Self-assembling systems based on diquaternized derivatives of 1,4-diazabicyclo[2.2.2]octane

Journal of Molecular Liquids

Volumn 210, Issue , 2015, Pages 136-142

  Zhiltsova, Elena P ^a   Lukashenko, Svetlana S ^a   Pashirova, Tatiana N ^a   Valeeva, Farida G ^a   Zakharova, Lucia Ya ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

1,4 Diazabicyclo 2.2.2 octane; Cationic surfactant; Critical micelle concentration; Self assembly

Indexed keywords

AGGREGATES; CATIONIC SURFACTANTS; CRITICAL MICELLE CONCENTRATION; DRUG DELIVERY; DYES; LIGHT SCATTERING; PHASE INTERFACES; SELF ASSEMBLY; SOLUBILITY; SURFACE ACTIVE AGENTS;

1 ,4-DIAZABICYCLO[2.2.2]OCTANE; AGGREGATION BEHAVIOR; CONCENTRATION FACTORS; DICATIONIC SURFACTANTS; MORPHOLOGICAL CHANGES; SOLUBILIZATION CAPACITIES; STRUCTURAL REARRANGEMENT; SURFACTANT CONCENTRATIONS;

MICELLES;

EID: 84941599796     PISSN: 01677322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molliq.2015.01.018     Document Type: Article

References (61)

1. V. Chauhan, S. Singh, R. Kamboj, R. Mishra, and G. Kaur Self-assembly, DNA binding and cytotoxicity trends of ether functionalized gemini pyridinium amphiphiles J. Colloid Interface Sci. 417 2014 385 395 10.1016/j.jcis.2013.11.059
2. P. Parvizi, E. Jubeli, L. Raju, N.A. Khalique, A. Almeer, H. Allam, M.A. Manaa, H. Larsen, D. Nicholson, M.D. Pungente, and T.M. Fyles Aspects of nonviral gene therapy: correlation of molecular parameters with lipoplex structure and transfection efficacy in pyridinium-based cationic lipids Int. J. Pharm. 461 2014 145 156 10.1016/j.ijpharm.2013.11.045
3. I. Jevremovic, M. Singer, S. Nešic, and V. Miškovic-Stankovic Inhibition properties of self-assembled corrosion inhibitor talloil diethylenetriamine imidazoline for mild steel corrosion in chloride solution saturated with carbon dioxide Corros. Sci. 77 2013 265 272 10.1016/j.corsci.2013.08.012
4. A.O.W. Neto, E.F. Moura, H.S. Júnior, T.N.C. Dantas, A.A.D. Neto, and A. Gurgel Preparation and application of self-assembled systems containing dodecylammonium bromide and chloride as corrosion inhibitors of carbon-steel Colloids Surf. A 398 2012 76 83 10.1016/j.colsurfa.2012.02.014
5. X. Zhang, T.J. McIntosh, and M.W. Grinstaff Functional lipids and lipoplexes for improved gene delivery Biochimie 94 2012 42 58 10.1016/j.biochi.2011.05.005
6. T. Yoshimura, T. Kusano, H. Iwase, M. Shibayama, T. Ogawa, and H. Kurata Star-Shaped trimeric quaternary ammonium bromide surfactants: adsorption and aggregation properties Langmuir 28 2012 9322 9331 10.1021/la301220y
7. V.I. Martin, A. Rodriguez, A. Laschewsky, and M.L. Moya Self-aggregation of cationic dimeric surfactants in water-ionic liquid binary mixtures J. Colloid Interface Sci. 430 2014 326 336 10.1016/j.jcis.2014.05.064
8. Y. Fan, Y. Hou, J. Xiang, D. Yu, C. Wu, M. Tian, Y. Han, and Y. Wang Synthesis and aggregation behavior of a hexameric quaternary ammonium surfactant Langmuir 27 2011 10570 10579 10.1021/la202453c
9. B. Cai, X. Li, Y. Yang, and J. Dong Surface properties of Gemini surfactants with pyrrolidinium head groups J. Colloid Interface Sci. 370 2012 111 116 10.1016/j.jcis.2011.12.025
10. S. Zhang, H. Yan, M. Zhao, and L. Zheng Aggregation behavior of gemini pyrrolidine-based ionic liquids 1,1 0-(butane-1,4-diyl)bis(1-alkylpyrrolidinium) bromide ([C(n)py-4-C(n)py][Br2]) in aqueous solution J. Colloid Interface Sci. 372 2012 52 57 10.1016/j.jcis.2012.01.040
11. L. Mivehi, R. Bordes, and K. Holmberg Adsorption of cationic gemini surfactants at solid surfaces studied by QCM-D and SPR - effect of the presence of hydroxyl groups in the spacer Colloids Surf. A 419 2013 21 27 10.1016/j.colsurfa.2012.11.044
12. L. Zakharova, A. Mirgorodskaya, E. Zhiltsova, L. Kudryavtseva, and A. Konovalov Reactions in Supramolecular Systems, Molecular Encapsulation: Organic Reactions in Constrained Systems Udo H. Brinker, Jean-Luc Mieusset, 2010 John Wiley @ Sons, Ltd. United Kingdom 397 420
13. L.Ya. Zakharova, and A.I. Konovalov Supramolecular systems based on cationic surfactants and amphiphilic macrocycles Colloid J. (Engl. Transl.) 74 2 2012 194 206 10.1134/S1061933X12020147
14. T.N. Pashirova, E.P. Zhiltsova, R.R. Kashapov, S.S. Lukashenko, A.I. Litvinov, M.K. Kadirov, L.Ya. Zakharova, and A.I. Konovalov Supramolecular systems based on 1-alkyl-4-aza-1-azoniabicyclo[2.2.2]octane bromides Russ. Chem. Bull. Int. Ed. 59 9 2010 1745 1752 10.1007/s11172-010-0307-9
15. L.Ya. Zakharova, T.N. Pashirova, R.R. Kashapov, E.P. Zhil'tsova, N.K. Gaisin, O.I. Gnezdilov, A.B. Konov, S.S. Lukashenko, and I.M. Magdeev Catalytic properties of micellar systems based on 4-aza-1-alkyl-1-azoniabicyclo[2.2.2]octane bromides Kinet. Catal. (Engl. Transl.) 52 2 2011 179 185 10.1134/S0023158411020236
16. E.P. Zhiltsova, T.N. Pashirova, R.R. Kashapov, N.K. Gaisin, O.I. Gnezdilov, S.S. Lukashenko, A.D. Voloshina, N.V. Kulik, V.V. Zobov, L.Ya. Zakharova, and A.I. Konovalov Alkylated 1,4-diazabicyclo[2.2.2]octanes: self-association, catalytic properties, and biological activity Russ. Chem. Bull. Int. Ed. 61 2012 113 120 10.1007/s11172-012-0016-7
17. R. Engel, I. Ghani, D. Montenegro, M. Thomas, B. Klaritch-Vrana, A. Castaño, L. Friedman, J. Leb, L. Rothman, H. Lee, C. Capodiferro, D. Ambinder, E. Cere, C. Awad, F. Sheikh, J. Rizzo, L. Nisbett, E. Testani, and K. Melkonian Polycationic glycosides Molecules 16 2011 1508 1518 10.3390/molecules16021508
18. A.A. Fedorova, E.P. Goncharova, E.I. Ryabchikova, V.V. Vlasov, and M.A. Zenkova Novel amphiphilic compounds effectively inactivate the vaccinia virus FEBS Lett. 586 2012 1669 1673 10.1016/j.febslet.2012.04.047
19. M. Thomas, D. Montenegro, A. Castaño, L. Friedman, J. Leb, M.L. Huang, L. Rothman, H. Lee, C. Capodiferro, D. Ambinder, E. Cere, J. Galante, J. Rizzo, K. Melkonian, and R. Engel Polycations. 17. Synthesis and properties of polycationic derivatives of carbohydrates Carbohydr. Res. 344 2009 1620 1627 10.1016/j.carres.2009.04.021
20. N.A. Kovalev, D.A. Medvedeva, M.A. Zenkova, and V.V. Vlassov Cleavage of RNA by an amphiphilic compound lacking traditional catalytic groups Bioorg. Chem. 36 2008 33 45 10.1016/j.bioorg.2007.10.003
21. K. Ohta, T. Sugiyama, and T. Nogami A smectic T phase of 1,4-dialkyl-1,4-diazoniabicyclo[2.2.2]octane dibromides J. Mater. Chem. 10 2000 613 616 10.1039/A906922D
22. J. Shimizu, T. Nogami, and H. Mikawa Phase transition of quaternary alkyl halide salts of diazabicyclo[2.2.2]octane Solid State Commun. 54 11 1985 1009 1011 10.1016/0038-1098(85)90175-9
23. D.B. Robinson, J.L. Rognlien, C.A. Bauer, and B.A. Simmons Dependence of amine-accelerated silicate condensation on amine structure J. Mater. Chem. 17 2007 2113 2119 10.1039/B700514H
24. F.M. Menger, and R.A. Persichetti Two new amphiphilic catalysts for ester hydrolysis J. Org. Chem. 52 15 1987 3451 3452 10.1021/jo00391a055
25. E.A. Burakova, N.A. Kovalev, I.L. Kuznetsova, M.A. Zenkova, V.V. Vlasov, and V.N. Sil'nikov, Polycationic catalysts for phosphodiester bond cleavage on the basis of 1,4-diazabicyclo[2.2.2]octane, Russian Journal of Bioorganic Chemistry, 33(5), 523-530
26. L. Zakharova, F. Valeeva, A. Zakharov, A. Ibragimova, L. Kudryavtseva, and H. Harlampidi Micellization and catalytic activity of the cetyltrimethylammonium bromide-Brij 97-water mixed micellar system J. Colloid Interface Sci. 263 2003 597 605 10.1016/S0021-9797(03)00343-6
27. L.Ya. Zakharova, N.K. Gaysin, O.I. Gnezdilov, F.I. Bashirov, R.R. Kashapov, E.P. Zhiltsova, T.N. Pashirova, and S.S. Lukashenko Micellization of alkylated 1.4-diazabicyclo[2.2.2]octane by nuclear magnetic resonance technique using pulsed gradient of static magnetic field J. Mol. Liq. 167 2012 89 93 10.1016/j.molliq.2011.12.015
28. G.A. Gainanova, G.I. Vagapova, V.V. Syakaev, A.R. Ibragimova, F.G. Valeeva, E.V. Tudriy, I.V. Galkina, O.N. Kataeva, L.Ya. Zakharova, Sh.K. Latypov, and A.I. Konovalov Self-assembling systems based on amphiphilic alkyltriphenylphosphonium bromides: elucidation of the role of head group J. Colloid Interface Sci. 367 2012 327 336 10.1016/j.jcis.2011.10.074
29. T.N. Pashirova, A.Yu. Ziganshina, E.D. Sultanova, S.S. Lukashenko, Yu.R. Kudryashova, E.P. Zhiltsova, L.Ya. Zakharova, and A.I. Konovalov Supramolecular systems based on calix[4]resorcine with mono-, di-, and tetracationic surfactants: synergetic structural and solubilization behavior Colloids Surf. A 448 2014 67 72 10.1016/j.colsurfa.2014.02.012
30. A. Callaghan, R. Doyle, E. Alexander, and R. Palepu Thermodynamic properties of micellization and adsorption and electrochemical studies of hexadecylpyridinium bromide in binary mixtures of 1,2-ethanediol with water Langmuir 9 12 1993 3422 3426 10.1021/la00036a016
31. S.P. Moulik, M.E. Haque, P.K. Jana, and A.R. Das Micellar properties of cationic surfactants in pure and mixed states J. Phys. Chem. 100 2 1996 701 708 10.1021/jp9506494
32. B.W. Barry, J.C. Morrison, and G.F.J. Russell Prediction of the critical micelle concentration of mixtures of alkyltrimethylammonium salts J. Colloid Interface Sci. 33 4 1970 554 561 10.1016/0021-9797(70)90007-X
33. I.G. Mateos, M.M. Velazquez, and L.J. Rodriguez Critical micelle concentration determination in binary mixtures of ionic surfactants by deconvolution of conductivity/concentration curves Langmuir 6 6 1990 1078 1083 10.1021/la00096a009
34. E.P. Zhil'tsova, R.F. Gimranova, S.S. Lukashenko, T.N. Pashirova, K.E. Kharlampidi, and L.Ya. Zakharova Supramolecular catalytic systems based on alkylated diquaternary 1,4-diazabicyclo[2.2.2]octane derivatives Kinet. Catal. (Engl. Transl.) 54 5 2013 552 558 10.1134/S0023158413050200
35. K. Shinoda, T. Nakagawa, B. Tamamushi, and T. Isemura Colloidal Surfactants 1963 Academic Press New York - London
36. M.J. Rosen, M. Dahanayake, and A.W. Cohen Relationship of structure to properties in surfactants. 11. Surface and thermodynamic properties of N-dodecyl-pyridinium bromide and chloride Colloids Surf. 5 1982 159 172 10.1016/0166-6622(82)80071-1
37. P.K. Jana, and S.P. Moulik Interaction of bile salts with hexadecyltrimethylammonium bromide and sodium dodecyl sulfate J. Phys. Chem. 95 1991 9525 9532 10.1021/j100176a089
38. R. Zana Dimeric (gemini) surfactants: effect of the spacer group on the association behavior in aqueous solution J. Colloid Interface Sci. 248 2002 203 220 10.1006/jcis.2001.8104
39. L.Ya. Zakharova, V.E. Semenov, M.A. Voronin, F.G. Valeeva, A.R. Ibragimova, R.Kh. Giniatullin, A.V. Chernova, S.V. Kharlamov, L.A. Kudryavtseva, Sh.K. Latypov, V.S. Reznik, and A.I. Konovalov Nanoreactors based on amphiphilic uracilophanes: self-organization and reactivity study J. Phys. Chem. B 111 2007 14152 14162 10.1021/jp076592q
40. S. Ghosh Surface chemical and micellar properties of binary and ternary surfactant mixtures (cetyl pyridinium chloride, Tween-40, and Brij-56) in an aqueous medium J. Colloid Interface Sci. 244 2001 128 138 10.1006/jcis.2001.7855
41. S. Ghosh, and S.P. Moulik Interfacial and micellization behaviors of binary and ternary mixtures of amphiphiles (Tween-20, Brij-35, and sodium dodecyl sulfate) in aqueous medium J. Colloid Interface Sci. 208 1998 357 366 10.1006/jcis.1998.5752
42. R. Zana Critical micellization concentration of surfactants in aqueous solution and free energy of micellization Langmuir 12 5 1996 1208 1211 10.1021/la950691
43. R. Zana Ionization of cationic micelles: effect of the detergent structure J. Colloid Interface Sci. 78 2 1980 330 337 10.1016/0021-9797(80)90571-8
44. P.A. Kooreman, J.B.F.N. Engberts, and N.M. van Os Synthesis, physicochemical properties, and detergency of disodium 2-alkyl-1,3-propanediyl bissulfates J. Surfactant Deterg. 1 1998 23 28 10.1007/s11743-998-0003-9
45. F.G. Valeeva, A.V. Zakharov, M.A. Voronin, L.Ya. Zakharova, L.A. Kudryavtseva, O.G. Isaikina, A.A. Kalinin, and V.A. Mamedov Catalytic effect of supramolecular system based on cationic surfactant and monopodands in nucleophilic substitution of phosphorus esters Russ. Chem. Bull. 53 7 2004 1563 1571 10.1023/B:RUCB.0000046255.85293.5f
46. K. Holmberg, B. Jönsson, B. Kronberg, and B. Lindman Surfactants and Polymers in Aqueous Solution 2nd ed. 2002 Wiley 562
47. K. Matsuoka, T. Yoshimura, T. Shikimoto, J. Hamada, M. Yamawaki, C. Honda, and K. Endo Molecular aggregates of partially fluorinated quaternary ammonium salt gemini surfactants Langmuir 23 22 2007 10990 10994 10.1021/la701525c
48. I. Tabushi, J. Imuta, N. Seko, and Y. Kobuke Highly discriminative binding of nucleoside phosphates by a lipophilic diammonium salt embedded in a bicyclic skeleton J. Am. Chem. Soc. 100 19 1978 6287 6288 10.1021/ja00487a083
49. H. Schot Solubilization of a water-insoluble dye. II J. Phys. Chem. 71 1967 3611 3617 10.1021/j100870a041
50. J. Swarbrick, J. Galownia, and T.R. Bates Micellar solubilization of orange OT by a series of N-alkyl betaines J. Colloid Interface Sci. 41 3 1972 609 611 10.1016/0021-9797(72)90385-2
51. P.T. Jacobs, and E.W. Anacker The role of polar head structure in dye solubilization by cationic surfactants J. Colloid Interface Sci. 43 1 1973 105 112 10.1016/0021-9797(73)90353-6
52. J.P. Salvage, S.F. Rose, G.J. Phillips, G.W. Hanlon, A.W. Lloyd, T.I.Y. Ma, S.P. Armes, N.C. Billingham, and A.L. Lewis Novel biocompatible phosphorylcholine-based self-assembled nanoparticles for drug delivery J. Control. Release 104 2005 259 270 10.1016/j.jconrel.2005.02.003
53. J. Mata, D. Varade, and P. Bahadur Aggregation behavior of quaternary salt based cationic surfactants Thermochim. Acta 428 2005 147 155 10.1016/j.tca.2004.11.009
54. K. Kalyanasundaran, and J.K. Thomas Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems J. Am. Chem. Soc. 99 1977 2039 2044 10.1021/ja00449a004
55. J. van Stam, S. Depaemelaere, and F.C. De Schryver Micellar aggregation numbers - a fluorescence study J. Chem. Educ. 75 1 1998 93 98 10.1021/ed075p93
56. T. Sakai, M. Miyaki, H. Tajima, and M. Shimizu Precipitate deposition around CMC and vesicle-to-micelle transition of monopotassium monododecyl phosphate in water J. Phys. Chem. B 116 2012 11225 11233 10.1021/jp307070e
57. T. Sakai, R. Ikoshi, N. Toshida, and M. Kagaya Thermodynamically stable vesicle formation and vesicle-to-micelle transition of single-tailed anionic surfactant in water J. Phys. Chem. B 117 2013 5081 5089 10.1021/jp402314f
58. A. Mohanty, T. Patra, and J. Dey Salt-induced vesicle to micelle transition in aqueous solution of sodium N-(4-n-octyloxybenzoyl)-l-valinate J. Phys. Chem. B 111 2007 7155 7159 10.1021/jp071312s
59. S. Ghosh, and J. Dey Interaction of sodium N-lauroylsarcosinate with N-alkylpyridinium chloride surfactants: spontaneous formation of pH-responsive, stable vesicles in aqueous mixtures J. Colloid Interface Sci. 358 2011 208 216 10.1016/j.jcis.2011.02.054
60. A. Ghosh, and J. Dey Effect of hydrogen bonding on the physicochemical properties and bilayer self-assembly formation of N-(2-hydroxydodecyl)-l-alanine in aqueous solution Langmuir 24 2008 6018 6026 10.1021/la800232x
61. A. Ghosh, S. Shrivastava, and J. Dey Concentration and pH-dependent aggregation behavior of an l-histidine based amphiphile in aqueous solution Chem. Phys. Lipids 163 6 2010 561 568 10.1016/j.chemphyslip.2010.04.003