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PMID: 20088605 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Inclusion of solvation and entropy in the knowledge-based scoring function for protein-ligand interactions.

Journal of chemical information and modeling ·Vol. 50 ·No. 2 ·2010-02-22 ·Pages 262-73

Huang SY, Zou X

Abstract

The effects of solvation and entropy play a critical role in determining the binding free energy in protein-ligand interactions. Despite the good balance between speed and accuracy, no current knowledge-based scoring functions account for the effects of solvation and configurational entropy explicitly due to the difficulty in deriving the corresponding pair potentials and the resulting double counting problem. In the present work, we have included the solvation effect and configurational entropy in the knowledge-based scoring function by an iterative method. The newly developed scoring function has yielded a success rate of 91% in identifying near-native binding modes with Wang et al.'s benchmark of 100 diverse protein-ligand complexes. The results have been compared with the results of 15 other scoring functions for validation purpose. In binding affinity prediction, our scoring function has yielded a correlation of R(2) = 0.76 between the predicted binding scores and the experimentally measured binding affinities on the PMF validation sets of 77 diverse complexes. The results have been compared with R(2) of four other well-known knowledge-based scoring functions. Finally, our scoring function was also validated on the large PDBbind database of 1299 protein-ligand complexes and yielded a correlation coefficient of 0.474. The present computational model can be applied to other scoring functions to account for solvation and entropic effects.

MeSH Terms
Computational Biology Computer Simulation Databases, Protein Entropy Ligands Models, Molecular Protein Binding Protein Conformation Proteins/chemistry,metabolism Reproducibility of Results Solvents/chemistry
Chemicals
Ligands Proteins Solvents
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Huang Sheng-You
Department of Physics and Astronomy, Department of Biochemistry, Dalton Cardiovascular Research Center, and Informatics Institute, University of Missouri, Columbia, Missouri 65211, USA.
Zou Xiaoqin
References (64)
64 references, click to expand
  1. Scoring noncovalent protein-ligand interactions: a continuous differentiable function tuned to compute binding affinities.
    J Comput Aided Mol Des. 1996 Oct;10(5):427-40 PMID: 8951652
  2. PMF scoring revisited.
    J Med Chem. 2006 Oct 5;49(20):5895-902 PMID: 17004705
  3. The Protein Data Bank.
    Nucleic Acids Res. 2000 Jan 1;28(1):235-42 PMID: 10592235
  4. SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.
    J Med Chem. 2002 Jun 20;45(13):2770-80 PMID: 12061879
  5. Electrostatics of ligand binding: parametrization of the generalized Born model and comparison with the Poisson-Boltzmann approach.
    J Phys Chem B. 2006 May 11;110(18):9304-13 PMID: 16671749
  6. Role of binding entropy in the refinement of protein-ligand docking predictions: analysis based on the use of 11 scoring functions.
    J Comput Chem. 2007 Jun;28(8):1364-72 PMID: 17342720
  7. Determination of the interaction potential from the pair distribution function: an inverse Monte Carlo technique.
    Phys Rev E Stat Nonlin Soft Matter Phys. 2003 Jul;68(1 Pt 1):011202 PMID: 12935127
  8. The price of lost freedom: entropy of bimolecular complex formation.
    Protein Eng. 1989 Oct;3(1):1-3 PMID: 2813338
  9. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases.
    J Comput Aided Mol Des. 2001 May;15(5):411-28 PMID: 11394736
  10. Development of a quantum mechanics-based free-energy perturbation method: use in the calculation of relative solvation free energies.
    J Am Chem Soc. 2004 May 26;126(20):6224-5 PMID: 15149207
  11. Molecular recognition of the inhibitor AG-1343 by HIV-1 protease: conformationally flexible docking by evolutionary programming.
    Chem Biol. 1995 May;2(5):317-24 PMID: 9383433
  12. Ligand configurational entropy and protein binding.
    Proc Natl Acad Sci U S A. 2007 Jan 30;104(5):1534-9 PMID: 17242351
  13. Empirical free energy calculations of ligand-protein crystallographic complexes. I. Knowledge-based ligand-protein interaction potentials applied to the prediction of human immunodeficiency virus 1 protease binding affinity.
    Protein Eng. 1995 Jul;8(7):677-91 PMID: 8577696
  14. Continuum solvent studies of the stability of RNA hairpin loops and helices.
    J Biomol Struct Dyn. 1998 Dec;16(3):671-82 PMID: 10052623
  15. An iterative knowledge-based scoring function to predict protein-ligand interactions: II. Validation of the scoring function.
    J Comput Chem. 2006 Nov 30;27(15):1876-82 PMID: 16983671
  16. Statistical potentials extracted from protein structures: how accurate are they?
    J Mol Biol. 1996 Mar 29;257(2):457-69 PMID: 8609636
  17. Recent advances in the development and application of implicit solvent models in biomolecule simulations.
    Curr Opin Struct Biol. 2004 Apr;14(2):217-24 PMID: 15093837
  18. Use of MM-PB/SA in estimating the free energies of proteins: application to native, intermediates, and unfolded villin headpiece.
    Proteins. 2000 Jun 1;39(4):309-16 PMID: 10813813
  19. Ensemble docking of multiple protein structures: considering protein structural variations in molecular docking.
    Proteins. 2007 Feb 1;66(2):399-421 PMID: 17096427
  20. Computational methods to predict binding free energy in ligand-receptor complexes.
    J Med Chem. 1995 Dec 22;38(26):4953-67 PMID: 8544170
  21. Estimating protein-ligand binding free energy: atomic solvation parameters for partition coefficient and solvation free energy calculation.
    Proteins. 2004 Dec 1;57(4):651-64 PMID: 15390269
  22. Empirical entropic contributions in computational docking: evaluation in APS reductase complexes.
    J Comput Chem. 2008 Aug;29(11):1753-61 PMID: 18351616
  23. UCSF Chimera--a visualization system for exploratory research and analysis.
    J Comput Chem. 2004 Oct;25(13):1605-12 PMID: 15264254
  24. Solvation energy in protein folding and binding.
    Nature. 1986 Jan 16-22;319(6050):199-203 PMID: 3945310
  25. Development and validation of a genetic algorithm for flexible docking.
    J Mol Biol. 1997 Apr 4;267(3):727-48 PMID: 9126849
  26. Biomolecular simulations: recent developments in force fields, simulations of enzyme catalysis, protein-ligand, protein-protein, and protein-nucleic acid noncovalent interactions.
    Annu Rev Biophys Biomol Struct. 2001;30:211-43 PMID: 11340059
  27. Lead discovery using molecular docking.
    Curr Opin Chem Biol. 2002 Aug;6(4):439-46 PMID: 12133718
  28. A semiempirical free energy force field with charge-based desolvation.
    J Comput Chem. 2007 Apr 30;28(6):1145-52 PMID: 17274016
  29. DrugScore(CSD)-knowledge-based scoring function derived from small molecule crystal data with superior recognition rate of near-native ligand poses and better affinity prediction.
    J Med Chem. 2005 Oct 6;48(20):6296-303 PMID: 16190756
  30. M-score: a knowledge-based potential scoring function accounting for protein atom mobility.
    J Med Chem. 2006 Oct 5;49(20):5903-11 PMID: 17004706
  31. Prediction of new serine proteinase inhibitors.
    Nat Struct Biol. 1994 Oct;1(10):735-43 PMID: 7634078
  32. Rapid grid-based construction of the molecular surface and the use of induced surface charge to calculate reaction field energies: applications to the molecular systems and geometric objects.
    J Comput Chem. 2002 Jan 15;23(1):128-37 PMID: 11913378
  33. Comparative evaluation of 11 scoring functions for molecular docking.
    J Med Chem. 2003 Jun 5;46(12):2287-303 PMID: 12773034
  34. Efficient molecular docking of NMR structures: application to HIV-1 protease.
    Protein Sci. 2007 Jan;16(1):43-51 PMID: 17123961
  35. Revisiting free energy calculations: a theoretical connection to MM/PBSA and direct calculation of the association free energy.
    Biophys J. 2004 Jan;86(1 Pt 1):67-74 PMID: 14695250
  36. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes.
    J Comput Aided Mol Des. 1997 Sep;11(5):425-45 PMID: 9385547
  37. The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure.
    J Comput Aided Mol Des. 1994 Jun;8(3):243-56 PMID: 7964925
  38. The PDBbind database: methodologies and updates.
    J Med Chem. 2005 Jun 16;48(12):4111-9 PMID: 15943484
  39. A fast flexible docking method using an incremental construction algorithm.
    J Mol Biol. 1996 Aug 23;261(3):470-89 PMID: 8780787
  40. A preference-based free-energy parameterization of enzyme-inhibitor binding. Applications to HIV-1-protease inhibitor design.
    Protein Sci. 1995 Sep;4(9):1881-903 PMID: 8528086
  41. An iterative knowledge-based scoring function for protein-protein recognition.
    Proteins. 2008 Aug;72(2):557-79 PMID: 18247354
  42. Hydrogen Bonding, Hydrophobic Interactions, and Failure of the Rigid Receptor Hypothesis.
    Angew Chem Int Ed Engl. 1999 Mar 15;38(6):736-749 PMID: 29711793
  43. General and targeted statistical potentials for protein-ligand interactions.
    Proteins. 2005 Nov 1;61(2):272-87 PMID: 16106379
  44. PLASS: protein-ligand affinity statistical score--a knowledge-based force-field model of interaction derived from the PDB.
    J Comput Aided Mol Des. 2004 Apr;18(4):261-70 PMID: 15562990
  45. Calculation of conformational ensembles from potentials of mean force. An approach to the knowledge-based prediction of local structures in globular proteins.
    J Mol Biol. 1990 Jun 20;213(4):859-83 PMID: 2359125
  46. Empirical potentials and functions for protein folding and binding.
    Curr Opin Struct Biol. 1997 Apr;7(2):222-8 PMID: 9094333
  47. The PDBbind database: collection of binding affinities for protein-ligand complexes with known three-dimensional structures.
    J Med Chem. 2004 Jun 3;47(12):2977-80 PMID: 15163179
  48. Electrostatics of nanosystems: application to microtubules and the ribosome.
    Proc Natl Acad Sci U S A. 2001 Aug 28;98(18):10037-41 PMID: 11517324
  49. A model binding site for testing scoring functions in molecular docking.
    J Mol Biol. 2002 Sep 13;322(2):339-55 PMID: 12217695
  50. An all atom force field for simulations of proteins and nucleic acids.
    J Comput Chem. 1986 Apr;7(2):230-252 PMID: 29160584
  51. Knowledge-based scoring function to predict protein-ligand interactions.
    J Mol Biol. 2000 Jan 14;295(2):337-56 PMID: 10623530
  52. An iterative method for extracting energy-like quantities from protein structures.
    Proc Natl Acad Sci U S A. 1996 Oct 15;93(21):11628-33 PMID: 8876187
  53. Calculations of protein-ligand binding entropy of relative and overall molecular motions.
    J Comput Aided Mol Des. 2007 Jul;21(7):361-70 PMID: 17503189
  54. A general and fast scoring function for protein-ligand interactions: a simplified potential approach.
    J Med Chem. 1999 Mar 11;42(5):791-804 PMID: 10072678
  55. Knowledge-based potentials--back to the roots.
    Biochemistry (Mosc). 1998 Mar;63(3):247-52 PMID: 9526121
  56. Medium- and long-range interaction parameters between amino acids for predicting three-dimensional structures of proteins.
    Macromolecules. 1976 Nov-Dec;9(6):945-50 PMID: 1004017
  57. An iterative knowledge-based scoring function to predict protein-ligand interactions: I. Derivation of interaction potentials.
    J Comput Chem. 2006 Nov 30;27(15):1866-75 PMID: 16983673
  58. Crystal structure of a T cell receptor bound to an allogeneic MHC molecule.
    Nat Immunol. 2000 Oct;1(4):291-7 PMID: 11017099
  59. A set of van der Waals and coulombic radii of protein atoms for molecular and solvent-accessible surface calculation, packing evaluation, and docking.
    Proteins. 1998 Jul 1;32(1):111-27 PMID: 9672047
  60. A knowledge-based energy function for protein-ligand, protein-protein, and protein-DNA complexes.
    J Med Chem. 2005 Apr 7;48(7):2325-35 PMID: 15801826
  61. Molecular recognition and docking algorithms.
    Annu Rev Biophys Biomol Struct. 2003;32:335-73 PMID: 12574069
  62. Further development and validation of empirical scoring functions for structure-based binding affinity prediction.
    J Comput Aided Mol Des. 2002 Jan;16(1):11-26 PMID: 12197663
  63. The statistical-thermodynamic basis for computation of binding affinities: a critical review.
    Biophys J. 1997 Mar;72(3):1047-69 PMID: 9138555
  64. Prediction of binding constants of protein ligands: a fast method for the prioritization of hits obtained from de novo design or 3D database search programs.
    J Comput Aided Mol Des. 1998 Jul;12(4):309-23 PMID: 9777490
Article Info
Journal
Journal of chemical information and modeling
Abbr.
J Chem Inf Model
ISSN
1549-960X
Published
2010-02-22
Pages
262-73
Language
English
Region
United States
NLM ID
101230060
PMCID
PMC3199178
Subset
IM
Grants
NIGMS NIH HHS · R21 GM088517 · United States
NIGMS NIH HHS · GM088517 · United States
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