Thermodynamics and biological properties of the aqueous solutions of new glucocationic surfactants

Journal of Physical Chemistry B

Volumn 112, Issue 31, 2008, Pages 9360-9370

  Fisicaro, Emilia ^a   Compari, Carlotta ^a   Biemmi, Mariano ^a   Duce, Elenia ^a   Peroni, Monica ^a   Donofrio, Gaetano ^a   Sansone, Francesco ^a   Rózycka Roszak, Bozenna ^b   Pruchnik, Hanna ^b   Barbero, Nadia ^c   Viscardi, Guido ^c   Quagliotto, Pierluigi ^c  

^a UNIVERSITY OF PARMA   (Italy)

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

^c UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; SURFACE ACTIVE AGENTS; THERMODYNAMIC PROPERTIES; THERMODYNAMICS;

ALKYLAMMONIUM; AQUEOUS SOLUTIONS; BIOLOGICAL PROPERTIES; HYDROPHOBIC TAILS;

SOLUTIONS;

EID: 49649128138     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp800470a     Document Type: Article

References (47)

1. Schmidt-Wolf, G. D.; Schmidt-Wolf, I. G. Non-viral and hybrid vectors in human gene therapy: An update. Trends Mol. Med. 2003, 67-72.
2. Mansouri, S.; Lavigne, P.; Corsi, K.; Benderdour, M.; Beaumont, E.; Fernandes, J. Chitosan-DNA nanoparticles as non-viral vectors in gene therapy: Strategies to improve transfection efficacy. Eur. J. Pharm. Biopharm. 2004, 57, 1-8.
3. Miller, A. D. Cationic liposomes for gene therapy. Angew. Chem., Int. Ed. 1998, 37, 1768-1785.
4. Pouton, C. W.; Seymour, L. W. Key issues in non-viral gene delivery. Adv. Drug. Deliv. Rev. 2001, 46, 187-203.
5. Kitamoto, D.; Isoda, H.; Nakahara, T. Functions and potential applications of glycolipid biosurfactants-From energy-saving materials to gene delivery carriers. J. Biosci. Bioeng 2002, 94 (3), 187-201.
6. Viscardi, G.; Quagliotto, P.; Barolo, C.; Savarino, P.; Barni, E.; Fisicaro, E. Synthesis and Surface and Antimicrobial Properties of Novel Cationic Surfactants. J. Org. Chem. 2000, 65 (24), 8197-8203.
7. Singh, P.; Cameotra, S. S. Potential applications of microbial surfactants in biomedical sciences. Trends Biotechnol. 2004, 22 3(, 142-146.
8. Bell, P. C.; Bergsma, M.; Dolbnya, I. P.; Bras, W.; Stuart, M. C. A.; Rowan, A. E.; Feiters, M. C.; Engberts, J. B. F. N. Transfection mediated by gemini surfactants: Engineered escape from the endosomal compartment. J. Am. Chem. Soc. 2003, 125, 1551-1558.
9. Remy, J. S.; Kichler, A.; Mordvinov, V.; Schuber, F.; Behr, J. P. Targeted gene transfer into hepatoma cells with lipopolyamine-condensed DNA particles presenting galactose ligands: A stage toward artificial viruses. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1744-1748.
10. Ferkol, T.; Perales, J. C.; Mularo, F.; Hanson, R. W. Receptor-mediated gene transfer into macrophages. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 101-105.
11. Liang, W.; Shi, X.; Deshpande, D.; Malanga, C. J.; Rojanasakul, Y. Oligonucleotide targeting to alveolar macrophages by mannose receptor-mediated endocytosis. Biochim. Biophys. Acta 1996, 1279, 227-234.
12. Quagliotto, P.; Viscardi, G.; Barolo, C.; D'Angelo, D.; Barni, E.; Compari, C.; Duce, E.; Fisicaro, E. Synthesis and Properties of New Glucocationic Surfactants: Model Structures for Marking Cationic Surfactants with Carbohydrates. J. Org. Chem. 2005, 70 (24), 9858-9866.
13. Dahmen, J.; Frejd, T.; Magnusson, G.; Noori, G.; Carlström, A. S. 2-Bromoethyl glycosides part 5. Synthesis of spacer-arm lipid and ethyl glycosides of the trisaccharide portion [α-D-Gal-(1→4)-β-D-Gal- (1→4)-β-D-Glc] of the blood-group Pk antigen: Preparation of neoglycoproteins. Carbohydr. Res. 1984, 127, 15-25.
14. Dahmen, J.; Frejd, T.; Magnusson, G.; Noori, G. Boron trifluoride etherate-induced glycosidation: Formation of alkyl glycosides and thioglycosides of 2-deoxy-2-phthalimidoglycopyranoses. Carbohydr. Res. 1983, 114, 328-330.
15. Schmidt, R. R.; Michel, J.; Roos, M. Glycosyl imidates, 12. Direct synthesis of O-α - and O-β-gIycosyl imidates. Liebigs Ann. Chem. 1984, 1343-1357.
16. Schmidt, R. R.; Michel, J. Synthesis of linear and branched cellotetraoses. Angew. Chem., Int. Ed. 1982, 21 (1), 72-73.
17. Blanzat, M.; Perez, E.; Rico-Lattes, I.; Prome, D.; Prome, J. C.; Lattes, A. New catanionic glycolipids. 1. Synthesis, characterization, and biological activity of double-chain and gemini catanionic analogues of galactosylceramide (gal β 1 cer). Langmuir 1999, 15, 6163-6169.
18. Pasc-Banu, A.; Blanzat, M.; Belloni, M.; Perez, E.; Mingotaud, C.; Rico-Lattes, I.; Labrot, T.; Oda, R. Spontaneous vesicles of single-chain sugar-based fluorocarbon surfactants. J. Fluorine Chem. 2005, 126, 33-38.
19. Rico-Lattes, I.; Blanzat, M.; Franceschi-Messant, S.; Perez, E.; Lattes, A. Catanionic sugar derived surfactants, polymers and dendrimers: From molecules to targeted self-organized systems. C. R. Chim. 2005, 8, 807-814.
20. Fisicaro, E.; Compari, C.; Duce, E.; Donofrio, G.; Rǒøycka- Roszak, B.; Woüniak, E. Biologically Active Bisquaternary Ammonium Chlorides: Physico-Chemical Properties of Long Chain Amphiphiles and Their Evaluation as Non-Viral Vectors for Gene Delivery. Biochim. Biophys. Acta: Gen. Subj. 2005, 1722, 224-233.
21. Martin, B.; Silos, M.; Aissaoui, A.; Oudrhiri, N.; Hauchecorne, M.; Vigneron, J. P.; Lehn, J. M.; Lehn, P. Curr. Pharm. Des. 2005, 11, 375-394.
22. Rǒøycka-Roszak, B.; Pruchnik, H. Effect of counterions on the influence of dodecyltrimethylammonium halides on thermotropic phase behaviour of phosphatidylcholine bilayers. Z. Naturforsch. 2000, 55c, 240-244.
23. Rǒøycka-Roszak, B.; Przyczyna, A. Interaction between N-dodecyl-N,N-dimethyl-N-benzylammonium halides and phosphatidylcholine bilayers-The effect of counterions. Chem. Phys. Lipids 2003, 123, 209-221.
24. Desnoyers, J. E.; Perron, G. In Surfactant Solutions-New Methods of Investigation; R. Zana, Ed.; Marcel Dekker Inc.: New York, 1987; p 1, and references therein.
25. Fisicaro, E.; Biemmi, M.; Compari, C.; Duce, E.; Peroni, M.; Viscardi, G.; Quagliotto, P. L. Thermodynamic Properties of Aqueous Micellar Solutions of Some New Acetylated Gluco-Cationic Surfactants. Colloids Surf. A: Physicochem. Eng. Aspects 2007, 301, 129-136.
26. Fisicaro, E.; Biemmi, M.; Compari, C.; Duce, E.; Peroni, M. Thermodynamics of Aqueous Solutions of Dodecyldimethylethylammonium Bromide. J Colloid Surface Sci. 2007, 305, 301-307.
27. Fisicaro, E.; Ghiozzi, A.; Pelizzetti, E.; Viscardi, G.; Quagliotto, P. Effect of the Counterion on Thermodynamic Properties of Aqueous Micellar Solutions of 1(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-Pyridinium Halides. Part 1: Apparent and Partial Molar Enthalpies and Volumes at 298 K. J. Colloid Interface Sci. 1996, 182, 549-557.
28. Fisicaro, E.; Compari, C.; Duce, E.; Contestabili, C.; Quagliotto, P.; Viscardi, G. First Evaluation of Thermodynamic Properties for Spheres to Elongated Micelles Transition of Some Propanediyl-α ω- bis(dimethylalkylammonium bromide) Surfactants in Aqueous Solutions. J. Phys. Chem. B 2005, 109, 1744-1749.
29. Wetting, S. D.; Verrall, R. E. Thermodynamic Studies of Aqueous m-s-m Gemini Surfactant Systems. J. Colloid Interface Sci. 2001, 235, 310-316.
30. De Lisi, R.; Milioto, S.; Verrall, R. E. Partial molar volumes and compressibilities of alkyltrimethylammonium bromides. J. Solution Chem. 1990, 19, 665-692.
31. Chalikian, T. V.; Sarvazyan, A. P.; Breslauer, K. Partial molar volumes, expansibilities, and compressibilities of α,ω-aminocarboxylic acids in aqueous solutions between 18 and 55 °C. J. Phys. Chem. 1993, 97, 13017-13026.
32. Bustamante, C.; Rivetti, C. Visualizing protein-nucleic acid interactions on a large scale with the scanning force microscope. Annu. Rev. Biophys. Biomol. Struct. 1996, 25, 395-429.
33. Hansma, H. G. Surface biology of DNA by atomic force microscopy. Annu. Rev. Phys. Chem. 2001, 52, 71-92.
34. Sansone, F.; Dudič, M.; Donofrio, G.; Rivetti, C.; Baldini, L.; Casnati, A.; Cellai, S.; Ungaro, R. DNA Condensation and Cell Transfection Properties of Guanidinium Calixarenes: Dependence on Macrocycle Lipophilicity, Size, and Conformation. J. Am. Chem. Soc. 2006, 128, 14528-14536.
35. Volcke, C.; Pirotton, S.; Grandfils, Ch.; Humbert, C.; Thiry, P. A.; Ydens, I.; Dubois, P.; Raes, M. Influence of DNA condensation state on transfection efficiency in DNA/polymer complexes: An AFM and DLS comparative study. J. Biotechnol. 2006, 125, 11-21.
36. Ceci, P.; Cellai, S.; Falvo, E.; Rivetti, C.; Rossi, G. L.; Chiancone, E. DNA condensation and self-aggregation of Escherichia coli Dps are coupled phenomena related to the properties of the N-terminus. Nucleic Acids Res. 2004, 32, 5935-5944.
37. De Lisi, R.; Fisicaro, E.; Milioto, S. Thermodynamic Properties and Conductivities of some Dodecylsurfactants in Water. J. Solution Chem. 1988, 17, 1015-1041.
38. Fisicaro, E.; Compari, C.; Quagliotto, P.; Viscardi, G. Thermodynamic Properties of the Aqueous Solution of Potassium Salts of Some 4-((alkylcarbonyl)amino)-2-hydroxybenzoic Acids at 298 and 313 K. J. Colloid Interface Sci. 2002, 255 (2), 410-416.
39. Fisicaro, E.; Compari, C.; Moroi, Y. Apparent and Partial Molar enthalpies of some Potassium p-n-Alkyl-Benzoate Aqueous Solutions. Polyhedron 2002, 21, 1497-1502.
40. Řøycka-Roszak, B.; Fisicaro, E. Thermochemical Study of Aqueous Micellar Solutions of Some Amphiphilic Quaternary Ammonium Chlorides at 313 K. Thermochim. Acta 1992, 205, 19-31.
41. Kudryashov, E.; Kapustina, T.; Morrissey, S.; Buckin, V.; Dawson, K. The Compressibility of Alkyltrimethylammonium Bromide Micelles. J. Colloid Interface Sci. 1998, 203, 59-68.
42. Zielinski, R.; Ikeda, S.; Nomura, H.; Kato, S. Temperature Dependence of Adiabatic Compressibility of Aqueous Solutions of Alkyltrimethylamrnonium Bromides. J. Chem. Soc. Faraday Trans. 1 1988, 84, 151-164.
43. Fukada, K.; Li, J.; Fujii, M.; Kato, T.; Seimiya, T. Adiabatic Compressibility of Aqueous solutions of Amphiphiles with an Ammonium Group as the Hydrophilic Domain. J. Oleo Sci. 2002, 51, 103-111.
44. Gianni, P.; Lepori, L. Group contributions to the partial molar volume of ionic organic solutes in aqueous solution. J. Solution Chem. 1996, 25, 1-42.
45. Evans, D. F.; Wennerström, H., Eds. The Colloidal Domain, where Physics, Chemistry, Biology and Technology Meet; VCH Publishers: New York, 1994; p 438.
46. Inoue, T.; Miyakawa, K.; Shimozawa, R. Interaction of surfactants with vesicle membrane of dipalmitoylphosphatidylcholine. Effect on gel-to-liquid-crystalline phase transition of lipid bilayer. Chem. Phys. Lipids 1986, 42, 261-270.
47. Bryszewska, M.; Epand, R. M. Effects of sugar alcohols and disaccharides in inducing the hexagonal phase and altering membrane properties implications for diabetes mellitus. Biochim. Biophys. Acta 1988, 943, 485-492, and references therein.