New gluconamide-type cationic surfactants: Interactions with DNA and lipid membranes

Biophysical Chemistry

Volumn 180-181, Issue , 2013, Pages 44-54

  Misiak, Paweł ^a   Wilk, Kazimiera A ^b   Kral, Teresa ^a,c   Woźniak, Edyta ^a   Pruchnik, Hanna ^a   Frackowiak, Renata ^b   Hof, Martin ^c   Rózycka Roszak, Bozenna ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

Cationic surfactant; DNA compaction; Glucose derived surfactant; Lipid bilayer; Molecular modeling; Soft surfactant

Indexed keywords

BROMINE DERIVATIVE; CATIONIC SURFACTANT; PLASMID DNA;

ARTICLE; CONTROLLED STUDY; GENE DELIVERY SYSTEM; INTERACTIONS WITH DNA; LIPID BILAYER; LIPID MEMBRANE; MEMBRANE MODEL; MEMBRANE STRUCTURE; PHASE TRANSITION; PRIORITY JOURNAL; SURFACE PROPERTY; SYNTHESIS; TEMPERATURE;

CATIONIC SURFACTANT; DNA COMPACTION; GLUCOSE-DERIVED SURFACTANT; LIPID BILAYER; MOLECULAR MODELING; SOFT SURFACTANT;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CALORIMETRY, DIFFERENTIAL SCANNING; CATIONS; DNA; GLUCONATES; LIPID BILAYERS; MODELS, MOLECULAR; PHASE TRANSITION; PLASMIDS; SPECTROMETRY, FLUORESCENCE; SURFACE-ACTIVE AGENTS; TRANSITION TEMPERATURE;

EID: 84882512650     PISSN: 03014622     EISSN: 18734200     Source Type: Journal    
DOI: 10.1016/j.bpc.2013.06.010     Document Type: Article

References (60)

1. B. Lindman, K. Thalberg, in: E.D. Goddard, K.P. Ananthapadamanabhan (Eds.), Interactions of Surfactants with Polymers and Proteins, CRC Press, Boca Raton, FL, 1993, pp. 203-276.
2. V. Labhasetwar, Nanotechnology for drug and gene therapy: the importance of understanding molecular mechanisms of delivery, Current Opinion in Biotechnology 16 (2005) 674-680.
3. M.L. Read, A. Logan, L.W. Seymour, Barriers to gene delivery using synthetic vectors, Advances in Genetics 53PA (2005) 19-46.
4. E. Wagner, M. Cotten, R. Foisner, M.L. Birnstiel, Transferrin-polycation- DNA complexes: the effect of polycations on the structure of the complex and DNA delivery to cells, Proceedings of the National Academy of Sciences of the United States of America 88 (1991) 4255-4259.
5. M. Köping-Höggård, Y.S. Mel'nikova, K.M. Vårum, B. Lindman, P. Artursson, Relationship between the physical shape and the efficiency of oligomeric chitosan as a gene delivery system in vitro and in vivo, The Journal of Gene Medicine 5 (2003) 130-141.
6. M. Morille, C. Passirani, A. Vonarbourg, A. Clavreul, J.-P. Benoit, Progress in developing cationic vectors for non-viral systemic gene therapy against cancer, Biomaterials 29 (2008) 3477-3496.
7. A.N. Zelikin, A.L. Becker, A.P.R. Johnston, K.L. Wark, F. Turatti, F. Caruso, A general approach for DNA encapsulation in degradable polymer microcapsules, ACS Nano 1 (2007) 63-69.
8. D.D. Lasic, H. Strey, M.C.A. Stuart, R. Podgornik, P.M. Frederik, The structure of DNA-liposome complexes, Journal of the American Chemical Society 119 (1997) 832-833.
9. C.-Y. Huang, T. Uno, J.E. Murphy, S. Lee, J.D. Hamer, J.A. Escobedo, et al., Lipitoids-novel cationic lipids for cellular delivery of plasmid DNA in vitro, Chemistry & Biology 5 (1998) 345-354.
10. Y. Zhou, Y. Li, Studies of interaction between poly(allylamine hydrochloride) and double helix DNA by spectral methods, Biophysical Chemistry 107 (2004) 273-281.
11. A. Colomer, A. Pinazo, M.T. García, M. Mitjans, M.P. Vinardell, M.R. Infante, et al., pH-sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior, Langmuir 28 (2012) 5900-5912.
12. J.J. McManus, J.O. Rädler, K.A. Dawson, Does calcium turn a zwitterionic lipid cationic? The Journal of Physical Chemistry. B 107 (2003) 9869-9875.
13. J.J. McManus, J.O. Rädler, K.A. Dawson, Observation of a rectangular columnar phase in a DNA-calcium-zwitterionic lipid complex, Journal of the American Chemical Society 126 (2004) 15966-15967.
14. E. Fisicaro, C. Compari, M. Biemmi, E. Duce, M. Peroni, G. Donofrio, et al., Thermodynamics and biological properties of the aqueous solutions of new glucocationic surfactants, The Journal of Physical Chemistry. B 112 (2008) 9360-9370.
15. U. Bazylińska, R. Skrzela, K. Szczepanowicz, P. Warszýski, K.A. Wilk, Novel approach to long sustained multilayer nanocapsules: influence of surfactant head groups and polyelectrolyte layer number on the release of hydrophobic compounds, Soft Matter 7 (2011) 6113-6124.
16. K.A. Wilk, K. Zielińska, A. Hamerska-Dudra, A. Jezierski, Biocompatible microemulsions of dicephalic aldonamide-type surfactants: formulation, structure and temperature influence, Journal of Colloid and Interface Science 334 (2009) 87-95.
17. K.A. Wilk, K. Zielińska, J. Pietkiewicz, N. Skołucka, A. Choromańska, J. Rossowska, et al., Photo-oxidative action in MCF-7 cancer cells induced by hydrophobic cyanines loaded in biodegradable microemulsion-templated nanocapsules, International Journal of Oncology 41 (2012) 105-116.
18. U. Laska, K.A. Wilk, I. Maliszewska, L. Syper, Novel glucose-derived gemini surfactants with a 1,1′-ethylenebisurea spacer: preparation, thermotropic behavior, and biological properties, Journal of Surfactants and Detergents 9 (2006) 115-124.
19. P.C. Bell, M. Bergsma, I.P. Dolbnya, W. Bras, M.C.A. Stuart, A.E. Rowan, et al., Transfection mediated by gemini surfactants: engineered escape from the endosomal compartment, Journal of the American Chemical Society 125 (2003) 1551-1558.
20. N. Adjimatera, A. Benda, I.S. Blagbrough, M. Langner, M. Hof, T. Kral, Fluorescence correlation spectroscopic studies of a single lipopolyamine-DNA nanoparticle, in: M.N. Berberan-Santos (Ed.), Fluorescence of Supermolecules, Polymers, and Nanosystems, Springer, Berlin/Heidelberg, 2008, pp. 381-413.
21. A. Benda, M. Hof, M. Wahl, M. Patting, R. Erdmann, P. Kapusta, TCSPC upgrade of a confocal FCS microscope, The Review of Scientific Instruments 76 (2005), (033106-1-4).
22. T. Kral, J. Leblond, M. Hof, D. Scherman, J. Herscovici, N. Mignet, Lipopolythiourea/DNA interaction: a biophysical study, Biophysical Chemistry 148 (2010) 68-73.
23. D. Magde, E.L. Elson, W.W. Webb, Fluorescence correlation spectroscopy. II. An experimental realization, Biopolymers 13 (1974) 29-61.
24. J. Humpolíčková, A. Benda, J. Sýkora, R. Machán, T. Kral, B. Gasinska, et al., Equilibrium dynamics of spermine-induced plasmid DNA condensation revealed by fluorescence lifetime correlation spectroscopy, Biophysical Journal 94 (2008) L17-L19.
25. N. Adjimatera, T. Kral, M. Hof, I. Blagbrough, Lipopolyamine-mediated single nanoparticle formation of calf thymus DNA analyzed by fluorescence correlation spectroscopy, Pharmaceutical Research 23 (2006) 1564-1573.
26. R. Winkler, S. Keller, J. Rädler, Intramolecular dynamics of linear macromolecules by fluorescence correlation spectroscopy, Physical Review E 73 (2006) 41919.
27. J. Humpolíčková, M. Stepánek, T. Kral, A. Benda, K. Procházka, M. Hof, Onmechanismof intermediate-sized circular DNA compactionmediated by spermine: contribution of fluorescence lifetime correlation spectroscopy, Journal of Fluorescence 18 (2008) 679-684.
28. B. Różycka-Roszak, A. Przyczyna, Interaction between N-dodecyl-N, N-dimethyl-N-benzylammonium halides and phosphatidylcholine bilayers-the effect of counterions, Chemistry and Physics of Lipids 123 (2003) 209-221.
29. E. Fisicaro, C. Compari, E. Duce, G. Donofrio, B. Różycka- Roszak, E. Woźniak, Biologically active bisquaternary ammonium chlorides: physico-chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery, Biochimica et Biophysica Acta, General Subjects 1722 (2005) 224-233.
30. B. Różycka-Roszak, H. Pruchnik, Effect of counterions on the influence of dodecyltrimethylammonium halides on thermotropic phase behaviour of phosphatidylcholine bilayers, Zeitschrift fur Naturforschung. Section C. Journal of Biosciences 55 (2000) 240-244.
31. T. Parasassi, E.K. Krasnowska, L.A. Bagatolli, Laurdan and Prodan as polarity-sensitive fluorescent membrane probes, Journal of Fluorescence 8 (1998) 365-373.
32. E.K. Krasnowska, L.A. Bagatolli, E. Gratton, T. Parasassi, Surface properties of cholesterol-containing membranes detected by Prodan fluorescence, Biochimica et Biophysica Acta-Biomembranes 1511 (2001) 330-340.
33. J.R. Lakowicz, Fluorescence anisotropy, Principles of Fluorescence Spectroscopy, Springer, New York, 2006, pp. 353-382.
34. Materials Studio Release Notes, Release 6.0, Accelrys Software Inc., San Diego, 2012.
35. J.J.P. Stewart, MOPAC2009, MOPAC2009, Stewart Computational Chemistry, Version 11.366W. Web: http://openmopac.net.
36. A. Pedretti, L. Villa, G. Vistoli, VEGA-an open platform to develop chemo-bioinformatics applications, using plug-in architecture and script programming, Journal of Computer-Aided Molecular Design 18 (2004) 167-173.
37. B. Różycka-Roszak, P. Misiak, E. Woźniak, A. Mozrzymas, Z. Dega-Szafran, Calorimetric and molecular modeling studies of N-alkoxycarbonylmethyl-N-alkylpiperidinium chlorides, Colloids and Surfaces A: Physicochemical and Engineering Aspects 318 (2008) 301-306.
38. B. Różycka-Roszak, P. Misiak, B. Jurczak, K.A. Wilk, Aggregation studies of n-alkanoyl-N-methyllactitolamine surfactants, The Journal of Physical Chemistry. B 112 (2008) 16546-16551.
39. B. Delley, An all-electron numerical method for solving the local density functional for polyatomic molecules, The Journal of Chemical Physics 92 (1990) 508-517.
40. B. Delley, Ground-state enthalpies: evaluation of electronic structure approaches with emphasis on the density functional method, The Journal of Physical Chemistry. A 110 (2006) 13629-13632.
41. S.H. Vosko, L. Wilk, M. Nusair, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Canadian Journal of Physics 58 (1980) 1200-1211.
42. A.D. Becke, A multicenter numerical integration scheme for polyatomic molecules, The Journal of Chemical Physics 88 (1988) 2547-2553.
43. J.P. Perdew, Y. Wang, Accurate and simple analytic representation of the electrongas correlation energy, Physics Review B 45 (1992) 13244-13249.
44. A. Klamt, G. Schüürmann, COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient, Journal of the Chemical Society, Perkin Transactions 2 (1993) 799-805.
45. E. Mullins, R. Oldland, Y.A. Liu, S. Wang, S.I. Sandler, C.-C. Chen, et al., Sigma-profile database for using COSMO-based thermodynamic methods, Industrial and Engineering Chemistry Research 45 (2006) 4389-4415.
46. E. Mullins, Y.A. Liu, A. Ghaderi, S.D. Fast, Sigma profile database for predicting solid solubility in pure and mixed solvent mixtures for organic pharmacological compounds with COSMO-based thermodynamic methods, Industrial and Engineering Chemistry Research 47 (2008) 1707-1725.
47. Y.T. Sato, T. Hamada, K. Kubo, A. Yamada, T. Kishida, O. Mazda, et al., Folding transition into a loosely collapsed state in plasmid DNA as revealed by single-molecule observation, FEBS Letters 579 (2005) 3095-3099.
48. C. Schweitzer, J.C. Scaiano, Selective binding and local photophysics of the fluorescent cyanine dye Pico Green in double-stranded and single-stranded DNA, Physical Chemistry Chemical Physics 5 (2003) 4911-4917.
49. H. Nakanishi, K. Tsuchiya, T. Okubo, H. Sakai, M. Abe, Cationic surfactant changes the morphology of DNA molecules, Langmuir 23 (2007) 345-347.
50. P. Misiak, B. Różycka-Roszak, E. Woźniak, R. Skrzela, K.A. Wilk, Aggregation study of omega-(alkyldimethylamonium)alkylaldonamide bromides, European Biophysics Journal with Biophysics Letters 40 (2011) 54.
51. D. Matulis, I. Rouzina, V.A. Bloomfield, Thermodynamics of cationic lipid binding to DNA and DNA condensation: roles of electrostatics and hydrophobicity, Journal of the American Chemical Society 124 (2002) 7331-7342.
52. S. Husale, W. Grange, M. Karle, S. Bürgi, M. Hegner, Interaction of cationic surfactants with DNA: a single-molecule study, Nucleic Acids Research 36 (2008) 1443-1449.
53. J. Humpolíčková, L. Beranová, M. Stěpánek, A. Benda, K. Procházka, M. Hof, Fluorescence lifetime correlation spectroscopy reveals compaction mechanism of 10 and 49 kbp DNA and differences between polycation and cationic surfactant, The Journal of Physical Chemistry. B 112 (2008) 16823-16829.
54. A.A. Zinchenko, V.G. Sergeyev, S. Murata, K. Yoshikawa, Controlling the intrachain segregation on a single DNA molecule, Journal of the American Chemical Society 125 (2003) 4414-4415.
55. N. Miyazawa, T. Sakaue, K. Yoshikawa, R. Zana, Rings-on-a-string chain structure in DNA, The Journal of Chemical Physics 122 (2005) 44902.
56. T. Parasassi, G. De Stasio, G. Ravagnan, R.M. Rusch, E. Gratton, Quantitation of lipid phases in phospholipid vesicles by the generalized polarization of Laurdan fluorescence, Biophysical Journal 60 (1991) 179-189.
57. M. Suwalsky, C. Rodríguez, F. Villena, F. Aguilar, C.P. Sotomayor, The organochlorine pesticide lindane interacts with the human erythrocyte membrane, Pesticide Biochemistry and Physiology 62 (1998) 87-95.
58. C.S. Pereira, P.H. Hünenberger, Interaction of the sugars trehalose, maltose and glucose with a phospholipid bilayer: a comparative molecular dynamics study, The Journal of Physical Chemistry. B 110 (2006) 15572-15581.
59. K. Lohner, Effects of small organic molecules on phospholipid phase transitions, Chemistry and Physics of Lipids 57 (1991) 341-362.
60. M.K. Jain, N.M. Wu, Effect of small molecules on the dipalmitoyl lecithin liposomal bilayer: III. Phase transition in lipid bilayer, The Journal of Membrane Biology 34 (1977) 157-201.