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Document Figure 9 Stereo view of the minimized complex between the putative ligand shown in Figure 8 and thrombin (thin lines). Intermolecular hydrogen bonds are drawn by dashed lines. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_554.html (2 of 2) [4/9/2004 12:53:32 AM]
Document Page 555 N-acylpyrrolidine ring in S2 by a single methylene linker. This is a novel design and the candidate ligand appears to be more rigid than NAPAP, since it has a smaller number of rotatable bonds. Hence, the penalty paid for the loss in entropy upon binding should be smaller for this CCLD hit than for NAPAP. In a study with a more diverse set of starting molecular fragments, ligands containing both a “core” similar to known inhibitors and additional intermolecular hydrogen bonds and/or van der Waals interactions were generated [28]. IV. Conclusion A combinatorial approach for the computer-aided design of putative ligands of proteins or receptors of known three-dimensional structure has been presented. Diversity of these candidate ligands is provided by first docking a set of diverse molecular fragments. For aliphatic functional groups a modified force field (switching off the attractive part of the van der Waals interaction with polar atoms of the protein) was introduced to better approximate solvation effects, thereby avoiding the docking of apolar fragments into hydrophilic cavities of the macromolecular target. The second part of the present ligand design approach consists of a combinatorial strategy for the connection of optimally docked molecular fragments by small linkage elements having optimal interactions with the target molecule. An application was presented in which candidate inhibitors of thrombin were found. It is important to note that the most difficult part of ligand design is the prediction of binding affinity. A method to estimate relative binding constants has recently been applied to a series of similar inhibitors of HIV-1 aspartic proteinase [41]. Our own efforts are concentrated on the development of an approach that will predict relative binding affinities and will be general enough to be used for any enzyme or receptor of known structure (A. Caflisch, D. Arosio, and C. Ehrhardt, work in progress). One of the purposes of this chapter was to show that structure-based ligand design is a fascinating and progressing research field. It is fascinating not only for its ultimate goal, i.e., the discovery of ethical drugs, but also because it is based on, and thereby increases, our understanding of molecular interactions and recognition phenomena on an atomic level. Another reason is its multidisciplinary character, which requires skills in different branches of science, from theoretical physics and chemistry to computer science and statistics. That structure-based computer-aided ligand design is a progressing field is evident in many chapters of this book. This is mainly a consequence of the methodological developments and the ever-increasing performance of computers. http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_555.html [4/9/2004 12:53:33 AM]
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