Mechanisms of liposomes/water partitioning of (p- methylbenzyl)alkylamines

Pharmaceutical Research

Volumn 15, Issue 9, 1998, Pages 1407-1413

  Fruttero, Roberta ^a   Caron, Giulia ^b   Fornatto, Elisa ^a   Boschi, Donatella ^a   Ermondi, Giuseppe ^a   Gasco, Alberto ^a   Carrupt, Pierre Alain ^b   Testa, Bernard ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Hydrogen bonds; Hydrophobic interactions; Intermolecular forces; Ionic bonds; Lipophilicity; Liposomes; NMR relaxation rates; pH metric method

Indexed keywords

ALIPHATIC AMINE; AMPHOLYTE; AMPHOPHILE; ANTIDEPRESSANT AGENT; CARDIOVASCULAR AGENT; LIPOSOME; NEUROLEPTIC AGENT; OCTANOL;

ARTICLE; CHEMICAL BOND; DRUG ACTIVITY; HYDROGEN BOND; HYDROPHOBICITY; LIPID MEMBRANE; LIPOPHILICITY; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PARTITION COEFFICIENT; PH; POTENTIOMETRY; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

1-OCTANOL; ALKANES; DRUG CARRIERS; LIPIDS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; WATER;

EID: 0031753162     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011953622052     Document Type: Article

References (24)

1. U. P. Kodavanti and H. M. Mehendale. Cationic amphiphilic drugs and phospholipid storage disorder. Pharmacol. Rev. 42:327-354 (1990).
2. R. P. Mason, D. G. Rhodes, and L. G. Herbette. Reevaluating equilibrium and kinetic binding parameters for lipophilic drugs based on a structural model for drug interaction with biological membranes. J. Med. Chem. 34:869-877 (1991).
3. R. P. Austin, A. M. Davis, and C. N. Manners. Partitioning of ionizing molecules between aqueous buffers and phospholipid vesicles. J. Pharm. Sci. 84:1180-1183 (1995).
4. Y. Boulanger, S. Schreier, L. C. Leitch, and I. C. P. Smith. 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 (1980).
5. F. Barbato, M. I. La Rotonda, and F. Quaglia. Chromatographic indices determined on an immobilized artificial membrane (IAM) column as descriptors of lipophilic and polar interactions of 4-phenyldihydropyridine calcium-channel dockers with biomembranes. Eur. J. Med. Chem. 31:311-318 (1996).
6. Liposomes. A Practical Approach. New, R. R. C. (ed.). IRL Press, Oxford, 1990.
7. B. I. Escher and R. P. Schwarzenbach. Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems. Environ. Sci. Technol. 30:260-270 (1996).
8. A. Avdeef. pH-Metric log P. Part 1. Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances. Quant. Struct.-Act. Relat. 11:510-517 (1992).
9. A. Avdeef. Assessment of distribution-pH profiles. In V. Pliska, B. Testa, and H. van de Waterbeemd (eds.), In: Lipophilicity in Drug Action and Toxicology Vol. VCH Publishers, Weinheim, 1996, pp. 109-139.
10. J. K. Seydel, H. P. Cordes, M. Wiese, H. Chi, N. Croes, R. Hanpft, H. Lüllmann, K. Mohr, M. Patten, Y. Padberg, R, Lüllmann-Rauch, S. Vellguth, W. R. Meindl, and H. Schönenberger. QSAR and multivariate data analysis of amphiphilic benzylamines and their interaction with various phospholipids determined by different methods. Quant. Struct.-Act. Relat. 8:266-278 (1989).
11. W. R. Meindl, E. von Angerer, H. Schönenberger, and G. Ruckdeschel. Benzylamines: synthesis and evaluation of antimycobacterial properties. J. Med. Chem. 27:1111-1118 (1984).
12. J. V. Braun and A. Friedsam. Haftfestigkeit organischer Reste (VII. Mitteil.). Chem. Ber. 639:2407-2412 (1930).
13. C. Ottiger and H. Wunderli-Allenspach. Ideal partition behaviour of acids and bases in a phosphatidylcholine liposome/buffer equilibrium dialysis system. Eur. J. Pharm. Sci. 5:223-231 (1997).
14. P. Gaillard, P. A. Carrupt, and B. Testa. The conformational-dependent lipophilicity of morphine glucuronides as calculated from their molecular lipophilicity potential. Bioorg. Med. Chem. Lett. 4:737-742 (1994).
15. C. Altomare, S. Cellamare, A. Carotti, G. Casini, M. Ferappi, E. Gavuzzo, F. Mazza, P. A. Carrupt, P. Gaillard, and B. Testa. X-ray crystal structure, partitioning behavior, and molecular modeling study of piracetam-type nootropics: insights into the pharmacophore. J. Med. Chem. 38:170-179 (1995).
16. G. Caron, P. Gaillard, P. A. Carrupt, and B. Testa. Lipophilicity behavior of model and medicinal compounds containing a sulfide, sulfoxide, or sulfone moiety. Helv. Chim. Acta 80:449-462 (1997).
17. P. A. Carrupt, B. Testa, and P. Gaillard. Computational approaches to lipophilicity: methods and applications. In D. B. Boyd and K. B. Lipkowitz (eds.), In: Reviews in Computational Chemistry Vol. 11, Wiley-VCH, New York, 1997, pp. 241-315.
18. P. Gaillard, P. A. Carrupt, B. Testa, and A. Boudon. Molecular lipophilicity potential, a tool in 3D-QSAR. Method and applications. J. Comput.-Aided Mol. Design 8:83-96 (1994).
19. B. Testa, P. A. Carrupt, P. Gaillard, F. Billois, and P. Weber. Lipophilicity in molecular modeling. Pharm. Res. 13:335-343 (1996).
20. CLIPI.0. Institute of Medicinal Chemistry, University of Lausanne, 1996.
21. A. Avdeef, K.J. Box, J. E. A. Comer, C. Hibbert, and K. Y. Tam. pH-metric log P. 10. Determination of vesicle membrane-water partition coefficients of ionizable drugs. Pharm. Res. 15:209-215 (1998).
22. J. J. Fischer and O. Jardetzky. Nuclear magnetic relaxation study of intermolecular complexes. The mechanism of penicillin binding to serum albumin. J. Am. Chem. Soc. 87:3237-3244 (1965).
23. DAYLIGHT Software 4.41. Daylight Chemical Information System, Inc., Irvine, California, 1995.
24. M. Recanatini. Partition and distribution coefficients of aryloxypropanolamine β-adrenceptor antagonists. J. Pharm. Pharmacol. 44:68-70 (1992).