Comparison of prediction models for blood brain barrier permeability and analysis of the molecular descriptors

Pharmazie

Volumn 67, Issue 7, 2012, Pages 628-634

  Wu, Ze Yu ^a   Pan, Jian ^a   Yuan, Yuan ^a   Hui, Ai Ling ^a   Yang, Yi ^a   Zhou, An ^b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b ANHUI UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OCTANOL; WATER; GLYCOPROTEIN P; PLASMA PROTEIN;

ACTIVE TRANSPORT; ARTICLE; BLOOD BRAIN BARRIER; CHEMICAL PARAMETERS; COMPARATIVE STUDY; COMPUTER MODEL; CONTROLLED STUDY; HIGH AFFINITY P GLYCOPROTEIN SUBSTRATE PROBABILITY; MEMBRANE PERMEABILITY; MULTIPLE LINEAR REGRESSION ANALYSIS; PARTITION COEFFICIENT; PLASMA PROTEIN BINDING RATIO; PREDICTION; ALGORITHM; CHEMICAL MODEL; CHEMISTRY; FACTUAL DATABASE; FORECASTING; HUMAN; METABOLISM; MOLECULAR WEIGHT; PERMEABILITY; PROTEIN BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SOLUBILITY; STATISTICAL MODEL;

ALGORITHMS; BIOLOGICAL TRANSPORT, ACTIVE; BLOOD PROTEINS; BLOOD-BRAIN BARRIER; DATABASES, FACTUAL; FORECASTING; HUMANS; LINEAR MODELS; MODELS, CHEMICAL; MOLECULAR WEIGHT; OCTANOLS; P-GLYCOPROTEIN; PERMEABILITY; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SOLUBILITY; WATER;

EID: 84865653455     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: 10.1691/ph.2012.1726     Document Type: Article

References (35)

1. Abraham MH, Chadha HS, Mitchell RC (1994) Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain. J Pharm Sci 83: 1257-1268.
2. Abraham MH, Chadha HS, Mitchell RC (1995) Hydrogen bonding. Part 36. Determination of blood brain distribution using octanol-water partition coefficients. Drug Des Discov 13: 123-131.
3. Abraham MH, Takács-Novák K, Mitchell RC (1997) On the partition of ampholytes: application to blood-brain distribution. J Pharm Sci 86: 310-315.
4. Abraham MH, Ibrahim A, Zissimos AM, Zhao YH, Comer J, Reynolds DP (2002) Application of hydrogen bonding calculations in property based drug design. Drug Discov Today 7: 1056-1063.
5. AbrahamMH(2004) The factors that influence permeation across the bloodbrain barrier. Eur J Med Chem 39: 235-240.
6. Adenot M, Lahana R (2004) Blood-brain barrier permeation models: discriminating between potential CNS and non-CNS drugs including P-glycoprotein substrates. J Chem Inf Comput Sci 44: 239-248.
7. Ambudkar SV, Kimchi-Sarfaty C, Sauna ZE, Gottesman MM (2003) Pglycoprotein: from genomics to mechanism. Oncogene 22: 7468-7485.
8. Bendels S, Kansy M, Wagner B, Huwyler J (2008) In silico prediction of brain and CSF permeation of small molecules using PLS regression models. Eur J Med Chem 43: 1581-1592.
9. Boccard J, Bajot F, Di Pietro A, Rudaz S, Boumendjel A, Nicolle E, Carrupt PA (2009) A 3D linear solvation energy model to quantify the affinity of flavonoid derivatives toward P-glycoprotein. Eur J Pharm Sci 36: 254-264.
10. Calder JAD, Ganellin CR (1994) Predicting the brain-penetrating capability of histaminergic compounds. Drug Des Discov 11: 259-268.
11. ChemBioOffice Ultra Version 12.0, CambridgeSoft Inc, Cambridge, USA. Clark DE (1999) 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 88: 815-821.
12. ClarkDE(2003) In silico prediction of blood-brain barrier permeation. Drug Discov Today 8: 927-933.
13. Crivori P, Cruciani G, Carrupt PA, Testa B (2000) Predicting blood-brain barrier permeation from three-dimensional molecular structure. J Med Chem 43: 2204-2216.
14. Dureja H, Madan AK (2006) Topochemical models for the prediction of permeability through blood-brain barrier. Int J Pharm 323: 27-33.
15. Fu XC, Wang GP, Shan HL, Liang WQ, Gao JQ (2008) Predicting bloodbrain barrier penetration from molecular weight and number of polar atoms. Eur J Pharm Biopharm 70: 462-466.
16. Garg P, Verma J (2006) In silico prediction of blood brain barrier permeability: an artificial neural network model. J Chem Inf Model 46: 289-297.
17. Glynn SL, Yazdanian M (1998) In vitro blood-brain barrier permeability of nevirapine compared to other HIV antiretroviral agents. J Pharm Sci 87: 306-310.
18. Greig NH, Brossi A, Pei XF, Ingram DK, Soncrant TT (1995) Designing drugs for optimal nervous system activity. In: Greenwood J, Begley DJ, Segal MB (eds.) New concepts of a blood-brain barrier, New York: Plenum, pp. 251-264.
19. Hemmateenejad B, Miri R, Safarpour MA, Mehdipour AR (2006) Accurate prediction of the blood-brain partitioning of a large set of solutes using ab initio calculations and genetic neural network modeling. J Comput Chem 27: 1125-1135.
20. Iyer M, Mishru R, Han Y, Hopfiger AJ (2002) Predicting blood-brain barrier partitioning of organic molecules using membrane-interaction QSAR analysis. Pharm Res 19: 1611-1621.
21. Kaznessis YN, Snow ME, BlankleyCJ (2001) Prediction of blood-brain partitioning using Monte Carlo simulations of molecules in water. J Comput Aided Mol Des 15: 697-708.
22. Kelder J, Grootenhuis PD, Bayada DM, Delbressine LP, Ploeman JP (1999) Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm Res 16: 1514-1519.
23. Levin VA (1980) Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability. J Med Chem 23: 682-684.
24. Lobell M, Molnár L, Keserü GM (2003) Recent advances in the prediction of blood-brain partitioning from molecular structure. J Pharm Sci 92: 360-370.
25. Lombardo F, Blake JF, Curatolo WJ (1996) Computation of brain-blood partitioning of organic solutes via free energy calculations. J Med Chem 39: 4750-4755.
26. Platts JA, Abraham MH, Zhao YH, Hersey A, Ijaz L, Butina D (2001) Correlation and prediction of a large blood-brain distribution data set - an LFER study. Eur J Med Chem 36: 719-730.
27. Ramakrishnan P (2003) The role of P-glycoprotein in the blood-brain barrier. Einstein Q J Biol Med 19: 160-165.
28. Rose K, Hall LH, Kier LB (2002) Modeling blood-brain barrier partitioning using the electrotopological state. J Chem Inf Comput Sci 42: 651-666.
29. Salminen T, Pulli A, Taskinen J (1997) Relationship between immobilised artificial membrane chromatographic retention and the brain penetration of structurally diverse drugs. J Pharm Biomed Anal 15: 469-477.
30. Sharom FJ, Lugo MR, Eckford PD (2005) New insights into the drug binding, transport and lipid flippase activities of the p-glycoprotein multidrug transporter. J Bioenerg Biomembr 37: 481-487.
31. Von Sprecher A, Gerpacher M, Anderson GP (1998) Neurokinin antagonists as potential therapies for inflammation and rheumatoid arthritis. IDrugs 1: 73-91.
32. Wan H, Rehngren M, Giordanetto F, Bergström F, Tunek A (2007) High-throughput screening of drug-brain tissue binding and in silico prediction for assessment of central nervous system drug delivery. J Med Chem 50: 4606-4615.
33. Winkler DA, Burden FR (2004) Modelling blood-brain barrier partitioning using Bayesian neural nets. J Mol Graph Model 22: 499-505.
34. Young RC, Mitchell RC, BrownTH, Ganellin CR, Griffiths R, JonesM,Rana KK, Saunders D, Smith IR, Sore NE, Wilks TJ (1988) 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: 656-671.
35. Zhang HB (2004) A new nonlinear equation for the tissue/blood partition coefficients of neutral compounds. J Pharm Sci 93: 1595-1604.