Abstract
New methods for docking, template fitting and building pseudo-receptors are described. Full conformational searches are carried out for flexible cyclic and acyclic molecules. QXP (quick explore) search algorithms are derived from the method of Monte Carlo perturbation with energy minimization in Cartesian space. An additional fast search step is introduced between the initial perturbation and energy minimization. The fast search produces approximate low-energy structures, which are likely to minimize to a low energy. For template fitting, QXP uses a superposition force field which automatically assigns short-range attractive forces to similar atoms in different molecules. The docking algorithms were evaluated using X-ray data for 12 protein-ligand complexes. The ligands had up to 24 rotatable bonds and ranged from highly polar to mostly nonpolar. Docking searches of the randomly disordered ligands gave rms differences between the lowest energy docked structure and the energy-minimized X-ray structure, of less than 0.76 A for 10 of the ligands. For all the ligands, the rms difference between the energy-minimized X-ray structure and the closest docked structure was less than 0.4 A, when parts of one of the molecules which are in the solvent were excluded from the rms calculation. Template fitting was tested using four ACE inhibitors. Three ACE templates have been previously published. A single run using QXP generated a series of templates which contained examples of each of the three. A pseudo-receptor, complementary to an ACE template, was built out of small molecules, such as pyrrole, cyclopentanone and propane. When individually energy minimized in the pseudo-receptor, each of the four ACE inhibitors moved with an rms of less than 0.25 A. After random perturbation, the inhibitors were docked into the pseudo-receptor. Each lowest energy docked structure matched the energy-minimized geometry with an rms of less than 0.08 A. Thus, the pseudo-receptor shows steric and chemical complementarity to all four molecules. The QXP program is reliable, easy to use and sufficiently rapid for routine application in structure-based drug design.
MeSH Terms
Algorithms
Angiotensin-Converting Enzyme Inhibitors/chemistry,metabolism
Binding Sites
Computer Simulation
Drug Design
HIV Protease/chemistry
HIV Protease Inhibitors/chemistry,metabolism
Ligands
Methylurea Compounds/chemistry,metabolism
Models, Molecular
Molecular Structure
Monte Carlo Method
Proteins/chemistry
Pyridines/chemistry,metabolism
Software
Thermodynamics
Valine/analogs & derivatives
X-Ray Diffraction
Chemicals
Angiotensin-Converting Enzyme Inhibitors
HIV Protease Inhibitors
Ligands
Methylurea Compounds
Proteins
Pyridines
Abbott 77003
HIV Protease
Valine
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
McMartin C
Research Department, Novartis Pharmaceuticals Corporation, Summit, NJ 07901, USA.
Bohacek R S
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