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Combinatorial Chemistry & High Throughput Screening, Vol. 4, No. 7, 2001

 

Contents

 

Parsing Intermolecular Interactions

 

Guest Editors: Diane J. Rodi / Lee Makowski

 

Identification of Enzyme Inhibitors from Phage-Displayed Combinatorial Peptide Libraries Pp. 535-543

Brian K. Kay and Paul T. Hamilton

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Identification of a Novel Human Peroxisomal 2,4-Dienoyl-CoA Reductase Related Protein Using the M13

Phage Protein VI Phage Display Technology Pp. 545-552

L. Amery, G. P. Mannaerts, S. Subramani, P. P. Van Veldhoven  and M. Fransen

[Abstract] [Purchase Issue/Articles]

 

Identification of Small Molecule Binding Sites within Proteins Using Phage Display Technology Pp. 553-572

D. J. Rodi, G. E. Agoston, R. Manon, R. Lapcevich, S. J. Green  and L. Makowski

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Substrate Phage as a Tool to Identify Novel Substrate Sequences of Proteases Pp. 573-583

Shuichi Ohkubo, Kazutaka Miyadera, Yoshikazu Sugimoto, Ken-ichi Matsuo, Konstanty Wierzba and Yuji Yamada

[Abstract] [Purchase Issue/Articles]

 

Predicting In Vivo Protein-Peptide Interactions with Random Phage Display Pp. 100%-591

James F. Smothers and Steven Henikoff

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The Cloning of Human Genes Using cDNA Phage Display and Small-molecule Chemical Probes Pp. 593-597

Sergey N. Savinov and David J. Austin

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Caveat Receptor: Proteomes on Display Pp. 599-602                                                                          

F. J. Stevens

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Abstracts

 

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Identification of Enzyme Inhibitors from Phage-Displayed Combinatorial Peptide Libraries

Brian K. Kay and Paul T. Hamilton

 

In recent years, there have been a growing number of examples of the successful isolation of peptide ligands for enzymes from phage-displayed combinatorial peptide libraries. These peptides typically bind at or near the active site of the enzymes and can inhibit their activity. We review the literature on peptide ligands that have been isolated for enzymes other than proteases as well as present data on peptide ligands we have identified for E. coli dihydrofolate reductase (DHFR) which bind at, or near, the same site as the known inhibitors methotrexate or trimethoprim. Thus, while the peptide ligand isolated from phage-displayed libraries may not resemble the chemical structure of the normal substrate of the enzyme, the peptide can be used as an inhibitor to evaluate the function of the enzyme or for drug discovery efforts (i.e., as a lead compound for peptidomimetic design or as displaceable probe in high-throughput screens of libraries of small molecules).

 

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Identification of a Novel Human Peroxisomal 2,4-Dienoyl-CoA Reductase Related Protein Using the M13 Phage Protein VI Phage Display Technology

L. Amery, G. P. Mannaerts, S. Subramani, P. P. Van Veldhoven  and M. Fransen

 

Recently, we reported the successful use of the gVI-cDNA phage display technology to clone cDNAs coding for novel peroxisomal enzymes by affinity selection using immobilized antisera directed against peroxisomal subfractions (Fransen, M.; Van Veldhoven, P.P.; Subramani, S. Biochem. J., 1999, 340, 561‑568). To identify other unknown peroxisomal enzymes, we further exploited this promising approach. Here we report the isolation and cloning of another novel human cDNA encoding a protein ending in the tripeptide AKL, a C-terminal peroxisomal targeting signal (PTS1). Primary structure analysis revealed that this molecule shared the highest sequence similarity to members of the 2,4-dienoyl-CoA reductase (DCR) family. However, functional analysis indicated that a recombinantly expressed version of the novel protein did not possess DCR activity with either 2-trans,4-trans-hexadienoyl-CoA or 2-trans,4-trans-decadienoyl-CoA as a substrate. The recombinant protein interacted with HsPex5p, the human PTS1-binding protein. Binding was competitively inhibited by a PTS1-containing peptide and was abolished when the last amino acid of the PTS1 signal was deleted. Transfection of mammalian cells with gene fusions between green fluorescent protein (GFP) and the human cDNA confirmed a peroxisomal localization and, therefore, the functionality of the PTS1. These results further demonstrate the suitability of the gVI-cDNA phage display technology for cDNA expression cloning using an antibody as a probe.

 

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Identification of Small Molecule Binding Sites within Proteins Using Phage Display Technology

D. J. Rodi, G. E. Agoston, R. Manon, R. Lapcevich, S. J. Green  and L. Makowski

 

Affinity selection of peptides displayed on phage particles was used as the basis for mapping molecular contacts between small molecule ligands and their protein targets. Analysis of the crystal structures of complexes between proteins and small molecule ligands revealed that virtually all ligands of molecular weight 300 Da or greater have a continuous binding epitope of 5 residues or more. This observation led to the development of a technique for binding site identification which involves statistical analysis of an affinity-selected set of peptides obtained by screening of libraries of random, phage-displayed peptides against small molecules attached to solid surfaces. A random sample of the selected peptides is sequenced and used as input for a similarity scanning program which calculates cumulative similarity scores along the length of the putative receptor. Regions of the protein sequence exhibiting the highest similarity with the selected peptides proved to have a high probability of being involved in ligand binding. This technique has been employed successfully to map the contact residues in multiple known targets of the anticancer drugs paclitaxel (Taxol™), docetaxel (Taxotere™) and 2-methoxyestradiol and the glycosaminoglycan hyaluronan, and to identify a novel paclitaxel receptor [1]. These data corroborate the observation that the binding properties of peptides displayed on the surface of phage particles can mimic the binding properties of peptides in naturally occurring proteins. It follows directly that structural context is relatively unimportant for determining the binding properties of these disordered peptides. This technique represents a novel, rapid, high resolution method for identifying potential ligand binding sites in the absence of three-dimensional information and has the potential to greatly enhance the speed of development of novel small molecule pharmaceuticals.

 

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Substrate Phage as a Tool to Identify Novel Substrate Sequences of Proteases

Shuichi Ohkubo, Kazutaka Miyadera, Yoshikazu Sugimoto, Ken-ichi Matsuo, Konstanty Wierzba and Yuji Yamada

 

Combinatorial phage peptide libraries have been used to identify the ligands for specific target molecules. These libraries are also useful for identification of the specific substrates of various proteases. A “substrate phage library” has a random peptide sequence at the N-terminus of the phage coat protein and an additional tag sequence that enables attachment of the phage to an immobile phase. When these libraries are incubated with a specific enzyme, such as a protease, the uncleaved phage is excluded from the solution with tag-binding macromolecules. This provides a novel approach to define substrate specificity. The aim of this review is to summarize recent progress on the application of the substrate phage technique to identify specific substrates of proteolytic enzymes. As an example, some of our own experimental data on the selection and characterization of substrate sequences for thrombin, a serine protease, and membrane type-1 matrix metalloproteinase (MT1-MMP) will be presented. Using this approach, the canonical consensus substrate sequence for thrombin was deduced from the selected clones. As expected from the collagenolytic activity of MT1-MMP, a collagen-like sequence was identified in the case of MT1-MMP. A more selective substrate sequence for MT1-MMP was identified during a substrate phage screen. The delineation of the substrate specificity of proteases will help to elucidate the enzymatic properties and the physiological roles of these enzymes. Comprehensive screening of very large numbers of potential substrate sequences is possible with substrate phage libraries. Thus, this approach allows novel substrate sequences and previously unknown target molecules to be defined.

 

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Predicting In Vivo Protein-Peptide Interactions with Random Phage Display

James F. Smothers and Steven Henikoff

 

Binding sites in protein complexes occasionally map to small peptides within one or more proteins. Random peptide display methods simulate binding interactions by providing all possible peptide combinations with an equal opportunity to bind a protein of interest. The natural substrates for the protein are typically known in advance. However, it is often the case that such substrates are identified as putative partner proteins by using in vivo methods such as yeast two‑hybrid screening. Unfortunately, such methods often produce lengthy datasets of protein sequences and offer little mechanistic insight into how such interactions might take place in vivo. Here, we review an approach that addresses this problem. First, sequence alignment tools identify and characterize blocks of conserved sequences among peptides recovered during random peptide display. Next, searching programs detect similar blocks of conserved sequences within naturally‑occurring proteins to predict partner proteins. Finally, the significance of an interaction is tested using site‑specific mutagenesis, binding competition or co‑immunoprecipitation experiments. This strategy should become increasingly powerful with the growing popularity of interaction studies, sequencing projects and microarray analyses in modern biology.

 

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The Cloning of Human Genes Using cDNA Phage Display and Small-molecule Chemical Probes

Sergey N. Savinov and David J. Austin

 

The cloning of genes based on protein function has become a powerful tool for protein discovery and should play an important role in proteomics in general. We have recently reported a technique for the functional identification of protein targets by combining traditional affinity chromatography with cDNA phage display. This procedure, referred to as display cloning, directly couples biologically active natural products to the gene of their protein cellular target. We now report the cloning of a human gene, the a domain of F1 ATP synthase, using a synthetic scaffold molecule which serves as a prototype for a diverse chemical library. The ability to select genes from cDNA libraries using probes from combinatorial libraries would greatly increase the number of small molecule/protein interactions that can be identified. This method might prove valuable in furthering our understanding of biology and its application toward drug development.

 

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Caveat Receptor: Proteomes on Display                                                                         

F. J. Stevens

 

Display methods development is currently extending the application of this strategy beyond the generation of ligand binding reagents for research, clinical, or biotechnological purposes to its use as a primary research tool. Peptide- and cDNA display methods have the potential to contribute to understanding the mechanisms of certain classes of drugs and to help map protein-protein interactions of physiological importance. Although the critical contribution of comprehensive amino acid sequence databases has been recognized, of equal importance might be structural genomics concepts in the application of display system technology to proteomics research. Lessons learned from the study of antibody-antigen interactions are reviewed here and applied to the field of display technology with the goal of delineating major factors involved in the successful mimicry of natural protein-ligand interactions.