Glycoarray by DNA-directed immobilization

Methods in Molecular Biology

Volumn 808, Issue , 2012, Pages 195-219

  Morvan, François ^a   Chevolot, Yann ^b   Zhang, Jing ^b   Meyer, Albert ^a   Vidal, Sébastien ^c   Praly, Jean Pierre ^c   Vasseur, Jean Jacques ^a   Souteyrand, Eliane ^b  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b ECOLE CENTRALE DE LYON   (France)

^c UNIVERSITÉ LYON 1   (France)

Author keywords

Click chemistry; DNA directed immobilization; Glycoarrays; Glycomimetics

Indexed keywords

CARBOHYDRATE; DNA;

ARTICLE; CHEMISTRY; METHODOLOGY; MICROARRAY ANALYSIS;

CARBOHYDRATES; DNA; MICROARRAY ANALYSIS;

EID: 82355193816     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-61779-373-8_14     Document Type: Article

References (49)

1. Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3: 93-130.
2. Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G. W., and Marth, J. (1999) Essentials of glycobiology, Cold Spring Harbor Laboratory Press, New York.
3. Sharon, N., and Lis, H. (2004) History of lectins: from hemagglutinins to biological recognition molecules. Glycobiology 14: 53R-62R. (Pubitemid 39430025)
4. Werz, D., B., and Seeberger, P., H. (2005) Carbohydrates as the Next Frontier in Pharmaceutical Research. Chemistry 11: 3194-3206. (Pubitemid 40750980)
5. Pohl, N., L., and Kiessling, L., L. (1999) Scope of multivalent ligand function: lactose-bearing neoglycopolymers by ring-opening metathesis polymerization. Synthesis 1515-1519. (Pubitemid 29390165)
6. Ratner, D., M., Adams, E., W., Disney, M., D., and Seeberger, P., H. (2004) Tools for Glycomics: Mapping Interactions of Carbohydrates in Biological Systems. ChemBioChem 5: 1375-1383. (Pubitemid 39377754)
7. Ratner, D., M., Adams, E., W., Su, J., O'Keefe, B., R., Mrksich, M., and Seeberger, P., H. (2004) Probing Protein-Carbohydrate Interactions with Microarrays of Synthetic Oligosaccharides. ChemBioChem 5: 379-383.
8. Disney, M., D., and Seeberger, P., H. (2004) The Use of Carbohydrate Microarrays to Study Carbohydrate-Cell Interactions and to Detect Pathogens. Chemistry and Biology 11: 1701-1707. (Pubitemid 39651304)
9. de Paz, J. L., Horlacher, T., and Seeberger, P. H. (2006) Oligosaccharide microarrays to map interactions of carbohydrates in biological systems. Methods in Enzymology 415: 269-292. (Pubitemid 44751103)
10. Uttamchandani, M., Neo, J. L., Zhung Ong, B., N., and Moochhala, S. (2008) Applications of microarrays in pathogen detection and biodefence. Trends in Biotechnology 27: 53-61.
11. Parthasarathy, N., DeShazer, D., Peacock, S. J., Wuthiekanun, V., England, M. J., Norris, S. L., and Waag, D. M. (2008) Application of Polysaccharide Microarray Technology for the Serodiagnosis of Burkholderia pseudomallei Infection (Melioidosis) in Humans. Journal of Carbohydrate Chemistry 27: 32-40. (Pubitemid 351891534)
12. Liang, P.-H., Wu, C.-Y., A, G. W., and Wong, C.-H. (2008) Glycan arrays: biological and medical applications. Current Opinion in Chemical Biology 12: 86-92.
13. Laurent, N., Voglmeir, J., and Flitsch, S. L. (2008) Glycoarrays-tools for determining protein-carbohydrate interactions and glycoenzyme specificity. Chem. Commun. 4400-4412.
14. Wang, D., Liu, S. y., Trummer, B. J., Deng, C., and Wang, A. (2002) Carbohydrate microarrays for the recognition of cross-reactive molecular markers of microbes and host cells. Nature Biotechnology 20: 275-281. (Pubitemid 34205421)
15. Park, S., Lee, M. R., Pyo, S. J., and Shin, I. (2004) Carbohydrate Chips for Studying High- Throughput Carbohydrate-Protein Interactions. Journal of the American Chemical Society 126: 4812-4819. (Pubitemid 38490147)
16. Wang, D. (2003) Carbohydrate microarrays. Proteomics 3: 2167-2175. (Pubitemid 37414083)
17. Fukui, S., Feizi, T., Galustian, C., Lawson, A. M., and Chai, W. (2002) Oligosaccharide microarrays for high-throughput detection and specificity assignments of carbohydrate-protein interactions. Nature Biotechnology 20: 1011-1017.
18. Feizi, T., Fazio, F., Chai, W., and Wong, C.-H. (2003) Carbohydrate microarrays - a new set of technologies at the frontiers of glycomics. Current Opinion in Structural Biology 13: 637-645. (Pubitemid 37244119)
19. Larsen, K., Thygesen, M. B., Guillaumie, F., Willats, W. G. T., and Jensen, K. J. (2006) Solid-phase chemical tools for glycobiology. Carbohydrate Research 341: 1209-1234. (Pubitemid 43795413)
20. Palma, A., S., Feizi, T., Zhang, Y., Stoll, M., S., Lawson, A., M., Diaz-Rodriguez, E., Campanero-Rhodes, M., A., Costa, J., Gordon, S., Brown, G., D., and Chai, W. (2006) Ligands for the b-Glucan Receptor, Dectin-1, Assigned Using "Designer" Microarrays of Oligosaccharide Probe (Neoglycolipids) Generated from Glucan Polysaccharides. Journal of Biological Chemistry 281: 5771-5779. (Pubitemid 43847676)
21. Jaipuri, F., A., Collet, B., Y., M., and Pohl, N., L. (2008) Synthesis and Quantitative Evaluation of Glycero-d-manno-heptose Binding to Concanavalin A by Fluorous-Tag Assistance. Angewandte Chemie, International Edition in English 47: 1707-1710.
22. Blixt, O., Head, S., Mondala, T., Scanlan, C., Huflejt, M. E., Alvarez, R., Bryan, M. C., Fazio, F., Calarese, D., Stevens, J., Razi, N., Stevens, D. J., Skehel, J. J., Van Die, I., Burton, D. R., Wilson, I. A., Cummings, R., Bovin, N., Wong, C.-H., and Paulson, C. (2004) Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proceedings of the National Academy of Sciences of the United States of America 10: 17033-17038. (Pubitemid 39627769)
23. Park, S., and Shin, I. (2007) Carbohydrate Microarrays for Assaying Galactosyltransferase Activity. Organic Letters 9: 1675-1678.
24. Seo, J. H., Adachi, K., Lee, B. K., Kang, D. G., Kim, Y. K., Kim, K. R., Lee, H. Y., Kawai, T., and Cha, H. J. (2007) Facile and Rapid Direct Gold Surface Immobilization with Controlled Orientation for Carbohydrates. Bioconjugate Chemistry 18: 2197-2201. (Pubitemid 350220025)
25. Smith, E. A., Thomas, W. D., Kiessling, L. L., and Corn, R. M. (2003) Surface Plasmon Resonance Imaging Studies of Protein- Carbohydrate Interactions. Journal of the American Chemical Society 125: 6140-6148. (Pubitemid 36582986)
26. Chevolot, Y., Bucher, O., Léonard, D., Mathieu, H.-J., and Sigrist, H. (1999) Synthesis and Characterization of a Photoactivatable Glycoaryldiazirine for Surface Glycoengineering. Bioconjugate Chemistry 10: 169-175. (Pubitemid 29147718)
27. Chevolot, Y., Martins, J., Milosevic, N., Leonard, D., Zeng, S., Malissard, M., Berger, E., G., Maier, P., Mathieu, H., J., Crout, D., H., and Sigrist, H. (2001) Immobilisation on Polystyrene of Diazirine Derivatives of MonoandDisaccharides: Biological Activities of Modified Surfaces. Bioorganic and Medicinal Chemistry 9: 2943-2953.
28. Leonard, D., Chevolot, Y., Bucher, O., Haenni, W., Sigrist, H., and Mathieu, H. J. (1998) ToFSIMS and XPS study of photoactivatable reagents designed for surface glycoengineering - Part 2. N-[m-(3-(trifluoromethyl) diazirine-3-yl) phenyl]-4-(-3-thio(-1 -D-galactopyrannosyl)- maleimidyl)butyramide (MAD-Gal) on diamond. Surface and Interface Analysis 26: 793-799. (Pubitemid 128627907)
29. Léonard, D., Chevolot, Y., Bucher, O., Sigrist, H., and Mathieu, H.-J. (1998) ToF-SIMS and XPS study of photoactivatable reagents designed for surface glycoengineering. Part I. N-(m-(3-(trifluoromethyl)diazirine-3-yl) phenyl)-4-maleimido-butyramide (mad) on silicon, silicon nitride and diamond. Surface and Interface Analysis 26: 783-792. (Pubitemid 128627906)
30. Léonard, D., Chevolot, Y., Heger, F., Martins, J., Crout, D., H., G., Sigrist, H., and Mathieu, H., J. (2001) ToF-SIMS and XPS Study of Photoactivatable Reagents Designed for Surface Glycoengineering: Part III: 5-carboxamidopentyl N-[m-[3-(trifluoromethyl) diazirin-3-yl] phenyl b-D-galactopyranosyl]-(1->4)-1-thiob- D-glucopyranoside (Lactose aryl diazirine) on Diamond. Surface and Interface Analysis 31: 457-464. (Pubitemid 32610664)
31. Manimala, J., C., Li, Z., Jain, A., VedBrat, S., and Gildersleeve, J., C. (2005) Carbohydrate Array Analysis of Anti-Tn Antibodies and Lectins Reveals Unexpected Specificities: Implications for Diagnostic and Vaccine Development. ChemBioChem 6: 2229-2241.
32. Manimala, J., C., Roach, T., A., Li, Z., and Gildersleeve, J., C. (2006) High-Throughput Carbohydrate Microarray Analysis of 24 Lectins. Angewandte Chemie, International Edition in English 45: 3607-3610. (Pubitemid 44105721)
33. Manimala, J. C., Roach, T. A., Li, Z., and Gildersleeve, J. C. (2001) High-throughput carbohydrate microarray profiling of 27 antibodies demonstrates widespread specificity problems. Glycobiology 17: 17C-23C.
34. Bochner, B., S., Alvarez, R., A., Mehta, P., Bovin, N., V., Blixt, O., White, J., R., and Schnaar, R., L. (2005) Glycan Array Screening Reveals a Candidate Ligand for Siglec-8. Journal of Biological Chemistry 280: 4307-4312. (Pubitemid 40288598)
35. Zhang, J., Pourceau, G., Meyer, A., Vidal, S., Praly, J. P., Souteyrand, E., Vasseur, J. J., Morvan, F., and Y., C. (2009) DNA-directed immobilisation of glycomimetics for glycoarrays application: Comparison with covalent immobilisation, and development of an on-chip IC(50) measurement assay. Biosensors and Bioelectronics 24: 2515-2521.
36. Chevolot, Y., Bouillon, C., Vidal, S., Morvan, F., Meyer, A., Cloarec, J.-P., Jochum, A., Praly, J.-P., Vasseur, J.-J., and Souteyrand, E. (2007) DNA-Based Carbohydrate Biochips: A Platform for Surface Glyco-Engineering. Angewandte Chemie, International Edition in English 46: 2398-2402. (Pubitemid 46973578)
37. Zhang, J., Pourceau, G., Meyer, A., Vidal, S., Praly, J. P., Souteyrand, E., Vasseur, J. J., Morvan, F., and Chevolot, Y. (2009) Specific recognition of lectins by oligonucleotide glycoconjugates and sorting on a DNA microarray. Chem. Commun. 28: 6795-6797.
38. Moni, L., Pourceau, G., Zhang, J., Meyer, A., Vidal, S., Souteyrand, E., Dondoni, A., Morvan, F., Chevolot, Y., Vasseur, J. J., and Marra, A. (2009) Design of Triazole-Tethered Glycoclusters Exhibiting Three Different Spatial Arrangements and Comparative Study of their Affinities towards PA-IL and RCA 120 by Using a DNA-Based Glycoarray. ChemBioChem 10: 1369-1378.
39. Niemeyer, C. M., Boldt, L., Ceyhan, B., and Blohm, D. (1999) DNA-Directed Immobilization: Efficient, Reversible, and Site- Selective Surface Binding of Proteins by Means of Covalent DNA-Streptavidin Conjugates. Analytical Chemistry 268: 54-63. (Pubitemid 29115510)
40. Wacker, R., Schröder, H., and Niemeyer, C. M. (2004) Performance of antibody microarrays fabricated by either DNA-directed immobilization, direct spotting, or streptavidin-biotin attachment: a comparative study. Analytical Biochemistry 330: 281-287. (Pubitemid 38760103)
41. Seela, F., and Kaiser, K. (1987) Oligodeoxyribonucleotides Containing 1,3-Propanediol as Nucleoside Substitute. Nucleic Acids Research 15: 3113-3129.
42. Mazurczyk, R., El Khoury, G., Dugasb, V., Hannes, B., Laurenceau, E., Cabrera, M., Krawczyk, S., Souteyrand, E., Cloarec, J. P., and Chevolot, Y. (2008) Low-cost, fast prototyping method of fabrication of the microreactor devices in soda-lime glass. Sensors and Actuators, B: Chemical Sensors and Materials 128: 552-559.
43. Vieillard, J., Mazurczyk, R., Morin, C., Hannes, B., Chevolot, Y., DesbèneP-L., and Krawczyk, S. (2007) Application of microfluidic chip with integrated optics for electrophoretic separations of proteins. Journal of Chromatography B: Biomedical Applications 845: 218-225. (Pubitemid 46073917)
44. Morvan, F., Meyer, A., Jochum, A., Sabin, C., Chevolot, Y., Imberty, A., Praly, J.-P., Vasseur, J.-J., Souteyrand, E., and Vidal, S. (2007) Fucosylated Pentaerythrityl Phosphodiester Oligomers (PePOs): Automated Synthesis of DNA-Based Glycoclusters and Binding to Pseudomonas aeruginosa Lectin (PA-IIL). Bioconjugate Chemistry 18: 1637-1643. (Pubitemid 47464074)
45. Dugas, V., Depret, G., Chevalier, Y., Nesme, X., and Souteyrand, E. (2004) Immobilization of single-stranded DNA fragments to solid surfaces and their repeatable specific hybridization:covalent binding or adsorption. Sensors and Actuators, B: Chemical Sensors and Materials 112-121.
46. Szurmai, Z., Szabo, L., and Liptak, A. (1989) Diethylene and Triethylene Glycol Spacers for the Preparation of Neoglycoproteins. Acta Chimica Hungarica-Models in Chemistry 126: 259-269.
47. Cecioni, S., Lalor, R., Blanchard, B., Praly, J. P., Imberty, A., Matthews, S. E., and Vidal, S. (2009) Achieving High Affinity towards a Bacterial Lectin through Multivalent Topological Isomers of Calix[4]arene Glycoconjugates. Chemistry-a European Journal 15: 13232-13240.
48. Salo, H., Virta, P., Hakala, H., Prakash, T. P., Kawasaki, A. M., Manoharan, M., and Lonnberg, H. (1999) Aminooxy functionalized oligonucleotides: Preparation, on-support derivatization, and postsynthetic attachment to polymer support. Bioconjugate Chemistry 10: 815-823. (Pubitemid 29456369)
49. Dugas, V., and Chevalier, Y. (2003) Surface hydroxylation and silane grafting on fumed and thermal silica. Journal of Colloid and Interface Science 264: 354-361. (Pubitemid 36959973)