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

Paweł Szymański; Robert Skibiński; Małgorzata Liszka; Izabela Jargieło; Elżbieta Mikiciuk-Olasik; Łukasz Komsta

doi:10.2478/s11532-013-0218-3

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Journal

Open Chemistry

2013 | 11 | 6 | 927-934

Article title

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

Content

http://www.degruyter.com/view/j/chem.2013.11.issue-6/s11532-013-0218-3/s11532-013-0218-3.pdf [remote]

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Abstracts

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

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

Publisher

De Gruyter Open

Journal

Open Chemistry

Year

2013

Volume

Issue

Pages

927-934

Physical description

Dates

published

1 - 6 - 2013

online

28 - 3 - 2013

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]

Document Type

Publication order reference

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-013-0218-3

Identifiers

DOI

10.2478/s11532-013-0218-3