Blood-Brain Barrier Permeation Models: Discriminating between Potential CNS and Non-CNS Drugs Including P-Glycoprotein Substrates

Journal of Chemical Information and Computer Sciences

Volumn 44, Issue 1, 2004, Pages 239-248

  Adenot, Marc ^a   Lahana, Roger ^a  

^a Synt:em   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BRAIN; CARBOHYDRATES; DIFFUSION; DRUG PRODUCTS; MATHEMATICAL MODELS; METABOLISM; NEUROLOGY; PROTEINS; SCREENING; SUBSTRATES; VIRTUAL REALITY;

BLOOD-BRAIN BARRIER; VIRTUAL SCREENING;

BLOOD;

CENTRAL NERVOUS SYSTEM AGENTS; GLYCOPROTEIN P;

ARTICLE; BIOLOGICAL MODEL; BLOOD BRAIN BARRIER; CENTRAL NERVOUS SYSTEM; DRUG EFFECT; METABOLISM;

BLOOD-BRAIN BARRIER; CENTRAL NERVOUS SYSTEM; CENTRAL NERVOUS SYSTEM AGENTS; MODELS, BIOLOGICAL; P-GLYCOPROTEINS;

EID: 1542426103     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci034205d     Document Type: Article

References (34)

1. Grassy, G.; Calas, B.; Yasri, A.; Lahana, R.; Woo, J.; Iyer, S.; Kaczorek, M.; Floch, R.; Buelow, R. Computer-Assisted Rational Design of Immunosuppressive Compounds. Nat. Biotechnol. 1998, 16, 748-752.
2. Levin, V. A. Relationship of Octanol/Water Partition Coefficient and molecular Weight to Rat Brain Capillary Permeability. J. Med. Chem. 1980, 23, 682-684.
3. Young, R. C.; Mitchell, R. C.; Brown, T. H.; Ganellin, C. R.; Griffiths, R.; Jones, M.; Rana, K. K.; Saunders, 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.
4. Van de Waterbeemd, H.; Kansy, M. Hydrogen-Bonding Capacity and Brain Penetration. Chimia 1992, 46, 299-303.
5. Kelder, J.; Grootenhuis, P. D. J.; Bayada, D. M.; Delbressine, L. P. C.; Ploemen, J. P. Polar Molecular Surface as a Dominating Determinant for Oral Absorption and Brain Penetration of Drugs. Pharm. Res. 1999, 16, 1514-1519.
6. Clark, D. E. Rapid Calculation of Polar Molecular Surface Area and Its Application to the Prediction of Transport Phenomena. 2. Prediction of Blood-Brain Barrier Penetration. J. Pharm. Sci. 1999, 88, 8, 815-821.
7. Liu, R.; Sun, H.; So, S. Development of Quantitative Structure-Property relationship Models for early ADME Evakluation in drug Discovery. 2. Blood-Brain Barrier Penetration. J. Chem. Inf. Comput. Sci. 2001, 41, 1623-1632.
8. Jorgensen, F. S.; Jensen, L. H.; Capion, D.; Christensen, I. T. Prediction of Blood-Brain Barrier Penetration. In Rational Approaches to drug Design; Höltje H.-D., Sippl, W., Eds.; 2001; pp 281-285.
9. Abraham, M. H.; Chadha, H. S.; Mitchell, R. C. Hydrogen Bonding. 33. Factors that Influence the Distribution of Solutes Between Blood and Brain. J. Pharm. Sci. 1994, 83, 1257-1268.
10. Van de Waterbeemd, H.; Camenish, G.; Folkers, G.; Chretien, J. R.; Raevsky, O. A. Estimation of Blood-Brain Barrier Crossing of Drugs Using Molecular Size and Shape, and H-bonding descriptors. J. Drugs Target. 1998, 6, 2, 151-165.
11. Lombarde, F.; Blake, J. F.; Curatolo, W. Computation of Brain-Blood Partitioning of Organic Solutes via Free-Energy Calculations. J. Med. Chem. 1996, 39, 4750-4755.
12. Keseru, G. M.; Molnar, L. High-Througput Prediction of Blood-Brain Partitioning: A Thermodynamic Approach. J. Chem. Inf. Comput. Sci. 2001, 41, 120-128.
13. Norinder, U.; Sjöberg, P.; Osterberg, T. Theoritical Calculations and Prediction of brain-blood partitionning of organic solutes using MolSurf parametrization and PLS statistics. J. Pharm. Sci. 1998, 88, 815-821.
14. Crivori, P.; Cruciani, G.; Carrupt, P.-A.; Testa, B. Predicting Blood-Brain Permeation from Three-Dimensional Molecular Structure. J. Med. Chem. 2000, 43, 2204-2216.
15. Osterberg, T.; Norinder, U. Prediction of Polar Surface Area and Drug Transport Processes using Simple Parameters and PLS Statistics. J. Chem. Inf. Comput. Sci. 2000, 40, 1408-1411.
16. Rose, K.; Hall, L. H.; Kier, L. B. Modeling Blood_Brain Barrier Partitioning Using the Electrotopological State. J. Chem. Inf. Comput. Sci. 2002, 42, 651-666.
17. Ajay, Bemis, G. W.; Murcko, M. A. Designing Libraries with CNS Activity. J. Med. Chem. 1999, 42, 4942-4951.
18. Basak, S. C.; Gute, B. D.; Drewes, L. R. Predicting Blood_Brain Transport of drugs: A Computational approach. Pharm. Res. 1996, 13, 5, 775-778.
19. Comprehensive Medicinal Chemistry Release 94.1 available from MDL Information Systems Inc., San Leandro, CA 94577.
20. MACCS-II Drug Data report available from MDL Information Systems Inc., San Leandro, CA 94577.
21. WDI, Daylight Chemical Information Systems, Inc., 27401 Los Altos, #360, Mission Viejo, CA 92691, U.S.A. E-mail: info@daylight.com.
22. Guidelines for ATC classification and DDD assignment. WHO Collaborating Centre for Drug Statistics Methodology: Oslo, Norway 2001; ISBN 82 90312 32 6 (www.whocc.no/atcddd/).
23. Willett, P.; Barnard, J. M.; Downs, G. M. Chemical Similarity Searching. J. Chem. Inf. Comput. Sci. 1998, 38, 983-996.
24. Seelig, A. A General Pattern for Substrate Recognition by PGlycoprotein, Eur. J. Biochem. 1998, 251, 252-261.
25. Accelrys, 9685 Scranton Road, San Diego, California, U.S.A. http://www.accelrys.com.
26. Lipinski, C. A.; Lombarde, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Adv. Drug Delivery Rev. 1997, 23 (1-3), 3-25.
27. Lahana, R.; Grassy, G. In QSAR: Quantitative Structure-Activity Relationships in Drug Design: Proceedings of the 7th European Symposium on QSAR; Interlaken, Switzerland, 5-9 September 1988, Fauchère, J. L. Ed.; Liss: New York.
28. Penzotti, J. E.; Lamb, M. L.; Evensen, E.; Grootenhuis, P. D. J. A Computational Ensemble Pharmacophore Model for Identifying Substrates of P-Glycoprotein. J. Med. Chem. 2002, 45(9), 1737-1740.
29. Ecker, G.; Huber, M.; Schmid, D.; Chiba, P. The Importance of a Nitrogen Atom in Modulators of Multidrug Resistance. Mol. Pharmacol. 1999, 56, 791-796.
30. Osterberg, T.; Norinder, U. Theoritical Calculation and Prediction of P-Glycoprotein-Interacting Drugs using MolSurf Parametrization and PLS Statistics. Eur. J. Pharm. Sci. 2000, 10, 295-303.
31. Litman, T.; Zuthen, T.; Skovsgaard, T.; Stein, W. Structure-Activity Relationships of P-Glycoprotein Interacting Drugs: Kinetic Characterization of their Effects on ATP-ase Activity. Biochim. Biophys. Acta 1997, 1361, 159-168.
32. Stouch, T. R.; Gudmundsson, O. Progress in Understanding the Structure-Activity Relationships of P-Glycoprotein. Adv. Drug Delivery Rev. 2002, 54(3), 315-328.
33. Palm, K.; Luthman, K.; Ungell, A. L.; Strandlund, G.; Beigi, F.; Lundahl, P.; Artursson, P. Evaluation of Dynamic Polar Molecular Surface Area as Predictor of Drug Absorption: Comparison with Other Computational and Experimental Predictors. J. Med. Chem. 1998, 41(27), 5382-5392.
34. Norinder, U.; Haeberlein, M. Computational approaches to the prediction of blood-brain distribution. Adv. Drug Delivery Rev. 2002. 54(3), 291-313.