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Document A. Molecular Diversity and Screening-Based Identification of Nonpeptide Ligands Page 586 Precedence for the success of nonpeptide drug discovery can be traced to the identification of morphine (75; Figure 17) as nonpeptide natural product agonist at μ-opioid peptide receptors [90]. To date, the robust momentum of nonpeptide drug discovery continues to be accelerated by sophisticated biochemical screening technologies. The scope of molecular diversity as well as therapeutic targets for such screening-based nonpeptide ligand lead compounds includes the following examples (Figure 17): substance P (NK 1 antagonist, 76 [91]; angiotensin AT 1 antagonist, 77 [92]; growth hormone-releasing peptide (GHRP) agonist, 78 [93]; cholecystokinin CCK A antagonist, 79 [94]; CCK B/gastrin antagonist, 80 [95]; CCK A agonist, 81 [96]; endothelin antagonist, 82 [97]; gonadotropin-releasing hormone (GnRH) antagonist, 83 [98]; vasopressin V 1 antagonist, 84 [99]; gastrin-releasing peptide antagonist, 85 [100]; glucagon antagonist, 86 [101], neurotensin antagonist, 87 [102]; angiotensin AT 1 agonist, 88 [103]; oxytocin antagonist, 89 [104]; and HIV protease inhibitor, 90 [105]. A significant number of screening-derived nonpeptide leads have been identified for G-protein-coupled receptors (GPCRs), and in a majority of cases these compounds have been determined to be competitive antagonists. Albeit the 3D structures of this receptor superfamily have not been directly determined, homology model-building and site-directed mutagenesis studies are impacting structure-activity analysis of agonist and antagonist ligands (peptide, peptidomimetic, and nonpeptide) for several GPCR targets (see below). B. Nonpeptides: Exploring Pharmacophore Relationships to Peptide Ligands Relative to a number of GPCR targets, there exists significant opportunity to compare chemical structures and 3D pharmacophore models of both peptide and nonpeptide ligands. Such comparative analyses can explore the possibility of similar 3D substructural elements that may account for their molecular recognition at the binding site(s) of the receptor. The fact that a vast number of screeningderived nonpeptide leads are multifunctionalized 5- to 7-membered ring heterocycles (e.g., alkaloid and benzodiazepine) and contain conformationally rigid substructural elements (e.g., biphenyl, spiro-bicyclic rings, and N-substituted amide or amine linkages) suggests the likelihood that such compounds are binding with highly favorable entropic driving forces as compared to the more conformationally flexible peptide ligands. In this regard, efforts to “rigidify” peptide-based scaffolding or replace it by nonpeptide templates has been the underlying theme of peptidomimetic design strategies, and concepts for the latter approach date back to the proposed used of cycloaliphatic ring systems that might be multifunctionalized to create “topographi- http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_586.html [4/9/2004 1:16:39 AM]
Document Figure 17 Nonpeptide drug discovery: examples from screening-based approaches http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_587.html [4/9/2004 1:17:33 AM] Page 587
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Page 689 and 690: Document Page 555 N-acylpyrrolidine
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Page 693 and 694: Document structure. 2. Ligand probe
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Page 739 and 740: Document Figure 22 Protease 3D stru
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Page 743 and 744: Document Page 603 hydroxymethyl sub
Page 745 and 746: Document Page 605 For other serinyl
Page 747 and 748: Document Page 607 scopic studies pr
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Page 755 and 756: Document (Ser/Thr) peptide 2.9 Å 2
Page 761 and 762: Document Page 617 Val (131) showed
Page 763 and 764: Document Figure 32 PTP and PTB 3D s
Page 765 and 766: Document Acknowledgments Page 620 I
Page 767 and 768: Document 18. Sawyer TK. In: Peptide
Page 769 and 770: Document Page 622 Fukuroda T, Fukam
Page 771 and 772: Document Page 623 53. Bird J, Harpe
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Document Cyclotheonamide A (CtA), 2
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Document D ddI, 152 tumour necrosis
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Document antistasin peptides, 281 c
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Document Kininogen, 119 high molecu
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Document Phosphoglycerate kinase (P
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Document [Protease targets] serinyl
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