Prediction of blood-brain partitioning and human serum albumin binding based on COSMO-RS σ-moments

Journal of Chemical Information and Modeling

Volumn 47, Issue 1, 2007, Pages 228-233

  Wichmann, Karin ^a   Diedenhofen, Michael ^a   Klamt, Andreas ^a,b  

^a COSMOlogic GmbH and Co KG ^*  (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD; BODY FLUIDS; CONTINUUM MECHANICS; ERROR ANALYSIS; MOLECULAR STRUCTURE; STATISTICAL METHODS;

BLOOD BRAIN PARTITIONING; DRUG SOLUBILITY; HUMAN SERUM ALBUMIN; NEUTRAL MOLECULES;

NEUROPHYSIOLOGY;

SERUM ALBUMIN;

ARTICLE; ARTIFICIAL INTELLIGENCE; BLOOD BRAIN BARRIER; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; HUMAN; INTESTINE ABSORPTION; METABOLISM; PROTEIN BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM THEORY; SOLUBILITY;

ARTIFICIAL INTELLIGENCE; BLOOD-BRAIN BARRIER; ELECTRONS; HUMANS; INTESTINAL ABSORPTION; MODELS, MOLECULAR; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; SERUM ALBUMIN; SOLUBILITY;

EID: 33846856720     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci600385w     Document Type: Article

References (30)

1. Kaznessis, Y. N.; Snow, M. E.; Biankley, J. C. Prediction of blood-brain partitioning using Monte-Carlo simulations of molecules in water. J. Comput.-Aided Mol. Des. 2001, 15, 697-708.
2. Ertl, P.; Rohde, B.; Selzer, P. Fast contribution of molecular polar surface area as a sum of fragment-based contributions and its applications to the prediction of drug transport. J. Med. Chem. 2000, 43, 3714-3717.
3. Keserü, G. M.; Molnár, L. High-Throughput Prediction of Blood-Brain Partitioning: A Thermodynamic Approach. J. Chem. Inf. Comput. Sci. 2001, 47, 120-128.
4. Ooms, F.; Weber, P.; Carrupt, P.-A.; Testa, B. A simple model to predict blood-brain barrier permeation from 3D molecular fields. Biochim. Biophys. Acta 2002, 1587, 118-125.
5. Aureli, L.; Cruciani, G.; Candida Cesta, M.; Anacardio, R.; De Simone, L.; Moriconi, A. Predicting Human Serum Albumin Affinity of Interleukin-8 (CXCL8) Inhibitors by 3D-QSPR Approach. J. Med. Chem. 2005, 48, 2469-2479.
6. Rose, K.; Hall, L. H.; Hall, L. M.; Kier, L. B. Modeling Blood-Brain Barrier Partitioning Using Topological Structure Descriptors, 2003. Elsevier MDL Web Site, http://www.mdl.com/solutions/white_papers/MDLQSARreprint.jsp (accessed Feb 13, 2004).
7. Kier, L. B.; Hall, L. H.; Hall, L. M. QSAR Modeling of Drug Binding to Protein. β-Lactam Serum Binding and Albumin Binding Affinity, 2002. Elsevier MDL Web Site, http://www.mdl.com/solutions/white-_papers/ ML233QM3_white_paper.jsp (accessed Oct 7, 2004).
8. Hutter, M. C. Prediction of blood-brain barrier permeation using quantum chemically derived information. J. Comput.-Aided Mol. Des. 2003, 17, 415-433.
9. Colmenarejo, G.; Alvarez-Pedraglio, A.; Lavandera, J.-L. Chemin-formatic Models to Predict Binding Affinities to Human Serum Albumin. J. Med. Chem. 2001, 44, 4370-4378.
10. Klamt, A.; Eckert, F.; Hornig, M. COSMO-RS: A novel view to physiological solvation and partition questions. J. Comput.-Aided Mol. Des. 2001, 15, 355-365.
11. Jones, R.; Connolly, P. C.; Klamt, A.; Diedenhofen, M. Use of Surface Charges from DFT Calculations To Predict Intestinal Absorption. J. Chem. Inf. Model. 2005, 45, 1337-1342.
12. Klamt, A.; Schuü̈rmann, G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc., Perkin Trans. 1993, 2, 799-805.
13. Klamt, A. Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena. J. Phys. Chem. 1995, 99, 2224-2235.
14. Klamt, A. COSMO and COSMO-RS. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, L., Eds.; Wiley: New York, 1998; Vol. 2, pp 604-615.
15. Klamt, A.; Jonas, V.; Buerger, T.; Lohrenz, J. C. W. Refinement and Parameterization of COSMO-RS. J. Phys. Chem. A 1998, 102, 5074-5085.
16. Klamt, A.; Eckert, F. COSMO-RS: a novel and efficient method for the a priori prediction of thermophysical data of liquids. Fluid Phase Equilib. 2000, 172, 43-72.
17. Klamt, A. COSMO-RS. From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design', Elsevier. Amsterdam, The Netherlands, 2005; pp 49-147.
18. Mehler, C.; Klamt, A.; Peukert, W. Use of COSMO-RS for the prediction of adsorption equilibria. A1CHE J. 2002, 48, 1093-1099.
19. Klamt, A.; Eckert, F.; Diedenhofen, M. Prediction of Soil Sorption Coefficients with COSMO-RS. Environ. Toxicol. Chem. 2002, 21, 2562-2566.
20. Zissimos, A. M.; Abraham, M. H.; Klamt, A.; Eckert, F.; Wood, J. A Comparison between the Two General Sets of Linear Free Energy Descriptors of Abraham and Klamt. J. Chem. Inf. Comput. Sci. 2002, 42, 1320-1331.
21. Colmenarejo, G.; Alvarez-Pedraglio, A.; Lavandera, J.-L. Chemin-formatic Models to Predict Binding Affinities to Human Serum Albumin. J. Med. Chem. 2001, 44, 4370-4378.
22. Sadowski, J.; Gasteiger, J. From atoms and bonds to three-dimensional atomic coordinates: automatic model builders. Chem. Rev. 1993, 93, 2567-2581.
23. MOPAC 2002, version 2.00; Fujitsu: Tokyo, Japan, 2002.
24. Klamt, A.; Eckert, F. Fast Solvent Screening via Quantum Chemistry: The COSMO-RS approach. AIChE J. 2002, 48, 369-385.
25. For Selen a recently optimized COSMO radius of 2.200 Å was used.
26. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Electronic structure calculations on workstation computers: The program system turbomole. Chem. Phys. Lett. 1989, 162, 165-169.
27. COSMOtherm, version C2.0 release 01.04;
28. COSMOhgic GmbH & Co. KG: Leverkusen, Germany, 2004.
29. Clark, D. E. In-silico prediction of blood-brain barrier permeation. Drug Discovery Today 2003, 8, 927-933.
30. Hornig, M.; Klamt, A. COSMOfrag: A Novel Tool for High Throughput ADME Property Prediction and Similarity Screening Based on Quantum Chemistry. J. Chem. Inf. Model. 2005, 45, 1169-1177.