Double-chain surfactants with two carboxylate head groups that form vesicles

Langmuir

Volumn 12, Issue 8, 1996, Pages 1976-1980

  Jaeger, David A ^a   Brown, Ethan L G ^a,b  

^a UNIVERSITY OF WYOMING   (United States)

^b Hickson Danchem Corp   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONATES; CARBOXYLIC ACIDS; CHARACTERIZATION; DIFFERENTIAL SCANNING CALORIMETRY; GEL PERMEATION CHROMATOGRAPHY; LIGHT SCATTERING; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL);

CARBOXYLATE HEAD; DOUBLE CHAIN SURFACTANTS; DYNAMIC LIGHT SCATTERING; GEL FILTRATION CHROMATOGRAPHY; VESICLES;

SURFACE ACTIVE AGENTS;

EID: 0030127105     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la950872s     Document Type: Article

References (44)

1. (a) Bosch, M. A.; Parra, J. L.; Sánchez-Baeza, F. Can J. Chem. 1993, 71, 2095.
2. (b) de Groot, R. W.; Wagenaar, A.; Sein, A.; Engberts, J. B. F. N. Recl. Trav. Chim. Pays-Bas 1995, 114, 371.
3. (c) Zhu, Y.-P.; Masuyama, A.; Kobata, Y.; Nakatsuji, Y.; Okahara, M.; Rosen, M. J. J. Colloid Interface. Sci. 1993, 158, 40.
4. (d) Porter, N. A.; Ok, D.; Huff, J. B.; Adams, C. M.; McPhail, A. T.; Kim, K. J. Am. Chem. Soc. 1988, 110, 1896.
5. (e) Ringsdorf, H.; Schlarb, B.; Venzmer, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 113 and references therein.
6. (a) Danino, D.; Talmon, Y.; Zana, R. Langmuir 1995, 11, 1448.
7. (b) Zana, R.; Talmon, Y. Nature 1993, 362, 228.
8. (c) Menger, F. M.; Littau, C. A. J. Am. Chem. Soc. 1993, 115, 10083.
9. (d) Devínsky, F.; Lacko, I.; Imam, T. J. Colloid Interface. Sci. 1991, 143, 336.
10. (e) Abid, S. K.; Hamid, S. M.; Sherrington, D. C. J. Colloid Interface. Sci. 1987, 120, 245.
11. (f) Imam, T.; Devínsky, F.; Lacko, I.; Mlynarcik, D.; Krasnec, L. Pharmazie 1983, 38, 308 and references therein.
12. (a) Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1525.
13. (b) Israelachvili, J. N. Intermodular and Surface Forces, 2nd ed.; Academic Press: New York, 1992; Chapter 17.
14. 1s and NOEs of the carbons involved are comparable, thus allowing quantitation based on their intensities.
15. On dissolution of 3 into the carbonate buffers, deprotonation of the two carboxyl groups is likely incomplete at pH 9.2 and may or may not be complete at pH 10.7 (see Discussion). In any event, the resulting system is designated as 1.
16. (a) Chattopadhyay, A.; London, E. Anal. Biochem. 1984, 139, 408.
17. (b) Goodling, K.; Johnson, K.; Lefkowitz, L.; Williams, B. R. J. Chem. Ed. 1994, 71, A8.
18. Wang, G.-J.; Engberts, J. B. F. N. Langmuir 1994, 10, 2583.
19. Browning, J. L. In Liposomes: From Physical Structure to Therapeutic Applications; Knight, C. G., Ed.; Elsevier/North Holland: New York, 1981; Chapter 7.
20. Wilkinson, D. A.; Nagle, J. F. In ref 9; Chapter 9.
21. Weinstein, J. N.; Ralston, E.; Leserman, L. D.; Klausner, R. D.; Dragsten, P.; Henkart, P.; Blumenthal, R. In Liposome Technology; Gregoriadis, G., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 3, p 183.
22. Weinstein, J. N.; Yoshikami, S.; Henkart, P.; Blumenthal, R.; Hagins, W. A. Science (Washington, D.C.) 1977, 195, 489.
23. Fendler, J. H. Membrane Mimetic Chemistry; Wiley-Interscience: New York, 1982; Chapter 6.
24. Briggs, J.; Dorshow, R. B.; Bunton, C. A.; Nicoli, D. F. J. Chem. Phys. 1982, 76, 775.
25. However, endotherms due to clusters of micelles have been observed in DSC thermograms of moderately concentrated solutions of single-chain surfactants: Blandamer, M. J.; Briggs, B.; Burgess, J.; Butt, M. D.; Brown, H. R.; Cullis, P. M.; Engberts, J. B. F. N. J. Colloid Interface Sci. 1992, 150, 285.
26. CF could be adsorbed to the surface of open bilayers. For an example in a related system, see: Carmona-Ribeiro, A. M.; Chaimovich, H. Biochim. Biophys. Acta. 1983, 733, 172.
27. For examples, see: (a) Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Biochemistry 1988, 27, 1881. (b) Edwards, K.; Silvander, M.; Karlsson, G. Langmuir 1995, 11, 2429. (c) Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759. (d) Wick, R.; Walde, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435 and references therein.
28. For examples, see: (a) Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Biochemistry 1988, 27, 1881. (b) Edwards, K.; Silvander, M.; Karlsson, G. Langmuir 1995, 11, 2429. (c) Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759. (d) Wick, R.; Walde, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435 and references therein.
29. For examples, see: (a) Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Biochemistry 1988, 27, 1881. (b) Edwards, K.; Silvander, M.; Karlsson, G. Langmuir 1995, 11, 2429. (c) Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759. (d) Wick, R.; Walde, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435 and references therein.
30. For examples, see: (a) Cistola, D. P.; Hamilton, J. A.; Jackson, D.; Small, D. M. Biochemistry 1988, 27, 1881. (b) Edwards, K.; Silvander, M.; Karlsson, G. Langmuir 1995, 11, 2429. (c) Hargreaves, W. R.; Deamer, D. W. Biochemistry 1978, 17, 3759. (d) Wick, R.; Walde, P.; Luisi, P. L. J. Am. Chem. Soc. 1995, 117, 1435 and references therein.
31. Haines, T. H. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 160.
32. Cistola, D. P.; Small, D. M.; Hamilton, J. A. J. Biol. Chem. 1987, 262, 10971.
33. (a) Glasoe, P. K.; Eberson, L. J. Phys. Chem. 1964, 68, 1560.
34. (b) Glasoe, P. K.; Hutchison, J. R. J. Phys. Chem. 1964, 68, 1562.
35. (c) Eyring, E. M.; Haslam, J. L. J. Phys. Chem. 1966, 70, 293.
36. (d) Haslam, J. Li,; Eyring, E. M.; Epstein, W. W.; Jensen, R. P.; Jaget, C. W. J. Am. Chem. Soc. 1965, 87, 4247.
37. Rebek, J., Jr.; Duff, R. J.; Gordon, W. E.; Parris, K. J. Am. Chem. Soc. 1986, 108, 6088.
38. Jaeger, D. A. Supramol.Chem. 1995, 5, 27.
39. Jaeger, D. A.; Sayed, Y. M. J. Org. Chem. 1993, 58, 2619.
40. (a) McElhaney, R. N. Chem. Phys. Lipids 1982, 30, 229.
41. (b) Takahashi, K.; Sturtevant, J. M. Biochemistry 1981, 20, 6185.
42. Palameta, B.; Prostenik, M. Tetrahedron 1963, 19, 1463.
43. Utaka, M.; Watabu, H.; Higashi, H.; Sakai, T.; Tsuboi, S.; Torii, S. J. Org. Chem. 1990, 55, 3917.
44. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.