Hitting the SPOT: small-molecule macroarrays advance combinatorial synthesis

Current Opinion in Chemical Biology

Volumn 10, Issue 3, 2006, Pages 203-212

  Blackwell, Helen E ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELLULOSE; PEPTIDE;

ANALYTIC METHOD; AUTOMATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; COMPLEX FORMATION; COST; DNA MICROARRAY; MACROMOLECULE; MICROWAVE RADIATION; MOLECULAR SIZE; REVIEW; SCREENING; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE;

EID: 33744540320     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2006.04.026     Document Type: Review

References (51)

1. Lee A., and Breitenbucher J.G. The impact of combinatorial chemistry on drug discovery. Curr Opin Drug Discov Devel 6 (2003) 494-508
2. Kramer R., and Cohen D. Functional genomics to new drug targets. Nat Rev Drug Discov 3 (2004) 965-972
3. Boyle N.A., and Janda K.D. Formats for combinatorial synthesis: solid-phase, liquid-phase and surface. Curr Opin Chem Biol 6 (2002) 339-346
4. Yu Z., and Bradley M. Solid supports for combinatorial chemistry. Curr Opin Chem Biol 6 (2002) 347-352
5. Li W.B., and Yan B. Effects of polymer supports on the kinetics of solid-phase organic reactions: a comparison of polystyrene- and tentagel-based resins. J Org Chem 63 (1998) 4092-4097
6. Frank R. SPOT-synthesis: an easy technique for the positionally addressable, parallel chemical synthesis on a membrane support. Tetrahedron 48 (1992) 9217-9232
7. Frank R. The SPOT-synthesis technique. Synthetic peptide arrays on membrane supports-principles and applications. J Immunol Methods 267 (2002) 13-26
8. Pirrung M.C. Spatially addressable combinatorial libraries. Chem Rev 97 (1997) 473-488
9. Lebl M. Solid-phase synthesis on planar supports. Biopolymers 47 (1998) 397-404
10. Min D.H., and Mrksich M. Peptide arrays: towards routine implementation. Curr Opin Chem Biol 8 (2004) 554-558
11. Reimer U., Reineke U., and Schneider-Mergener J. Peptide arrays: from macro to micro. Curr Opin Biotechnol 13 (2002) 315-320
12. Reineke U., Volkmer-Engert R., and Schneider-Mergener J. Applications of peptide arrays prepared by the SPOT-technology. Curr Opin Biotechnol 12 (2001) 59-64
13. Heine N., Ast T., Schneider-Mergener J., Reineke U., Germeroth L., and Wenschuh H. Synthesis and screening of peptoid arrays on cellulose membranes. Tetrahedron 59 (2003) 9919-9930
14. Uttamchandani M., Walsh D.P., Yao S.Q., and Chang Y.-T. Small molecule microarrays: recent advances and applications. Curr Opin Chem Biol 9 (2005) 4-13. The authors provide a comprehensive review of the complementary small-molecule microarray technique, including a detailed analysis of recent applications and a thoughtful discussion of future areas for development.
15. Lam K.S., and Renil M. From combinatorial chemistry to chemical microarray. Curr Opin Chem Biol 6 (2002) 353-358
16. Stoughton R.B. Applications of DNA microarrays in biology. Ann Rev Biochem 74 (2005) 53-82
17. Lovrinovic M., and Niemeyer C.M. DNA microarrays as decoding tools in combinatorial chemistry and chemical biology. Angew Chem Int Ed 44 (2005) 3179-3183
18. MacBeath G., Koehler A.N., and Schreiber S.L. Printing small molecules as microarrays and detecting protein-ligand interactions en masse. J Am Chem Soc 121 (1999) 7967-7968
19. Hergenrother P.J., Depew K.M., and Schreiber S.L. Small-molecule microarrays: covalent attachment and screening of alcohol-containing small molecules on glass slides. J Am Chem Soc 122 (2000) 7849-7850
20. Laird E.R., and Blake J.F. Structure-based generation of viable leads from small combinatorial libraries. Curr Opin Drug Discov Devel 7 (2004) 354-359
21. Schutkowski M., Reimer U., Panse S., Dong L.Y., Lizcano J.M., Alessi D.R., and Schneider-Mergener J. High-content peptide microarrays for deciphering kinase specificity and biology. Angew Chem Int Ed Engl 43 (2004) 2671-2674
22. Zander N. New planar substrates for the in situ synthesis of peptide arrays. Mol Divers 8 (2004) 189-195
23. Scharn D., Wenschuh H., Reineke U., Schneider-Mergener J., and Germeroth L. Spatially addressed synthesis of amino- and amino-oxy-substituted 1,3 5-triazine arrays on polymeric membranes. J Comb Chem 2 (2000) 361-369
24. Niggemann J., Michaelis K., Frank R., Zander N., and Höfle G. Natural product-derived building blocks for combinatorial synthesis. Part 1. Fragmentation of natural products from mycobacteria. J Chem Soc, Perkin Trans 1 (2002) 2490-2503
25. La Clair J.J., and Burkart M.D. Molecular screening on a compact disc. Org Biomol Chem 1 (2003) 3244-3249
26. Tesfu E., Maurer K., Ragsdale S.R., and Moeller K.D. Building addressable libraries: the use of electrochemistry for generating reactive Pd(II) reagents at preselected sites on a chip. J Am Chem Soc 126 (2004) 6212-6213
27. Coulon E., Pinson J., Bourzat J.D., Commercon A., and Pulicani J.P. Surface-modified carbon felts: possible supports for combinatorial chemistry. J Org Chem 67 (2002) 8513-8518
28. Williams L. Thin layer chromatography as a tool for reaction optimisation in microwave assisted synthesis. Chem Commun (2000) 435-436
29. Williams L., and Bergersen O. Towards an integrated platform for combinatorial library synthesis and screening. J Planar Chromatogr-Mod TLC 14 (2001) 318-321
30. Ast T., Heine N., Germeroth L., Schneider-Mergener J., and Wenschuh H. Efficient assembly of peptomers on continuous surfaces. Tetrahedron Lett 40 (1999) 4317-4318
31. Bowman M.D., Jeske R.C., and Blackwell H.E. Microwave-accelerated spot-synthesis on cellulose supports. Org Lett 6 (2004) 2019-2022. This paper reports that MW-assisted reactions can be utilized as a general approach to dramatically accelerate the macroarray synthesis process. This work represents the first use of a commercial MW reactor for macroarray synthesis.
32. Lin Q., O'Neill J.C., and Blackwell H.E. Small molecule macroarray construction via Ugi four-component reactions. Org Lett 7 (2005) 4455-4458. The authors report the first use of multicomponent reactions for the construction of small-molecule macroarrays. The Ugi four-component reaction was found to proceed efficiently on cellulose support in the presence of water.
33. Heine N., Germeroth L., Schneider-Mergener J., and Wenschuh H. A modular approach to the spot synthesis of 1,3, 5-trisubstituted hydantoins on cellulose membranes. Tetrahedron Lett 42 (2001) 227-230
34. Scharn D., Germeroth L., Schneider-Mergener J., and Wenschuh H. Sequential nucleophilic substitution on halogenated triazines, pyrimidines, and purines: a novel approach to cyclic peptidomimetics. J Org Chem 66 (2001) 507-513
35. Wenschuh H., Volkmer-Engert R., Schmidt M., Schulz M., Schneider-Mergener J., and Reineke U. Coherent membrane supports for parallel microsynthesis and screening of bioactive peptides. Biopolymers 55 (2000) 188-206
36. Blankemeyer-Menge B., and Frank R. Simultaneous multiple synthesis of protected peptide-fragments on allyl-functionalized cellulose disk supports. Tetrahedron Lett 29 (1988) 5871-5874
37. Volkmer-Engert R., Hoffmann B., and Schneider-Mergener J. Stable attachment of the HMB-linker to continuous cellulose membranes for parallel solid phase spot synthesis. Tetrahedron Lett 38 (1997) 1029-1032
38. Blackwell H.E. Out of the oil bath and into the oven - microwave-assisted combinatorial chemistry heats up. Org Biomol Chem 1 (2003) 1251-1255
39. Kappe C.O. Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed Engl 43 (2004) 6250-6284
40. Kappe C.O., and Dallinger D. The impact of microwave synthesis on drug discovery. Nat Rev Drug Discov 5 (2006) 51-63. This is an outstanding review of the current state of microwave-assisted organic chemistry that also highlights the utility of microwave-assisted solid-phase organic reactions in medicinal and combinatorial chemistry.
41. Borman S. Combinatorial synthesis hits the spot. Chem Eng News 78 (2000) 25-27
42. Hoffmann S.R.K. High-density compound arrays of combinatorial chemical libraries by a new pen-directed and computer-navigated plotter device. In: Lebl M., and Houghten R.A. (Eds). Peptides: The wave of the future (2001), American Peptide Society 210-211
43. Pirrung M.C., and Das Sarma K. Aqueous medium effects on multi-component reactions. Tetrahedron 61 (2005) 11456-11472
44. Reineke U., Sabat R., Misselwitz R., Welfle H., Volk H.-D., and Schneider-Mergener J. A synthetic mimic of a discontinuous binding site on interleukin-10. Nat Biotechnol 17 (1999) 271-275
45. Weiser A.A., Or-Guil M., Tapia V., Leichsenring A., Schuchhardt J., Frömmel C., and Volkmer-Engert R. Spot synthesis: reliability of array-based measurement of peptide binding affinity. Anal Biochem 342 (2005) 300-311
46. Reineke U., Ivascu C., Schlief M., Landgraf C., Gericke S., Zahn G., Herzel H., Volkmer-Engert R., and Schneider-Mergener J. Identification of distinct antibody epitopes and mimotopes from a peptide array of 5520 randomly generated sequences. J Immunol Methods 267 (2002) 37-51
47. Malin R., Steinbrecher R., Jannsen J., Semmler W., Noll B., Johannsen B., Frommel C., Hohne W., and Schneider-Mergener J. Identification of Tc-99m binding peptides using combinatorial cellulose-bound peptide libraries. J Am Chem Soc 117 (1995) 11821-11822
48. Hilpert K., Volkmer-Engert R., Walter T., and Hancock R.E.W. High-throughput generation of small antibacterial peptides with improved activity. Nat Biotechnol 23 (2005) 1008-1012. The authors report an efficient screening approach for antibacterial cationic peptides using peptide macroarrays - this assay would be easily translatable to small-molecule macroarrays.
49. Bailey S.N., Sabatini D.M., and Stockwell B.R. Microarrays of small molecules embedded in biodegradable polymers for use in mammalian cell-based screens. Proc Natl Acad Sci USA 101 (2004) 16144-16149
50. Bowman M.D., Jacobson M.M., Pujanuaski B.G., and Blackwell H.E. Efficient synthesis of small molecule macroarrays: optimization of the macroarray synthesis platform and examination of microwave and conventional heating methods. Tetrahedron 62 (2006) 4715-4727. The authors demonstrate that conventional drying ovens and MW reactors both have utility for the heating of reactions during macroarray synthesis.
51. Bowman M.D., Jacobson M.M., and Blackwell H.E. Discovery of fluorescent cyanopyridine and deazalumazine dyes using small molecule macroarrays. Org Lett 8 (2006) 1645-1648. This paper is the first to report the use of small-molecule macroarrays as a platform for the discovery of fluorescence dyes. A straightforward method for the bench-top identification of fluorescence dyes is described.