Does transbilayer diffusion have a role in membrane transport of drugs?

Drug Discovery Today

Volumn 17, Issue 19-20, 2012, Pages 1079-1087

  Balaz, Stefan ^a  

^a ALBANY COLLEGE OF PHARMACY AND HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOPHILE; OCTANOL;

ADRENERGIC NERVE CELL; AORTA STRIP; CELL STRAIN; CELL STRAIN CACO 2; CELL SUSPENSION; CORNEA EPITHELIUM; CORRELATION COEFFICIENT; DRUG ACCUMULATION; DRUG BINDING SITE; DRUG DIFFUSION; DRUG PENETRATION; DRUG TRANSPORT; ELECTRON SPIN RESONANCE; ESCHERICHIA COLI; HUMAN; HYPOTHESIS; KIDNEY CELL; LIPID BILAYER; LIPID MEMBRANE; LIPID RAFT; LIPOPHILICITY; LIVER CELL; MEMBRANE TRANSPORT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PATCH CLAMP; PH; PHOSPHOLIPID BILAYER; PLACENTA; PROTEIN LIPID INTERACTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; SPECTROSCOPY; X RAY DIFFRACTION;

ANIMALS; BIOLOGICAL TRANSPORT; CELL MEMBRANE; DIFFUSION; HUMANS; LIPID BILAYERS; PHARMACEUTICAL PREPARATIONS;

EID: 84866731309     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2012.06.003     Document Type: Review

References (59)

1. S. Balaz Modeling kinetics of subcellular disposition of chemicals Chem. Rev. 109 2009 1793 1899
2. P.D. Dobson, and D.B. Kell Carrier-mediated cellular uptake of pharmaceutical drugs: an exception or the rule? Nat. Rev. Drug Discov. 7 2008 205 220
3. P. Dobson Implications of the dominant role of transporters in drug uptake by cells Curr. Top. Med. Chem. 9 2009 163 181
4. D.B. Kell Pharmaceutical drug transport: the issues and the implications that it is essentially carrier-mediated only Drug Discov. Today 16 2011 704 714
5. P. Mueller Reconstitution of cell membrane structure in vitro and its transformation into an excitable system Nature 194 1962 979 980
6. J.F. Nagle, and H.L. Scott Jr. Lateral compressibility of lipid mono- and bilayers. Theory of membrane permeability Biochim. Biophys. Acta Biomembr. 513 1978 236 243
7. D.W. Deamer, and J. Bramhall Permeability of lipid bilayers to water and ionic solutes Chem. Phys. Lipids 40 1986 167 188
8. S. Paula Permeation of protons, potassium ions, and small polar molecules through phospholipid bilayers as a function of membrane thickness Biophys. J. 70 1996 339 348
9. S. Paula Permeation of halide anions through phospholipid bilayers occurs by the solubility-diffusion mechanism Biophys. J. 74 1998 319 327
10. M.K. Jain The Bimolecular Lipid Membrane 1972 Van Nostrand Reinhold
11. H.T. Tien, and A. Ottova-Leitmannova Planar Lipid Bilayers (BLMs) and Their Applications 2003 Elsevier
12. F. Bordi Ionic transport in lipid bilayer membranes Biophys. J. 74 1998 1358 1370
13. H. Leontiadou Molecular dynamics simulations of hydrophilic pores in lipid bilayers Biophys. J. 86 2004 2156 2164
14. H. Leontiadou Ion transport across transmembrane pores Biophys. J. 92 2007 4209 4215
15. W.H.J. Vaes Solid phase microextraction as a tool to determine membrane/water partition coefficients and bioavailable concentrations in in vitro systems Chem. Res. Toxicol. 10 1997 1067 1072
16. P.L. Yeagle Molecular dynamics of the local anesthetic tetracaine in phospholipid vesicles Biochim. Biophys. Acta 465 1977 173 178
17. R.S. Phadke Structure and function of propranolol: a β-adrenergic blocking drug Int. J. Quant. Chem. 20 1981 85 92
18. R. Welti Partition of amphiphilic molecules into phospholipid vesicles and human erythrocyte ghosts: measurements by ultraviolet difference spectroscopy Biochemistry 23 1984 6086 6091
19. X. Michalet The power and prospects of fluorescence microscopies and spectroscopies Annu. Rev. Biophys. Biomol. Struct. 32 2003 161 182
20. A. Sujak Studies on canthaxanthin in lipid membranes Biochim. Biophys. Acta Biomembr. 1712 2005 17 28
21. P. Muller Continuous measurement of rapid transbilayer movement of a pyrene-labeled phospholipid analogue Chem. Phys. Lipids 106 2000 89 99
22. C. Ho, and C.D. Stubbs Effect of n-alkanols on lipid bilayer hydration Biochemistry 36 1997 10630 10637
23. S.H. White Location of hexane in lipid bilayers determined by neutron diffraction Nature 1981 161 163
24. M. Trumbore Structure and location of amiodarone in a membrane bilayer as determined by molecular mechanics and quantitative X-ray diffraction Biophys. J. 54 1988 535 543
25. E. Asuncion-Punzalan, and E. London Control of the depth of molecules within membranes by polar groups: determination of the location of anthracene-labeled probes in model membranes by parallax analysis of nitroxide-labeled phospholipid induced fluorescence quenching Biochemistry 34 1995 11460 11466
26. C. Hansch, and T. Fujita ρ-σ-π analysis. A method for the correlation of biological activity and chemical structure J. Am. Chem. Soc. 86 1964 1616 1626
27. M.V. Serra Pathways for flip-flop of mono- and di-anionic phospholipids in the erythrocyte membrane Biochim. Biophys. Acta 1282 1996 263 273
28. P.A. Shore The gastric secretion of drugs: a pH partition hypothesis J. Pharmacol. Exp. Ther. 119 1957 361 369
29. T.X. Xiang, and B.D. Anderson Influence of a transmembrane protein on the permeability of small molecules across lipid membranes J. Membr. Biol. 173 2000 187 201
30. J. Gutknecht Aspirin, acetaminophen and proton transport through phospholipid bilayers and mitochondrial membranes Mol. Cell. Biochem. 114 1992 3 8
31. V. Lukacova Partitioning of organic compounds in phases imitating the headgroup and core regions of phospholipid bilayers Langmuir 22 2006 1869 1874
32. W.M. Yau The preference of tryptophan for membrane interfaces Biochemistry 37 1998 14713 14718
33. O.G. Mouritsen, and M. Bloom Mattress model of lipid-protein interactions in membranes Biophys. J. 46 1984 141 153
34. W.A. Daniel Mechanisms of cellular distribution of psychotropic drugs: significance for drug action and interactions Prog. Neuropsychopharmacol. Biol. Psychiatry 27 2003 65 73
35. S. Balaz, and V. Lukacova A model-based dependence of the human tissue/blood partition coefficients of chemicals on lipophilicity and tissue composition Quant. Struct.-Act. Relat. 18 1999 361 368
36. A.C. MacIntyre, and D.J. Cutler The potential role of lysosomes in tissue distribution of weak bases Biopharm. Drug Dispos. 9 1988 513 526
37. P. Kannan Lysosomal trapping of a radiolabeled substrate of P-glycoprotein as a mechanism for signal amplification in PET Proc. Natl. Acad. Sci. U. S. A. 108 2011 2593 2598
38. S. Trapp Quantitative modeling of selective lysosomal targeting for drug design Eur. Biophys. J. 37 2008 1317 1328
39. J. Wojcikowski, and W.A. Daniel Distribution interactions between perazine and antidepressant drugs. In vivo studies Pol. J. Pharmacol. 52 2000 449 457
40. L.S. Maynard, and G. Cotzias The partition of manganese among organs and intracellular organelles of the rat J. Biol. Chem. 214 1955 489 495
41. J. Baik, and G.R. Rosania Molecular imaging of intracellular drug-membrane aggregate formation Mol. Pharm. 8 2011 1742 1749
42. S. Balaz Hansch approach and kinetics of biological activities Quant. Struct.-Act. Relat. 4 1985 77 81
43. G.M. Maggiora On outliers and activity cliffs: why QSAR often disappoints J. Chem. Inf. Model. 46 2006 1535
44. C. Hansch, and T.E. Klein Quantitative structure-activity relationships and molecular graphics in evaluation of enzyme-ligand interactions Methods Enzymol. 202 1991 512 543
45. H. Kubinyi 3D-QSAR in Drug Design Vols. 1-3 1993 Escom
46. Bio-Loom for Windows Version 1.5 2006 BioByte Corp.
47. K. Pirselova Quantitative structure-time-activity relationships (QSTAR): growth inhibition of Escherichia coli by nonionizable kojic acid derivatives Quant. Struct.-Act. Relat. 15 1996 87 93
48. S. Natesan Cellular quantitative structure-activity relationship (cell-QSAR): conceptual dissection of receptor binding and intracellular disposition in antifilarial activities of selwood antimycins J. Med. Chem. 55 2012 3699 3712
49. J.D. Irvine MDCK (Madin-Darby canine kidney) cells: a tool for membrane permeability screening J. Pharm. Sci. 88 1999 28 33
50. W.G. Hill, and M.L. Zeidel Reconstituting the barrier properties of a water-tight epithelial membrane by design of leaflet-specific liposomes J. Biol. Chem. 275 2000 30176 30185
51. E. Orbach, and A. Finkelstein The nonelectrolyte permeability of planar lipid bilayer membranes J. Gen. Physiol. 75 1980 427 436
52. M.C. Blok Effect of the gel to liquid crystalline phase transition on the osmotic behavior of phosphatidylcholine liposomes Biochim. Biophys. Acta Biomembr. 433 1976 1 12
53. M.C. Blok The effect of cholesterol incorporation on the temperature dependence of water permeation through liposomal membranes prepared from phosphatidylcholines Biochim. Biophys. Acta 464 1977 509 518
54. J. Cuppoletti Transport of ions and nonelectrolytes N. Sperelakis, Cell Physiology 1995 Academic Press 139 147
55. K. Sugano Coexistence of passive and carrier-mediated processes in drug transport Nat. Rev. Drug Discov. 9 2010 597 614
56. S. Balaz Subcellular pharmacokinetics and drug properties: numerical simulations in multicompartment systems Quant. Struct.-Act. Relat. 13 1994 381 392
57. H. Kubinyi Quantitative structure-activity relationships. 7. The bilinear model, a new model for nonlinear dependence of biological activity on hydrophobic character J. Med. Chem. 20 1977 625 629
58. S. Balaz, and E. Sturdik Lipophilicity and drug distribution M. Tichy, QSAR in Toxicology and Xenobiochemistry 1985 Elsevier 257 267
59. S. Balaz Quantitative relationships between lipophilicity and mutagenic effects of N-substituted amides of 3-(5-nitro-2-furyl)-acrylic acid on Salmonella typhimurium Chem. Biol. Interact. 55 1985 93 108