Penetration of dimyristoylphosphatidylcholine monolayers and bilayers by model β-blocker agents of varying lipophilicity

Journal of Pharmaceutical Sciences

Volumn 87, Issue 6, 1998, Pages 751-756

  Krill, Steven L ^a   Lau, Ka Yan ^a   Plachy, William Z ^a,b   Rehfeld, Selwyn J ^a,b  

^a ABBOTT LABORATORIES   (United States)

^b SAN FRANCISCO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ADRENERGIC RECEPTOR BLOCKING AGENT; DIMYRISTOYLPHOSPHATIDYLCHOLINE; METOPROLOL; NADOLOL; OXPRENOLOL; PROPRANOLOL;

ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG PENETRATION; LIPID BILAYER; LIPOPHILICITY; PARTITION COEFFICIENT; SURFACE PROPERTY;

EID: 14444285474     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970374z     Document Type: Article

References (39)

1. De Young, L. R.; Dill, K. A. Solute Partitioning into Lipid Bilayer Membranes. Biochemistry 1988, 27, 5281-5289.
2. Marqusee, J. A.; Dill, K. A. Solute Partitioning into Chain Molecule Interphases: Monolayers, Bilayer Membranes, and Micelles. J. Chem. Phys. 1986, 85, 434-444.
3. Smejtek, P.; Wang, S. Distribution of Hydrophobic Ionizable Xenobiotics between Water and Lipid Membranes: Pentachlorophenol and Pentachlorophenate. A Comparison with Octanol-Water Partition. Arch. Environ. Contam. Toxicol. 1993, 25, 394-404.
4. Wimley, W. C.; White, S. H. Membrane Partitioning: Distinguishing Bilayer Effects from the Hydrophobic Effect. Biochemistry 1993, 32, 6307-6312.
5. MacDonald, R. C.; Simon, S. A. Lipid Monolayer States and their Relationships to Bilayers. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4089-4093.
6. Chiu, S. W.; Clark, M.; Balaji, V.; Subramaniam, S.; Scott, H. L.; Jakobsson, E. Incorporation of Surface Tension into Molecular Dynamics Simulation of an Interface: A Fluid Phase Lipid Bilayer Membrane. Biophys. J. 1995, 69, 1230-1245.
7. Zografi, G.; Auslander, D. E. Surface Activity of Chlorpromazine and Chlorpromazine Sulfoxide in the Presence of Insoluble Monomolecular Films. J. Pharm. Sci. 1965, 54, 1313-1318.
8. Attwood, D.; Udeala, O. K. The Interaction of Antihistamines with Lecithin Monolayers. J. Pharm. Pharmacol. 1975, 27, 806-810.
9. Lodhi, S.; Weiner, N. D.; Schacht, J. Interactions of Neomycin with Monomolecular Films of Polyphosphoinositides and Other Lipids. Biochim. Biophys. Acta 1979, 557, 1-8.
10. Vilallonga, F. A.; Phillips, E. W. Interaction of Doxorubicin with Phospholipid Monolayers. J. Pharm. Sci. 1978, 67, 773-775.
11. Williams, N. A.; Weiner, N. D. Interaction of Recombinant Leukocyte A Interferon with Lipid Monolayers. Int. J. Pharm. 1989, 51, 241-244.
12. Sicre, P.; Cordoba, J. Association of Indomethacin and Flurbiprofen to Phospholipid Membrane Models. J. Colloid Interface Sci. 1989, 132, 94-99.
13. Reig, F.; Busquets, M. A.; Haro, I.; Rabanal, F.; Alsina, M. A. Interaction of Opiate Molecules with Lipid Monolayers and Liposomes. J. Pharm. Sci. 1992, 81, 546-550.
14. Colome, C.; Alsina, M. A.; Busquets, M. A.; Haro, I.; Reig, F. Interaction of Aminoglycosides and Colistin with Model Membranes: Liposomes and Monolayers. Int. J. Pharm. 1993, 90, 59-71.
15. Mestres, C.; Alsina, M. A.; Busquets, M. A.; Haro, I.; Reig, F. Interaction of Enrofloxacin with Phospholipid Mono-and Bilayers. Langmuir 1994, 10, 767-772.
16. Takao, Y.; Yamauchi, H.; Manosroi, J.; Manosroi, A.; Abe, M. Molecular Interactions between Lipids and Some Steroids in a Monolayer and a Bilayer. 2. Langmuir 1995, 11, 912-916.
17. Doisy, A.; Proust, J. E.; Ivanova, T.; Panaiotov, I.; Dubois, J. L. Phospholipid/Drug Interactions in Liposomes Studied by Rheological Properties of Monolayers. Langmuir 1996, 12, 6098-6103.
18. Betageri, G. V.; Rogers, J. A. The Liposome as a Distribution Model in QSAR Studies. Int. J. Pharm. 1988, 46, 95-102.
19. Huang, H.; Schoenwald, R. D.; Lach, J. L. Corneal Penetration Behavior of β-Blocking Agents II: Assessment of Barrier Contributions. J. Pharm. Sci. 1983, 72, 1272-1278.
20. Luan, C. C.; Harris, R. D.; Prasad, K. U.; Urry, D. W. Differential Scanning Calorimetry Studies of the Inverse Temperature Transition of the Polypentapeptide of Elastin and Its Analogues. Biopolymers 1990, 29, 1699-1706.
21. Luan, C. C.; Urry, D. W. Solvent Deuteration Enhancement of Hydrophobicity: DSC Study of the Inverse Temperature Transition of Elastin-Based Polypeptides. J. Phys. Chem. 1991, 95, 7896-7900.
22. Pethica, B. A. The Thermodynamics of Monolayer Penetration at Constant Area. Trans. Faraday Soc. 1955, 51, 1402-1411.
23. Sabra, M. C.; Jorgensen, K.; Mouritsen, O. G. Lindane Suppresses the Lipid-Bilayer Permeability in the Main Transition Region. Biochim. Biophys. Acta 1996, 1282, 85-92.
24. Lee, A. G. Lipid Phase Transitions and Phase Diagrams II. Mixtures Involving Lipids. Biochim. Biophys Acta 1977, 472, 285-344.
25. Betageri, G. V.; Rogers, J. A. Thermodynamics of Partitioning of β-Blockers in the n-Octanol-Buffer and Liposome Systems. Int. J. Pharm. 1987, 36, 165-173.
26. Saija, A.; Bonina, F.; Trombetta, D.; Tomaino, A.; Montenegro, L.; Smeriglio, P.; Castelli, F. Flavonoid-Biomembrenae Interactions: A Calorimetric Study on Dipalmitoylphosphatidylcholine Vesicles. Int. J. Pharm. 1995, 124, 1-8.
27. Bloom, M.; Evans, E.; Mouritsen, O. G. Physical Properties of the Fluid Lipid-Bilayer Component of Cell Membranes: A Perspective. Q. Rev. Biophys. 1991, 24, 293-397.
28. Bondar, O. P.; Rowe, E. S. Differential Scanning Calorimetric Study of the Effect of Vitamin DS on the Thermotropic Phase Behavior of Lipids Model Systems. Biochim. Biophys. Acta 1995, 1240, 125-132.
29. Herbette, L.; Katz, A. M.; Sturtevant, J. M. Comparisons of the Interaction of Propranolol and Timolol with Model and Biological Membrane Systems. Mol. Pharmacol. 1983, 24, 259-269.
30. Nag, K.; Boland, C.; Rich, N.; Keough, M. W. Epifluorescence Microscopic Observation of Monolayers of Dipalmitoylphosphatidylcholine: Dependence of Domain Size on Compression Rates. Biochim. Biophys. Acta 1991, 1068, 157-160.
31. McConnell, H. M. Structures and Transitions in Lipid Monolayers at the Air-Water Interface. Annu. Rev. Phys. Chem. 1991, 42, 171-195.
32. Von Tscharner, V.; McConnell, H. M. An Alternative View of Phospholipid Phase Behavior at the Air-Water Interface. Biophys. J. 1981, 36, 409-419.
33. Hwang, J.; Tamm, L. K; B̂hm, C.; Ramalingam, R. S.; Betzig, E.; Edidin, M. Nanoscale Compexity of Phospholipid Monolayers Investigated by Near-Field Scanning Optical Microscopy. Science 1995, 270, 610-614.
34. Charron, J. R.; Tilton, R. D. A Scanning Angle Reflectometry Investigation of Block Copolymer Adsorption to Insoluble Lipid Monolayers at the Air-Water Interface. J. Phys. Chem. 1996, 100, 3179-3189.
35. McGregor, M. A.; Barnes, G. T. Equilibrium Penetration of Monolayers VI: Cholesterol-Cetrimonium Bromide System. J. Pharm. Sci. 1978, 67, 1054-1056.
36. McGregor, M. A.; Barnes, G. T. The Equilibrium Penetration of Monolayers V. The Sodium Docosyl Sulfate/Sodium Dodecyl Sulfonate System. J. Colloid Interface Sci. 1978, 65, 291-295.
37. Sundaram, S.; Stebe, K. J. Equations for the Equilibrium Surface Pressure Increase on the Penetration of an Insoluble Monolayer by a Soluble Surfactant. Langmuir 1996, 12, 2028-2034.
38. Santos Magalhaes, N. S.; de Oliveira, H. M.; Baszkin, A. Colloids and Surfaces A: Physicochem. Eng. Aspects 1996, 118, 63-73.
39. Davies, J. T.; Rideal, E. K. Reactions in Liquid Surfaces. In Interfacial Phenomena; Academic Press Inc.: San Diego, 1961; pp 282-300.