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2010 | 8 | 1 | 194-201
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
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. [...]
Wydawca

Czasopismo
Rocznik
Tom
8
Numer
1
Strony
194-201
Opis fizyczny
Daty
wydano
2010-02-01
online
2010-02-16
Twórcy
  • Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia, lukac@fpharm.uniba.sk
autor
  • Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
  • Department of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
  • Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
  • Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
  • Institute of Chemistry, Faculty of Natural Science, Comenius University, Bratislava, 842 15, Slovakia
  • Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia
Bibliografia
  • [1] J. Pernak, J. Rogoża, I. Mirska, Eur. J. Med. Chem. 36, 313 (2001) http://dx.doi.org/10.1016/S0223-5234(01)01226-0[Crossref]
  • [2] C.J. Ioannou, G.W. Hanlon, S.P. Denyer, Antimicrob. Agents Chemother. 51, 296 (2007) http://dx.doi.org/10.1128/AAC.00375-06[Crossref]
  • [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.2005.10.021[Crossref]
  • [4] F. Devínsky, I. Lacko, F. Bittererová, D. Mlynarčík, Chem. Pap. 41, 803 (1987)
  • [5] F. Šeršeň, A. Leitmanová, F. Devínsky, I. Lacko, P. Balgavý, Gen. Physiol. Biophys. 8, 133 (1989)
  • [6] F. Kopecký, Pharmazie 51, 135 (1996)
  • [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.3620320113[Crossref]
  • [8] J. Gallová, F. Devínsky, P. Balgavý, Chem. Phys. Lipids 53, 231 (1990) http://dx.doi.org/10.1016/0009-3084(90)90049-W[Crossref]
  • [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.x[Crossref]
  • [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.x[Crossref]
  • [11] L. Marcotte, J. Barbeau, M. Lafleur, J. Colloid Interface Sci. 292, 219 (2005) http://dx.doi.org/10.1016/j.jcis.2005.05.060[Crossref]
  • [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.2004.09.015[Crossref]
  • [13] A.D. Russell, J. Antimicrob. Chemother. 52, 750 (2003) http://dx.doi.org/10.1093/jac/dkg422[Crossref]
  • [14] P. Gilbert, L.E. Moore, J. Appl. Microbiol. 99, 703 (2005) http://dx.doi.org/10.1111/j.1365-2672.2005.02664.x[Crossref]
  • [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.2008.05.007[Crossref]
  • [16] J.J. Merianos, In: S.S. Block (Ed.), Desinfection, Sterilisation and Preservation, 5th edition, (Lippincott Williams & Wilkins, Philadelphia, 2001) 283
  • [17] F. Devínsky, I. Lacko, D. Mlynarčík, V. Račanský, L. Krasnec, Tenside Detergents 22, 10 (1985)
  • [18] P. Balgavý, F. Devínsky, Adv. Colloid Interface Sci. 66, 23 (1996) http://dx.doi.org/10.1016/0001-8686(96)00295-3[Crossref]
  • [19] M.J. Pringle, K.B. Brown, K.W. Miller, Mol. Pharmacol. 19, 49 (1980)
  • [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.47.8.2598-2605.2003[Crossref]
  • [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.00919-06[Crossref]
  • [22] M. Miko, F. Devínsky, Drug Metab. Drug Interact. 9, 333 (1991)
  • [23] M. Miko, F. Devínsky, Drug Metab. Drug Interact. 10, 237 (1992) [Crossref]
  • [24] K.W. Yip et al., Clin. Cancer Res. 12, 5557 (2006) http://dx.doi.org/10.1158/1078-0432.CCR-06-0536[Crossref]
  • [25] M. Ferenčík, I. Lacko, F. Devínsky, Pharmazie 45, 695 (1990)
  • [26] L. Gyermek, C. Lee, Y.M. Cho, N. Nguyen, Life Sci. 79, 559 (2006) http://dx.doi.org/10.1016/j.lfs.2006.01.038[Crossref]
  • [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.271.48.30392[Crossref]
  • [28] F. Zheng et al., Biorg. Med. Chem. 14, 3017 (2006) http://dx.doi.org/10.1016/j.bmc.2005.12.036[Crossref]
  • [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.2007.10.062[Crossref]
  • [30] D. Uhríková et al., Colloids Surf., B 42, 59 (2005) http://dx.doi.org/10.1016/j.colsurfb.2005.02.002[Crossref]
  • [31] S.J. Ryhanen et al., Biophys. J. 84, 578 (2003) http://dx.doi.org/10.1016/S0006-3495(03)74878-4[Crossref]
  • [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.2004.05.012[Crossref]
  • [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/s11532-009-0045-8[Crossref]
  • [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.2000.7285[Crossref]
  • [35] R. Mikláš, M. Srnák, I. Lacko, F. Devínsky, Acta Facult. Pharm. Univ. Comenianae 50, 111 (2003)
  • [36] H. Tan, H. Xiao, Tetrahedron Lett. 49, 1759 (2008) http://dx.doi.org/10.1016/j.tetlet.2008.01.079[Crossref]
  • [37] Y. Yang, M. Suzuki, S. Owa, H. Shirai, K. Hanabusa, Chem. Commun. 4462 (2005) [Crossref]
  • [38] K. Kurata, J. Ono, A. Dobashi, J. Chromatogr. A 1080, 140 (2005) http://dx.doi.org/10.1016/j.chroma.2005.04.095[Crossref]
  • [39] A. Azalamira et al., Tetrahedron: Asymmetry 18, 1868 (2007) http://dx.doi.org/10.1016/j.tetasy.2007.07.026[Crossref]
  • [40] M. J. McKennon, A.I. Mayers, K. Drauz, M. Schwarm, J. Org. Chem. 58, 3568 (1993) http://dx.doi.org/10.1021/jo00065a020[Crossref]
  • [41] D. Mlynarčík, S.P. Denyer, W.B. Hugo, Microbios 30, 27 (1981)
  • [42] F. Devínsky, I. Lacko, D. Mlynarčík, E. Švajdlenka, V. Borovská, Chem. Pap. 44, 159 (1990)
  • [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
  • [44] D. Demberelnyanba et al., Biorg. Med. Chem. 12, 853 (2004) http://dx.doi.org/10.1016/j.bmc.2004.01.003[Crossref]
  • [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.2005.02.012[Crossref]
  • [46] C. Hansh, J.M. Clayton, J. Pharm. Sci. 62, 1 (1973) http://dx.doi.org/10.1002/jps.2600620102[Crossref]
  • [47] H.H. Laycock, B.A. Mulley, J. Pharm. Pharmac. 22, 157 (1970) [Crossref]
  • [48] N.N. Daoud, N.A. Dickinson, P. Gilbert, Microbios. 37, 73 (1983)
  • [49] H. Kubinyi, Arzneim.-Forsch. 26, 1991 (1976)
  • [50] H. Kubinyi, Arzneim.-Forsch. 29, 1067 (1979)
  • [51] F. Devínsky, I. Lacko, D. Mlynarčík, E. Švajdlenka, L. Masárová, Acta Facult. Pharm. Univ. Comenianae 44, 127 (1990)
  • [52] F. Devínsky, A. Kopecká-Leitmanová, F. Šeršeň, P. Balgavý, J. Pharm. Pharmacol. 42, 790 (1990) [Crossref]
  • [53] F. Devínsky, L. Masárová, I. Lacko, D. Mlynarčík, J. Biopharm. Sci. 2, 1 (1991)
  • [54] M. Pavlíková, I. Lacko, F. Devínsky, D. Mlynarčík, Collect. Czech. Chem. Commun. 60, 1213 (1995) http://dx.doi.org/10.1135/cccc19951213[Crossref]
  • [55] M. Pavlíková-Mořická, I. Lacko, F. Devínsky, L. Masárová, D. Mlynarčík, Folia Microbiol. 39, 176 (1994) http://dx.doi.org/10.1007/BF02814644[Crossref]
  • [56] S. Osanai, Y. Abe, J. Chem. Tech. Biotechnol. 35B, 43 (1985) [Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-009-0126-8
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