Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Open Chemistry

formerly Central European Journal of Chemistry


IMPACT FACTOR 2017: 1.425
5-year IMPACT FACTOR: 1.511

CiteScore 2017: 1.45

SCImago Journal Rank (SJR) 2017: 0.349
Source Normalized Impact per Paper (SNIP) 2017: 0.812

ICV 2017: 165.27

Open Access
Online
ISSN
2391-5420
See all formats and pricing
More options …
Volume 8, Issue 1

Issues

Volume 13 (2015)

Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine

Miloš Lukáč / Ivan Lacko / Marián Bukovský
  • Department of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Zuzana Kyselová / Janka Karlovská / Branislav Horváth / Ferdinand Devínsky
Published Online: 2010-02-16 | DOI: https://doi.org/10.2478/s11532-009-0126-8

Abstract

We synthesized nine quaternary ammonium compounds (QUATs) starting from phenylalanine, N-alkyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromides, which were prepared as optically pure substances. Five compounds were prepared as S-enantiomers and four compounds as R-enantiomers. These compounds were evaluated by their activities against bacteria and fungi. Three microbial strains were used in the study: the gram-negative bacteria Escherichia coli, the gram-positive bacteria Staphylococcus aureus and the fungi Candida albicans. The activities were expressed as minimum bactericidal or fungicidal concentrations (MBC). The most active compounds were (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide and (2R)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide, with MBC values exceeding those of commercial benzalkoniumbromide (BAB) used as standard. The relationships between structure and biological activity of the tested QUATs were quantified by the bilinear model (QSAR) and are discussed.

Keywords: Microbicidal activity; Enantiomers; Phenylalanine; Quaternary ammonium compounds; Quantitative structure activity relationships (QSAR)

  • [1] J. Pernak, J. Rogoża, I. Mirska, Eur. J. Med. Chem. 36, 313 (2001) http://dx.doi.org/10.1016/S0223-5234(01)01226-0CrossrefGoogle Scholar

  • [2] C.J. Ioannou, G.W. Hanlon, S.P. Denyer, Antimicrob. Agents Chemother. 51, 296 (2007) http://dx.doi.org/10.1128/AAC.00375-06CrossrefGoogle Scholar

  • [3] H. Kourai, T. Yabuhara, A. Shirai, T. Maeda, H. Nagamune, Eur. J. Med. Chem. 41, 437 (2006) http://dx.doi.org/10.1016/j.ejmech.2005.10.021CrossrefGoogle Scholar

  • [4] F. Devínsky, I. Lacko, F. Bittererová, D. Mlynarčík, Chem. Pap. 41, 803 (1987) Google Scholar

  • [5] F. Šeršeň, A. Leitmanová, F. Devínsky, I. Lacko, P. Balgavý, Gen. Physiol. Biophys. 8, 133 (1989) Google Scholar

  • [6] F. Kopecký, Pharmazie 51, 135 (1996) Google Scholar

  • [7] D. Mlynarčik, L. Sirotková, F. Devínsky, L. Masárová, A. Pikulíková, I. Lacko, J. Basic. Microbiol. 32, 43 (1992) http://dx.doi.org/10.1002/jobm.3620320113CrossrefGoogle Scholar

  • [8] J. Gallová, F. Devínsky, P. Balgavý, Chem. Phys. Lipids 53, 231 (1990) http://dx.doi.org/10.1016/0009-3084(90)90049-WCrossrefGoogle Scholar

  • [9] J.T. Walton, D.J. Hill, R.G. Protheroe, A. Nevill, H. Gibson, J. Appl. Microbiol. 105, 309 (2008) http://dx.doi.org/10.1111/j.1365-2672.2008.03805.xCrossrefGoogle Scholar

  • [10] L.A. Bjergbæk, J.A.J. Haagensen, S. Molin, P. Roslev, J. Appl. Microbiol. 105, 1310 (2008) http://dx.doi.org/10.1111/j.1365-2672.2008.03901.xCrossrefGoogle Scholar

  • [11] L. Marcotte, J. Barbeau, M. Lafleur, J. Colloid Interface Sci. 292, 219 (2005) http://dx.doi.org/10.1016/j.jcis.2005.05.060CrossrefGoogle Scholar

  • [12] A. Shirai, T. Maeda, H. Nagamune, H. Matsuki, S. Kaneshina, H. Kourai, Eur. J. Med. Chem. 40, 113 (2005) http://dx.doi.org/10.1016/j.ejmech.2004.09.015CrossrefGoogle Scholar

  • [13] A.D. Russell, J. Antimicrob. Chemother. 52, 750 (2003) http://dx.doi.org/10.1093/jac/dkg422CrossrefGoogle Scholar

  • [14] P. Gilbert, L.E. Moore, J. Appl. Microbiol. 99, 703 (2005) http://dx.doi.org/10.1111/j.1365-2672.2005.02664.xCrossrefGoogle Scholar

  • [15] P. Thebault, E.G. Givenchi, R. Levy, Y. Vandenberghe, F. Guittard, S. Géribaldi, Eur. J. Med. Chem. 44, 717 (2009) http://dx.doi.org/10.1016/j.ejmech.2008.05.007CrossrefGoogle Scholar

  • [16] J.J. Merianos, In: S.S. Block (Ed.), Desinfection, Sterilisation and Preservation, 5th edition, (Lippincott Williams & Wilkins, Philadelphia, 2001) 283 Google Scholar

  • [17] F. Devínsky, I. Lacko, D. Mlynarčík, V. Račanský, L. Krasnec, Tenside Detergents 22, 10 (1985) Google Scholar

  • [18] P. Balgavý, F. Devínsky, Adv. Colloid Interface Sci. 66, 23 (1996) http://dx.doi.org/10.1016/0001-8686(96)00295-3CrossrefGoogle Scholar

  • [19] M.J. Pringle, K.B. Brown, K.W. Miller, Mol. Pharmacol. 19, 49 (1980) Google Scholar

  • [20] M.L. Ancelin, M. Calas, A. Bonhoure, S. Herbute, H.J. Vial, Antimicrob. Agents Chemother. 47, 2598 (2003) http://dx.doi.org/10.1128/AAC.47.8.2598-2605.2003CrossrefGoogle Scholar

  • [21] V. Choubey, P. Maity, M. Guha, S. Kumar, K. Srivastava, S.K. Puri, U. Bandyopadhyay, Antimicrob. Agents Chemother. 51, 696 (2007) http://dx.doi.org/10.1128/AAC.00919-06CrossrefGoogle Scholar

  • [22] M. Miko, F. Devínsky, Drug Metab. Drug Interact. 9, 333 (1991) Google Scholar

  • [23] M. Miko, F. Devínsky, Drug Metab. Drug Interact. 10, 237 (1992) CrossrefGoogle Scholar

  • [24] K.W. Yip et al., Clin. Cancer Res. 12, 5557 (2006) http://dx.doi.org/10.1158/1078-0432.CCR-06-0536CrossrefGoogle Scholar

  • [25] M. Ferenčík, I. Lacko, F. Devínsky, Pharmazie 45, 695 (1990) Google Scholar

  • [26] L. Gyermek, C. Lee, Y.M. Cho, N. Nguyen, Life Sci. 79, 559 (2006) http://dx.doi.org/10.1016/j.lfs.2006.01.038CrossrefGoogle Scholar

  • [27] S.J. Wood, L. MacKenzie, B. Maleeff, M.R. Hurle, R. Wetzel, J. Biol. Chem. 271, 4086 (1996) http://dx.doi.org/10.1074/jbc.271.48.30392CrossrefGoogle Scholar

  • [28] F. Zheng et al., Biorg. Med. Chem. 14, 3017 (2006) http://dx.doi.org/10.1016/j.bmc.2005.12.036CrossrefGoogle Scholar

  • [29] G. Zheng, P. Sangeetha, S.P. Sumithran, A.G. Deaciuc, L.P. Dwoskin, P.A. Crooks, Biorg. Med. Chem. 17, 6701 (2007) http://dx.doi.org/10.1016/j.bmcl.2007.10.062CrossrefGoogle Scholar

  • [30] D. Uhríková et al., Colloids Surf., B 42, 59 (2005) http://dx.doi.org/10.1016/j.colsurfb.2005.02.002CrossrefGoogle Scholar

  • [31] S.J. Ryhanen et al., Biophys. J. 84, 578 (2003) http://dx.doi.org/10.1016/S0006-3495(03)74878-4CrossrefGoogle Scholar

  • [32] D. Uhríková, M. Hanulová, S.S. Funari, I. Lacko, F. Devínsky, P. Balgavý, Biophys. Chem. 111, 197 (2004) http://dx.doi.org/10.1016/j.bpc.2004.05.012CrossrefGoogle Scholar

  • [33] Y.H. Liu, X.H. Cao, D.F. Peng, W.Y. Xu, Cent. Eur. J. Chem. 7, 532 (2009) http://dx.doi.org/10.2478/s11532-009-0045-8CrossrefGoogle Scholar

  • [34] M.J. Diego-Castro, H.C. Hailes, M.J. Lawrence, J. Colloid Interface Sci. 234, 122 (2001) http://dx.doi.org/10.1006/jcis.2000.7285CrossrefGoogle Scholar

  • [35] R. Mikláš, M. Srnák, I. Lacko, F. Devínsky, Acta Facult. Pharm. Univ. Comenianae 50, 111 (2003) Google Scholar

  • [36] H. Tan, H. Xiao, Tetrahedron Lett. 49, 1759 (2008) http://dx.doi.org/10.1016/j.tetlet.2008.01.079CrossrefGoogle Scholar

  • [37] Y. Yang, M. Suzuki, S. Owa, H. Shirai, K. Hanabusa, Chem. Commun. 4462 (2005) CrossrefGoogle Scholar

  • [38] K. Kurata, J. Ono, A. Dobashi, J. Chromatogr. A 1080, 140 (2005) http://dx.doi.org/10.1016/j.chroma.2005.04.095CrossrefGoogle Scholar

  • [39] A. Azalamira et al., Tetrahedron: Asymmetry 18, 1868 (2007) http://dx.doi.org/10.1016/j.tetasy.2007.07.026CrossrefGoogle Scholar

  • [40] M. J. McKennon, A.I. Mayers, K. Drauz, M. Schwarm, J. Org. Chem. 58, 3568 (1993) http://dx.doi.org/10.1021/jo00065a020CrossrefGoogle Scholar

  • [41] D. Mlynarčík, S.P. Denyer, W.B. Hugo, Microbios 30, 27 (1981) Google Scholar

  • [42] F. Devínsky, I. Lacko, D. Mlynarčík, E. Švajdlenka, V. Borovská, Chem. Pap. 44, 159 (1990) Google Scholar

  • [43] F. Devínsky, I. Lacko, D. Mlynarčík, In: M. Kuchař, V. Rejholec (Eds.), QSAR in Design of Bioactive Compounds (Prous Int. Pub., Barcelona, 1992) 233 Google Scholar

  • [44] D. Demberelnyanba et al., Biorg. Med. Chem. 12, 853 (2004) http://dx.doi.org/10.1016/j.bmc.2004.01.003CrossrefGoogle Scholar

  • [45] S. Rodríguez-Morales, R.L. Compadre, R. Castillo, P.J. Breen, C.M. Compadre, Eur. J. Med. Chem. 40, 840 (2005) http://dx.doi.org/10.1016/j.ejmech.2005.02.012CrossrefGoogle Scholar

  • [46] C. Hansh, J.M. Clayton, J. Pharm. Sci. 62, 1 (1973) http://dx.doi.org/10.1002/jps.2600620102CrossrefGoogle Scholar

  • [47] H.H. Laycock, B.A. Mulley, J. Pharm. Pharmac. 22, 157 (1970) CrossrefGoogle Scholar

  • [48] N.N. Daoud, N.A. Dickinson, P. Gilbert, Microbios. 37, 73 (1983) Google Scholar

  • [49] H. Kubinyi, Arzneim.-Forsch. 26, 1991 (1976) Google Scholar

  • [50] H. Kubinyi, Arzneim.-Forsch. 29, 1067 (1979) Google Scholar

  • [51] F. Devínsky, I. Lacko, D. Mlynarčík, E. Švajdlenka, L. Masárová, Acta Facult. Pharm. Univ. Comenianae 44, 127 (1990) Google Scholar

  • [52] F. Devínsky, A. Kopecká-Leitmanová, F. Šeršeň, P. Balgavý, J. Pharm. Pharmacol. 42, 790 (1990) CrossrefGoogle Scholar

  • [53] F. Devínsky, L. Masárová, I. Lacko, D. Mlynarčík, J. Biopharm. Sci. 2, 1 (1991) Google Scholar

  • [54] M. Pavlíková, I. Lacko, F. Devínsky, D. Mlynarčík, Collect. Czech. Chem. Commun. 60, 1213 (1995) http://dx.doi.org/10.1135/cccc19951213CrossrefGoogle Scholar

  • [55] M. Pavlíková-Mořická, I. Lacko, F. Devínsky, L. Masárová, D. Mlynarčík, Folia Microbiol. 39, 176 (1994) http://dx.doi.org/10.1007/BF02814644CrossrefGoogle Scholar

  • [56] S. Osanai, Y. Abe, J. Chem. Tech. Biotechnol. 35B, 43 (1985) CrossrefGoogle Scholar

About the article

Published Online: 2010-02-16

Published in Print: 2010-02-01


Citation Information: Open Chemistry, Volume 8, Issue 1, Pages 194–201, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-009-0126-8.

Export Citation

© 2010 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Ewa Obłąk, Agata Piecuch, Justyna Rewak-Soroczyńska, and Emil Paluch
Applied Microbiology and Biotechnology, 2018
[2]
Martin Pisárčik, Miloš Lukáč, Josef Jampílek, František Bilka, Andrea Bilková, Ľudmila Pašková, Ferdinand Devínsky, Renáta Horáková, and Tomáš Opravil
Journal of Molecular Liquids, 2018
[3]
Martin Pisárčik, Josef Jampílek, Miloš Lukáč, Renáta Horáková, Ferdinand Devínsky, Marián Bukovský, Michal Kalina, Jakub Tkacz, and Tomáš Opravil
Molecules, 2017, Volume 22, Number 10, Page 1794
[4]
Miloš Lukáč, Ferdinand Devínsky, Martin Pisárčik, Aspasia Papapetropoulou, Marián Bukovský, and Branislav Horváth
Journal of Surfactants and Detergents, 2017, Volume 20, Number 1, Page 159
[5]
Łukasz Pałkowski, Jerzy Błaszczyński, Andrzej Skrzypczak, Jan Błaszczak, Alicja Nowaczyk, Joanna Wróblewska, Sylwia Kożuszko, Eugenia Gospodarek, Roman Słowiński, and Jerzy Krysiński
BioMed Research International, 2015, Volume 2015, Page 1
[6]
Lukáš Timko, Eva Fischer-Fodor, Mária Garajová, Martin Mrva, Gabriela Chereches, František Ondriska, Marián Bukovský, Miloš Lukáč, Janka Karlovská, Janka Kubincová, and Ferdinand Devínsky
European Journal of Medicinal Chemistry, 2015, Volume 93, Page 263
[8]
R. Mikláš, N. Miklášová, M. Bukovský, B. Horváth, J. Kubincová, and F. Devínsky
European Journal of Pharmaceutical Sciences, 2014, Volume 65, Page 29
[10]
R. Mikláš, N. Miklášová, M. Bukovský, and F. Devínsky
Acta Facultatis Pharmaceuticae Universitatis Comenianae, 2012, Volume 59, Number 1
[11]
M. Pisárčik, M. Polakovičová, M. Lukáč, F. Devínsky, and M. Pupák
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2012, Volume 407, Page 169
[12]
Miloš Lukáč, Martin Pisárčik, Ivan Lacko, and Ferdinand Devínsky
Journal of Colloid and Interface Science, 2010, Volume 347, Number 2, Page 233
[13]
Yi Zhang, Mingming Ding, Lijuan Zhou, Hong Tan, Jiehua Li, Huining Xiao, Jianshu Li, and James Snow
Polymer Chemistry, 2012, Volume 3, Number 4, Page 907
[14]
Miloš Lukáč, Mária Garajová, Martin Mrva, Marián Bukovský, František Ondriska, Eszter Máriássy, Ferdinand Devínsky, and Ivan Lacko
International Journal of Pharmaceutics, 2012, Volume 423, Number 2, Page 247

Comments (0)

Please log in or register to comment.
Log in