A TLC Study of the lipophilicity of thirty-two acetylcholinesterase inhibitors - 1,2,3,4-tetrahydroacridine and 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives

• Authors: Paweł Szymański , Robert Skibiński , Małgorzata Liszka , Izabela Jargieło , Elżbieta Mikiciuk-Olasik , Łukasz Komsta
• Languages of publication: EN

Abstracts

EN

The lipophilicity of thirty-two novel acetylcholinesterase (AChE) inhibitors - 1,2,3,4-tetrahydroacridine and 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives was studied by thin layer chromatography. The analyzed compounds were chromatographed on RP-18, RP-8, RP-2, CN and NH2 stationary phases with dioxane - citric buffer pH 3.0 binary mobile phases containing different proportions of dioxane. RM values for pure water were extrapolated from the linear Soczewiński-Wachtmeister equation and six compounds with known literature log P values were used as reference calibration data set for computation of experimental log P values. [...] The obtained results were compared with computationally calculated partition coefficients values (AlogPs, AClogP, AlogP, MlogP, KOWWIN, XlogP2, XlogP3) by PCA and significant differences between them were observed.

Keywords

EN

Lipophilicity; Calculated partition coefficients; AChE inhibitors; Tetrahydroacridine; Cyclopenta[b]quinoline

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 6
• Pages: 927-934

Dates

published

1 - 6 - 2013

online

28 - 3 - 2013

Contributors

author

Paweł Szymański

• Department of Pharmaceutical Chemistry and Drug Analyses, Medical University, 90-151, Łódź, Poland

author

Robert Skibiński

• Department of Medicinal Chemistry, Faculty of Pharmacy, Medical University of Lublin, 20-090, Lublin, Poland

author

Małgorzata Liszka

• Department of Medicinal Chemistry, Faculty of Pharmacy, Medical University of Lublin, 20-090, Lublin, Poland

author

Izabela Jargieło

• Department of Medicinal Chemistry, Faculty of Pharmacy, Medical University of Lublin, 20-090, Lublin, Poland

author

Elżbieta Mikiciuk-Olasik

• Department of Pharmaceutical Chemistry and Drug Analyses, Medical University, 90-151, Łódź, Poland

author

Łukasz Komsta

• Department of Medicinal Chemistry, Faculty of Pharmacy, Medical University of Lublin, 20-090, Lublin, Poland

References

• [1] D.S. Knopman, Am J Med. 104, 2 (1998) http://dx.doi.org/10.1016/S0002-9343(98)00022-9[Crossref]
• [2] Y.Y Na, N. Dai-Nghiep, K. Se-Kwon, Carbohydrate Polymers 78, 869 (2009) http://dx.doi.org/10.1016/j.carbpol.2009.07.004[Crossref]
• [3] R. S. Shah, H. Lee, Z. Xiongwei, G. Perry, M.A. Smith, R. J. Castellani, Biomed. Pharmacotherapy 62, 199 (2008) http://dx.doi.org/10.1016/j.biopha.2008.02.005[Crossref]
• [4] L. Mucke, Nature 461, 895 (2009) http://dx.doi.org/10.1038/461895a[Crossref]
• [5] K. Jin, L. Xie, X.O. Mao, D.A. Greenberg, Brain Reaserch 1085, 183 (2006) http://dx.doi.org/10.1016/j.brainres.2006.02.081[Crossref]
• [6] L. Shin-Hua, J.W. Wu, H.L. Liu, J.H. Zhao, K.T. Liu, Ch.K. Chuang, H.Y. Lin, W.B. Tsai, Y. Ho, J. Biomed. Sci. 18, 1 (2011) http://dx.doi.org/10.1186/1423-0127-18-1[Crossref]
• [7] M. Waksumndzka-Hajnos, D. Matosiuk, A. Petruczynik, U. Kijkowska-Murak, Acta Chromatogr. 20, 563 (2008) http://dx.doi.org/10.1556/AChrom.20.2008.4.3[Crossref]
• [8] E. Pękala, H. Marona, Biomed. Chromatogr. 23, 543 (2009) http://dx.doi.org/10.1002/bmc.1153[Crossref]
• [9] K. Kulig, B. Malawska, J. Planar Chromatogr. 22, 141 (2009) http://dx.doi.org/10.1556/JPC.22.2009.2.12[Crossref]
• [10] R. Skibiński, T. Sławik, M. Kaczkowska, J. Planar Chromatogr. 24, 348 (2011) http://dx.doi.org/10.1556/JPC.24.2011.4.14[Crossref]
• [11] A. Pyka, J. Planar Chromatogr. 22, 211 (2009) http://dx.doi.org/10.1556/JPC.22.2009.3.10[Crossref]
• [12] C. Sârbu, B. Tiperciuc, J. Planar Chromatogr. 19, 342 (2006) http://dx.doi.org/10.1556/JPC.19.2006.5.2[Crossref]
• [13] J.V. OdoviĆ, B.B. StojimiroviĆ, M.B. AleksiĆ, D.M. Milojković-Opsenica, Z.Lj. Tešić, J. Planar Chromatogr. 18, 98 (2005) http://dx.doi.org/10.1556/JPC.18.2005.2.2[Crossref]
• [14] P. Szymański, E. Żurek, E. Mikiciuk-Olasik, Die Pharmazie, 61, 269 (2006)
• [15] P. Szymański, A. Karpiński, E. Mikiciuk-Olasik, Eur. J. Med. Chem. 46, 3250 (2011) http://dx.doi.org/10.1016/j.ejmech.2011.04.038[Crossref]
• [16] P. Szymański, M. Markowicz, E. Mikiciuk-Olasik, Bioorg. Chem. 39, 138 (2011) http://dx.doi.org/10.1016/j.bioorg.2011.05.001[Crossref]
• [17] P. Szymański, M. Markowicz, M. Bajda, B. Malawska, E. Mikiciuk-Olasik, Lett. Drug Design Discovery 9, 645 (2012) http://dx.doi.org/10.2174/157018012801319454[Crossref]
• [18] P. Szymański, A. Laznickova, M. Laznicek, M. Bajda, B. Malawska, M. Markowicz, E. Mikiciuk-Olasik, Int. J. Mol. Sci. 13, 10067 (2012) http://dx.doi.org/10.3390/ijms130810067[Crossref]
• [19] Ł. Komsta, R. Skibiński, A. Berecka, A. Gumieniczek, B. Radkiewicz, M. Radoń, J. Pharm. Biomed. Anal. 53, 911 (2010) http://dx.doi.org/10.1016/j.jpba.2010.06.024[Crossref]
• [20] E.C. Bate-Smith, R.G. Westall, Biochim. Biophys. Acta. 4, 427 (1950) http://dx.doi.org/10.1016/0006-3002(50)90049-7[Crossref]
• [21] E. Soczewiński, C.A. Wachtmeister, J. Chromatogr. A 7, 311 (1962) http://dx.doi.org/10.1016/S0021-9673(01)86422-0[Crossref]
• [22] A.C. Moffat (Ed.), Clarke’s Analysis of Drugs and Poisons (Pharmaceutical Press, London, 2004)
• [23] M. Daszykowski, B. Walczak, D.L. Massart, Chemom. Intell. Lab. Syst. 65, 97 (2003) http://dx.doi.org/10.1016/S0169-7439(02)00107-7[Crossref]

Identifiers

DOI

10.2478/s11532-013-0218-3