The permeation of neutral molecules, ions, and ionic species through membranes: Brain permeation as an example

Journal of Pharmaceutical Sciences

Volumn 100, Issue 5, 2011, Pages 1690-1701

  Abraham, Michael H ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Absorption; ADME; Blood brain barrier; Membrane transport; Passive diffusion transport; Permeability; Physicochemical properties

Indexed keywords

ACETIC ACID; ACETONE; ALCOHOL; ALDOSTERONE; ANION; CARBAMAZEPINE; CARBOXYLIC ACID; CATION; CLOZAPINE; CORTICOSTERONE; DIAZEPAM; DIGOXIN; ERYTHRITOL; ESTRADIOL; ETHOSUXIMIDE; HYPOXANTHINE; ISOCARBOXAZID; MANNITOL; MEPROBAMATE; PHENAZONE; PROGESTERONE; PYRIDINE DERIVATIVE; QUETIAPINE; THEOBROMINE; THIOUREA; TRAZODONE; WARFARIN; XANTHINE; ZIPRASIDONE;

ARTICLE; ARTIFICIAL MEMBRANE; BLOOD BRAIN BARRIER; BRAIN; MEMBRANE TRANSPORT; PARTITION COEFFICIENT;

EID: 79952213236     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22404     Document Type: Article

References (39)

1. Abbott NJ. 2004. Prediction of blood-brain barrier permeation in drug discovery from in vivo, in vitro, and in silico models. Drug Discov Today Technol 1:407-416.
2. Abraham MH, Hersey A. 2006. In Silico models to predict brain uptake. In Comprehensive Medicinal Chemistry II; Triggle DJ, Taylor JB, Eds. Oxford: Elsevier:745-766.
3. Abraham MH. 2006. In silico models to predict brain uptake. In Virtual ADMET assessment in target selection and maturation; B.Testa, L.Turski, Eds. Amsterdam: Solvay Pharmaceuticals Conferences, IOS Press 163-185.
4. Abraham MH. 2004. The factors that influence permeation across the blood-brain barrier. Eur J Med Chem 39:235-240.
5. Lanevskij K, Japertas P, Didziapetris R, Petrauskas A. 2009. Ionization-specific prediction of blood-brain permeability. J Pharm Sci 98:4039-4054.
6. Dagenais C, Avdeef A, Tsinman O, Dudley A, Beliveau R. 2009. P-glycoprotein deficient in situ blood-brain barrier permeability and its prediction using an in combo PAMPA model. Eur J Pharm Sci 38:121-137.
7. Schaper K-J, Zhang H, Raevsky OA. 2001. pH-dependent partitioning of acidic and basic drugs into liposomes-A quantitative structure-activity relationship. Quant Struct-Act Relat 20:46-54.
8. Balon K, Riebesehl BU, Muller BW. 1999. Determination of liposome partitioning of ionizable drugs by titration. J Pharm Sci 88:802-806.
9. Balon K, Riebesehl BU, Muller BW. 1999. Drug liposome partitioning as a tool for the prediction of human passive intestinal absorption. Pharm Res 16:882-888.
10. Abraham MH, Acree Jr. WE. 2010. The transfer of neutral molecules, ions and ionic species from water to wet octanol. Phys Chem Chem Phys. In press.
11. Pardridge WM, Triguero D, Yang J, Cancilla PA. 1990. Comparison of in vitro and in vivo models of drug transctosis through the blood-brain barrier. J Pharmacol Exp Ther 253:884-891.
12. Gratton JA, Lightman SL, Bradbury MW. 1993. Transport into retina measured by short vascular perfusion in the rat. J Physiol 470:651-663.
13. Chikhale EG, Ng KY, Burton PS, Borchardt RT. 1994. Hydrogen-bonding potential as a determinant of the in vitro and in vivo blood-brain permeability of peptides. Pharm Res 11:412-419.
14. Gratton JA, Abraham MH, Bradbury MW, Chadha HS. 1997. Molecular factors influencing drug transport across the blood-brain barrier. J Pharm Pharmacol 49:1211-1216.
15. Abraham MH. 1993. Scales of hydrogen bonding: Their construction and application to physicochemical and biochemical processes. Chem Soc Rev 22:73-83.
16. Abraham MH, Ibrahim A, Zissimos AM. 2004. The determination of sets of solute descriptors from chromatographic measurements. J Chromatogr A 1037:29-47.
17. Abraham MH, Platts JA. 2001. Hydrogen bond structural group constants. J Org Chem 66:3484-3491.
18. ADME Boxes, version 5.0, Advanced Chemistry Development, 110 Yonge Street, 14th Floor, Toronto, Ontario, M5C 1T4, Canada.
19. Abraham MH, Acree Jr. WE. 2010. Equations for the transfer of neutral molecules and ionic species from water to organic phases. J Org Chem 75:1006-1015.
20. Abraham MH, Acree Jr. WE. 2010. Solute descriptors for phenoxide anions and their use to establish correlations of rates of reaction of anions with iodomethane. J Org Chem 75:3021-3026.
21. Abraham MH, Acree Jr. WE. 2010. The transfer of neutral molecules, ions and ionic species from water to ethylene glycol and to propylene carbonate; descriptors for pyridinium cations. New J Chem 34:2298-2305.
22. Habgood MD, Liu ZD, Dehkordi LS, Khodr HH, Abbott J, Hider RC. 1999. Investigation into correlation between the structure of hydroxypyridinones and blood-brain barrier permeability. Biochem Pharmacol 57:1305-1310.
23. Murakami H, Takanaga H, Matsou H, Ohtani O, Sawada Y. 2000. Comparison of blood-brain barrier permeability in mice and rats using as in situ brain perfusion technique. Am J Physiol Heart Circ Physiol 279:H1022-H1028.
24. Liu X, Tu M, Kelly RS, Chen C, Smith BJ. 2004. Development of a computational approach to predict blood-brain barrier permeability. Drug Metab Dispos 32:132-139.
25. Sommerfield SG, Read K, Begley DJ, Obradovic T, Hidalgo IJ, Coggan S, Lewis AV, Porter RA, Jeffrey P. 2007. Central nervous system drug disposition: The relationship between in situ brain permeability and brain free fraction. J Pharmacol Exp Ther 322:205-213. Erratum, same page.
26. Ohno K, Pettigrew KD, Rapoport SI. 1978. Lower limits of cerebrovascular permeability to nonelectrolytes in the conscious rat. Am J Physiol 235:H299-H307.
27. Espenson JH. 1981. Chemical kinetics and reaction mechanisms. New York: McGraw-Hill.
28. Di L, Kerns EH, Bezar IF, Petusky SL, Huang Y. 2009. Comparison of blood-brain barrier permeability assays: In situ brain perfusion, MDR1-MDCKII and PAMPA-BBB. J Pharm Sci 98:1980-1991.
29. Cussler EL. 2009. Diffusion: Mass transfer in Fluid Systems. Cambridge: Cambridge University Press.
30. Pardridge WM. 2005. The blood-brain barrier: Bottleneck in brain drug development. NeuroRx 2:3-14.
31. Li G, Yuan W, Fu BM. 2010. A model for the blood-brain barrier permeability to water and small solutes. J Biomech 43: 2133-2140.
32. Bassolino D, Alper H, Stouch TR. 1996. Drug-membrane interactions studied by molecular dynamics simulation: Size dependence of diffusion. Drug Des Discov 13:135-141.
33. Hills EE, Abraham MH, Hersey A, Bevan CD. Diffusion coefficients in ethanol and in water at 298K: Linear free energy relationships. In preparation.
34. Hawes JL, Kay RL. 1965. Ionic association of potassium and cesium chloride in ethanol-water mixtures from conductance measurements at 25°. J Phys Chem 69:2420-2431.
35. Levin VA. 1980. Relationship of octanol-water partition coefficients and molecular weight to rat brain capillary permeation. J Med Chem 23:682-684.
36. Pardridge VM. 1998. Drug delivery to the brain. J Cereb Blood Flow Metab 17:713-731.
37. Ishihara K, Kushida H, Yuzurihara M, Wakui Y, Yanagisawa T, Kamei H, Ohmori S, Kitada M. 2000. Interaction of drugs and Chinese herbs: Pharmacokinetic changes of tolbutamide and diazepam caused by extract of Angelica dahurica. J Pharm Pharmacol 52:1023-1029.
38. Wang JS, Zhu HJ, Gibson BB, Markowitz JS, Donovan JL, DeVane CL. 2008. Sertraline and its metabolite desmethylsertraline, but not buproprion or its three major metabolites have high affinity for p-glycoprotein. Biol Pharm Bull 31:231-234.
39. Vaes WHJ, Ramos EU, Verhaar JM, Cramer CJ, Hermans HJM. 1998. Understanding and estimating membrane/water partition coefficients: Approaches to derive quantitative structure property relationships. Chem Res Toxicol 11:847-854.