ENCODING TECHNIQUES FOR POOL LIBRARIES OF SMALL ORGANIC MOLECULES*

REFERENCES

• Seneci P. Direct Deconvolution Technique for Pool Libraries of Small Organic Molecules. Combinatorial Chemistry and Technology: Principles, Methods, and Applications, S. Miertus, G. Fassina. Marcel Dekker, Inc. 1999; 91–125
   Google Scholar
• Selway C. N., Terrett N. K. Parallel-Compound Synthesis: Methodology for Accelerating Drug Discovery. Bioorg. Med. Chem. 1996; 4: 645–654
   PubMed Web of Science ®Google Scholar
• Sashar S., Mjalli A. M.M. Techniques for Single-Compound Synthesis. Annual Reports in Combinatorial Chemistry and Molecular Diversity, W. H. Moos, M. R. Pavia, B. K. Kay, A. D. Ellington. ESCOM, Leiden 1997; 19–29
   Google Scholar
• Cargill J. F., Lebl M. New Methods In Combinatorial Chemistry: Robotics And Parallel Synthesis. Curr. Opin. Chem. Biol. 1997; 1: 67–71
   PubMed Web of Science ®Google Scholar
• Janda K. D. Tagged Versus Untagged Libraries: Methods for the Generation and Screening Of Combinatorial Chemical Libraries. Proc. Natl. Acad. Sci. USA 1994; 91: 10779–10785
   PubMed Web of Science ®Google Scholar
• Baldwin J. J., Dolle R. E. Deconvolution Methods In Solid-Phase Synthesis. Annual Reports in Combinatorial Chemistry and Molecular Diversity, W. H. Moos, M. R. Pavia, B. K. Kay, A. D. Ellington. ESCOM, Leiden 1997; 287–297
   Google Scholar
• Xiao X-Y., Nova M. P. Radiofrequency Encoding and Additional Techniques for the Structure Elucidation of Synthetic Combinatorial Libraries. Combinatorial Chemistry: Synthesis and Application, S. R. Wilson, A. W. Czarnik. Wiley, New York 1997; 135–152
   Google Scholar
• van Breemen R. B., Huang C. R., Nikolic D., Woodbury C. P., Zhao Y. Z., Venton D. L. Pulsed Ultrafiltration Mass Spectrometry: A New Method for Screening Combinatorial Libraries. Anal. Chem. 1997; 69: 2159–2164
   PubMed Web of Science ®Google Scholar
• Dunayevskiy Y. M., Lai J-J., Quinn C., Talley F., Vouros P. Mass Spectrometric Identification of Ligand Selected from Combinatorial Libraries using Gel Filtration. Rapid Commun. Mass Spectrom. 1997; 11: 1178–1184
   Web of Science ®Google Scholar
• Chu Y. H., Dunayevskiy Y. M., Kirby D. P., Vouros P., Karger B. L. Affinity Capillary Electrophoresis-Mass Spectrometry for Screening Combinatorial Libraries. J. Am. Chem. Soc. 1996; 118: 7827–7835
   Web of Science ®Google Scholar
• Brummel C. L., Vickerman J. C., Carr S. A., et al. Evaluation of Mass Spectrometric Methods Applicable to the Direct Analysis of Non-Peptide Bead-Bound Combinatorial Libraries. Anal. Chem. 1996; 68: 237–242
   Google Scholar
• Lam K. S., Salmon S. E., Hersh E. M., Hruby V. J., Kazmierski W. M., Knapp R. J. A New Type of Synthetic Peptide Library for Identifying Ligand-Binding Activity. Nature 1991; 354: 82–84
   PubMed Web of Science ®Google Scholar
• Lam K. S., Lebl M., Krchnak V. The “One-Bead One-Compound” Combinatorial Library Method. Chem. Rev. 1998; 97: 411–448
   Google Scholar
• Ruvo M., Fassina G. Synthesis and Characterization of Peptide Libraries. Combinatorial Chemistry and Technology: Principles, Methods, and Applications, S. Miertus, G. Fassina. Marcel Dekker, Inc. 1999; 7–21
   Google Scholar
• From here on the concept “one Bead, one Compound” will be used also in place of the more common synonym, “Mix and Split” technique, for library synthesis
   Google Scholar
• Brenner S., Lerner R. A. Encoded Combinatorial Chemistry. Proc. Nati. Acad. Sci. USA 1992; 89: 5381–5383
   PubMed Web of Science ®Google Scholar
• Nielsen J., Brenner S., Janda K. D. Synthetic Methods for the Implementation of Encoded Combinatorial Chemistry. J. Am. Chem. Soc. 1993; 115: 9812–9813
   Web of Science ®Google Scholar
• Jones D. G. Applications of Encoded Synthetic Libraries in Ligand Discovery. Polymer Prep. 1994; 35: 981–982
   Google Scholar
• Fenniri H., Janda K. D., Lerner R. A. Encoded Reaction Cassette for the Highly Sensitive Detection of the Making and Breaking of Chemical Bonds. Proc. Natl. Acad. Sci. USA 1995; 92: 2278–2282
   Google Scholar
• Fenniri H. Rapid Screening of Biocatalysts. CHEMTECH 1996; 26: 15–25
   Google Scholar
• Needels M. C., Jones D. G., Tate E. H., et al. Generation and Screening of an Oligonucleotide-Encoded Synthetic Peptide Library. Proc. Natl. Acad. Sci. USA 1993; 90: 107000–10704
   Google Scholar
• Nielsen J., Janda K. D. Toward Chemical Implementation of Encoded Combinatorial Libraries. Methods: Meth. Enzymol. 1994; 6: 361–371
   Google Scholar
• Dani M. Peptide Display Libraries: Design and Construction. Combinatorial Chemistry and Technology: Principles, Methods, and Applications, S. Miertus, G. Fassina. Marcel Dekker, Inc. 1999; 301–322
   Google Scholar
• Ruvo M., Fassina G. Synthesis and Characterization of Peptide Libraries. Combinatorial Chemistry and Technology; Principles, Methods, and Applications, S. Mirtus, G Fassina. Marcel Dekker, Inc. 1999; 7–21
   Google Scholar
• Nikolaiev V., Stierandova A., Krchnak V., et al. Peptide-Encoding for Structure Determination of Nonsequenceable Polymers within Libraries Synthesized and Tested on Solid-Phase Supports. Peptide Res. 1993; 6: 161–170
   Google Scholar
• Kerr J. M., Banville S. C., Zuckermann R. N. Encoded Combinatorial Peptide Libraries Containing Non-Natural Amino Acids. J. Am. Chem. Soc. 1993; 115: 2529–2531
   Google Scholar
• Hornik V., Hadas E. Self-encoded, Highly Condensed Solid Phase-Supported Peptide Library for Identification of Ligand-Specific Peptides. Reaction Polymers 1994; 22: 213–220
   Google Scholar
• Felder E. R., Heizmann G., Matthews I. T., Rink H., Spieser E. A New Combination of Protecting Groups and Links for Encoded Synthetic Libraries Suited for Consecutive Tests on the Solid Phase and in Solution. Molec Diversity 1996; 1: 109–112
   Google Scholar
• Vagner J., Barany G., Lam K. S., et al. Enzyme-Mediated Spatial Segregation on Individual Polymeric Support Beads: Application to Generation and Screening of Encoded Combinatorial Libraries. Proc. Natl. Acad. Sci. USA 1996; 93: 8194–8199
   Google Scholar
• Ohlmeyer M. J.H., Swanson R. N., Dillard L. W., et al. Complex Synthetic Chemical Libraries Indexed with Molecular Tags. Proc. Natl. Acad. Sci. USA 1993; 90: 10922–10926
   PubMed Web of Science ®Google Scholar
• Nestler H. P., Bartlett P. A., Still W. C. A General Method For Molecular Tagging of Encoded Combinatorial Chemistry Libraries. J. Org. Chem. 1994; 59: 4723–4724
   Web of Science ®Google Scholar
• Yoon S. S., Still W. C. Sequence-Selective Binding with a Synthetic Receptor. Tetrahedron 1995; 51: 567–578
   Web of Science ®Google Scholar
• Hill H. H., McMinn D. G. Detectors For Capillary Chromatography. Chem. Anal. 1992; 121: 83–107
   Google Scholar
• Yoon S. S., Still W. C. An Exceptional Synthetic Receptor for Peptides. J. Am. Chem. Soc. 1993; 115: 823–824
   Web of Science ®Google Scholar
• Yoon S. S., Still W. C. Cyclooligomeric Receptors for the Sequence Selective Binding of Peptides. A Tetrahedral Receptor from Trimesic Acid and 1,2-Diamines. Tetrahedron Lett. 1994; 35: 8557–8560
   Google Scholar
• Baldwin J. J. Design, Synthesis and Use of Binary Encoded Synthetic Chemical Libraries. Molec Diversity 1996; 2: 81–88
   Google Scholar
• Still W. C. Discovery of Sequence-Selective Peptide Binding by Synthetic Receptors Using Encoded Combinatorial Libraries. Accounts Chem. Res. 1996; 29: 155–163
   Web of Science ®Google Scholar
• Burbaum J. J., Ohlmeyer M. H.J., Reader J. C., et al. A Paradigm for Drug Discovery Employing Encoded Combinatorial Libraries. Proc. Natl. Acad. Sci. USA 1995; 92: 6027–6031
   Google Scholar
• Burger M. T., Still W. C. Synthetic Ionophores. Encoded Combinatorial Libraries of Cyclen-Based Receptors for Cu(2+) And Co(2+). J. Org. Chem. 1995; 60: 7382–7383
   Web of Science ®Google Scholar
• Appell K. C., Chung T. D.Y., Ohlmeyer M. J.H., Sigal N. H., Baldwin J. J., Chelsky D. Biological Screening of a Large Combinatorial Library. J. Biomolec Screening 1996; 1: 27–31
   Google Scholar
• Nestler H. P. Sequence-Selective Nonmacrocyclic Two-Armed Receptors for Peptides. Molec Diversity 1996; 2: 35–40
   Google Scholar
• Liang R., Yan L., Loebach J. Parallel Synthesis and Screening of a Solid Phase Carbohydrate Library. Science 1996; 274: 1520–1522
   PubMed Web of Science ®Google Scholar
• Ni Z. J., Maclean D., Holmes C. P. Versatile Approach to Encoding Combinatorial Organic Syntheses Using Chemically Robust Secondary Amine Tags. J. Med. Chem. 1996; 39: 1601–1608
   PubMed Web of Science ®Google Scholar
• Maclean D., Schullek J. R., Murphy M. M., Ni Z. J., Gordon E. M., Gallop M. A. Encoded Combinatorial Chemistry: Synthesis and Screening of a Library of Highly Functionalized Pyrrolidines. Proc. Natl. Acad. Sci. USA 1997; 94: 2805–2810
   PubMed Web of Science ®Google Scholar
• Murphy M. M., Schullek J. R., Gordon E. M., Gallop M. A. Combinatorial Oganic Synthesis of Highly Functionalized Pyrrolidines: Identification of a Potent Angiotensin Converting Enzyme Inhibitor from a Mercaptoacyl Proline Library. J. Am. Chem. Soc. 1995; 117: 7029–7030
   Web of Science ®Google Scholar
• Atuegbu A., Maclean D., Nguyen C., Gordon E. M., Jacobs J. W. Combinatorial Modification of Natural Products: Preparation of Unencoded and Encoded Libraries of Rauwolfia Alkaloids. Bioorg. Med. Chem. 1996; 4: 1097–1106
   Google Scholar
• Schullek J. R., Butler J. H., Ni Z. J., Chen D., Yuan Z. Y. A High-Density Screening Format for Encoded Combinatorial Libraries: Assay Miniaturization and its Application to Enzymatic Reactions. Anal. Biochem. 1997; 246: 20–29
   PubMedGoogle Scholar
• Geysen H. M., Wagner C. D., Bodnar W. M., et al. Isotope or Mass Encoding of Combinatorial Libraries. Chem. and Biol. 1996; 3: 679–688
   Google Scholar
• Garigipati R. S., Sarkar S. K. A Binary Coding Method for Use in Combinatorial Chemistry. WO 9714814 1997; A1: 970, 424
   Google Scholar
• Seneci P., Sizemore C., Islam K., Kocis P. Combinatorial Chemistry and Natural Products. Teicoplanin Aglycone as a Molecular Scaffold for Solid Phase Synthesis of Cornbinatorial Libraries. Tetrahedron Lett. 1996; 37: 6319–6322
   Google Scholar
• Kocis P., Krchnak V., LebI M. Symmetrical Structure Allowing the Selective Multiple Release of a Defined Quantity of Peptide from a Single Bead of Polymeric Support. Tetrahedron Lett. 1993; 34: 7251–7252
   Google Scholar
• Malabarba A., Strazzolini P., Depaoli A., Landi M., Berti M., Cavalleri B. Teicoplanin, Antibiotics from Actinoplanes teichomyceticus Nov. sp. VI. Chemical Degradation: Physicochemical and Biological Properties of Acid Hydrolysis Products. J. Antibiot. 1984; 37: 988–999
   Google Scholar
• Malabarba A., Ferrari P., Gallo G. G., Kettenring J., Cavalleri B. Teicoplanin, Antibiotics from Actinoplones teichomyceticus nov. sp. VII. Preparation and NMR Characteristics of the Aglycon of Teicoplanin. J. Antibiot. 1986; 39: 1430–1442
   Google Scholar
• Seneci P., Trani A., Ferrari P., Scotti R., Ciabatti R. Synthesis and Biological Activity of 0-56-Substituted Carboxy Esters and Carboxamides of Teicoplanin Aglycone. J. Antibiot. 1992; 45: 1633–1644
   Google Scholar
• Sizemore C. F., Seneci P., Kocis P., Wertman K. F., Islam K. Combinatorial Chemistry and Natural Products: Determination of the Biological Activity of On-Bead, Double Cleavable Teicoplanin Aglycon (TD). Protein Peptide Lett. 1996; 3: 253–260
   Web of Science ®Google Scholar
• Lebl M., Krchnak V., Salmon S. E., Lam K. S. Screening of Completely Random One-Bead One-Peptide Libraries for Activities in Solution. Methods: Meth. Enzymol., 6: 381–387
   Google Scholar
• Salmon S. E., Lam K. S., Lebl M., et al. Discovery Of Biologically Active Peptides in Random Libraries: Solution-Phase Testing after Staged Orthogonal Release from Resin Beads. Proc. Natl. Acad. Sci. USA 1993; 90: 11708–11712
   PubMedGoogle Scholar
• Brown B. B., Wagner D. S., Geysen H. M. A Single-Bead Decode Strategy using Electrospray Ionization Mass Spectrometry and a New Photolabile Linker: 3-Amino-3-(2-nitrophenyl)-propionic Acid. Molec Diversity 1995; 1: 4–12
   Google Scholar
• Cardno M., Bradley M. A Simple Multiple Release System For Combinatorial Library and Peptide Analysis. Tetrahedron Lett. 1996; 37: 135–138
   Google Scholar
• Rink H., Vetter D., Gercken B., Felder E. Preparation of Combinatorial Compound Libraries Coded with Element Atom Tags. WO 9630392 1996; A1: 961, 003
   Google Scholar
• Garigipati R. S., Adams J. L. Photolytically Cleavable Arylsulfonamide Encoding and Linking Agents for Use in Combinatorial Chemistry. WO 9630337 1996; A1: 961003
   Google Scholar
• Yamashita D. S., Weinstock J. Encoded Combinatorial Libraries. WO 9532425 1995; Al: 951, 130
   Google Scholar
• Scott R. H., Balasubramanian S. Properties of Fluorophores on Solid Phase Resins: Implications for Screening, Encoding and Reaction Monitoring. Bioorg. Med. Chem. Lett. 1997; 7: 1567–1572
   Google Scholar
• Egner B. J., Rana S., Smith H., et al. Tagging in Combinatorial Chemistry: The Use of Colored and Fluorescent Beads. Chem. Commun. 1997; 735–736
   Google Scholar
• Edwards P. N., Main B. G., Shute R. E. Chemical Libraries, Labelling and Deconvolution Thereof. WO 9623749 1996; A1: 960, 808
   Google Scholar
• Main B. G., Shute R. E. Intrinsically Labelled Solid Support. WO 9703931 1997; A1: 970, 602
   Google Scholar
• Kaye P. H., Tracey M. C. Coded Particles for Process Sequence Tracking in Combinatorial Compound Library Preparation. WO 9715390 1997; A1: 970501
   Google Scholar
• Nicolaou K. C., Xiao X. Y., Parandoosh Z., Senyei A., Nova M. P. Radiofrequency Encoded Combinatorial Chemistry. Angew. Chem. Int. Ed. 1995; 34: 2289–2291
   Google Scholar
• Moran E. J., Sarshar S., Cargill J. F., et al. Radio Frequency Tag Encoded Combinatorial Library Method for the Discovery Of Tripeptide-Substitued Cinnamic Acid Inhibitors of the Protein Tyrosine Phosphatase PTP1b. J. Am. Chem. Soc. 1995; 117: 10787–10788
   Google Scholar
• Felder E. R. Resins, Linkers, and Reactions for Solid-Phase Synthesis of Organic Libraries. Combinatorial Chemistry and Technology: Principles, Methods, and Applications, S. Miertus, G. Fassina. Marcel Dekker, Inc. 1999; 35–51
   Google Scholar
• Rapp W. PEG Grafted Polystyrene Tentacle Polymers: Physico-Chemical Properties and Application in Chemical Synthesis. Molecular Diversity and Combinatorial Chemistry, I. W. Chaiken, K. D. Janda. American Chemical Society, Washington, DC 1996; 425–464
   Google Scholar
• Porco J. A., Jr., Deegan T. L., Gooding O. W., et al. New Poly(Styrene-oxyethylene) Graft Copolymers for Solid-Phase Organic Synthesis: Linkers and Applications. Book of Abstracts, 212th ACS National Meeting, Orlando, FL, August, 25–29. American Chemical Society, Washington, DC 1996
   Google Scholar
• Kempe M., Barany G. CLEAR: A Novel Family of Highly Cross-Linked Polymeric Supports for Solid-Phase Peptide Synthesis. J. Am. Chem. Soc. 1996; 118: 7083–7093
   Web of Science ®Google Scholar
• Backes B. J., Ellman J. A. Solid Support Linker Strategies. Curr. Opin. Chem. Biol. 1997; 1: 86–93
   PubMed Web of Science ®Google Scholar
• Blackburn C., Albericlo F., Kates S. A. Functionalized Resins and Linkers for Solid-Phase Synthesis of Small Molecules. Drugs Future 1997; 22: 1007–1025
   Google Scholar
• Geysen H. M., Meloen R. H., Barteling S. J. Use of Peptide Synthesis to Probe Viral Antigens for Epitopes to a Resolution of a Single Amino Acid. Proc. Natl. Acad. Sci. USA 1984; 81: 3998–4002
   PubMed Web of Science ®Google Scholar
• Valerio R. M., Bray A. M., Campbell R. A., et al. Multipin Peptide Synthesis at the Micromole Scale Using 2-Hydroxyethyl Methacrylate Grafted Polyethylene Supports. Int. J. Peptide Protein Res. 1993; 42: 1–9
   Google Scholar
• Chin J., Fell B., Shapiro M. J., Tomesch J., Wareing J. R., Bray A. M. Magic Angle Spinning NMR for Reaction Monitoring and Structure Determination of Molecules attached to Multipin Crowns. J. Org. Chem. 1997; 62: 538–539
   Google Scholar
• Frank R. Spot Synthesis: An Easy Technique for the Positionally Addressable, Parallel Chemical Synthesis on a Membrane Support. Tetrahedron 1992; 48: 9217–9232
   Web of Science ®Google Scholar
• Frank R. Strategies and Techniques in Simultaneous Multiple Peptide Synthesis Based on the Segmentation of Membrane type Supports. Bioorg. Med. Chem. Lett. 1993; 3: 425–430
   Google Scholar
• Gravert D. J., Janda K. D. Synthesis on Soluble Polymers: New Reactions and the Construction of Small Molecules. Curr. Opin. Chem. Biol. 1997; 1: 107–113
   PubMedGoogle Scholar
• Gravert D. J., Janda K. D. Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies. Chem. Rev. 1997; 97: 489–509
   PubMed Web of Science ®Google Scholar
• Kim R. M., Manna M., Hutchins S. M., et al. Dendrimer-Supported Combinatorial Chemistry. Proc. Natl. Acad. Sci. USA 1996; 93: 10012–10017
   PubMedGoogle Scholar
• French P. J., Gennissen P. T.J., Sarro P. M. New Silicon Micromachining Techniques for Microsystems. Sens. Actuators A 1997; 62: 652–662
   Google Scholar
• Bao M., Li X., Shen S., Chen H. A Novel Micromachining Technology For Multilevel Structures Of Silicon. Sens. Actuators A 1997; 63: 217–221
   Google Scholar
• Navarro M., Lopez-Villegas J. M., Samitier J., Morante J. R., Bausells J., Merlos A. Electrochemical Etching of Porous Silicon Sacrificial Layers for Micromachining Applications. J. Micromech Microeng. 1997; 7: 131–132
   Google Scholar
• Xiao X., Zhao C., Potash H., Nova M. P. Combinatorial Chemistry with Laser Optical Encoding. Angew. Chem. Int. Ed. 1997; 36: 780–782
   Google Scholar
• Xiao X., Parandoosh Z., Nova M. P. Design and Synthesis of a Taxoid Library using Radiofrequency Encoded Combinatorial Chemistry. J. Org. Chem. 1997; 62: 6029–6033
   Google Scholar
• Armstrong R. W., Tempest P. A., Cargill J. F. Microchip Encoded Combinatorial Libraries. Generation of a Spatially Encoded Library from a Pool Synthesis. Chimia 1996; 50: 258–260
   Web of Science ®Google Scholar
• Nicolaou K. C., Vourloumis D., Li T. Designed Epothilones: Combinatorial Synthesis, Tubulin Assembly Properties, and Cytotoxic Action Against Taxol-Resistant Tumor Cells. Angew. Chem. Int. Ed. 1997; 36: 2097–2103
   Google Scholar
• Radiofrequence-Based Parallel Synthesis Tools are Commercialized by IRORI Quantum Microchemistry, 11025 North Torrey Pines Road, La Jolta CA 92037, USA
   Google Scholar
• Burgess K., Liaw A. I., Wang N. Combinatorial Technologies Involving Reiterative Division/Coupling/Recombination: Statistical Considerations. J. Med. Chem. 1994; 37: 2985–2987
   Google Scholar