Artículos de revistas
Use Of A Novel Method For Determination Of Partition Coefficients To Compare The Effect Of Local Anesthetics On Membrane Structure
Registro en:
Bba - Biomembranes. , v. 1240, n. 1, p. 25 - 33, 1995.
52736
10.1016/0005-2736(95)00155-6
2-s2.0-0028818451
Autor
Paula E.d.
Schreier S.
Institución
Resumen
A new, simple procedure for the determination of partition coefficients (P) was developed based on spectral effects caused upon addition of solutes to spin labeled model lipid membranes, and on the knowledge of their water solubility. Values of P were determined for nine local anesthetics (LA), amino-esters and amino-amides. The results were in good agreement with those found by phase separation and by a more complex, previously reported, methodology (Lissi et al. (1990) Biochim. Biophys. Acta 1021, 46-50) applied to either EPR or fluorescence spectra of probes incorporated in the bilayers. Both the present and the previously reported procedures make use of effects on membrane structure evaluated by spectroscopic techniques and offer the advantage of not requiring phase separation. The spectral effects, indicative of a decrease in bilayer organization increased with LA concentration, reaching a maximum at the drug water solubility, indicating that partitioning in the membrane is limited by saturation of the aqueous phase. A thermodynamic analysis of the partition data according to Hill (Hill, M.W. (1974) Biochim. Biophys. Acta 356, 117-124) showed that the LAs did not display ideal behavior. Knowledge of the partition coefficients allowed a comparison between effects at the same drug concentration in the membrane. Within a given family (esters, acyclic amides, cyclic amides) no clear proportionality was observed between effect and LA hydrophibicity, as reflected in the partition coefficient. Rather, the membrane perturbing ability is a result of steric effects originating in the mismatch between anesthetic and phospholipid shapes. © 1995. 1240 1 25 33 Frazier, Narahashi, Yamada, (1970) J. Pharmacol. Exp. Ther., 171, pp. 45-51 Narahashi, Frazier, Yamada, (1970) J. Pharmacol. Exp. Ther., 171, pp. 32-44 Ritchie, Greengard, (1961) J. Pharmacol. Exp. Ther., 133, pp. 241-245 Strichartz, Ritchie, Local Anesthetics (1987) Handbook of Experimental Pharmacology, 81, pp. 21-52. , G.R. Strichartz, Springer-Verlag, Berlin Courtney, (1980) J. Pharmacol. Exp. Ther., 213, pp. 114-119 Courtney, Strichartz, Local Anesthetics (1987) Handbook of Experimental Pharmacology, 81, pp. 53-94. , G.R. Strichartz, Springer-Verlag, Berlin Wildsmith, Gissen, Takman, Covino, (1987) Br. J. Anaesth., 59, pp. 379-384 Gupta, (1991) Chem. Rev., 91, pp. 1109-1119 Frezzatti, Jr., Toselli, Schreier, (1986) Biochim. Biophys. Acta, 860, pp. 531-538 Skou, Local Anaesthetics. V. The Action of Local Anaesthetics on Monomolecular Layers of Stearic Acid. (1954) Acta Pharmacologica et Toxicologica, 10, pp. 317-324 Seelig, (1987) Biochim. Biophys. Acta, 899, pp. 196-204 Papahadjopoulos, Jacobson, Poste, Shepherd, (1975) Biochim. Biophys. Acta, 394, pp. 504-519 Dörfler, Brezesinski, Jantschke, Calorimetric studies of the thermodynamic properties of lamellar lecithin/local anaesthetic/water mixtures (1990) Liquid Crystals, 8, pp. 263-277 Kaminoh, Inoue, Ma, Ueda, Lin, (1988) Biochim. Biophys. Acta, 946, pp. 337-344 Lee, (1978) Biochim. Biophys. Acta, 514, pp. 95-104 Sikaris, Sawyer, (1982) Biochem. Pharmacol., 31, pp. 2625-2631 Fernandez, Calderon, The local anaesthetic tetracaine as a quencher of perylene fluorescence in micelles (1990) Journal of Photochemistry and Photobiology B: Biology, 7, pp. 75-86 Barghouthi, Eftink, (1993) Biophys. Chem., 46, pp. 13-19 Schöpflin, Fingeli, Perlia, (1987) J. Am. Chem. Soc., 109, pp. 2375-2380 Auger, Smith, Mantsch, Wong, (1990) Biochemistry, 29, pp. 2008-2015 Coster, James, Berthet, Mille, (1981) Biochim. Biophys. Acta, 641, pp. 281-287 Dörfler, Förster, Jantschke, X-ray studies on polymorphism of lamellar lecithin/local anaesthetic/water mixtures (1990) Liquid Crystals, 8, pp. 279-297 Butler, Schneider, Smith, (1973) Arch. Biochem. Biophys., 154, pp. 548-554 Giotta, Chan, Wang, (1974) Arch. Biochim. Biophys., 163, pp. 453-458 Neal, Butler, Polnaszek, Smith, (1976) Mol. Pharmacol., 12, pp. 144-155 Schreier, Frezzatti, Jr., Araujo, Chaimovich, Cuccovia, (1984) Biochim. Biophys. Acta, 769, pp. 231-237 Limbacher, Blickenstaff, Bowen, Wang, (1985) Biochim. Biophys. Acta, 812, pp. 268-276 Schreier, Amaral, Stachissini, Bianconi, (1986) Bull. Magn. Reson., 8, pp. 166-171 Bianconi, Amaral, Schreier, (1988) Biochem. Biophys. Res. Commun., 152, pp. 344-350 Lissi, Bianconi, Amaral, de Paula, Blanch, Schreier, (1990) Biochim. Biophys. Acta, 1021, pp. 46-50 Bianconi, Schreier, (1991) J. Phys. Chem., 95, pp. 2483-2487 Boulanger, Schreier, Leitch, Smith, (1980) Can. J. Biochem., 58, pp. 986-995 Boulanger, Schreier, Smith, (1981) Biochemistry, 20, pp. 6824-6830 Browning, Akutsu, (1982) Biochim. Biophys. Acta, 684, pp. 172-178 Kelusky, Smith, (1984) Mol. Pharmacol., 26, pp. 314-321 Kelusky, Boulanger, Schreier, Smith, (1986) Biochim. Biophys. Acta, 856, pp. 85-90 Kuroda, Fujikawa, (1987) Biochim. Biophys. Acta, 903, pp. 395-410 Auger, Jarrell, Smith, Siminovitch, Mantsch, Wong, (1988) Biochemistry, 27, pp. 6086-6090 Auger, Smith, Jarrell, (1989) Biochim. Biophys. Acta, 981, pp. 351-357 Yokono, Ogli, Miura, Ueda, (1989) Biochim. Biophys. Acta, 982, pp. 300-302 Wakita, Kuroda, Fujiwara, Nakagawa, (1992) Chem. Phys. Lipids, 62, pp. 45-54 Singleton, Gray, Brown, White, (1965) J. Am. Oil. Chem. Soc., 42, pp. 53-56 Kamp, Wirtz, Baer, Slotboom, Rosenthal, Paltauf, Van Deenen, (1977) Biochemistry, 16, pp. 1310-1316 Rabjohn, Fronabarger, Lingsfromberg, β-DIETHYLAMINOETHYL ESTERS OF STERICALLY HINDERED ALKYL SUBSTITUTED BENZOIC ACIDS (1955) The Journal of Organic Chemistry, 20, pp. 171-173 Rouser, Fleischer, Yamamoto, (1970) Lipids, 5, pp. 494-496 Hubbell, McConnell, (1971) J. Am. Chem. Soc., 93, pp. 314-320 Schreier, Polnaszek, Smith, (1978) Biochim. Biophys. Acta, 515, pp. 375-436 Agin, Hersh, Holtzman, (1965) Proc. Natl. Acad. Sci. USA, 53, pp. 952-958 Strichartz, Sanchez, Arthur, Chafetz, Martin, (1990) Anesth. Analg., 71, pp. 158-170 Rooney, Lee, (1983) Biochim. Biophys. Acta, 732, pp. 428-432 Eriksson, Westman, (1981) Biophys. Chem., 13, pp. 253-264 Lee, Schreier, (1993) Liposome Technology, Entrapment of drugs and other materials, 2, pp. 1-25. , G. Gregoriadis, CRC Press, Boca Raton, FL Abuin, Lissi, (1983) J. Colloid Interface Sci., 57, pp. 11-19 Fernandez, Formation of micelles and membrane action of the local anesthetic tetracaine hydrochloride (1980) Biochimica et Biophysica Acta (BBA) - Biomembranes, 597, pp. 83-91 Schreier, Amaral, Stachissimi, Bianconi, (1986) Bull. Magn. Res., 8, pp. 166-171 Van Hoogevest, De Kruijff, (1978) Biochim. Biophys. Acta, 511, pp. 397-407 Hill, (1974) Biochim. Biophys. Acta, 356, pp. 117-124 Pringle, Brown, Miller, (1980) Mol. Pharmacol., 19, pp. 49-55 Jones, Lee, (1985) Biochim. Biophys. Acta, 812, pp. 731-739 Lee, (1976) Biochemistry, 15, pp. 2448-2454 Seeman, Roth, Schneider, (1971) Biochim. Biophys. Acta, 225, pp. 171-184 Lee, (1977) Biochemistry, 16, pp. 835-841 Kaminoh, Tashiro, Kamaya, Ueda, (1988) Biochim. Biophys. Acta, 946, pp. 215-220 Kaminoh, Kamaya, Ueda, (1989) Biochim. Biophys. Acta, 987, pp. 63-68 Uhrikova, Cherezov, Yaradaikin, Balgavý, (1993) Pharmazie, 48, pp. 446-450