-
661 Accesses
Abstract
The myriad functions of cell-surface glycans have rendered them attractive targets for in vivo molecular imaging. Until very recently, methods for specifically visualizing this class of biomolecules were lacking. The advent of bioorthogonal chemistry, i.e., reactions among functional groups that do not interact with or interfere with biological systems, provided a platform for probing glycans on cells and in animals. Herein, the progression of bioorthogonal reaction development and use of these chemistries for glycan imaging are described.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Bioorthogonal Chemistry in Cellular Organelles
Chemical editing of proteoglycan architecture
Bioorthogonal Reactions in Bioimaging
Explore related subjects
Discover the latest articles, books and news in related subjects, suggested using machine learning.References
Agarwal P, van der Weijden J, Sletten EM, Rabuka D, Bertozzi CR (2013) A Pictet-Spengler ligation for protein chemical modification. Proc Natl Acad Sci U S A 110:46–51
Baskin JM, Dehnert KW, Laughlin ST, Amacher SL, Bertozzi CR (2010) Visualizing enveloping layer glycans during zebrafish early embryogenesis. Proc Natl Acad Sci U S A 107:10360–10365
Beahm BJ, Dehnert KW, Derr NL, Kuhn J, Eberhart JK, Spillmann D, Amacher SL, Bertozzi CR (2014) A visualizable chain-terminating inhibitor of glycosaminoglycan biosynthesis in developing zebrafish. Angew Chem Int Ed 53(13):3347–3352
Chang PV, Prescher JA, Sletten EM, Baskin JM, Miller IA, Agard NJ, Lo A, Bertozzi CR (2010) Copper-free click chemistry in living animals. Proc Natl Acad Sci U S A 107:1821–1826
Dehnert KW, Beahm BJ, Huynh TT, Baskin JM, Laughlin ST, Wang W, Wu P, Amacher SL, Bertozzi CR (2011) Metabolic labeling of fucosylated glycans in developing zebrafish. ACS Chem Biol 6:547–552
Dehnert KW, Baskin JM, Laughlin ST, Beahm BJ, Naidu NN, Amacher SL, Bertozzi CR (2012) Imaging the sialome during zebrafish development with copper-free click chemistry. Chembiochem 13:353–357
Devaraj NK, Weissleder R, Hilderbrand SA (2008) Tetrazine-based cycloadditions: application to pretargeted live cell imaging. Bioconjug Chem 19:2297–2299
Hsu T-L, Hanson SR, Kishikawa K, Wang S-K, Sawa M, Wong C-H (2007) Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells. Proc Natl Acad Sci 104:2614–2619
Jewett JC, Sletten EM, Bertozzi CR (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. J Am Chem Soc 132:3688–3690
Kayser H, Zeitler R, Kannicht C, Grunow D, Nuck R, Reutter W (1992) Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-d-hexosamines as precursors. J Biol Chem 267:16934–16938
Koo H, Lee S, Na JH, Kim SH, Hahn SK, Choi K, Kwon IC, Jeong SY, Kim K (2012) Bioorthogonal copper-free click chemistry in vivo for tumor-targeted delivery of nanoparticles. Angew Chem Int Ed Engl 51:11836–11840
Laughlin ST, Bertozzi CR (2009) Imaging the glycome. Proc Natl Acad Sci U S A 106:12–17
Laughlin ST, Baskin JM, Amacher SL, Bertozzi CR (2008) In vivo imaging of membrane-associated glycans in developing zebrafish. Science 320:664–667
Mahal LK, Yarema KJ, Bertozzi CR (1997) Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis. Science 276:1125–1128
Patterson DM, Nazarova LA, Xie B, Kamber DN, Prescher JA (2012) Functionalized cyclopropenes as bioorthogonal chemical reporters. J Am Chem Soc 134:18638–18643
Prescher JA, Dube DH, Bertozzi CR (2004) Chemical remodelling of cell surfaces in living animals. Nature 430:873–877
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed 41:2596–2599
Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 48:6974–6998
Soriano del Amo D, Wang W, Jiang H, Besanceney C, Yan AC, Levy M, Liu Y, Marlow FL, Wu P (2010) Biocompatible copper(I) catalysts for in vivo imaging of glycans. J Am Chem Soc 132:16893–16899
Yang J, Šečkutė J, Cole CM, Devaraj NK (2012) Live-cell imaging of cyclopropene tags with fluorogenic tetrazine cycloadditions. Angew Chem Int Ed Engl 51:7476–7479
Editor information
Editors and Affiliations
Tokyo Metropolitan Institute of Gerontology, Tokyo Metropolitan Geriatric Hospital, Tokyo, Japan
Tamao Endo
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Potsdam, Germany
Peter H. Seeberger
Dept. Biological Chemistry, Johns Hopkins University School of Medicine, Baltimore, Maryland, USA
Gerald W. Hart
Academia Sinica, Nankang, Taipei, Taiwan
Chi-Huey Wong
Systems Glycobiology Group, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, Wako, Saitama, Japan
Naoyuki Taniguchi
Rights and permissions
Copyright information
© 2014 Springer Japan
About this entry
Cite this entry
Beahm, B.J., Bertozzi, C.R. (2014). Imaging Cell-Surface Glycans in Animals with Bioorthogonal Chemistry. In: Endo, T., Seeberger, P., Hart, G., Wong, CH., Taniguchi, N. (eds) Glycoscience: Biology and Medicine. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54836-2_109-1
Download citation
DOI: https://doi.org/10.1007/978-4-431-54836-2_109-1
Received:
Accepted:
Published:
Publisher Name: Springer, Tokyo
Online ISBN: 978-4-431-54836-2
eBook Packages: Living Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences