Monitoring dynamic glycosylation in vivo using supersensitive click chemistry

Bioconjugate Chemistry

Volumn 25, Issue 4, 2014, Pages 698-706

  Jiang, Hao ^a   Zheng, Tianqing ^a   Lopez Aguilar, Aime ^a   Feng, Lei ^a   Kopp, Felix ^a   Marlow, Florence L ^a   Wu, Peng ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CELL MEMBRANES; COPPER COMPOUNDS; CYTOLOGY; LIGANDS; MAMMALS;

BIOLOGICAL PROCESS; CELL SURFACES; CLICK CHEMISTRY; GLYCANS; GLYCOSYLATIONS; IN-VIVO; MAMMALIAN CELLS; SIMPLE++; SYNTHESISED; TIME-SCALES;

POLYSACCHARIDES;

ALKYNE; AZIDE; COPPER; GLYCAN DERIVATIVE; LIGAND; POLYSACCHARIDE;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CELL LYSATE; CELL SURFACE; CLICK CHEMISTRY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYCLOADDITION; ELECTRON; EMBRYO DEVELOPMENT; FEMALE; FLOW CYTOMETRY; GLYCOSYLATION; HUMAN; HUMAN CELL; IN VIVO STUDY; LIMIT OF DETECTION; MAMMAL CELL; MONITORING; NONHUMAN; PH; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTON TRANSPORT; ZEBRA FISH; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; EMBRYOLOGY; JURKAT CELL LINE; METABOLISM;

ALKYNES; ANIMALS; AZIDES; CLICK CHEMISTRY; COPPER; CYCLIZATION; FLOW CYTOMETRY; GLYCOSYLATION; HUMANS; JURKAT CELLS; MOLECULAR STRUCTURE; POLYSACCHARIDES; ZEBRAFISH;

EID: 84899010849     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400502d     Document Type: Article

References (38)

1. Haltiwanger, R. S. and Lowe, J. B. (2004) Role of glycosylation in development Annu. Rev. Biochem. 73, 491-537
2. Hakomori, S. (1989) Aberrant glycosylation in tumors and tumor-associated carbohydrate antigens Adv. Cancer Res. 52, 257-331
3. Dube, D. H. and Bertozzi, C. R. (2005) Glycans in cancer and inflammation - potential for therapeutics and diagnostics Nat. Rev. Drug Discovery 4, 477-88
4. Fishman, J. B. and Cook, J. S. (1986) The sequential transfer of internalized, cell surface sialoglycoconjugates through the lysosomes and Golgi complex in HeLa cells J. Biol. Chem. 261, 11896-905
5. Reichner, J. S., Whiteheart, S. W., and Hart, G. W. (1988) Intracellular trafficking of cell surface sialoglycoconjugates J. Biol. Chem. 263, 16316-26
6. Huang, K. M. and Snider, M. D. (1993) Glycoprotein recycling to the galactosyltransferase compartment of the Golgi complex J. Biol. Chem. 268, 9302-10
7. Pakula, T. M., Uusitalo, J., Saloheimo, M., Salonen, K., Aarts, R. J., and Penttila, M. (2000) Monitoring the kinetics of glycoprotein synthesis and secretion in the filamentous fungus Trichoderma reesei: cellobiohydrolase I (CBHI) as a model protein Microbiology 146 (Pt 1) 223-32
8. Laughlin, S. T. and Bertozzi, C. R. (2009) Imaging the glycome Proc. Natl. Acad. Sci. U.S.A. 106, 12-7
9. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective â€ligation†of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-9
10. Tornoe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-64
11. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 104, 16793-7
12. Ning, X., Guo, J., Wolfert, M. A., and Boons, G. J. (2008) Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions Angew. Chem., Int. Ed. 47, 2253-5
13. Jewett, J. C., Sletten, E. M., and Bertozzi, C. R. (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones J. Am. Chem. Soc. 132, 3688-90
14. Presolski, S. I., Hong, V., Cho, S. H., and Finn, M. G. (2010) Tailored ligand acceleration of the Cu-catalyzed azide-alkyne cycloaddition reaction: practical and mechanistic implications J. Am. Chem. Soc. 132, 14570-6
15. Chan, T. R., Hilgraf, R., Sharpless, K. B., and Fokin, V. V. (2004) Polytriazoles as copper(I)-stabilizing ligands in catalysis Org. Lett. 6, 2853-5
16. Hong, V., Presolski, S. I., Ma, C., and Finn, M. G. (2009) Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation Angew. Chem., Int. Ed. 48, 9879-83
17. Soriano del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A., Levy, M., Liu, Y., Marlow, F. L., and Wu, P. (2010) Biocompatible copper(I) catalysts for in vivo imaging of glycans J. Am. Chem. Soc. 132, 16893-9
18. Worrell, B. T., Malik, J. A., and Fokin, V. V. (2013) Direct evidence of a dinuclear copper intermediate in Cu(I)-catalyzed azide-alkyne cycloadditions Science 340, 457-60
19. Brotherton, W. S., Michaels, H. A., Simmons, J. T., Clark, R. J., Dalal, N. S., and Zhu, L. (2009) Apparent copper(II)-accelerated azide-alkyne cycloaddition Org. Lett. 11, 4954-7
20. Kuang, G. C., Michaels, H. A., Simmons, J. T., Clark, R. J., and Zhu, L. (2010) Chelation-assisted, copper(II)-acetate-accelerated azide-alkyne cycloaddition J. Org. Chem. 75, 6540-8
21. Kuang, G. C., Guha, P. M., Brotherton, W. S., Simmons, J. T., Stankee, L. A., Nguyen, B. T., Clark, R. J., and Zhu, L. (2011) Experimental investigation on the mechanism of chelation-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition J. Am. Chem. Soc. 133, 13984-4001
22. Michaels, H. A. and Zhu, L. (2011) Ligand-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition Chem.î - ̧Asian J. 6, 2825-34
23. Uttamapinant, C., Tangpeerachaikul, A., Grecian, S., Clarke, S., Singh, U., Slade, P., Gee, K. R., and Ting, A. Y. (2012) Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling Angew. Chem., Int. Ed. 51, 5852-6
24. Wang, W., Hong, S., Tran, A., Jiang, H., Triano, R., Liu, Y., Chen, X., and Wu, P. (2011) Sulfated ligands for the copper(I)-catalyzed azide-alkyne cycloaddition Chem.î - ̧Asian J. 6, 2796-802
25. Qi, J. and Tung, C. H. (2011) Development of benzothiazole ’click-on’ fluorogenic dyes Bioorg. Med. Chem. Lett. 21, 320-3
26. Besanceney-Webler, C., Jiang, H., Zheng, T., Feng, L., Soriano Del Amo, D., Wang, W., Klivansky, L. M., Marlow, F. L., Liu, Y., and Wu, P. (2011) Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study Angew. Chem., Int. Ed. 50, 8051-6
27. Dirks, A. J., van Berkel, S. S., Hatzakis, N. S., Opsteen, J. A., van Delft, F. L., Cornelissen, J. J., Rowan, A. E., van Hest, J. C., Rutjes, F. P., and Nolte, R. J. (2005) Preparation of biohybrid amphiphiles via the copper catalysed Huisgen [3 + 2] dipolar cycloaddition reaction Chem. Commun. 4172-4
28. Brahma, A., Mandal, C., and Bhattacharyya, D. (2005) Characterization of a dimeric unfolding intermediate of bovine serum albumin under mildly acidic condition Biochim. Biophys. Acta 1751, 159-69
29. Hsu, T. L., Hanson, S. R., Kishikawa, K., Wang, S. K., Sawa, M., and Wong, C. H. (2007) Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells Proc. Natl. Acad. Sci. U.S.A. 104, 2614-9
30. Chang, P. V., Chen, X., Smyrniotis, C., Xenakis, A., Hu, T., Bertozzi, C. R., and Wu, P. (2009) Metabolic labeling of sialic acids in living animals with alkynyl sugars Angew. Chem., Int. Ed. 48, 4030-3
31. Du, J., Meledeo, M. A., Wang, Z., Khanna, H. S., Paruchuri, V. D. P., and Yarema, K. J. (2009) Metabolic glycoengineering: sialic acid and beyond Glycobiology 19, 1382-401
32. Sarkar, A. K., Fritz, T. A., Taylor, W. H., and Esko, J. D. (1995) Disaccharide uptake and priming in animal cells: inhibition of sialyl Lewis X by acetylated Gal beta 1 - >4GlcNAc beta-O-naphthalenemethanol Proc. Natl. Acad. Sci. U.S.A. 92, 3323-7
33. Jones, M. B., Teng, H., Rhee, J. K., Lahar, N., Baskaran, G., and Yarema, K. J. (2004) Characterization of the cellular uptake and metabolic conversion of acetylated N-acetylmannosamine (ManNAc) analogues to sialic acids Biotechnol. Bioeng. 85, 394-405
34. Tian, L., Yang, Y., Wysocki, L. M., Arnold, A. C., Hu, A., Ravichandran, B., Sternson, S. M., Looger, L. L., and Lavis, L. D. (2012) Selective esterase-ester pair for targeting small molecules with cellular specificity Proc. Natl. Acad. Sci. U.S.A. 109, 4756-61
35. Oetke, C., Brossmer, R., Mantey, L. R., Hinderlich, S., Isecke, R., Reutter, W., Keppler, O. T., and Pawlita, M. (2002) Versatile biosynthetic engineering of sialic acid in living cells using synthetic sialic acid analogues J. Biol. Chem. 277, 6688-95
36. North, S. J., Huang, H. H., Sundaram, S., Jang-Lee, J., Etienne, A. T., Trollope, A., Chalabi, S., Dell, A., Stanley, P., and Haslam, S. M. (2010) Glycomics profiling of Chinese hamster ovary cell glycosylation mutants reveals N-glycans of a novel size and complexity J. Biol. Chem. 285, 5759-75
37. Wang, W., Hu, T., Frantom, P. A., Zheng, T., Gerwe, B., Del Amo, D. S., Garret, S., Seidel, R. D., 3rd, and Wu, P. (2009) Chemoenzymatic synthesis of GDP-L-fucose and the Lewis X glycan derivatives Proc. Natl. Acad. Sci. U.S.A. 106, 16096-101
38. Yabe, T., Ge, X., Lindeman, R., Nair, S., Runke, G., Mullins, M. C., and Pelegri, F. (2009) The maternal-effect gene cellular island encodes aurora B kinase and is essential for furrow formation in the early zebrafish embryo PLoS Genet. 5, e1000518