Structural determinants of drug partitioning in n-hexadecane/water system

Journal of Chemical Information and Modeling

Volumn 53, Issue 6, 2013, Pages 1424-1435

  Natesan, Senthil ^a   Wang, Zhanbin ^a   Lukacova, Viera ^b,c   Peng, Ming ^b   Subramaniam, Rajesh ^a   Lynch, Sandra ^a   Balaz, Stefan ^a  

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

^b NORTH DAKOTA STATE UNIVERSITY   (United States)

^c Simulations Plus Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITES; BIOLOGICAL SYSTEMS; PARAFFINS; PHOSPHOLIPIDS; PROTEINS; SOLVATION;

CHEMICAL SIMILARITY; CORRECTION FACTORS; HIGH WATER CONTENT; PARTITION COEFFICIENT; PHOSPHOLIPID BILAYER; SOLVATION PARAMETERS; SOLVATOCHROMIC PARAMETERS; STRUCTURAL DETERMINANTS;

FORECASTING;

ALKANE; DRUG; N-HEXADECANE; OCTANOL; PHOSPHOLIPID; WATER; HEXADECANE;

CHEMICAL PHENOMENA; CHEMISTRY; ARTICLE;

1-OCTANOL; ALKANES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PHARMACEUTICAL PREPARATIONS; PHOSPHOLIPIDS; WATER;

EID: 84879581500     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci400112k     Document Type: Article

References (76)

1. Collander, R. Lipoid solubility Acta Physiol. Scand. 1947, 13, 363-381
2. Hansch, C.; Maloney, P. P.; Fujita, T.; Muir, R. M. Correlation of biological activity of phenoxyacetic acids with Hammett substituent constants and partition coefficients Nature 1962, 194, 178-180
3. Dallas, A. J.; Carr, P. W. A thermodynamic and solvatochromic investigation of the effect of water on the phase-transfer properties of octan-1-ol J. Chem. Soc., Perkin Trans 2 1992, 2155-2161
4. Sassi, P.; Paolantoni, M.; Cataliotti, R. S.; Palombo, F.; Morresi, A. Water/alcohol mixtures: A spectroscopic study of the water-saturated 1-octanol solution J. Phys. Chem. B 2004, 108, 19557-19565
5. Margolis, S. A.; Levenson, M. Certification by the Karl Fischer method of the water content in SRM 2890, water saturated 1-octanol, and the analysis of associated interlaboratory bias in the measurement process Fresen. J. Anal. Chem. 2000, 367, 1-7
6. Franks, N. P.; Abraham, M. H.; Lieb, W. R. Molecular organization of liquid n-octanol: An X-ray diffraction analysis J. Pharm. Sci. 1993, 82, 466-470
7. Hu, K.; Zhou, Y.; Shen, J.; Ji, Z.; Cheng, G. Microheterogeneous structure of 1-octanol in neat and water-saturated state J. Phys. Chem. B 2007, 111, 10160-10165
8. MacCallum, J. L.; Tieleman, D. P. Structures of neat and hydrated 1-octanol from computer simulations J. Am. Chem. Soc. 2002, 124, 15085-15093
9. Shallard-Brown, H. A.; Watkin, D. J.; Cowley, A. R. n-Octanol Acta Crystallogr., Sect. E 2005, 61, 213-214
10. DeBolt, S. E.; Kollman, P. A. Investigation of structure, dynamics, and solvation in 1-octanol and its water-saturated solution: Molecular dynamics and free-energy perturbation studies J. Am. Chem. Soc. 1995, 117, 5316-5340
11. Balaz, S. Lipophilicity in trans-bilayer transport and subcellular pharmacokinetics Perspect. Drug Discovery Des. 2000, 19, 157-177
12. Seelig, A.; Gatlik-Landwojtowicz, E. Inhibitors of multidrug efflux transporters: Their membrane and protein interactions Mini-Rev. Med. Chem. 2005, 5, 135-151
13. Cojocaru, V.; Balali-Mood, K.; Sansom, M. S. P.; Wade, R. C. Structure and dynamics of the membrane-bound cytochrome P450 2C9 PLoS Comput. Biol. 2011, 7, e1002152
14. Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.; Browner, M. F. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2 Nat. Struct. Biol. 1996, 3, 927-933
15. Marrink, S. J.; Berendsen, H. J. C. Simulation of water transport through a lipid membrane J. Phys. Chem. 1994, 98, 4155-4168
16. Scheuplein, R. J.; Blank, I. H.; Brauner, G. J.; MacFarlane, D. J. Percutaneous absorption of steroids J. Invest. Dermatol. 1969, 52, 63-70
17. Riebesehl, W.; Tomlinson, E.; Gruenbauer, H. J. M. Thermodynamics of solute transfer between alkanes and water J. Phys. Chem. 1984, 88, 4775-4779
18. Schulte, J.; Durr, J.; Ritter, S.; Hauthal, W. H.; Quitzsch, K.; Maurer, G. Partition coefficients for environmentally important, multifunctional organic compounds in hexane + water J. Chem. Eng. Data 1998, 43, 69-73
19. Runyan, A.; Perrin, J. H.; Vilallonga, F. A. Interfacial tensions and partition coefficients in water/heptane systems containing 2,6- diisopropylphenol, n-alkylphenols and cycloalkanols J. Pharm. Pharmacol. 1988, 40, 203-204
20. Chikhale, E. G.; Ng, K. Y.; Burton, P. S.; Borchardt, R. T. Hydrogen bonding potential as a determinant of the in vitro and in situ blood-brain barrier permeability of peptides Pharm. Res. 1994, 11, 412-419
21. Xiang, T. X.; Anderson, B. D. The relationship between permeant size and permeability in lipid bilayer membranes J. Membr. Biol. 1994, 140, 111-122
22. Abraham, M. H.; Acree, W. E., Jr.; Leo, A. J.; Hoekman, D.; Cavanaugh, J. E. Water-solvent partition coefficients and ΔLog P values as predictors for blood-brain distribution; application of the Akaike information criterion J. Pharm. Sci. 2010, 99, 2492-2501
23. Hafkenscheid, T. L.; Tomlinson, E. Correlations between alkane/water and 1-octanol/water distribution coefficients and isocratic reversed-phase liquid chromatographic capacity factors of acids, bases and neutrals Int. J. Pharm. 1983, 16, 225-239
24. Young, R. C.; Mitchell, R. C.; Brown, T. H.; Ganellin, C. R.; Griffiths, R.; Jones, M.; Rana, K. K.; Saundners, D. D.; Smith, I. R.; Sore, N. E.; Wilks, T. J. Development of a new physicochemical model for brain penetration and its application to the design of centrally acting H2 receptor histamine antagonists J. Med. Chem. 1988, 31, 656-671
25. van de Waterbeemd, H.; Kansy, M. Hydrogen-bonding capacity and brain penetration Chimia 1992, 46, 299-303
26. alk J. Med. Chem. 2005, 48, 3269-3279
27. Barry, J. A.; Gawrisch, K. Direct NMR evidence for ethanol binding to the lipid-water interface of phospholipid bilayers Biochemistry 1994, 33, 8082-8088
28. Balgavy, P.; Dubnickova, M.; Kucerka, N.; Kiselev, M. A.; Yaradaikin, S. P.; Uhrikova, D. Bilayer thickness and lipid interface area in unilamellar extruded 1,2-diacylphosphatidylcholine liposomes: A small-angle neutron scattering study Biochim. Biophys. Acta 2001, 1512, 40-52
29. Hristova, K.; White, S. H. Determination of the hydrocarbon core structure of fluid dioleoylphosphocholine (DOPC) bilayers by X-ray diffraction using specific bromination of the double-bonds: Effect of hydration Biophys. J. 1998, 74, 2419-2433
30. Eisenberg, D.; Weiss, R. M.; Terwilliger, T. C. The helical hydrophobic moment: A measure of the amphiphilicity of a helix Nature 1982, 299, 371-374
31. Brasseur, R.; Vandenbosch, C.; van den Bossche, H.; Ruysschaert, J.-M. Mode of inserion of miconazole ketonazole and deacylated ketoconazole in lipid layers. A conformational analysis Biochem. Pharmacol. 1983, 32, 2175-2180
32. Fischer, H.; Kansy, M.; Bur, D. CAFCA: A novel tool for the calculation of amphiphilic properties of charged drug molecules Chimia 2000, 54, 640-645
33. Kessel, A.; Musafia, B.; Ben-Tal, N. Continuum solvent model studies of the interactions of an anticonvulsant drug with a lipid bilayer Biophys. J. 2001, 80, 2536-2545
34. Oren, I.; Fleishman, S. J.; Kessel, A.; Ben Tal, N. Free diffusion of steroid hormones across biomembranes: A simplex search with implicit solvent model calculations Biophys. J. 2004, 87, 768-779
35. Tanaka, M.; Fukuda, H.; Nagai, T. Permeation of drug through a model membrane consisting of millipore filter with oil Chem. Pharm. Bull. 1978, 26, 9-13
36. Leahy, D. E.; Taylor, P. J.; Wait, A. R. Model solvent systems for QSAR. 1. Propylene glycol dipelargonate (PGDP). A new standard solvent for use in partition coefficient determination Quant. Struct.-Act. Relat. 1989, 8, 17-31
37. el-Tayar, N.; Tsai, R. S.; Testa, B.; Carrupt, P. A.; Hansch, C.; Leo, A. Percutaneous penetration of drugs: A quantitative structure-permeability relationship study J. Pharm. Sci. 1991, 80, 744-749
38. Seiler, P. Interconversion of lipophilicities from hydrocarbon/water systems into the octanol/water system Eur. J. Med. Chem. 1974, 9, 473-479
39. Lukacova, V.; Peng, M.; Tandlich, R.; Hinderliter, A.; Balaz, S. Partitioning of organic compounds in phases imitating the headgroup and core regions of phospholipid bilayers Langmuir 2006, 22, 1869-1874
40. Kakemi, K.; Sezaki, H.; Muranishi, S.; Tsujimura, Y. Absorption and excretion of drugs. XL. Enhancement of the rectal absorption of pharmaceutical amines with lauryl sulfate and saccharinate anions Chem. Pharm. Bull. 1969, 17, 1641-1650
41. Weilgung, F. The local stimulating effect of calcium salts in relation to their chemical constitution Arch. Exp. Pathol. Pharmakol. 1932, 167, 71-72
42. Burton, P. S.; Conradi, R. A.; Hilgers, A. R.; Ho, N. F. H.; Maggiora, L. L. The relationship between peptide structure and transport across epithelial cell monolayers J. Controlled Release 1992, 19, 87-97
43. Niimi, A. J. Solubility of organic chemicals in octanol, triolein and cod liver oil and relationships between solubility and partition coefficients Water Res. 1991, 25, 1515-1521
44. Poulin, P.; Krishnan, K. A biologically-based algorithm for predicting human tissue:blood partition coefficients of organic chemicals Hum. Exp. Toxicol. 1995, 14, 273-280
45. Poulin, P.; Krishnan, K. Molecular structure-based prediction of the partition coefficients of organic chemicals for physiological pharmacokinetic models Toxicol. Methods 1996, 6, 117-137
46. Poulin, P.; Theil, F. P. A priori prediction of tissue:plasma partition coefficients of drugs to facilitate the use of physiologically-based pharmacokinetic models in drug discovery J. Pharm. Sci. 2000, 89, 16-35
47. Mannhold, R.; van de Waterbeemd, H. Substructure and whole molecule approaches for calculating log P J. Comput.-Aided Mol. Des. 2001, 15, 337-354
48. Zerara, M.; Brickmann, J.; Kretschmer, R.; Exner, T. E. Parameterization of an empirical model for the prediction of n-octanol, alkane and cyclohexane/water as well as brain/blood partition coefficients J. Comput. -Aided Mol. Des. 2009, 23, 105-111
49. Abraham, M. H.; Acree, W. E. Linear free-energy relationships for water/hexadec-1-ene and water/deca-1,9-diene partitions, and for permeation through lipid bilayers; comparison of permeation systems New J. Chem. 2012, 36, 1798-1806
50. Nitsche, J. M.; Kasting, G. B. A correlation for 1,9-decadiene/water partition coefficients J. Pharm. Sci. 2013, 102, 136-144
51. Leo, A.; Jow, P. Y.; Silipo, C.; Hansch, C. Calculation of hydrophobic constant (log P) from π and f constants J. Med. Chem. 1975, 18, 865-868
52. Origin 7.0; Origin Lab: Northampton, MA, 2002.
53. Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the delta log P parameter of Seiler J. Pharm. Sci. 1994, 83, 1085-1100
54. Avdeef, A. pH-metric log P. Part 1. Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances Quant. Struct.-Act. Relat. 1992, 11, 510-517
55. Box, K.; Comer, J.; Huque, F. Correlations between PAMPA permeability and log P. In Pharmacokinetic Profiling in Drug Research; Wiley-VCH Verlag: 2006; pp 243-257.
56. Caron, G.; Carrupt, P. A.; Testa, B.; Ermondi, G.; Gasco, A. Insight into the lipophilicity of the aromatic N-oxide moiety Pharm. Res. 1996, 13, 1186-1190
57. Caron, G.; Gaillard, P.; Carrupt, P. A.; Testa, B. Lipophilicity behavior of model and medicinal compounds containing a sulfide, sulfoxide, or sulfone moiety Helv. Chim. Acta 1997, 80, 449-462
58. el Tayar, N.; Tsai, R. S.; Testa, B.; Carrupt, P. A.; Leo, A. Partitioning of solutes in different solvent systems. The contribution of hydrogen-bonding capacity and polarity J. Pharm. Sci. 1991, 80, 590-598
59. Gobas, F. A. P. C.; Lahittete, J. M.; Garofalo, G.; Shiu, W. Y.; Mackay, D. A novel method for measuring membrane-water partition coefficients of hydrophobic organic chemicals: Comparison with 1-octanol-water partitioning J. Pharm. Sci. 1988, 77, 265-272
60. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley: New York, 1979.
61. Leahy, D. E.; Morris, J. J.; Taylor, P. J.; Wait, A. R. Model solvent systems for QSAR 2. Fragment values ('f-values') for the 'critical quartet' J. Chem. Soc., Perkin Trans. 2 1992, 723-731
62. Lukacova, V.; Peng, M.; Fanucci, G.; Tandlich, R.; Hinderliter, A.; Maity, B.; Mannivanan, E.; Cook, G. R.; Balaz, S. Drug-membrane interactions studied in phospholipid monolayers adsorbed on nonporous alkylated microspheres J. Biomol. Screening 2007, 12, 186-202
63. Pagliara, A.; Testa, B.; Carrupt, P. A.; Jolliet, P.; Morin, C.; Morin, D.; Urien, S.; Tillement, J. P.; Rihoux, J. P. Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist J. Med. Chem. 1998, 41, 853-863
64. Ter Laak, A. M.; Tsai, R. S.; Donne-Op den Kelder, G. M.; Carrupt, P. A.; Testa, B.; Timmerman, H. Lipophilicity and hydrogen-bonding capacity of H1-antihistaminic agents in relation to their central sedative side-effects Eur. J. Pharm. Sci. 1994, 2, 373-384
65. ClogP, version 3.51; Daylight Chemical Information Systems: Irvine, CA, 1991.
66. Toulmin, A.; Wood, J. M.; Kenny, P. W. Toward prediction of alkane/water partition coefficients J. Med. Chem. 2008, 51, 3720-3730
67. Wohnsland, F.; Faller, B. High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes J. Med. Chem. 2001, 44, 923-930
68. Bio-Loom for Windows, version 1.5; BioByte Corp.: Claremont, CA, 2006.
69. SAS Enterprise Guide, version 4.3; SAS Institute Inc.: Cary, NC, 2010.
70. Kubinyi, H. Drug partitioning: Relationships between forward and reverse rate constants and partition coefficient J. Pharm. Sci. 1978, 67, 262-263
71. van de Waterbeemd, H.; van Bakel, H.; Jansen, A. Transport in quantitative structure-activity relationships VI: Relationship between transport rate constants and partition coefficients J. Pharm. Sci. 1981, 70, 1081-1082
72. Balaz, S. Modeling kinetics of subcellular disposition of chemicals Chem. Rev. 2009, 109, 1793-1899
73. de Bruijn, J.; Busser, F.; Seinen, W.; Hermens, J. Determination of octanol/water partition coefficients for hydrophobic organic chemicals with the ″slow-stirring″ method Environ. Toxicol. Chem. 1989, 8, 499-512
74. Leo, A. The octanol-water partition coefficient of aromatic solutes: The effect of electronic interactions, alkyl chains, hydrogen bonds, and ortho-substitution J. Chem. Soc., Perkin Trans. 2 1983, 825-838
75. Platts, J. A.; Butina, D.; Abraham, M. H.; Hersey, A. Estimation of molecular linear free energy relation descriptors using a group contribution approach J. Chem. Inf. Comput. Sci. 1999, 39, 835-845
76. Abraham, M. H.; Platts, J. A. Hydrogen bond structural group constants J. Org. Chem. 2001, 66, 3484-3491 General Medical Sciences