Skip to main content
NCBI home page
Springer Nature - PMC COVID-19 Collection logoLink to Springer Nature - PMC COVID-19 Collection
. 2007 Mar 10;278:311–342. doi: 10.1007/128_2007_109

Probing Biology with Small Molecule Microarrays (SMM)

Nicolas Winssinger 1,✉, Zbigniew Pianowski 1, Francois Debaene 1
Editor: Stefan Bräse
PMCID: PMC7122856

Abstract

In the continuous drive to increase screening throughput and reduce sample requirement, microarray-based technologies have risen to the occasion. In the past 7 years, a number of new methodologies have been developed for preparing small molecule microarrays from combinatorial and natural product libraries with the goal of identifying new interactions or enzymatic activities. Recent advances and applications of small molecule microarrays are reviewed.

Keywords: Activity profiling, Combinatorial libraries, Diagnostic, Screening, Small molecule microarray (SMM)

Contributor Information

Stefan Bräse, Email: braese@ioc.uka.de.

Nicolas Winssinger, Email: winssinger@isis.u-strasbg.fr.

References

  • 1.Heller MJ. DNA microarray technology: devices, systems, and applications. Ann Rev Biomed Eng. 2002;4:129–153. doi: 10.1146/annurev.bioeng.4.020702.153438. [DOI] [PubMed] [Google Scholar]
  • 2.Pirrung MC. How to make a DNA chip. Angew Chem Int Ed. 2002;41:1276–1289. doi: 10.1002/1521-3773(20020415)41:8<1276::AID-ANIE1276>3.0.CO;2-2. [DOI] [PubMed] [Google Scholar]
  • 3. Brown P (2004) The MGuide. Version 2.0. http://www.cmgm.stanford.edu/pbrown/mguide/index.html (last visited: 26 Jan 2007)
  • 4.Conzone SD, Pantano CG. Glass slides to DNA microarrays. Mater Today. 2004;7:20–26. doi: 10.1016/S1369-7021(04)00122-1. [DOI] [Google Scholar]
  • 5.Bradner JE, et al. A robust small-molecule microarray platform for screening cell lysates. Chem Biol. 2006;13:493–504. doi: 10.1016/j.chembiol.2006.03.004. [DOI] [PubMed] [Google Scholar]
  • 6.Lee MR, Shin I. Fabrication of chemical microarrays by efficient immobilization of hydrazide-linked substances on epoxide-coated glass surfaces. Angew Chem Int Ed. 2005;44:2881–2884. doi: 10.1002/anie.200462720. [DOI] [PubMed] [Google Scholar]
  • 7.Kanoh N, et al. Immobilization of natural products on glass slides by using a photoaffinity reaction and the detection of protein-small-molecule interactions. Angew Chem Int Ed. 2003;42:5584–5587. doi: 10.1002/anie.200352164. [DOI] [PubMed] [Google Scholar]
  • 8.Hergenrother PJ, Depew KM, Schreiber SL. Small-molecule microarrays: covalent attachment and screening of alcohol-containing small molecules on glass slides. J Am Chem Soc. 2000;122:7849–7850. doi: 10.1021/ja0014032. [DOI] [Google Scholar]
  • 9.Falsey JR, Renil M, Park S, Li S, Lam KS. Peptide and small molecule microarray for high throughput cell adhesion and functional assays. Bioconjugate Chem. 2001;12:346–353. doi: 10.1021/bc000141q. [DOI] [PubMed] [Google Scholar]
  • 10.Shin I, Park S, Lee MR. Carbohydrate microarrays: an advanced technology for functional studies of glycans. Chemistry. 2005;11:2894–2901. doi: 10.1002/chem.200401030. [DOI] [PubMed] [Google Scholar]
  • 11.Benters R, Niemeyer CM, Wohrle D. Dendrimer-activated solid supports for nucleic acid and protein microarrays. ChemBioChem. 2001;2:686–694. doi: 10.1002/1439-7633(20010903)2:9<686::AID-CBIC686>3.0.CO;2-S. [DOI] [PubMed] [Google Scholar]
  • 12.Hackler L, Jr, et al. Development of chemically modified glass surfaces for nucleic acid, protein and small molecule microarrays. Mol Divers. 2003;7:25–36. doi: 10.1023/B:MODI.0000006534.36417.06. [DOI] [PubMed] [Google Scholar]
  • 13.Houseman BT, Huh JH, Kron SJ, Mrksich M. Peptide chips for the quantitative evaluation of protein kinase activity. Nat Biotechnol. 2002;20:270–274. doi: 10.1038/nbt0302-270. [DOI] [PubMed] [Google Scholar]
  • 14.Lee K-B, Park S-J, Mirkin CA, Smith JC, Mrksich M. Protein nanoarrays generated by dip-pen nanolithography. Science. 2002;295:1702–1705. doi: 10.1126/science.1067172. [DOI] [PubMed] [Google Scholar]
  • 15.Lee SW, et al. Biologically active protein nanoarrays generated using parallel dip-pen nanolithography. Adv Mater. 2006;18:1133–1136. doi: 10.1002/adma.200600070. [DOI] [Google Scholar]
  • 16.Fodor SPA, et al. Light-directed, spatially addressable parallel chemical synthesis. Science. 1991;251:767–773. doi: 10.1126/science.1990438. [DOI] [PubMed] [Google Scholar]
  • 17.Cho CY, et al. An unnatural biopolymer. Science. 1993;261:1303–1305. doi: 10.1126/science.7689747. [DOI] [PubMed] [Google Scholar]
  • 18.Pease AC, et al. Light-generated oligonucleotide arrays for rapid DNA sequence analysis. Proc Natl Acad Sci USA. 1994;91:5022–5026. doi: 10.1073/pnas.91.11.5022. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 19.McGall G, et al. Light-directed synthesis of high-density oligonucleotide arrays using semiconductor photoresists. Proc Natl Acad Sci USA. 1996;93:13555–13560. doi: 10.1073/pnas.93.24.13555. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 20.Singh-Gasson S, et al. Maskless fabrication of light-directed oligonucleotide microarrays using a digital micromirror array. Nat Biotechnol. 1999;17:974–978. doi: 10.1038/13664. [DOI] [PubMed] [Google Scholar]
  • 21.Li S, et al. Photolithographic synthesis of peptoids. J Am Chem Soc. 2004;126:4088–4089. doi: 10.1021/ja039565w. [DOI] [PubMed] [Google Scholar]
  • 22. Li S, Marthandan N, Bowerman D, Garner HR, Kodadek T (2005) Photolithographic synthesis of cyclic peptide arrays using a differential deprotection strategy. Chem Comm pp 581–583 [DOI] [PubMed]
  • 23.LeProust E, et al. Digital light-directed synthesis. A microarray platform that permits rapid reaction optimization on a combinatorial basis. J Comb Chem. 2000;2:49–354. doi: 10.1021/cc000009x. [DOI] [PubMed] [Google Scholar]
  • 24.Pellois JP, Wang W, Gao X. Peptide synthesis based on t-Boc chemistry and solution photogenerated acids. J Comb Chem. 2000;2:355–360. doi: 10.1021/cc0000139. [DOI] [PubMed] [Google Scholar]
  • 25.Pellois JP, et al. Individually addressable parallel peptide synthesis on microchips. Nat Biotechnol. 2002;20:922–926. doi: 10.1038/nbt723. [DOI] [PubMed] [Google Scholar]
  • 26.Frank R, Gueler S, Krause S, Lindenmaier W. Facile and rapid spot-synthesis of large numbers of peptides on membrane sheets. Proc 21st Eur Pept Symp: Pept 1990; 1991. pp. 151–152. [Google Scholar]
  • 27.Frank R. Spot-synthesis: an easy technique for the positionally addressable, parallel chemical synthesis on a membrane support. Tetrahedron. 1992;48:9217–9232. doi: 10.1016/S0040-4020(01)85612-X. [DOI] [Google Scholar]
  • 28.Frank R. The SPOT-synthesis technique. Synthetic peptide arrays on membrane supports–principles and applications. J Immunol Methods. 2002;267:13–26. doi: 10.1016/S0022-1759(02)00137-0. [DOI] [PubMed] [Google Scholar]
  • 29.Scharn D, Wenschuh H, Reineke U, Schneider-Mergener J, Germeroth L. Spatially addressed synthesis of amino- and amino-oxy-substituted 1,3,5-triazine arrays on polymeric membranes. J Comb Chem. 2000;2:361–369. doi: 10.1021/cc000012g. [DOI] [PubMed] [Google Scholar]
  • 30.Scharn D, Germeroth L, Schneider-Mergener J, Wenschuh H. Sequential nucleophilic substitution on halogenated triazines, pyrimidines, and purines: a novel approach to cyclic peptidomimetics. J Org Chem. 2001;66:507–513. doi: 10.1021/jo005631q. [DOI] [PubMed] [Google Scholar]
  • 31.Heine N, Germeroth L, Schneider-Mergener J, Wenschuh H. A modular approach to the SPOT-synthesis of 1,3,5-trisubstituted hydantoins on cellulose membranes. Tetrahedron Lett. 2001;42:227–230. doi: 10.1016/S0040-4039(00)01960-2. [DOI] [Google Scholar]
  • 32.Niggemann J, Michaelis K, Frank R, Zander N, Hoefle G. Natural product-derived building blocks for combinatorial synthesis. Part 1. Fragmentation of natural products from myxobacteria. J Chem Soc. pp 2490–2503: Perkin Trans 1; 2002. [Google Scholar]
  • 33.Bowman Matthew D, Jeske Ryan C, Blackwell Helen E. Microwave-accelerated SPOT-synthesis on cellulose supports. Org Lett. 2004;6:2019–2022. doi: 10.1021/ol049313f. [DOI] [PubMed] [Google Scholar]
  • 34.Lin Q, O'Neill JC, Blackwell HE. Small molecule macroarray construction via Ugi four-component reactions. Org Lett. 2005;7:4455–4458. doi: 10.1021/ol051684o. [DOI] [PubMed] [Google Scholar]
  • 35.MacBeath G, Koehler AN, Schreiber SL. Printing small molecules as microarrays and detecting protein–ligand interactions en masse. J Am Chem Soc. 1999;121:7967–7968. doi: 10.1021/ja991083q. [DOI] [Google Scholar]
  • 36.Kuruvilla FG, Shamji AF, Sternson SM, Hergenrother PJ, Schreiber SL. Dissecting glucose signalling with diversity-oriented synthesis and small-molecule microarrays. Nature. 2002;416:653–657. doi: 10.1038/416653a. [DOI] [PubMed] [Google Scholar]
  • 37.Melnyk O, et al. Peptide arrays for highly sensitive and specific antibody-binding fluorescence assays. Bioconjugate Chem. 2002;13:713–720. doi: 10.1021/bc015584o. [DOI] [PubMed] [Google Scholar]
  • 38.de Araujo AD, et al. Diels–Alder ligation and surface immobilization of proteins. Angew Chem Int Ed. 2005;45:296–301. doi: 10.1002/anie.200502266. [DOI] [PubMed] [Google Scholar]
  • 39.Barnes-Seeman D, Park SB, Koehler AN, Schreiber SL. Expanding the functional group compatibility of small-molecule microarrays: discovery of novel calmodulin ligands. Angew Chem Int Ed. 2003;42:2376–2379. doi: 10.1002/anie.200351043. [DOI] [PubMed] [Google Scholar]
  • 40.Nilsson BL, Kiessling LL, Raines RT. Staudinger ligation: a peptide from a thioester and azide. Org Lett. 2000;2:1939–1941. doi: 10.1021/ol0060174. [DOI] [PubMed] [Google Scholar]
  • 41.Saxon E, Armstrong JI, Bertozzi CR. A traceless Staudinger ligation for the chemoselective synthesis of amide bonds. Org Lett. 2000;2:2141–2143. doi: 10.1021/ol006054v. [DOI] [PubMed] [Google Scholar]
  • 42.Soellner MB, Dickson KA, Nilsson BL, Raines RT. Site-specific protein immobilization by Staudinger ligation. J Am Chem Soc. 2003;125:11790–11791. doi: 10.1021/ja036712h. [DOI] [PubMed] [Google Scholar]
  • 43.Watzke A, et al. Site-selective protein immobilization by staudinger ligation. Angew Chem Int Ed. 2006;45:1408–1412. doi: 10.1002/anie.200502057. [DOI] [PubMed] [Google Scholar]
  • 44.Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew Chem Int Ed. 2002;41:2596–2599. doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. [DOI] [PubMed] [Google Scholar]
  • 45.Bryan MC, et al. Covalent display of oligosaccharide arrays in microtiter plates. J Am Chem Soc. 2004;126:8640–8641. doi: 10.1021/ja048433f. [DOI] [PubMed] [Google Scholar]
  • 46.Calarese DA, et al. Dissection of the carbohydrate specificity of the broadly neutralizing anti-HIV-1 antibody 2G12. Proc Natl Acad Sci USA. 2005;102:13372–13377. doi: 10.1073/pnas.0505763102. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 47.Feizi T, Fazio F, Chai W, Wong C-H. Carbohydrate microarrays – a new set of technologies at the frontiers of glycomics. Curr Opin Struct Biol. 2003;13:637–645. doi: 10.1016/j.sbi.2003.09.002. [DOI] [PubMed] [Google Scholar]
  • 48.Huang CY, et al. Carbohydrate microarray for profiling the antibodies interacting with Globo H tumor antigen. Proc Natl Acad Sci USA. 2006;103:15–20. doi: 10.1073/pnas.0509693102. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 49.Lee MR, Shin I. Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides. Org Lett. 2005;7:4269–4272. doi: 10.1021/ol051753z. [DOI] [PubMed] [Google Scholar]
  • 50.Winssinger N, Harris JL, Backes BJ, Schultz PG. From split-pool libraries to spatially addressable microarrays and its application to functional proteomic profiling. Angew Chem Int Ed. 2001;40:3152–3155. doi: 10.1002/1521-3773(20010903)40:17<3152::AID-ANIE3152>3.0.CO;2-P. [DOI] [PubMed] [Google Scholar]
  • 51.Harris JL, Winssinger N. PNA encoding (PNA=peptide nucleic acid): from solution-based libraries to organized microarrays. Chemistry. 2005;11:6792–6801. doi: 10.1002/chem.200500305. [DOI] [PubMed] [Google Scholar]
  • 52.Winssinger N, Ficarro S, Schultz PG, Harris JL. Profiling protein function with small molecule microarrays. Proc Natl Acad Sci USA. 2002;99:11139–11144. doi: 10.1073/pnas.172286899. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 53.Debaene F, Mejias L, Harris JL, Winssinger N. Synthesis of a PNA-encoded cysteine protease inhibitor library. Tetrahedron. 2004;60:8677–8690. doi: 10.1016/j.tet.2004.05.107. [DOI] [Google Scholar]
  • 54.Urbina HD, Debaene F, Jost B, Bole-Feysot C, Mason DE, Kuzmic P, Harris JL, Winssinger N. Self-assembled small molecule microarrays for protease screening and profiling. ChemBioChem. 2006;7(11):1790–1797. doi: 10.1002/cbic.200600242. [DOI] [PubMed] [Google Scholar]
  • 55.Winssinger N, et al. PNA-encoded protease substrate microarrays. Chem Biol. 2004;11:1351–1360. doi: 10.1016/j.chembiol.2004.07.015. [DOI] [PubMed] [Google Scholar]
  • 56.Harris J, et al. Activity profile of dust mite allergen extract using substrate libraries and functional proteomic microarrays. Chem Biol. 2004;11:1361–1372. doi: 10.1016/j.chembiol.2004.08.008. [DOI] [PubMed] [Google Scholar]
  • 57.Sano S, Tomizaki KY, Usui K, Mihara H. A PNA-DNA hybridization chip approach for the detection of beta-secretase activity. Bioorg Med Chem Lett. 2006;16:503–506. doi: 10.1016/j.bmcl.2005.10.064. [DOI] [PubMed] [Google Scholar]
  • 58.Diaz-Mochon JJ, Bialy L, Keinicke L, Bradley M. Combinatorial libraries – from solution to 2D microarrays. Chem Comm. 2005;7:1384–1386. doi: 10.1039/b415847d. [DOI] [PubMed] [Google Scholar]
  • 59.Bryan MC, et al. Saccharide display on microtiter plates. Chem Biol. 2002;9:713–720. doi: 10.1016/S1074-5521(02)00155-2. [DOI] [PubMed] [Google Scholar]
  • 60.Fazio F, Bryan MC, Blixt O, Paulson JC, Wong CH. Synthesis of sugar arrays in microtiter plate. J Am Chem Soc. 2002;124:14397–14402. doi: 10.1021/ja020887u. [DOI] [PubMed] [Google Scholar]
  • 61.Studer A, et al. Fluorous synthesis: a fluorous-phase strategy for improving separation efficiency in organic synthesis. Science. 1997;275:823–826. doi: 10.1126/science.275.5301.823. [DOI] [PubMed] [Google Scholar]
  • 62.Ko K-S, Jaipuri FA, Pohl NL. Fluorous-based carbohydrate microarrays. J Am Chem Soc. 2005;127:13162–13163. doi: 10.1021/ja054811k. [DOI] [PubMed] [Google Scholar]
  • 63.Gosalia DN, Diamond SL. Printing chemical libraries on microarrays for fluid phase nanoliter reactions. Proc Natl Acad Sci USA. 2003;100:8721–8726. doi: 10.1073/pnas.1530261100. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 64.Bailey SN, Sabatini DM, Stockwell BR. Microarrays of small molecules embedded in biodegradable polymers for use in mammalian cell-based screens. Proc Natl Acad Sci USA. 2004;101:16144–16149. doi: 10.1073/pnas.0404425101. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 65.Kumaresan PR, Lam KS. Screening chemical microarrays: methods and applications. In: Bartlett P, Entzeroth M, editors. Exploiting chemical diversity for drug discovery. UK: RSC; 2006. pp. 291–312. [Google Scholar]
  • 66.Kukar T, et al. Protein microarrays to detect protein–protein interactions using red and green fluorescent proteins. Anal Biochem. 2002;306:50–54. doi: 10.1006/abio.2002.5614. [DOI] [PubMed] [Google Scholar]
  • 67.Sielaff I, et al. Protein function microarrays based on self-immobilizing and self-labeling fusion proteins. Chem Bio Chem. 2006;7:194–202. doi: 10.1002/cbic.200500278. [DOI] [PubMed] [Google Scholar]
  • 68.Kawahashi Y, et al. In vitro protein microarrays for detecting protein–protein interactions: application of a new method for fluorescence labeling of proteins. Proteomics. 2003;3:1236–1243. doi: 10.1002/pmic.200300444. [DOI] [PubMed] [Google Scholar]
  • 69.Koehler AN, Shamji AF, Schreiber SL. Discovery of an inhibitor of a transcription factor using small molecule microarrays and diversity-oriented synthesis. J Am Chem Soc. 2003;125:8420–8421. doi: 10.1021/ja0352698. [DOI] [PubMed] [Google Scholar]
  • 70.Kato R, Kunimatsu M, Fujimoto S, Kobayashi T, Honda H. Angiotensin II inhibitory peptide found in the receptor sequence using peptide array. Biochem Biophys Res Commun. 2004;315:22–29. doi: 10.1016/j.bbrc.2004.01.016. [DOI] [PubMed] [Google Scholar]
  • 71.Reddy MM, Kodadek T. Protein fingerprinting in complex mixtures with peptoid microarrays. Proc Natl Acad Sci USA. 2005;102:12672–12677. doi: 10.1073/pnas.0501208102. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 72.Uttamchandani M, et al. Microarrays of tagged combinatorial triazine libraries in the discovery of small-molecule ligands of human IgG. J Comb Chem. 2004;6:862–868. doi: 10.1021/cc049900s. [DOI] [PubMed] [Google Scholar]
  • 73.Tegge W, Frank R, Hofmann F, Dostmann WR. Determination of cyclic nucleotide-dependent protein kinase substrate specificity by the use of peptide libraries on cellulose paper. Biochemistry. 1995;34:10569–10577. doi: 10.1021/bi00033a032. [DOI] [PubMed] [Google Scholar]
  • 74.Dostmann WR, et al. Highly specific, membrane-permeant peptide blockers of cGMP-dependent protein kinase Iα inhibit NO-induced cerebral dilation. Proc Natl Acad Sci USA. 2000;97:14772–14777. doi: 10.1073/pnas.97.26.14772. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 75.Mah AS, et al. Substrate specificity analysis of protein kinase complex Dbf2-Mob1 by peptide library and proteome array screening. BMC Biochem. 2005;6:22. doi: 10.1186/1471-2091-6-22. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 76.Panse S, et al. Profiling of generic anti-phosphopeptide antibodies and kinases with peptide microarrays using radioactive and fluorescence-based assays. Mol Divers. 2004;8:291–299. doi: 10.1023/B:MODI.0000036240.39384.eb. [DOI] [PubMed] [Google Scholar]
  • 77.Rychlewski L, Kschischo M, Dong L, Schutkowski M, Reimer U. Target specificity analysis of the Abl kinase using peptide microarray data. J Mol Biol. 2004;336:307–311. doi: 10.1016/j.jmb.2003.12.052. [DOI] [PubMed] [Google Scholar]
  • 78.Schutkowski M, et al. Automated synthesis: high-content peptide microarrays for deciphering kinase specificity and biology. Angew Chem Int Ed. 2004;43:2671–2674. doi: 10.1002/anie.200453900. [DOI] [PubMed] [Google Scholar]
  • 79.Schutkowski M, Reineke U, Reimer U. Peptide arrays for kinase profiling. ChemBioChem. 2005;6:513–521. doi: 10.1002/cbic.200400314. [DOI] [PubMed] [Google Scholar]
  • 80.Lesaicherre ML, Uttamchandani M, Chen GY, Yao SQ. Antibody-based fluorescence detection of kinase activity on a peptide array. Bioorg Med Chem Lett. 2002;12:2085–2088. doi: 10.1016/S0960-894X(02)00378-5. [DOI] [PubMed] [Google Scholar]
  • 81.Martin K, et al. Quantitative analysis of protein phosphorylation status and protein kinase activity on microarrays using a novel fluorescent phosphorylation sensor dye. Proteomics. 2003;3:1244–1255. doi: 10.1002/pmic.200300445. [DOI] [PubMed] [Google Scholar]
  • 82.Su J, Bringer MR, Ismagilov RF, Mrksich M. Combining microfluidic networks and peptide arrays for multi-enzyme assays. J Am Chem Soc. 2005;127:7280–7281. doi: 10.1021/ja051371o. [DOI] [PubMed] [Google Scholar]
  • 83.Salisbury CM, Maly DJ, Ellman JA. Peptide microarrays for the determination of protease substrate specificity. J Am Chem Soc. 2002;124:14868–14870. doi: 10.1021/ja027477q. [DOI] [PubMed] [Google Scholar]
  • 84.Gosalia DN, Salisbury CM, Maly DJ, Ellman JA, Diamond SL. Profiling serine protease substrate specificity with solution phase fluorogenic peptide microarrays. Proteomics. 2005;5:1292–1298. doi: 10.1002/pmic.200401011. [DOI] [PubMed] [Google Scholar]
  • 85.Gosalia DN, Salisbury CM, Ellman JA, Diamond SL. High throughput substrate specificity profiling of serine and cysteine proteases using solution-phase fluorogenic peptide microarrays. Mol Cell Proteomics. 2005;4:626–636. doi: 10.1074/mcp.M500004-MCP200. [DOI] [PubMed] [Google Scholar]
  • 86.Park S, Lee MR, Pyo SJ, Shin I. Carbohydrate chips for studying high-throughput carbohydrate–protein interactions. J Am Chem Soc. 2004;126:4812–4819. doi: 10.1021/ja0391661. [DOI] [PubMed] [Google Scholar]
  • 87.Park S, Shin I. Fabrication of carbohydrate chips for studying protein-carbohydrate interactions. Angew Chem Int Ed. 2002;41:3180–3182. doi: 10.1002/1521-3773(20020902)41:17<3180::AID-ANIE3180>3.0.CO;2-S. [DOI] [PubMed] [Google Scholar]
  • 88.Adams EW, et al. Oligosaccharide and glycoprotein microarrays as tools in HIV glycobiology; glycan-dependent gp120/protein interactions. Chem Biol. 2004;11:875–881. doi: 10.1016/j.chembiol.2004.04.010. [DOI] [PubMed] [Google Scholar]
  • 89.Houseman BT, Mrksich M. Carbohydrate arrays for the evaluation of protein binding and enzymatic modification. Chem Biol. 2002;9:443–454. doi: 10.1016/S1074-5521(02)00124-2. [DOI] [PubMed] [Google Scholar]
  • 90.Schwarz M, et al. A new kind of carbohydrate array, its use for profiling antiglycan antibodies, and the discovery of a novel human cellulose-binding antibody. Glycobiology. 2003;13:749–754. doi: 10.1093/glycob/cwg091. [DOI] [PubMed] [Google Scholar]
  • 91.Kohn M, et al. Staudinger ligation: a new immobilization strategy for the preparation of small-molecule arrays. Angew Chem Int Ed. 2003;42:5830–5834. doi: 10.1002/anie.200352877. [DOI] [PubMed] [Google Scholar]
  • 92.de Paz JL, Noti C, Seeberger PH. Microarrays of synthetic heparin oligosaccharides. J Am Chem Soc. 2006;128:2766–2767. doi: 10.1021/ja057584v. [DOI] [PubMed] [Google Scholar]
  • 93.Tully SE, Rawat M, Hsieh-Wilson LC. Discovery of a TNF-alpha antagonist using chondroitin sulfate microarrays. J Am Chem Soc. 2006;128:7740–7741. doi: 10.1021/ja061906t. [DOI] [PubMed] [Google Scholar]
  • 94.Love KR, Seeberger PH. Carbohydrate arrays as tools for glycomics. Angew Chem Int Ed. 2002;41:3583–3586. doi: 10.1002/1521-3773(20021004)41:19<3583::AID-ANIE3583>3.0.CO;2-P. [DOI] [PubMed] [Google Scholar]
  • 95.Manimala JC, Roach TA, Li Z, Gildersleeve JC. High-throughput carbohydrate microarray analysis of 24 lectins. Angew Chem Int Ed. 2006;45:3607–3610. doi: 10.1002/anie.200600591. [DOI] [PubMed] [Google Scholar]
  • 96.Simmons G, et al. Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry. Proc Natl Acad Sci USA. 2005;102:11876–11881. doi: 10.1073/pnas.0505577102. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 97.Yeo W-S, Min D-H, Hsieh RW, Greene GL, Mrksich M. Label-free detection of protein–protein interactions on biochips. Angew Chem Int Ed. 2005;44:5480–5483. doi: 10.1002/anie.200501363. [DOI] [PubMed] [Google Scholar]
  • 98.Becker CF, et al. Direct readout of protein–protein interactions by mass spectrometry from protein-DNA microarrays. Angew Chem Int Ed. 2005;44:7635–7639. doi: 10.1002/anie.200502908. [DOI] [PubMed] [Google Scholar]
  • 99.Inamori K, et al. Detection and quantification of on-chip phosphorylated peptides by surface plasmon resonance imaging techniques using a phosphate capture molecule. Anal Chem. 2005;77:3979–3985. doi: 10.1021/ac050135t. [DOI] [PubMed] [Google Scholar]
  • 100.Kanoh N, et al. SPR imaging of photo-cross-linked small-molecule arrays on gold. Anal Chem. 2006;78:2226–2230. doi: 10.1021/ac051777j. [DOI] [PubMed] [Google Scholar]

Articles from Combinatorial Chemistry on Solid Supports are provided here courtesy of Nature Publishing Group

RESOURCES