DNA-Encoded Chemical Libraries: Advancing beyond Conventional Small-Molecule Libraries

被引:189
作者
Franzini, Raphael M. [1 ]
Neri, Dario [1 ]
Scheuermann, Joerg [1 ]
机构
[1] ETH, Inst Pharmaceut Sci, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
基金
瑞士国家科学基金会;
关键词
IN-VITRO SELECTION; TEMPLATED ORGANIC-SYNTHESIS; DRUG DISCOVERY; COMBINATORIAL CHEMISTRY; HIGH-AFFINITY; TRYPSIN-INHIBITORS; BINDING-MOLECULES; CYCLIC-PEPTIDES; GENETIC-CODE; LIGANDS;
D O I
10.1021/ar400284t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
DNA-encoded chemical libraries (DECLs) represent a promising tool in drug discovery. DECL technology allows the synthesis and screening of chemical libraries of unprecedented size at moderate costs. In analogy to phage-display technology, where large antibody libraries are displayed on the surface of filamentous phage and are genetically encoded in the phage genome, DECLs feature the display of individual small organic chemical moieties on DNA fragments serving as amplifiable identification barcodes. The DNA-tag facilitates the synthesis and allows the simultaneous screening of very large sets of compounds (up to billions of molecules), because the hit compounds can easily be identified and quantified by PCR-amplification of the DNA-barcode followed by high-throughput DNA sequencing. Several approaches have been used to generate DECLs, differing both in the methods used for library encoding and for the combinatorial assembly of chemical moieties. For example, DECLs can be used for fragment-based drug discovery, displaying a single molecule on DNA or two chemical moieties at the extremities of complementary DNA strands. DECLs can vary substantially in the chemical structures and the library size. While ultralarge libraries containing billions of compounds have been reported containing four or more sets of building blocks, also smaller libraries have been shown to be efficient for ligand discovery. In general, it has been found that the overall library size is a poor predictor for library performance and that the number and diversity of the building blocks are rather important indicators. Smaller libraries consisting of two to three sets of building blocks better fulfill the criteria of drug-likeness and often have higher quality. In this Account, we present advances in the DECL field from proof-of-principle studies to practical applications for drug discovery, both in industry and in academia. DECL technology can yield specific binders to a variety of target proteins and is likely to become a standard tool for pharmaceutical hit discovery, lead expansion, and Chemical Biology research. The introduction of new methodologies for library encoding and for compound synthesis in the presence of DNA is an exciting research field and will crucially contribute to the performance and the propagation of the technology.
引用
收藏
页码:1247 / 1255
页数:9
相关论文
共 56 条
[1]   Yeast surface display for screening combinatorial polypeptide libraries [J].
Boder, ET ;
Wittrup, KD .
NATURE BIOTECHNOLOGY, 1997, 15 (06) :553-557
[2]   ENCODED COMBINATORIAL CHEMISTRY [J].
BRENNER, S ;
LERNER, RA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (12) :5381-5383
[3]   Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions [J].
Buller, Fabian ;
Mannocci, Luca ;
Zhang, Yixin ;
Dumelin, Christoph E. ;
Scheuermann, Joerg ;
Neri, Dario .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (22) :5926-5931
[4]   Selection of Carbonic Anhydrase IX Inhibitors from One Million DNA-Encoded Compounds [J].
Buller, Fabian ;
Steiner, Martina ;
Frey, Katharina ;
Mircsof, Dennis ;
Scheuermann, Joerg ;
Kalisch, Markus ;
Buehlmann, Peter ;
Supuran, Claudiu T. ;
Neri, Dario .
ACS CHEMICAL BIOLOGY, 2011, 6 (04) :336-344
[5]   High-throughput sequencing for the identification of binding molecules from DNA-encoded chemical libraries [J].
Buller, Fabian ;
Steiner, Martina ;
Scheuermann, Joerg ;
Mannocci, Luca ;
Nissen, Ina ;
Kohler, Manuel ;
Beisel, Christian ;
Neri, Dario .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (14) :4188-4192
[6]   Discovery of TNF Inhibitors from a DNA-Encoded Chemical Library based on Diels-Alder Cycloaddition [J].
Buller, Fabian ;
Zhang, Yixin ;
Scheuermann, Joerg ;
Schaefer, Juliane ;
Buehlmann, Peter ;
Neri, Dario .
CHEMISTRY & BIOLOGY, 2009, 16 (10) :1075-1086
[7]   An expanded eukaryotic genetic code [J].
Chin, JW ;
Cropp, TA ;
Anderson, JC ;
Mukherji, M ;
Zhang, ZW ;
Schultz, PG .
SCIENCE, 2003, 301 (5635) :964-967
[8]   Design, synthesis and selection of DNA-encoded small-molecule libraries [J].
Clark, Matthew A. ;
Acharya, Raksha A. ;
Arico-Muendel, Christopher C. ;
Belyanskaya, Svetlana L. ;
Benjamin, Dennis R. ;
Carlson, Neil R. ;
Centrella, Paolo A. ;
Chiu, Cynthia H. ;
Creaser, Steffen P. ;
Cuozzo, John W. ;
Davie, Christopher P. ;
Ding, Yun ;
Franklin, G. Joseph ;
Franzen, Kurt D. ;
Gefter, Malcolm L. ;
Hale, Steven P. ;
Hansen, Nils J. V. ;
Israel, David I. ;
Jiang, Jinwei ;
Kavarana, Malcolm J. ;
Kelley, Michael S. ;
Kollmann, Christopher S. ;
Li, Fan ;
Lind, Kenneth ;
Mataruse, Sibongile ;
Medeiros, Patricia F. ;
Messer, Jeffrey A. ;
Myers, Paul ;
O'Keefe, Heather ;
Oliff, Matthew C. ;
Rise, Cecil E. ;
Satz, Alexander L. ;
Skinner, Steven R. ;
Svendsen, Jennifer L. ;
Tang, Lujia ;
van Vloten, Kurt ;
Wagner, Richard W. ;
Yao, Gang ;
Zhao, Baoguang ;
Morgan, Barry A. .
NATURE CHEMICAL BIOLOGY, 2009, 5 (09) :647-654
[9]   Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metalloproteases as well as tyrosine phosphatases [J].
Debaene, Francois ;
Da Silva, Julien A. ;
Pianowski, Zbigniew ;
Duran, Fernando J. ;
Winssinger, Nicolas .
TETRAHEDRON, 2007, 63 (28) :6577-6586
[10]   Discovery of Highly Potent and Selective Small Molecule ADAMTS-5 Inhibitors That Inhibit Human Cartilage Degradation via Encoded Library Technology (ELT) [J].
Deng, Hongfeng ;
O'Keefe, Heather ;
Davie, Christopher P. ;
Lind, Kenneth E. ;
Acharya, Raksha A. ;
Franklin, G. Joseph ;
Larkin, Jonathan ;
Matico, Rosalie ;
Neeb, Michael ;
Thompson, Monique M. ;
Lohr, Thomas ;
Gross, Jeffrey W. ;
Centrella, Paolo A. ;
O'Donovan, Gary K. ;
Bedard, Katie L. ;
van Vloten, Kurt ;
Mataruse, Sibongile ;
Skinner, Steven R. ;
Belyanskaya, Svetlana L. ;
Carpenter, Tiffany Y. ;
Shearer, Todd W. ;
Clark, Matthew A. ;
Cuozzo, John W. ;
Arico-Muendel, Christopher C. ;
Morgan, Barry A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (16) :7061-7079