Thermodynamic protonation constants of vardenafil by the nonlinear regression of multiwavelength pH-spectrophotometric titration data

• Autorzy: Milan Meloun , Zuzana Ferenčíková , Irena Niesnerová , Tomáš Pekárek
• Języki publikacji: EN

Abstrakty

EN

pH-spectrophotometric titration data were used to determine protonation constants of vardenafil at different ionic strengths I and temperatures of 25°C and 37°C. The use of two different multiwavelength and the multivariate treatment of spectral data, SPECFIT32 and SQUAD(84) nonlinear regression analyses and INDICES factor analysis is presented. The reliability of the protonation constants of the drug was proven with goodness-of-fit tests of the pH-spectra. The thermodynamic protonation constants log K Ti were estimated by a nonlinear regression of (log K, I) data using the Debye-Hückel equation, yielding log K 4T = 3.59(1) and 3.26(1), log K 3T = 5.64(1) and 5.81(1), log K 2T = 9.41(1) and 8.59(2), log K 1T = 10.92(2) and 10.05(1) at 25°C and 37°C, where the figure in brackets is the standard deviation in last significant digit. Concurrently, the experimental determination of four thermodynamic protonation constants was combined with the computational prediction of the MARVIN program based on knowledge of the chemical structures of the drug and was in good agreement with its experimental value. The factor analysis of spectra in the INDICES program predicts the correct number of light-absorbing components when the instrument error is known and when the signal-to-error ratio SER is higher than 10. [...]

Słowa kluczowe

EN

Spectrophotometric titration; Protonation constant; Vardenafil; SPECFIT; SQUAD

• Czasopismo: Open Chemistry
• Rocznik: 2013
• Tom: 11
• Numer: 2
• Strony: 271-279

Daty

wydano

2013-02-01

online

2012-11-29

Twórcy

autor

Milan Meloun

• Department of Analytical Chemistry, University of Pardubice, CZ 532 10, Pardubice, Czech Republic,

autor

Zuzana Ferenčíková

• Department of Analytical Chemistry, University of Pardubice, CZ 532 10, Pardubice, Czech Republic

autor

Irena Niesnerová

• Department of Analytical Chemistry, University of Pardubice, CZ 532 10, Pardubice, Czech Republic

autor

Tomáš Pekárek

• Zentiva k.s., CZ 102 37, Prague, Czech Republic

Bibliografia

• [1] Z. Bartošová, D. Jirovský, A. Horna, J. Chrom. A 1218, 7996 (2011) http://dx.doi.org/10.1016/j.chroma.2011.09.001[Crossref]
• [2] G. M. Keating, L.J. Scott, Drugs 63, 2673 (2003) http://dx.doi.org/10.2165/00003495-200363230-00010[Crossref]
• [3] J. D. Corbin, A. Beasley, M.A. Blount, S.H. Francis, Neurochem. Int. 45, 859 (2004) http://dx.doi.org/10.1016/j.neuint.2004.03.016[Crossref]
• [4] T. Klotz, R. Sachse, A. Heidrich, F. Jockenhovel, G. Rohde, G. Wensing, R. Horstmann, R. Engelmann, World J. Urol. 19, 32 (2001) http://dx.doi.org/10.1007/s003450000168[Crossref]
• [5] K. R. Schonnemann, M. Andersen, M. Yilmaz, H.A. Jensen, L.W. Vestermark, P. Pfeiffer, J. Clin. Oncol. 27, (2009)
• [6] S. H. Hillal, S.W. Karickhoff, L.A. Carriera, in National Exposure Research Laboratory EPA/600/R-03/030 (Office of Research and Development, U.S. Enviromental protection Agency, NC 27711, USA, March 2003)
• [7] Z. Gulyás, G. Pöcze, A. Petz, F. Darvas, Pallas cluster-a new solution to accelerate the high-throughut ADME-TOX prediction, ComGenex-CompuDrug, PKALC/PALLAS 2.1 CompuDrug ChemistryLtd., 〈http://www.compudrug.com〉
• [8] B. Sirohi, S. Sutherland, E. Killick, C. Mikropoulos, A. Constantinodou, S. Ashley, N. Shaunak, M. O’Brien, S. Johnston, I.E. Smith, Ann. Oncol. 19, 133 (2008) http://dx.doi.org/10.1093/annonc/mdn328[Crossref]
• [9] United States Pharmacopeial Convention USP DI.: Drug information for the health care provider (University of Chicago, USA, 1996) vol. 3, p. 664, ISBN 0740-4174
• [10] Y. Hotta, M. Hattori, T. Kataoka, R. Ohno, M. Mikumo, Y. Maeda, K. Kimura, J. Sex. Med. 8, 705 (2011) http://dx.doi.org/10.1111/j.1743-6109.2010.02153.x[Crossref]
• [11] J. I. Martinez-Salamanca, J. Carballido, I. Eardley, F. Giuliano, C. Gratzke, R. Rosen, A. Salonia, C. Stief, Eur. Urol. 60, 527 (2011) http://dx.doi.org/10.1016/j.eururo.2011.05.054[Crossref]
• [12] Y. Ishibashi, T. Matsui, M. Takeuchi, S. Yamagishi, Clin. Exp. Med. 11, 131 (2011) http://dx.doi.org/10.1007/s10238-010-0109-2[Crossref]
• [13] M. Meloun, S. Bordovská, T. Syrový, A. Vrána, Anal. Chim. Acta 580, 107 (2006) http://dx.doi.org/10.1016/j.aca.2006.07.043[Crossref]
• [14] M. Meloun, T. Syrový, S. Bordovská, A. Vrána, Anal. Bioanal. Chem. 387, 941 (2007) http://dx.doi.org/10.1007/s00216-006-0993-1[Crossref]
• [15] M. Meloun, M. Javůrek, J. Havel, Talanta 33, 513 (1986) http://dx.doi.org/10.1016/0039-9140(86)80263-6[Crossref]
• [16] D. J. Leggett, Computational methods for the determination of formation constants (Plenum Press, New York, 1985) http://dx.doi.org/10.1007/978-1-4684-4934-1[Crossref]
• [17] H. Gampp, M. Maeder, C.J. Meyer, A.D. Zuberbuhler, Talanta 32, 95 (1985) http://dx.doi.org/10.1016/0039-9140(85)80035-7[Crossref]
• [18] H. Gampp, M. Maeder, C.J. Meyer, A.D. Zuberbuhler, Talanta 32, 257 (1985) http://dx.doi.org/10.1016/0039-9140(85)80077-1[Crossref]
• [19] H. Gampp, M. Maeder, C.J. Meyer, A.D. Zuberbuhler, Talanta 32, 1133 (1985) http://dx.doi.org/10.1016/0039-9140(85)80238-1[Crossref]
• [20] M. Meloun, Z. Ferenčíková, A. Vrána, J. Chem. Thermodyn 43, 930 (2011) http://dx.doi.org/10.1016/j.jct.2011.01.012[Crossref]
• [21] S-Plus (MathSoft, Seattle, USA, 1999)
• [22] M. Meloun, J. Čapek, P. Mikšík, R. G. Brereton, Analytica Chimica Acta 423, 51 (2000) http://dx.doi.org/10.1016/S0003-2670(00)01100-4[Crossref]
• [23] M. Meloun, V. Říha, J. Žáček, Chem Listy 82, 765 (1988)
• [24] M. Meloun, J. Havel, E. Högfeldt, Computation of Solution Equilibria: A Guide to Methods in Potentiometry, Extraction, and Spectrophotometry (Prentice Hall, UK, 1988)
• [25] J. J. Kankare, Analytical Chemistry 42, 1322 (1970) http://dx.doi.org/10.1021/ac60294a012[Crossref]
• [26] M. Meloun, J. Militký, M. Forina, Chemometrics for analytical chemistry, Volume 1: PC-Aided Statistical Data Analysis (Ellis Horwood, Chichester, 1992)
• [27] SPECFIT/32 (Spectrum Software Associates, 197M Boston Post Road West, Marlborough, MA, 01752 U. SPECFIT/32 (Spectrum Software Associates, 197M Boston Post Road West, Marlborough, MA, 01752 U.S.A., 2004)
• [28] Origin 8.0 (OriginLab Corporation, One Roundhouse Plaza, Suite 303, Northampton, MA 01060, USA.)
• [29] ADSTAT (TriloByte Statistical Software Ltd., Pardubice, Czech Republic)
• [30] M. Meloun, S. Bordovská, T. Syrový, J. Phys. Org. Chem. 43, 690 (2007) http://dx.doi.org/10.1002/poc.1235[Crossref]
• [31] M. Meloun, D. Burkoňová, T. Syrový, A. Vrána, Anal. Chim. Acta 486, 125 (2003) http://dx.doi.org/10.1016/S0003-2670(03)00470-7[Crossref]
• [32] M. Meloun, Z. Ferenčíková, H. Málková, T. Pekárek, Centr. Eur. J. Chem. 10, 338 (2012) http://dx.doi.org/10.2478/s11532-011-0150-3[Crossref]
• [33] M. Meloun, Z. Ferenčíková, A. Vrána, Am. J. Anal. Chem. 1, 14 (2010) http://dx.doi.org/10.4236/ajac.2010.11002[Crossref]

Identyfikatory

DOI

10.2478/s11532-012-0150-y