Catanionic gels based on cholic acid derivatives

Langmuir

Volumn 29, Issue 40, 2013, Pages 12342-12351

  Di Gregorio, M Chiara ^a   Pavel, N Viorel ^a   Miragaya, Javier ^b   Jover, Aida ^b   Meijide, Francisco ^b   Vázquez Tato, José ^b   Soto Tellini, Victor H ^c   Galantini, Luciano ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSIDAD DE COSTA RICA   (Costa Rica)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RESIDUES; ELECTROSTATIC COMPONENTS; GELATION CONCENTRATIONS; GYRATION RADII; LATERAL CHAINS; MOLAR FRACTIONS; PURE CATIONIC SURFACTANTS; SURFACTANT CONCENTRATIONS;

BODY FLUIDS; CATIONIC SURFACTANTS; CHEMICAL MODIFICATION; GELATION; GELS; MIXTURES; MOLECULES;

DYES;

CATION; CHOLIC ACID; SURFACTANT;

ARTICLE; CHEMISTRY; GEL;

CATIONS; CHOLIC ACID; GELS; SURFACE-ACTIVE AGENTS;

EID: 84885409068     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la402602d     Document Type: Article

References (60)

1. Natalini, B.; Sardella, R.; Camaioni, E.; Gioiello, A.; Pellicciari, R. Correlation between CMC and chromatographic index: Simple and effective evaluation of the hydrophobic/hydrophilic balance of bile acids Anal. Bioanal. Chem. 2007, 338, 1681-1688
2. Costantino, G.; Wolf, C.; Natalini, B.; Pellicciari, R. Evaluation of hydrophobic/hydrophilic balance of bile acids by comparative molecular field analysis (CoMFA) Steroids 2000, 65, 483-489
3. Carey, M. C. Aqueous bile salt-lecithin-cholesterol systems: Equilibrium aspects Hepatology 1984, 4, 151S-154S
4. Armstrong, M. J.; Carey, M. C. The hydrophobic-hydrophilic balance of bile salts. Inverse correlation between reverse-phase high performance liquid chromatographic mobilities and micellar cholesterol-solubilizing capacities J. Lipid Res. 1982, 23, 70-80
5. Attili, A. F.; Angelico, M.; Cantafora, A.; Alvaro, D.; Capocaccia, L. Bile acid-induced liver toxicity: relation to the hydrophobic-hydrophilic balance of bile acids Med. Hypotheses 1986, 19, 57-69
6. Donovan, J. M.; Jackson, A. A.; Carey, M. C. Molecular species composition of inter-mixed micellar/vesicular bile salt concentrations in model bile: dependence upon hydrophilic-hydrophobic balance J. Lipid Res. 1993, 34, 1131-1140
7. Luk, A. S.; Kaler, E. W.; Lee, S. P. Structural mechanisms of bile salt-induced growth of small unilamellar cholesterol-lecithin vesicles Biochemistry 1997, 36, 5633-5644
8. Fini, A.; Fazio, G.; Roda, A.; Bellini, A. M.; Mencini, E.; Guarneri, M. Basic cholane derivatives. XI: Comparison between acid and basic derivatives J. Pharm. Sci. 1992, 81, 726-730
9. Meijide, F.; Antelo, A.; Alvarez Alcalde, M.; Jover, A.; Galantini, L.; Pavel, N. V.; Vázquez Tato, J. Supramolecular structures generated by a p-tert-butylphenylamide derivative of deoxycholic acid: From planar sheets to tubular structures through helical ribbons Langmuir 2010, 26, 7768-7773
10. Alvarez Alcalde, M.; Jover, A.; Meijide, F.; Galantini, L.; Pavel, N. V.; Antelo, A.; Vázquez Tato, J. Synthesis and characterization of a new gemini surfactant derived from 3α,12α-dihydroxy-5β-cholan-24- amine (steroid residue) and ethylenediamintetraacetic acid (spacer) Langmuir 2008, 24, 6060-6066
11. Alcalde, M. A.; Jover, A.; Meijide, F.; Galantini, L.; Pavel, N. V.; Antelo, A.; Vázquez Tato, J. Aggregation behavior of tetracarboxylic surfactants derived from cholic and deoxycholic acids and ethylenediaminetetraacetic acid Langmuir 2009, 25, 9037-9044
12. Soto Tellini, V. H.; Jover, A.; Galantini, L.; Pavel, N. V.; Meijide, F.; Vázquez Tato, J. New lamellar structure formed by an adamantyl derivative of cholic acid J. Phys. Chem. B 2006, 110, 13679-13681
13. Meijide, F.; Trillo, J. V.; de Frutos, S.; Galantini, L.; Pavel, N. V.; Soto, V. H.; Jover, A.; Vázquez Tato, J. Formation of tubules by p-tert-butylphenylamide derivatives of chenodeoxycholic and ursodeoxycholic acids in aqueous solution Steroids 2012, 77, 1205-1211
14. Sobotka, H.; Czeczowiczka, N. The gelation of bile salt solutions J. Colloid Sci. 1958, 13, 188-191
15. Terech, P.; Sangeetha, N. M.; Maitra, U. Molecular hydrogels from bile acid analogues with neutral side chains: network architectures and viscoelastic properties. Junction zones, spherulites, and crystallites: Phenomenological aspects of the gel metastability J. Phys. Chem. B 2006, 110, 15224-15233
16. Sangeetha, N. M.; Balasubramanian, R.; Maitra, U.; Ghosh, S.; Raju, A. R. Novel cationic and neutral analogues of bile acids: Synthesis and preliminary study of their aggregation properties Langmuir 2002, 18, 7154-7157
17. Terech, P.; Sangeetha, N. M.; Demé, B.; Maitra, U. Self-assembled networks of ribbons in molecular hydrogels of cationic deoxycholic acid analogues J. Phys. Chem. B 2005, 109, 12270-12276
18. Terech, P.; Dourdain, S.; Maitra, U.; Bhat, S. Structure and rheology of cationic molecular hydrogels of quinuclidine grafted bile salts: Influence of the ionic strength and counter-ion type J. Phys. Chem. B 2009, 113, 4619-4630
19. Galantini, L.; Leggio, C.; Jover, A.; Meijide, F.; Pavel, N. V.; Soto Tellini, V. H.; Vázquez Tato, J.; Di Leonardo, R.; Ruocco, G. Kinetics of formation of supramolecular tubules of a sodium cholate derivative Soft Matter 2009, 5, 3018-3025
20. Soto Tellini, V. H.; Jover, A.; Meijide, F.; Vázquez Tato, J.; Galantini, L.; Pavel, N. V. Supramolecular structures generated by a p-tert-butylphenyl-amide derivative of cholic acid: From vesicles to molecular tubes Adv. Mater. 2007, 19, 1752-1756
21. Travaglini, L.; D'Annibale, A.; Schillén, K.; Olsson, U.; Sennato, S.; Pavel, N. V.; Galantini, L. Amino acid-bile acid based molecules: extremely narrow surfactant nanotubes formed by a phenylalanine-substituted cholic acid Chem. Commun. 2012, 48, 12011-12013
22. Manghisi, N.; Leggio, C.; Jover, A.; Meijide, F.; Pavel, N. V.; Soto Tellini, V. H.; Vázquez Tato, J.; Agostino, R. G.; Galantini, L. Catanionic tubules with tunable charge Angew. Chem., Int. Ed. 2010, 49, 6604-6607
23. Zemb, T. Self-assembly of flat nanodiscs in salt-free catanionic surfactant solutions Science 1999, 283, 816-819
24. Zemb, T.; Carrière, D.; Glinel, K.; Hartman, M.; Meister, A.; Vautrin, C.; Delorme, N.; Fery, A.; Dubois, M. Catanionic bilayers as micro-crystals with in-plane ordered alternated charges Colloids Surf., A 2007, 303, 37-45
25. Dubois, M.; Demé, B.; Gulik-Krzywicki, T.; Dedieu, J.-C.; Vautrin, C.; Désert, S.; Perez, E.; Zemb, T. Self-assembly of regular hollow icosahedra in salt-free catanionic solutions Nature 2001, 411, 672-675
26. Song, A.; Dong, S.; Jia, X.; Hao, J.; Liu, W.; Liu, T. An onion phase in salt-free zero-charged catanionic surfactant solutions Angew. Chem., Int. Ed. 2005, 44, 4018-4021
27. Kaler, E. W.; Murthy, A. K.; Rodriguez, B. E.; Zasadzinski, J. A. Spontaneous vesicle formation in aqueous mixtures of single-tailed surfactants Science 1989, 245, 1371-1374
28. Antunes, F. E.; Marques, E. F.; Miguel, M. G.; Lindman, B. Polymer-vesicle association Adv. Colloid Interface Sci. 2009, 147-148, 18-35
29. Vogel, A. I.; Smith, P. W.; Furniss, B. S.; Hannaford, A. J. Vogel's Textbook of Practical Organic Chemistry, 5 th ed.; Longman/Wiley: New York, 1989.
30. Bendedouch, D.; Chen, S. H. Effect of an attractive potential on the interparticle structure of ionic micelles at high salt concentration J. Phys. Chem. 1984, 88, 648-652
31. Bendedouch, D.; Chen, S.-H.; Koehler, W. C. Determination of interparticle structure factors in ionic micellar solutions by small angle neutron scattering J. Phys. Chem. 1983, 87, 2621-2828
32. Bendedouch, D.; Chen, S.-H. Study of intermicellar interaction and structure by small angle neutron scattering J. Phys. Chem. 1983, 87, 1653-1658
33. Lusvardi, K. M.; Full, A. P.; Kaler, E. W. Mixed micelles of dodecyltrimethylammonium bromide and didodecyldimethylammonium bromide Langmuir 1995, 11, 487-492
34. Caponetti, E.; Chillura-Martino, D.; Pedone, L. Partitioning of macrocyclic compounds in a cationic and an anionic micellar solution: A small-angle neutron scattering study Langmuir 2004, 20, 3854-3862
35. Haldar, J.; Aswal, V. K.; Goyal, P. S.; Bhattacharya, S. Aggregation properties of novel cationic surfactants with multiple pyridinium headgroups: Small-angle neutron scattering and conductivity studies J. Phys. Chem. B 2004, 108, 11406-11411
36. Ortega, F.; Bacaloglu, R.; McKenzie, D. C.; Bunton, C. A.; Nicoli, D. F. Static and dynamic light scattering study of strongly interacting micelles: Hypernetted chain vs dilute gas approximation J. Phys. Chem. 1990, 94, 501-504
37. Dhont, J. K. G. An Introduction to Dynamics of Colloids; Elsevier: Amsterdam, 1996.
38. Felderhof, B. U. Diffusion of interacting Brownian particles J. Phys. A: Math. Gen. 1978, 11, 929-937
39. Bonincontro, A.; D'Archivio, A. A.; Galantini, L.; Giglio, E.; Punzo, F. X-ray, electrolytic conductance, and dielectric studies of bile salt micellar aggregates Langmuir 2000, 16, 10436-10443
40. Leggio, C.; Galantini, L.; Zaccarelli, E.; Pavel, N. V. Small-angle X-ray scattering and light scattering on lysozyme and sodium glycocholate micelles J. Phys. Chem. B 2005, 109, 23857-23869
41. Cozzolino, S.; Galantini, L.; Leggio, C.; Pavel, N. V. Correlation between small-angle X-ray scattering spectra and apparent diffusion coefficients in the study of structure and interaction of sodium taurodeoxycholate micelles J. Phys. Chem. B 2005, 109, 6111-6120
42. Durchschlag, H.; Zipper, P. Calculation of partial specific volumes of detergents and lipids J. Com. Esp. Deterg. 1995, 26, 275-292
43. Perrin, F. Mouvement Brownien d'un ellipsoide (II). Rotation libre et dépolarisation des fluorescences. Translation et diffusion de molécules ellipsoidales J. Phys. Radium 1936, 7, 1-11
44. Terech, P.; Talmon, Y. Aqueous suspensions of steroid nanotubules: Structural and rheological characterizations Langmuir 2002, 18, 7240-7244
45. Sangeetha, N. M.; Bhat, S.; Choudhury, A. R.; Maitra, U.; Terech, P. Properties of hydrogels derived from cationic analogues of bile acid: Remarkably distinct flowing characteristics. J. Phys. Chem. B 2004, 108.
46. Terech, P.; Maitra, U. Structural and rheological properties of aqueous viscoelastic solutions and gels of tripodal cholamide-based self-assembled supramolecules J. Phys. Chem. B 2008, 112, 13483-13492
47. Terech, P.; Weiss, R. G. Low molecular mass gelators of organic liquids and the properties of their gels Chem. Rev. 1997, 97, 3133-3160
48. Jover, A.; Meijide, F.; Rodríguez Núñez, E.; Vázquez Tato, J. Aggregation kinetics of sodium deoxycholate in aqueous solution Langmuir 1998, 14, 4359-4363
49. Jover, A.; Meijide, F.; Rodríguez Nunez, E.; Vázquez Tato, J. Dynamic rheology of sodium deoxycholate gels Langmuir 2002, 18, 987-991
50. Bhata, S.; Maitra, U. Low molecular mass cationic gelators derived from deoxycholic acid: Remarkable gelation of aqueous solvents Tetrahedron 2007, 63, 7309-7320
51. Löfman, M.; Koivukorpi, J.; Noponen, V.; Salo, H.; Sievänen, E. Bile acid alkylamide derivatives as low molecular weight organogelators: Systematic gelation studies and qualitative structural analysis of the systems J. Colloid Interface Sci. 2011, 360, 633-644
52. Khatua, D.; Maiti, R.; Dey, J. A supramolecular hydrogel that responds to biologically relevant stimuli Chem. Commun. 2006, 4903-4905
53. Sangeetha, N. M.; Maitra, U. Supramolecular gels: Functions and uses Chem. Soc. Rev. 2005, 34, 821-836
54. Hoare, T. R.; Kohane, D. S. Hydrogels in drug delivery: Progress and challenges Polymer 2008, 49, 1993-2007
55. Brandl, F.; Sommer, F.; Goepferich, A. Rational design of hydrogels for tissue engineering: Impact of physical factors on cell behavior Biomaterials 2007, 28, 134-146
56. Dias, R. S.; Lindman, B.; Miguel, M. G. Compaction and decompaction of DNA in the presence of catanionic amphiphile mixtures J. Phys. Chem. B 2002, 106, 12608-12612
57. Liu, Y.-C.; Le Ny, A.-L. M.; Schmidt, J.; Talmon, Y.; Chmelka, B. F.; Lee, C. T. J. Photo-assisted gene delivery using light-responsive catanionic vesicles Langmuir 2009, 25, 5713-5724
58. Mel'nikov, S. M.; Dias, R.; Mel'nikov, Y. S.; Marques, E. F.; Miguel, M. G.; Lindman, B. DNA conformational dynamics in the presence of catanionic mixtures FEBS Lett. 1999, 453, 113-118
59. Bramer, T.; Dew, N.; Edsman, K. Pharmaceutical applications for catanionic mixtures J. Pharm. Pharmacol. 2007, 59, 1319-1334
60. Bramer, T.; Dew, N.; Edsman, K. Catanionic mixtures involving a drug: A rather general concept that can be utilized for prolonged drug release from gels J. Pharm. Sci. 2006, 95, 769-780