606nSearch in Google Scholar
[23] F.G. Banica, A. Ion, In: R.A. Meyers (Ed.), Encyclopedia of analytical chemistry (J. Wiley & Sons, Chichester, 2000) Search in Google Scholar
[24] G. Somer, Z. Almas, J. Electroanal. Chem. 593, 179 (2006) http://dx.doi.org/10.1016/j.jelechem.2006.03.04710.1016/j.jelechem.2006.03.047Search in Google Scholar
[25] D. Guziejewski, S. Skrzypek, W. Ciesielski, Food Anal. Methods, DOI: 10.1007/s12161-011-9253-x 10.1007/s12161-011-9253-xSearch in Google Scholar
[26] S. Skrzypek, J. Lewkowski, Electroanalysis 23(5), 1212 (2011) http://dx.doi.org/10.1002/elan.20100060210.1002/elan.201000602Search in Google Scholar
[27] L. H. Wang, S.J. Tsai, Anal. Chim. Acta 441, 107 (2001) http://dx.doi.org/10.1016/S0003-2670(01)01083-210.1016/S0003-2670(01)01083-2Search in Google Scholar
[28] G.B. El-Hefnawy, I.S. El-Hallag, E.M. Ghoneim, M.M. Ghoneim, J. Pharm. Biomed. Anal. 34, 899 (2004) http://dx.doi.org/10.1016/j.jpba.2003.09.00210.1016/j.jpba.2003.09.002Search in Google Scholar
[29] F. Vicente, C. Sanz, Electrochimica Acta 29, 1659 (1984) http://dx.doi.org/10.1016/0013-4686(84)89007-610.1016/0013-4686(84)89007-6Search in Google Scholar
[30] F.V. Pedros, C.S. Box, J.T. Monge, J. Electroanal. Chem. 182, 413 (1985) http://dx.doi.org/10.1016/0368-1874(85)87015-510.1016/0368-1874(85)87015-5Search in Google Scholar
[31] B. Baś, Z. Kowalski, Electroanalysis 14, 1067 (2002) http://dx.doi.org/10.1002/1521-4109(200208)14:15/16<1067::AID-ELAN1067>3.0.CO;2-510.1002/1521-4109(200208)14:15/16<1067::AID-ELAN1067>3.0.CO;2-5Search in Google Scholar
[32] B. Baś, Electrochem. Commun. 10, 156 (2008) http://dx.doi.org/10.1016/j.elecom.2007.10.02410.1016/j.elecom.2007.10.024Search in Google Scholar
[33] J.A. Squella, G. Valencia, I. Lemus, L.J. Nunez-Vergara, J. Assoc. Anal. Chem. 4, 72 (1989) 10.1093/jaoac/72.4.549Search in Google Scholar
[34] V. Mirceski, S. Skrzypek, W. Ciesielski, A. Sokołowski, J. Electroanal. Chem. 585, 97 (2005) http://dx.doi.org/10.1016/j.jelechem.2005.07.01710.1016/j.jelechem.2005.07.017Search in Google Scholar
[35] M. Lovric, S. Komorsky-Lovric, R.W. Murray, Electrochim. Acta 33, 739 (1988) http://dx.doi.org/10.1016/S0013-4686(98)80002-910.1016/S0013-4686(98)80002-9Search in Google Scholar
[36] V. Mirceski, R. Gulaboski, Electroanalysis 13, 1326 (2001) http://dx.doi.org/10.1002/1521-4109(200111)13:16<1326::AID-ELAN1326>3.0.CO;2-S10.1002/1521-4109(200111)13:16<1326::AID-ELAN1326>3.0.CO;2-SSearch in Google Scholar
[37] V. Mirceski, R. Gulaboski, J. Solid State Electrochem. 7, 157 (2003) 10.1007/s10008-002-0290-7Search in Google Scholar
[38] J.J. O’Dea, J. Osteryoung, Anal. Chem. 53, 695 (1981) http://dx.doi.org/10.1021/ac00227a02810.1021/ac00227a028Search in Google Scholar
[39] R. Gulaboski, V. Mirceski, M. Lovric, I. Bogeski, Electrochem. Commun. 7, 515 (2005) http://dx.doi.org/10.1016/j.elecom.2005.03.00910.1016/j.elecom.2005.03.009Search in Google Scholar
[40] R.S. Nicholson, M.L. Olmstead, In: J.S. Mattson, H.B. Mark, H.C. MacDonald (Eds), Electrochemistry: Calculations, Simulation and Instrumentation, 2nd edition (Marcel Dekker, New York, 1972) Search in Google Scholar
[41] B. Baś, Anal. Chim. Acta 570, 195 (2006) http://dx.doi.org/10.1016/j.aca.2006.04.01310.1016/j.aca.2006.04.013Search in Google Scholar
[42] P. Kapturski, A. Bobrowski, J. Electroanal. Chem. 617, 1 (2008) http://dx.doi.org/10.1016/j.jelechem.2008.01.00710.1016/j.jelechem.2008.01.007Search in Google Scholar
[43] R. Piech, B. Baś, E. Niewiara, W.W. Kubiak, Electroanalysis 20, 809 (2008) http://dx.doi.org/10.1002/elan.20070410610.1002/elan.200704106Search in Google Scholar
[44] P. Kapturski, A. Bobrowski, Electroanalysis 19, 1863 (2007) http://dx.doi.org/10.1002/elan.20070399210.1002/elan.200703992Search in Google Scholar
[45] R. Piech, B. Baś, W.W. Kubiak, J. Electroanal. Chem. 621, 43 (2008) http://dx.doi.org/10.1016/j.jelechem.2008.04.00810.1016/j.jelechem.2008.04.008Search in Google Scholar
[46] R. Piech, B. Baś, W.W. Kubiak, Talanta 76, 295 (2008) http://dx.doi.org/10.1016/j.talanta.2008.02.03810.1016/j.talanta.2008.02.038Search in Google Scholar PubMed
[47] R. Piech, Electroanalysis 20, 2475 (2008) http://dx.doi.org/10.1002/elan.20080436210.1002/elan.200804362Search in Google Scholar
[48] R. Piech, B. Baś, W.W. Kubiak, Electroanalysis 19, 2342 (2007) http://dx.doi.org/10.1002/elan.20070398810.1002/elan.200703988Search in Google Scholar
[49] A. Bobrowski, M. Gawlicki, P. Kapturski, V. Mirceski, F. Spasovski, J. Zarębski, Electroanalysis 21, 36 (2009) http://dx.doi.org/10.1002/elan.20080433610.1002/elan.200804336Search in Google Scholar
[50] R. Piech, Electroanalysis 22, 1851 (2010) http://dx.doi.org/10.1002/elan.20100017610.1002/elan.201000176Search in Google Scholar
[51] A. Navalon, R. EI-Khattabi, A. Gonzales-Casado, J.L. Vilchez, Microchim. Acta 130, 261 (1999) http://dx.doi.org/10.1007/BF0124291410.1007/BF01242914Search in Google Scholar
[52] M.M. Kamal, Electroanalysis 4, 563 (1992) http://dx.doi.org/10.1002/elan.114004050910.1002/elan.1140040509Search in Google Scholar
[53] K. Stojanova, R. Gulaboski, V. Mirceski, S. Petrovska-Jovanovic, Anal.Lett. 32, 2937 (1999) http://dx.doi.org/10.1080/0003271990854301810.1080/00032719908543018Search in Google Scholar
[54] S. Skrzypek, V. Mirceski, S. Smarzewska, D. Guziejewski, W. Ciesielski, Collect. Czech. Chem. Commun. 76(12), 1699 (2011) http://dx.doi.org/10.1135/cccc201112210.1135/cccc2011122Search in Google Scholar
[55] P. Zuman, In: M.M. Baizer, H. Lund (Eds.), Organic Electrochemistry, 2nd edition (Marcel Dekker, New York, 1983) 151 Search in Google Scholar
[56] P. Zuman, J. Ludvik, Electroanalysis 12, 879 (2000) http://dx.doi.org/10.1002/1521-4109(200008)12:12<879::AID-ELAN879>3.0.CO;2-O10.1002/1521-4109(200008)12:12<879::AID-ELAN879>3.0.CO;2-OSearch in Google Scholar
[57] S. Skrzypek, Electroanalysis, DOI: 10.1002/elan.201100343 10.1002/elan.201100343Search in Google Scholar
[58] R. Parson, Can. J. Chem. 59, 1898 (1981) http://dx.doi.org/10.1139/v81-28210.1139/v81-282Search in Google Scholar
[59] O. Ikeda, H. Limbo, H. Tamura, J. Electroanal. Chem. 137(1982) 127 http://dx.doi.org/10.1016/0022-0728(82)85072-910.1016/0022-0728(82)85072-9Search in Google Scholar
[60] A. Nosal -Wiercińska, G. Dalmata, Electroanalysis 22 (2010) 2081) http://dx.doi.org/10.1002/elan.20100006910.1002/elan.201000069Search in Google Scholar
[61] A. Nosal-Wiercinska, Cent. Eur. J. Chem. 8, 1 (2010) http://dx.doi.org/10.2478/s11532-009-0109-910.2478/s11532-009-0109-9Search in Google Scholar
[62] A. Nosal-Wiercińska, Z. Fekner, G. Dalmata, J. Electroanal. Chem. 584, 192 (2005) http://dx.doi.org/10.1016/j.jelechem.2005.01.04410.1016/j.jelechem.2005.01.044Search in Google Scholar
[63] H. Jehring, Elektrosorptionsanalyse mit der Wechselstrompolarographie. (Akademie Verlag, Berlin 1974) (In German) Search in Google Scholar
[64] J. Heyrovsky, P. Zuman, Practical polarography: an introduction for chemistry students (Academic Press, London and New York, 1968) 10.1016/B978-1-4832-2746-7.50004-XSearch in Google Scholar
[65] Z.P. Zagórski, Analiza polarograficzna (PWN, Warszawa, 1970) (In Polish) Search in Google Scholar
[66] O. Mikkelsen, K.H. Schroder, T.A. Aarhaug, Collect. Czech. Chem. Commun. 66, 465 (2001) http://dx.doi.org/10.1135/cccc2001046510.1135/cccc20010465Search in Google Scholar
[67] O. Mikkelsen, K.H. Schroder, Anal. Lett. 33, 3253 (2000) http://dx.doi.org/10.1080/00032719.2000.1039949910.1080/00032719.2000.10399499Search in Google Scholar
[68] O. Mikkelsen, K.H. Schroder, Electroanalysis 15, 679 (2003) http://dx.doi.org/10.1002/elan.20039008510.1002/elan.200390085Search in Google Scholar
[69] J. Barek, J. Fischer, T. Navratil, K. Peckova, B. Yosypchuk, Sensors 6, 445 (2006) http://dx.doi.org/10.3390/s604044510.3390/s6040445Search in Google Scholar
[70] B. Yosypchuk, L. Novotny, Electroanalysis 14, 1138 (2002) http://dx.doi.org/10.1002/1521-4109(200208)14:15/16<1138::AID-ELAN1138>3.0.CO;2-#Search in Google Scholar
[71] J. Barek, J. Fischer, T. Navratil, K. Peckova, B. Yosypchuk, J. Zima, Electroanalysis 19, 2003 (2007) http://dx.doi.org/10.1002/elan.20070391810.1002/elan.200703918Search in Google Scholar
[72] R. Piech, B. Baś, B. Paczosa-Bator, W. Kubiak, J. Electroanal. Chem. 633, 333 (2009) http://dx.doi.org/10.1016/j.jelechem.2009.06.02110.1016/j.jelechem.2009.06.021Search in Google Scholar
[73] B. Baś, Z. Kowalski, Electroanalysis 14, 1067 (2002) http://dx.doi.org/10.1002/1521-4109(200208)14:15/16<1067::AID-ELAN1067>3.0.CO;2-510.1002/1521-4109(200208)14:15/16<1067::AID-ELAN1067>3.0.CO;2-5Search in Google Scholar
[74] B. Baś, Electrochem. Commun. 10, 156 (2008) http://dx.doi.org/10.1016/j.elecom.2007.10.02410.1016/j.elecom.2007.10.024Search in Google Scholar
© 2012 Versita Warsaw
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.