Effect of anions from the hofmeister series and urea on the binding of the charged and uncharged forms of the local anesthetic tetracaine to zwitterionic micelles

Photochemistry and Photobiology

Volumn 63, Issue 6, 1996, Pages 755-761

  Graziela, S ^a   Ferreira, S ^a   Périgo, Daniel M ^a   Politi, Mario J ^a   Schreier, Shirley ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000684880     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1996.tb09627.x     Document Type: Conference Paper

References (44)

1. Collins, K. D. and M. W. Washabaugh (1985) The Hofmeister effect and the behaviour of water at interfaces. Q. Rev. Biophys. 18, 324-364.
2. Long, F. A. and W. F. McDevit (1952) Activity coefficients of nonelectrolyte solutes in aqueous salt solutions. Chem. Rev. 51, 119-169.
3. von Hippel, P. H and T Schleich (1969) Ion effects on the solution structure of biological macromolecules. Acc. Chem. Res 2, 257-265
4. Arakawa, T. and S. N. Timasheff (1985) Theory of protein solubility. Methods Enzymol. 114, 49-77.
5. Schrier, E. and E. B. Schrier (1967) The salting-out behavior of amides and its relation to the denaturation of proteins by salts. J. Phys. Chem. 71, 1851-1860.
6. Altekar, W. (1977) Fluorescence of proteins in aqueous neutral salt solutions. I. Influence of anions. Biopolymers 16, 341-368.
7. Damodaran, S. and J. E. Kinsella (1981) The effects of neutral salts on the stability of macromolecules. J. Biol. Chem. 256, 3394-3398.
8. Sihag, R. K. and P. Deutscher (1983) Perturbation of the aminoacyl-tRNA synthetase complex by salts and detergents. J. Biol. Chem. 258, 11846-11850.
9. Hatefi, Y. and W. G. Hanstein (1969) Solubilization of particulate proteins and nonelectrolytes by chaotropic agents Biochemistry 62, 1129-1136.
10. Damodaran, S. and J. E. Kinsella (1983) Dissociation of nucleoprotein complexes by chaotropic salts. FEBS Lett. 158, 53-57.
11. Nandi, P. K. and H. Edelhoch (1984) The effects of lyotropic (Hofmeister) salts on the stability of clathrin coat structure in coated vesicles and baskets. J. Biol. Chem. 259, 11290-11296.
12. Wetlaufer, D. B., S. K. Malik, L. Stoller and R. L. Coffin (1964) Nonpolar group participation in the denaturation of proteins by urea and guanidinium salts. Model compound studies. J. Am. Chem. Soc. 86, 508-514
13. Kuharski, R. A. and P. J. Rossky (1984) Solvation of hydrophobic species in aqueous urea solution: a molecular dynamics study J. Am. Chem. Soc. 106, 5794-5800.
14. Robinson, D. R. and W. P. Jencks (1965) The effect of compounds of the urea-guanidinium class on the activity coefficient of acetyltetraglycine ethyl ester and related compounds. J. Am. Chem. Soc. 87, 2462-2470.
15. Breslow, R. and T. Guo (1990) Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers. Proc. Natl. Acad. Sci. USA 87, 167-169.
16. Anacker, E. W. and H. M. Ghose (1963) Counterions and micelle size. I. Light scattering by solutions of dodecyltrimethylammonium salts. J. Phys. Chem. 67, 1713-1716.
17. Sudhölter, E. J. R. and B. F. N. Engberts (1979) Salt effects on the critical micellar concentration, iodide counterion binding, and surface micropolarity of 1-methyl-4-dodecylpyridinium iodide micelles. J. Phys. Chem. 83, 1854-1859.
18. Schott, H., A. E. Royce and S. K. Han (1984) Effect of inorganic additives on solutions of nonionic surfactants. J. Colloid Interface Sci. 98, 196-201.
19. Quina, F. H. and H. Chaimovich (1979) Ion exchange in micellar solutions. 1. Conceptual framework for ion exchange in micellar solutions. J. Phys. Chem. 83, 1844-1850.
20. Romsted, L. S. (1984) Micellar effects on reactions rates and equilibria. In Surfactants in Solution, Vol. 2 (Edited by K. L. Mittal and B. Lindman), pp. 1015-1068. Plenum Press, New York.
21. Brochsztain, S., P Berci-Filho, V. G. Toscano, H. Chaimovich and M. J. Politi (1990) Ion binding and selectivity in zwitterionic micelles. J. Phys. Chem. 94, 6781-6785.
22. Baglioni, P., E. Rivara-Minten, L. Dei and E. Ferroni (1990) ESR study of sodium dodecyl sulfate and dodecyltrimethylammonium bromide micellar solutions. Effect of urea. J. Phys. Chem 94, 8218-8222
23. Almeida, F. C. L., H. Chaimovich and S. Schreier (1994) Electron spin resonance study of the effect of urea on the properties of AOT reverse micelles in isooctane. Langmuir 10, 1786-1792
24. Tocanne, J. F. and J. Teissié (1990) Ionization of phospholipids and phospholipid-supported interfacial lateral diffusion of protons in membrane model systems. Biochim. Biophys Acta 1031, 111-142.
25. Tatulian, S A. (1993) Ionization and ion binding. In Phospholipid Handbook (Edited by G. Cevc), pp. 511-552. Marcel Dekker, New York.
26. McLaughlin, S., A. Bruder, S. Chen and C. Moser. (1975) Chaotropic anions and the surface potential of bilayer membranes. Biochim. Biophys. Acta 394, 304-313.
27. Simon, S. A., L J Lis, J. W. Kauffman and R. C. MacDonald (1975) A calorimetric and monolayer investigation of the influence of ions on the thermodynamic properties of phosphatidylcholine. Biochim. Biophys. Acta 375, 317-326.
28. Tatulian, S. A. (1983) Effect of lipid phase transition on the binding of anions to dimyristoylphosphatidylcholine liposomes. Biochim. Biophys. Acta 736, 189-195.
29. 2H NMR. Biochemistry 31, 1092-1099.
30. Cevc, G. (1990) Membrane electrostatics Biochim. Biophys. Ada 1031, 311-382.
31. Cunningham, B. A., W. Tamura-Lis, L. J. Lis and J. M. Collins (1989) Thermodynamic properties of acyl chain and mesophase transitions for phospholipids in KSCN. Biochim. Biophys. Acta 984, 109-112.
32. Bartucci, R. and L. Sportelli (1994) Spin label EPR study of the effects of monovalent cations, anions, and chaotropics on DPPC multilayers. Biochim. Biophys. Acta 1195, 229-236.
33. Lee, A. G. and S. Schreier (1993) Binding of charged molecules to lipid bilayers. In Liposome Technology, Vol. 2 (Edited by G. Gregoriadis), pp. 1-25. CRC Press, Boca Raton, FL.
34. Schreier, S., W. A. Frezzatti, Jr., P. S. Araújo and I. M Cuccovia (1984) Effect of lipid membranes on the apparent pK of the local anesthetic tetracaine - spin label and titration studies. Biochim. Biophys. Acta 769, 231-237.
35. Frezzatti, Jr., W. A., W. R. Toselli and S. Schreier (1986) Spin label study of local anesthetic-lipid membrane interactions. Phase separation of the uncharged form and bilayer micellization by the charged form of tetracaine. Biochim. Biophys. Acta 860, 531-538.
36. Tabak, M. and I. E. Borisevitch (1992) Interaction of dipyridamole with micelles of lysophosphatidylcholine and with bovine serum albumin: fluorescence studies. Biochim. Biophys. Acta 1116, 241-249.
37. Desai, S., T. Hadlock, C. Messam, R. Chafetz and G. Strichartz (1994) Ionization and adsorption of a series of local anesthetics in detergent micelles: studies of drug fluorescence. J. Pharm. Exp. Ther. 271, 220-228.
38. Boulanger, Y., S. Schreier and I. C. P. Smith (1981) Molecular details of anesthetic-lipid interaction as seen by deuterium and phosphorus nuclear magnetic resonance. Biochemistry 20, 6824-6839.
39. Boulanger, Y., S. Schreier, L. C. Leitch and I. C. P. Smith (1980) Multiple binding sites for local anesthetics in membranes: characterization of the sites and their equilibria by deuterium NMR of specifically deuterated procaine and tetracaine. Can. J. Biochem. 58, 986-995.
40. Schreier, S., C. F. Polnaszek and I. C. P. Smith (1978) Spin label studies in membranes. Problems in practice. Biochim. Biophys. Acta 515, 395-436.
41. García-Soto, J. and M. S. Fernández (1983) The effect of neutral and charged micelles on the acid-base dissociation of the local anesthetic tetracaine. Biochim. Biophys. Acta 731, 275-281.
42. 2H-NMR study on the interactions of the local anesthetic tetracaine with membranes containing phosphatidylserine. Biochim. Biophys. Acta 856, 85-90.
43. Bianconi, M. L. and S. Schreier (1991) EPR study of membrane partitioning, orientation and membrane-modulated alkaline hydrolysis of a spin-labeled benzoic acid ester. J. Phys. Chem. 95, 2483-2486.
44. Israelachvili, J. (1992) Intermolecular and Surface Forces. Academic Press, London.