Relationship between brain tissue partitioning and microemulsion retention factors of CNS drugs

Journal of Medicinal Chemistry

Volumn 52, Issue 6, 2009, Pages 1693-1700

  Wan, Hong ^a   Åhman, Madeleine ^a   Holmén, Anders G ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMANTADINE; AMOXAPINE; BUSPIRONE; CARBAMAZEPINE; CARISOPRODOL; CENTRAL NERVOUS SYSTEM AGENTS; CITALOPRAM; CLOZAPINE; CYCLOBENZAPRINE; DIAZEPAM; DOXEPIN; FLUOXETINE; HALOPERIDOL; HYDROXYZINE; LAMOTRIGINE; MAPROTILINE; MESORIDAZINE; METHYLPHENIDATE; METOCLOPRAMIDE; MIDAZOLAM; MIRTAZAPINE; NORTRIPTYLINE; OLANZAPINE; PAROXETINE; PERGOLIDE; PERPHENAZINE; PROPRANOLOL; QUETIAPINE; RISPERIDONE; UNINDEXED DRUG;

ARTICLE; BRAIN TISSUE; CAPILLARY ELECTROPHORESIS; DRUG RETENTION; LIPOPHILICITY; MASS SPECTROMETRY; MICROEMULSION; MICROEMULSION ELECTROKINETIC CHROMATOGRAPHY;

BRAIN; CENTRAL NERVOUS SYSTEM; CHROMATOGRAPHY, LIQUID; EMULSIONS; MASS SPECTROMETRY;

EID: 64349123113     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801441s     Document Type: Article

References (42)

1. Kalvass, J. C.; Maurer, T. S.; Pollack, G. M. Use of plasma and brain unbound fractions to assess the extent of brain distribution of 34 drugs: comparison of unbound concentration ratios to in vivo P-glycoprotein efflux ratios. Drug Metab. Dispos. 2007, 35 (4), 660-666.
2. Liu, X. R.; Chen, C. P. Strategies to optimize brain penetration in drug discovery. Curr. Opin. Drue Discovery Dev. 2005, 8 (4), 505-512.
3. Maurer, T. S.; DeBartolo, D. B.; Tess, D. A.; Scott, D. O. Relationship between exposure and nonspecific binding of 33 central nervous system drugs in mice. Drug Metab. Dispos. 2005, 33 (1), 175-181.
4. Summerfield, S. G.; Stevens, A. J.; Cutler, L.; Osuna, M. D.; Hammond, B.; Tang, S. P.; Hersey, A.; Spalding, D. J.; Jeffrey, P. Improving the in vitro prediction of in vivo central nervous system penetration: integrating permeability, P-glycoprotein efflux, and free fractions in blood and brain. J. Pharmacol. Exp. Ther. 2006, 316 (3), 1282-1290.
5. Summerfield, S. G.; Read, K.; Begley, D. J.; Obradovic, T.; Hidalgo, I. J.; Coggon, S.; Lewis, A. V.; Porter, R. A.; Jeffrey, P. Central nervous system drug disposition: The relationship between in situ brain permeability and brain free fraction. J. Pharmacol. Exp. Ther. 2007, 322 (1), 205-213.
6. Friden, M.; Gupta, A.; Antonsson, M.; Bredberg, U.; Hammarlund-Udenaes, M. In vitro methods for estimating unbound drug concentrations in the brain interstitial and intracellular fluids. Drug Metab. Dispos. 2007, 35 (9), 1711-1719.
7. Wan, H.; Rehngren, M.; Giordanetto, F.; Bergstrom, F.; Tunek, A. High-throughput screening of drug-brain tissue binding and in silico prediction for assessment of central nervous system drug delivery. J. Med. Chem. 2007, 50 (19), 4606-4615.
8. Hughes, J. D.; Blagg, J.; Price, D. A.; Bailey, S.; Decrescenzo, G. A.; Devraj, R. V.; Ellsworth, E.; Fobian, Y. M.; Gibbs, M. E.; Gilles, R. W.; Greene, N.; Huang, E.; Krieger-Burke, T.; Loesel, J.; Wager, T.; Whiteley, L.; Zhang, Y. Physiochemical drug properties associated with in vivo toxicological outcomes. Bioorg. Med. Chem. Lett. 2008, 18 (17), 4872-5.
9. Lewis, D. F. V.; Lake, B. G.; Ito, Y.; Dickins, M. Lipophilicity relationships in inhibitors of CYP2C9 and CYP2C19 enzymes. J. Enzyme Inhib. Med. Chem. 2006, 21 (4), 385-389.
10. Austin, R. P.; Barton, P.; Cockroft, S. L.; Wenlock, M. C.; Riley, R. J. The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties. Drug Metab. Dispos. 2002, 30 (12), 1497-1503.
11. Yamazaki, K.; Kanaoka, M. Computational prediction of the plasma protein-binding percent of diverse pharmaceutical compounds. J. Pharm. Sci. 2004, 93 (6), 1480-1494.
12. Carrozzino, J. M.; Khaledi, M. G. Interaction of basic drugs with lipid bilayers using liposome electrokinetic chromatography. Pharm. Res. 2004, 21 (12), 2327-2335.
13. Pascoe, R. J.; Masucci, J. A.; Foley, J. P. Investigation of vesicle electrokinetic chromatography as an in vitro assay for the estimation of intestinal permeability of pharmaceutical drug candidates. Electrophoresis 2006, 27 (4 Special Issue SI), 793-804.
14. Ornskov, E.; Gottfries, J.; Erickson, M.; Folestad, S. Experimental modelling of drug membrane permeability by capillary electrophoresis using liposomes, micelles and microemulsions. J. Pharm. Pharmacol. 2005, 57 (4), 435-442.
15. Wang, Y. J.; Sun, J.; Liu, H. Z.; He, Z. G. Prediction of human drug absorption using liposome electrokinetic chromatography. Chromatographia 2007, 65 (3 -4), 173-177.
16. Holland, L. A.; Leigh, A. M. Bilayered phospholipid micelles and capillary electrophoresis: a new additive for electrokinetic chroma-tography. Electrophoresis 2003, 24 (17), 2935-2939.
17. Avdeef, A.; Testa, B. Physicochemical profiling in drug research: a brief survey of the state-of-the-art of experimental techniques. Cell. Mol.Life Sci. 2002, 59 (10), 1681-1689.
18. Giaginis, C.; Tsantili-Kakoulidou, A. Current state of the art in HPLC methodology for lipophilicity assessment of basic drugs. A review. J. Liq. Chromatogr. Relat. Technol. 2008, 31 (1), 79-96.
19. Wan, H.; Holmen, A., High throughput screening of physicochemical properties and ADME profiling in drug discovery. Comb. Chem. High Troughput Screening 2009, 12, (3), (an invited review, in press).
20. Lombardo, F.; Shalaeva, M. Y.; Tupper, K. A.; Gao, F.; Abraham, M. H. ElogP(oct): A tool for lipophilicity determination in drug discovery. J. Med. Chem. 2000, 43 (15), 2922-2928.
21. Ishihama, Y.; Oda, Y.; Uchikawa, K.; Asakawa, N. Evaluation ofsolute hydrophobicity by microemulsion electrokinetic chromatography. Anal. Chem. 1995, 67 (9), 1588-1595.
22. Altria, K. D.; Mahuzier, P. E.; Clark, B. J. Background and operating parameters in microemulsion electrokinetic chromatography. Electrophoresis 2003, 24 (3), 315-324.
23. Klotz, W. L.; Schure, M. R.; Foley, J. P. Determination of octanol-water partition coefficients of pesticides by microemulsion electroki-netic chromatography. J. Chromatogr. 2001, 930 (1-2), 145-154.
24. Klotz, W. L.; Schure, M. R.; Foley, J. P. Rapid estimation of octanol-water partition coefficients using synthesized vesicles in electrokinetic chromatography. J. Chromatogr., A 2002, 962 (1-2), 207-219.
25. Hansen, S. H. Recent applications of microemulsion electrokinetic chromatography. Electrophoresis 2003, 24 (22-23), 3900-3907.
26. Poole, S. K.; Durham, D.; Kibbey, C. Rapid method for estimating the octanol-water partition coefficient (log Po/w) by microemulsion electrokinetic chromatography. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2000, 745 (1), 117-126.
27. Poole, S. K.; Poole, C. F. Separation methods for estimating octanol-water partition coefficients. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2003, 797 (1-2), 3-19.
28. Wong, K. S.; Kenseth, J.; Strasburg, R. Validation and long-term assessment of an approach for the high throughput determination of lipophilicity (log Po/w) values using multiplexed, absorbance-based capillary electrophoresis. J. Pharm. Sci. 2004, 93 (4), 916-931.
29. Wan, H.; Thompson, R. A. Capillary electrophoresis technologies for drug screening. Drug Discovery Today: Technol. 2005, 2 (2), 171-178, an invited review.
30. Goetzinger, W. K.; Cai, H. Buffer system for the separation of neutral and charged small molecules using micellar electrokinetic chroma-tography with mass spectrometric detection. J. Chromatogr. 2005, 1079 (1-2), 372-381.
31. Himmelsbach, M.; Haunschmidt, M.; Buchberger, W.; Klampfl, C. W. Microemulsion electrokinetic chromatography with on-line atmospheric pressure photoionization mass spectrometric detection. Anal. Chem. 2007, 79 (4), 1564-1568.
32. Schappler, J.; Guillarme, D.; Rudaz, S.; Veuthey, J. L. Microemulsion electrokinetic chromatography hyphenated to atmospheric pressure photoionization mass spectrometry. Electrophoresis 2008, 29 (1), 11-19.
33. a values of pharmaceuticals by pressure-assisted capillary electrophoresis and mass spectrometry. Rapid Commun. Mass Spectrom. 2003, 17 (23), 2639-2648.
34. Wan, H.; Bergstrom, F. High-throughput screening of drug-protein binding in drug discovery. J. Liq. Chromatogr. Rel. Technol. 2007, 30, 681-700.
35. Donovan, S. F.; Pescatore, M. C. Method for measuring the logarithm of the octanol-water partition coefficient by using short octadecyl-poly(vinyl alcohol) high-performance liquid chromatography columns. J. Chromatogr., A 2002, 952 (1-2), 47-61.
36. Ghasemi, J.; Saaidpour, S. Quantitative structure-property relationship study of n-octanol-water partition coefficients of some of diverse drugs using multiple linear regression. Anal. Chim. Acta 2007, 604 (2), 99-106.
37. ACD/LogP Database; Advanced Chemistry Developments, Inc.: Toronto, 2007.
38. Wan, H.; Ulander, J. High-throughput pKa screening and prediction amenable for ADME profiling. Exp. Opin. Drug Metab. Toxicol. 2006, 2 (2), 139-155, an invited review.
39. Yang, S.; Bumgarner, J. G.; Kruk, L. F. R.; Khaledi, M. G. Quantitative structure-activity relationships studies with micellar electrokinetic chromatography Influence of surfactant type and mixed micelles on estimation of hydrophobicity and bioavailability. J. Chromatogr., A 1996, 721, 323-335.
40. Gabel-Jensen, C.; Hansen, H. S.; Stig, P.-B. Separation of neutral compounds by microemulsion electrokinetic chromatography: fundamental studies on selectivity. Electrophoresis 2001, 22, 1330-1336.
41. 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 (1), 16-35.
42. Trainor, G. L. The importance of plasma protein binding in drug discovery. Exp. Opin. Drug Discovery 2007, 2 (1), 51-64.