Blood-brain barrier permeation: Molecular parameters governing passive diffusion

Journal of Membrane Biology

Volumn 165, Issue 3, 1998, Pages 201-211

  Fischer, H ^a   Gottschlich, R ^b   Seelig, A ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b MERCK KGAA   (Germany)

Author keywords

Amphiphilicity; Blood brain barrier; Cross sectional area; Drug screening; Internal lateral bilayer pressure; Molecular size; Monolayer bilayer equivalence pressure; Passive diffusion; pK(a)

Indexed keywords

AMITRIPTYLINE; APOMORPHINE; CHLORDIAZEPOXIDE; CHLORPROMAZINE; CLOMIPRAMINE; CLONIDINE; CLOZAPINE; DESIPRAMINE; DIAZEPAM; DOXYLAMINE; FLUNITRAZEPAM; FLUOXETINE; FLUPENTIXOL; HALOPERIDOL; HYDROXYZINE; IMIPRAMINE; LIDOCAINE; MEQUITAZINE; METOPROLOL; NALTREXONE; NOXIPTILINE; PERPHENAZINE; PIRACETAM; PROMAZINE; PROMETHAZINE; ROXINDOLE; SALBUTAMOL; SPIRADOLINE; THIOPENTAL; THIORIDAZINE; UNINDEXED DRUG;

ARTICLE; BLOOD BRAIN BARRIER; DIFFUSION; DISSOCIATION CONSTANT; HYDROPHILICITY; HYDROPHOBICITY; LIPID MEMBRANE; MEMBRANE TRANSPORT; MICELLE; MOLECULAR SIZE; PARTITION COEFFICIENT; SURFACE PROPERTY; THERMODYNAMICS;

AIR; AMIODARONE; ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; BUTYROPHENONES; DIFFUSION; DOMPERIDONE; HISTAMINE H1 ANTAGONISTS; HUMANS; KINETICS; LOPERAMIDE; MICELLES; MODELS, BIOLOGICAL; P-GLYCOPROTEIN; PIPERIDINES; SURFACE PROPERTIES; THERMODYNAMICS; WATER;

EID: 0031695039     PISSN: 00222631     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002329900434     Document Type: Article

References (50)

1. Altenbach, C., Seelig, J. 1985. Binding of the lipophilic cation tetraphenylphosphonium to phosphatidylcholine membranes. Biochim. Biophys. Acta 818:410-415
2. Barber, A., Bartoszyk, G.D., Bender, H.M., Gottschlich, R., Greiner, H.E., Harting, J., Mauler, F., Minck, K.O., Murray, R.D., Simon, M. 1994. A pharmacological profile of the novel, peripherally-selective kappa-opioid receptor agonist, EMD 61753. Br. J. Pharmacol. 113:1317-1327
3. Bassolino-Klimas, D., Alper, H.E., Stouch, T.R. 1993. Solute diffusion in lipid bilayer membranes: an atomic level study by molecular dynamics simulation. Biochemistry 32:12624-12637
4. Beschiaschvili, G., Seelig, J. 1992. Peptide binding to lipid bilayers. Nonclassical hydrophobic effect and membrane-induced pK shifts. Biochemistry 31:10044-10053
5. Boguslavsky, V., Rebecchi, M., Morris, A.J., Jhon, D.Y., Rhee, S.G., McLaughlin, S. 1994. Effect of monolayer surface pressure on the activities of phosphoinositide-specific phospholipase C-beta 1, -gamma 1, and -delta 1. Biochemistry 33:3032-3037
6. Broekhuysen, J., Laruel, R., Sion, R. 1969. [Research on the benzofuran series. XXXVII. Comparative study of transit and metabolism of amiodarone in different species of animals and humans]. Arch. Int. Pharmacodyn. Ther. 177:340-359
7. Büldt, G., Gally, H.U., Seelig, A., Seelig, J., Zaccai, G. 1978. Neutron diffraction studies on selectively deuterated phospholipid bilayers. Nature 271:182-184
8. Cevc, G., Marsh, D. 1987. Phospholipid Bilayers, Physical Principles and Models. Wiley, New York
9. Demel, R.A., Geurts van Kessel, W.S., Zwaal, R.F., Roelofsen, B., van Deenen, L.L. 1975. Relation between various phospholipase actions on human red cell membranes and the interfacial phospholipid pressure in monolayers. Biochim. Biophys. Acta 406:97-107
10. Fischer, H. 1998. Ph.D. Thesis University of Basel
11. Fuller, R.W. 1986. Substituted phenylpiperazines as serotonin agonists: structural determinants of potency and interaction with receptor subtypes. Psychopharmacol. Bull. 22:825-828
12. Gally, H.U., Seelig, A., Seelig, J. 1976. Cholesterol-induced rod-like motion of fatty acyl chains in lipid bilayers a deuterium magnetic resonance study. Hoppe Seylers Z. Physiol. Chem. 357:1447-1450
13. Gobas, F.A., Lahittete, J.M., Garofalo, G., Shiu, W.Y., Mackay, D. 1988. A novel method for measuring membrane-water partition coefficients of hydrophobic organic chemicals: comparison with 1-octanol-water partitioning. J. Phann. Sci. 77:265-272
14. Heykants, J., Michiels, M., Knaeps, A., Brugmans, J. 1974. Loperamide (R 18 553), a novel type of antidiarrheal agent. Part 5: the pharmacokinetics of loperamide in rats and man. Arzneimittelforschung 24:1649-1653
15. Huwyler, J., Fricker, G., Torok, M., Schneider, M., Drewe, J. 1997. Transport of clonidine across cultured brain microvessel endothelial cells. J. Pharmacol. Exp. Ther. 282:81-85
16. Kaliszan, R. 1990. High Performance Liquid Chromatographic Methods and Procedures of Hydrophobicity Determination. Quant. Struct.-Act. Relat. 9:83-87
17. Leeson, G.A., Chan, K.Y., Knapp, W.C., Biedenbach, S.A., Wright, G.J., Okerholm, R.A. 1982. Metabolic disposition of terfenadine in laboratory animals. Drug Res. 32:1173-1178
18. Lieb, W.R., Stein, W.D. 1986. Non-Stokesian nature of transverse diffusion within human red cell membranes. J. Membrane Biol. 92:111-119
19. Macdonald, R.C. 1996. The relationship and interactions between lipid bilayers vesicles and lipid monolayers at the air/water interface. Marcel Dekker, New York, Basel, Hong Kong
20. Marsh, D. 1996. Lateral pressure in membranes. Biochim. Biophys. Acta 1286:183-223
21. Martindale, N.O. 1996. The Extra Pharmacopoeia. The Royal Pharmaceutical Society, London Martinez-Tobed, A., Tarrus, E., Segura, J., Roberts, D.J. 1992. Pharmacokinetie studies of ebastine in rats, dogs and man. Drugs of Today 28:57-67
22. 1-receptor antagonist ebastine and its active metabolite carebastine in rats, guinea pigs, dogs and monkeys. Drug Res. 44:55-59
23. Mayer, L.D., Wong, K.F., Menon, K., Chong, C., Harrigan, P.R., Cullis, P.R. 1988. Influence of ion gradients on the transbilayer distribution of dibucaine in large unilamellar vesicles. Biochemistry 27:2053-2060
24. McLaughlin, S. 1989. The electrostatic properties of membranes. Annu. Rev. Biophys. Biophys. Chem. 18:113-136
25. Mooradian, A.D., Meredith, K.E. 1992. The effect of age on protein composition of rat cerebral microvessels. Neurochem. Res. 17:665-670
26. Moragues, J., Roberts, D.J. 1990. Ebastine. Drug Fut. 15:674-679
27. a values of medicinal compounds in pharmacy practice. Drug Intelligence & Clinical Pharmacy 12:546-554
28. Ong, S., Liu, H., Qui, X., Bhat, G., Pidgeon, C. 1995. Membrane partition coefficients chromatographically measured using immobilized artificial membrane surfaces. Anal. Chem. 67:755-762
29. Paula, S., Süs, W., Tuchtenhagen, J., Blume, A. 1995. Thermodynamics of Micelle Formation as a Function of Temperature: A High Sensitivity Titration Calorimetry Study. J. Phys. Chem. 99:11742-11751
30. Perrin, D.D., Dempsey, B., Serjeant, E.P. 1981. pKa Prediction for Organic Acids and Bases. Chapman and Hall, London and New York
31. Reece, P.A., Sedman, A.J., Rose, S., Wright, D.S., Dawkins, R., Rajagopalan, R. 1994. Diuretic effects, pharmacokinetics, and safety of a new centrally acting kappa-opioid agonist (CI-977) in humans. J. Clin. Pharmacol. 34:1126-1132
32. Reyntjens, A.J., Niemegeers, C.J., Van Neuten, J.M., Laduron, P., Heykants, J., Schellekens, K.H., Marsboom, R., Jageneau, A., Broekaert, A., Janssen, P.A. 1978. Domperidone, a novel and safe gastrokinetic anti-nauseant for the treatment of dyspepsia and vomiting. Arzneimittelforschung 28:1194-1196
33. Rosen, M.J. 1989. Surfactants and Interfacial Phenomena. John Wiley & Sons, New York
34. Schuermans, V., Van Lommel, R., Dom, J., Brugmans, J. 1974. Loperamide (R18553), a novel type of antidiarrheal agent. Arzneim. Forsch. 24:1653-1657
35. Seelig, A. 1987. Local anesthetics and pressure: a comparison of dibucaine binding to lipid monolayers and bilayers. Biochim. Biophys. Acta 899:196-204
36. Seelig, A. 1998. A general pattern for substrate recognition by P-glycoprotein. Eur. J. Biochem. 251:252-261
37. Seelig, J., Ganz, P. 1991. Nonclassical hydrophobic effect in membrane binding equilibria. Biochemistry 30:9354-359
38. Seelig, A., Gottschlich, R., Devant, R.M. 1994. A method to determine the ability of drugs to diffuse through the blood-brain barrier. Proc. Natl. Acad. Sci. USA 91:68-72
39. Seelig, J., Seelig, A. 1974. Deuterium magnetic resonance studies of phospholipid bilayers. Biochem. Biophys. Res. Commun. 57:406-411
40. Seelig, J., Seelig, A. 1980. Lipid conformation in model membranes and biological membranes. Q. Rev. Biophys. 13:19-61
41. Seppala, T., Savolainen, 1982. Effect of astemizole on human psychomotor performance. Curr. Ther. Res. 31:638-644
42. Simons, K., van Meer, G. 1988. Lipid sorting in epithelial cells. Biochemistry 27:6197-6202
43. Tanford, C. 1987. Amphiphile orientation: physical chemistry and biological function. Biochem. Soc. Trans. 15 Suppl:1S-7S
44. Taschner, N. 1993. Diploma Thesis University of Basel
45. Tausk, R.J., Karmiggelt, J., Oudshoorn, C., Overbeek, J.T. 1974. Physical chemical studies of short-chain lecithin homologues. I. Influence of the chain length of the fatty acid ester and of electrolytes on the critical micelle concentration. Biophys. Chem. 1:175-183
46. ter Laak, A.M., Tsia, R.S., Donne-Op den Kelder, G.M., Carrupt, P.-A., Testa, B., Timmerman, H. 1994. Lipophilicity and hydrogen-bonding capacity of H1-antihistaminic agents in relation to their central sedative side-effects. Eur. J. Pharm. Sci. 2:373-384
47. Tsuji, A., Kubo, O., Miyamoto, E., Yamana, T. 1977. Physicochemical properties of beta-lactam antibiotics: oil-water distribution. J. Pharm. Sci. 66:1675-1679
48. Von Voightlander, P.F., Lewis, R.A. 1988. Analgesic and mechanistic evaluation of spiradoline, a kappa opioid. J. Pharmacol. Exp. Ther. 246:259-262
49. Wenk, M.R., Alt, T., Seelig, A., Seelig, J. 1997. Octyl-beta-D-glucopyranoside partitioning into lipid bilayers: thermodynamics of binding and structural changes of the bilayer. Biophys. J. 72:1719-1731
50. Yang, C.Y., Cai, S.J., Liu, H., Pidgeon, C. 1997. Immobilized artificial membranes - screens for drug membrane interactions. Adv. Drug Delivery Rev. 23:229-256