Lipophilic and electrostatic forces encoded in IAM-HPLC indexes of basic drugs: Their role in membrane partition and their relationships with BBB passage data

European Journal of Pharmaceutical Sciences

Volumn 45, Issue 5, 2012, Pages 685-692

  Grumetto, Lucia ^a   Carpentiero, Carmen ^a   Barbato, Francesco ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

BBB passage; IAM HPLC; Lipophilicity; Membrane partition; Phospholipids

Indexed keywords

ATENOLOL; CHLORPROMAZINE; CIMETIDINE; CLONIDINE; HALOPERIDOL; IMIPRAMINE; MIANSERIN; MIDAZOLAM; MORPHINE; NICOTINE; PROMAZINE; PROMETHAZINE; PROPRANOLOL; RANITIDINE;

AQUEOUS SOLUTION; ARTICLE; BLOOD BRAIN BARRIER; CHEMICAL BOND; DRUG EFFICACY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; IN VIVO STUDY; IONIZATION; LIPOPHILICITY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PARTITION COEFFICIENT; PASSIVE TRANSPORT; PH; PHOSPHOLIPID MEMBRANE; PRIORITY JOURNAL; STATIC ELECTRICITY;

1-OCTANOL; BLOOD-BRAIN BARRIER; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; PHOSPHOLIPIDS; STATIC ELECTRICITY; WATER;

EID: 84857919473     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.01.008     Document Type: Article

References (25)

1. N.J. Abbott, A.A. Patabendige, D.E. Dolmen, S.R. Yusof, and D.J. Begley Structure and function in the blood-brain barrier Neurobiol. Dis. 37 1 2010 13 25
2. M.H. Abraham, H.S. Chadha, and R.C. Mitchell Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain J. Pharm. Sci. 83 1994 1257 1268 (Pubitemid 24282331)
3. A. Avdeef, K.J. Box, J.E.A. Comer, C. Hibbert, and K.Y. Tam PH-metric log P 10. Determination of liposomal membrane-water partition coefficients of ionizable drugs Pharm. Res. 15 1998 209 215 (Pubitemid 28144231)
4. M. Amato, F. Barbato, P. Morrica, F. Quaglia, and M.I. La Rotonda Interactions between amines and phospholipids: a chromatographic study on immobilized artificial membrane (IAM) stationary phase at various pH values Helv. Chim. Acta 83 2000 2836 2847
5. F. Barbato, M.I. La Rotonda, and F. Quaglia Chromatographic indices determined on an immobilized artificial membrane (IAM) column as descriptors of lipophilic and polar interactions of 4-phenyldihydropyridine calcium-channel blockers with biomembranes Eur. J. Med. Chem. 31 1996 311 318
6. F. Barbato, M.I. La Rotonda, and F. Quaglia Chromatographic indexes on immobilized artificial membranes for local anesthetics: relationships with activity data on closed sodium channels Pharm. Res. 14 1997 1699 1705 (Pubitemid 28062913)
7. F. Barbato, B. Cappello, A. Miro, M.I. La Rotonda, and F. Quaglia Chromatographic indexes on immobilized artificial membranes for the prediction of transdermal transport of drugs Il Farmaco. 53 1998 655 661 (Pubitemid 29139835)
8. F. Barbato, G. di Martino, L. Grumetto, and M.I. La Rotonda Prediction of drug-membrane interactions by IAM-HPLC: effects of different phospholipid stationary phases on the partition of bases Eur. J. Pharm. Sci. 22 2004 261 269 (Pubitemid 38758013)
9. F. Barbato, G. di Martino, L. Grumetto, and M.I. La Rotonda Can protonated beta-blockers interact with biomembranes stronger than neutral isolipophilic compounds? A chromatographic study on three different phospholipid stationary phases (IAM-HPLC) Eur. J. Pharm. Sci. 25 2005 379 386 (Pubitemid 40853865)
10. F. Barbato The use of immobilized artificial membrane (IAM) chromatography for determination of lipophilicity Curr. Comput.-Aided Drug Des. 02 4 2006 341 352 (Pubitemid 46029593)
11. F. Barbato, V. Cirocco, L. Grumetto, and M.I. La Rotonda Comparison between immobilized artificial membrane (IAM) HPLC data and lipophilicity in n-octanol for quinolone antibacterial agents Eur. J. Pharm. Sci. 31 2007 288 297 (Pubitemid 47068939)
12. w versus liquid-liquid partition coefficients as a model of the hydrophobicity of phenylureas, S-triazines and phenoxycarbonic acid derivatives J. Chromatogr. 261 1983 329 343 (Pubitemid 13054545)
13. A. Ducarme, M. Neuwels, S. Goldstein, and R. Massingham IAM retention and blood brain barrier penetration Eur. J. Med. Chem. 33 1998 215 223 (Pubitemid 28188258)
14. N. El Tayar, R.S. Tsai, B. Testa, P.-A. Carrupt, and A. Leo Partitioning of solutes in different solvent systems: the contribution of hydrogen bonding capacity and polarity J. Pharm. Sci. 80 6 1991 590 598
15. S.D. Krämer, N.J. Abbott, and D.J. Begley Biological models to study blood-brain barrier permeation B. Testa, H. van de Waterbeemd, G. Folkers, R.H. Guy, Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical and Computational Strategies 2001 Wiley-VHCA Zurich 127 153
16. A.J. Leo, C. Hansch, and D. Elkins Partition coefficients and their use Chem. Rev. 71 1971 525 616
17. A. Mälkiä, L. Murtomäki, A. Urtti, and K. Kontturi Drug permeation in biomembranes: in vitro and in silico prediction and influence of physicochemical properties Eur. J. Pharm. Sci. 23 2004 13 47 (Pubitemid 39485996)
18. S. Ong, H. Liu, and C. Pidgeon Immobilized-Artificial-Membrane Chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability J. Chromatogr. A 728 1996 113 128 (Pubitemid 26146680)
19. F. Pehourcq, M. Matoga, and B. Bannwarth Diffusion of arylproprionate non-steroidal anti-inflammatory drugs into the cerebrospinal fluid: a quantitative structure-activity relationship approach Fundam. Clin. Pharmacol. 18 1 2004 65 70 (Pubitemid 38200920)
20. J.A. Platts, M.H. Abraham, Y.H. Zhao, A. Hersey, L. Ijaz, and D. Butina Correlation and prediction of a large blood-brain distribution data set - an LFER study Eur. J. Med. Chem. 36 9 2001 719 730 (Pubitemid 32973863)
21. A. Taillardat-Bertschinger, F. Barbato, M.T. Quercia, P.A. Carrupt, M. Reist, M.I. La Rotonda, and B. Testa Structural properties governing retention mechanisms on immobilized artificial membrane (IAM) HPLC columns Helv. Chim. Acta 85 2002 519 532 (Pubitemid 34225480)
22. A. Taillardat-Bertschinger, P.A. Carrupt, F. Barbato, and B. Testa Immobilized artificial membrane HPLC in drug research J. Med. Chem. 46 2003 655 665 (Pubitemid 36258854)
23. J.B. van Bree, A.G. de Beer, M. Danhof, and D.D. Breiner Drug transport across the blood-brain barrier I. Anatomical and physiological aspects Pharm. Weekbl. Sci. 14 1992 305 310
24. C.Y. Yang, S.J. Cai, H. Liu, and C. Pidgeon Immobilized artificial membranes: screens for drug-membrane interactions Adv. Drug Deliv. Rev. 23 1996 229 256 (Pubitemid 27047005)
25. R.C. Young, R.C. Mitchell, T.H. Brown, C.R. Ganellin, R. Griffits, M. Jones, K.K. Rana, and D. Saunders 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. 31 3 1988 656 671 (Pubitemid 18070588)