Metabolic Labeling of Sialic Acids in Living Animals with Alkynyl Sugars

Chang, Pamela V.; Chen, Xing; Smyrniotis, Chris; Xenakis, Alexander; Hu, Tianshun; Bertozzi, Carolyn R.; Wu, Peng

doi:10.1002/anie.200806319

Cited by 205 publications

(176 citation statements)

References 29 publications

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“…Biotin-LC-alkyne has been described as a probe to detect azido-modified glycoconjugates [16]. In this study, biotin-LC-alkyne analogs were synthesized using the modified commercialized reagents sulfo-NHS-LC-biotin and sulfo-NHS-SS-biotin (see the electronic supplementary material), which can efficiently react with primary amino groups to form stable amide bonds.…”

Section: Methodsmentioning

confidence: 99%

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Cell surface glycoprotein profiling of cancer cells based on bioorthogonal chemistry

et al. 2012

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Bioorthogonal chemistry refers to chemical reactions that can occur within a living system without altering native biochemical processes. Applications of this concept extend to studies on a group of biomolecules that includes glycans, proteins, and lipids. In this study, a strategy for isolating cell surface glycoproteins and based on bioorthogonal chemistry was employed to identify new cancer-related glycoproteins. A novel alkyne reagent containing one disulfide bond was synthesized for the enrichment of glycoproteins metabolized with peracetylated N-azidoacetylmannosamine, which was applied on three different cancer cell lines, and all isolated proteins were analyzed by high-performance liquid chromatography-tandem mass spectrometry. The strategy of purifying cell surface glycoproteins introduced in this article was shown to be reliable, and a total of 56 cell surface glycoproteins were identified. Neuronal cell adhesion molecule was found uniquely expressed in A549 lung adenocarcinoma, and its expression in non-small-cell lung carcinomas was detected by immunohistochemistry. Furthermore, a significant increase of neuronal cell adhesion molecule expression was identified in non-small-cell lung adenocarcinoma compared with adjacent noncancerous tissues, and could be a novel potential target and marker in cancer treatment and detection.

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Section: Methodsmentioning

confidence: 99%

“…1b) [15]. This strategy has been validated and used in a number of in vitro and in vivo experiments [16][17][18].…”

Section: Introductionmentioning

confidence: 98%

Cell surface glycoprotein profiling of cancer cells based on bioorthogonal chemistry

et al. 2012

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“…Since both azide and alkyne groups (25-27) can be appended to biomolecules without altering their function or metabolic processing, it would be very useful if the CuAAC reaction could be adapted for this purpose. As a first step toward this goal, we describe here the application of optimized CuAAC reaction conditions (24) to the rapid and efficient labeling of cell-surface glycans on mammalian cells in culture.…”

Section: Introductionmentioning

confidence: 99%

Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry

et al. 2010

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The copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, optimized for biological molecules in aqueous buffers, has been shown to rapidly label mammalian cells in culture with no loss in cell viability. Metabolic uptake and display of the azide derivative of N-acetylmannosamine developed by Bertozzi, followed by CuAAC ligation using sodium ascorbate and the ligand tris(hydroxypropyltriazolyl)methylamine (THPTA), gave rise to abundant covalent attachment of dye-alkyne reactants. THPTA serves both to accelerate the CuAAC reaction and to protect the cells from damage by oxidative agents produced by the Cu-catalyzed reduction of oxygen by ascorbate, which is required to maintain the metal in the active +1 oxidation state. This procedure extends the application of this fastest of azide-based bioorthogonal reactions to the exterior of living cells.

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“…Under such circumstances in the molecular imaging and chemical biology fields, various bioorthogonal methods employing advanced organic reactions, including Sharpless/Meldal click reaction (for selected examples of protein labeling, see [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50]) and Bertozzi's Staudinger [51][52][53][54][55][56][57][58][59][60] and strain-releasing click ligation [25,[61][62][63][64][65][66][67][68][69][70][71], have been reported. Nevertheless, an efficient, rapid, and mild protocol not requiring bioengineering techniques and/or time-consuming procedures [63,[66][67][68] and is widely applicable for anyone in various buffer solutions had yet to be discovered.…”

Section: Azaelectrocyclization-based Labeling Of Lysines; New Microgrmentioning

confidence: 99%

Chemical Approach to a Whole Body Imaging of Sialo-N-Linked Glycans

Tanaka

Fukase

2014

Topics in Current Chemistry

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PET and noninvasive fluorescence imaging of the sialo-N-linked glycan derivatives are described. To establish the efficient labeling protocol for N-glycans and/or glycoconjugates, new labeling probes of fluorescence and ⁶⁸Ga-DOTA, as the positron emission nucleus for PET, through rapid 6π-azaelectrocyclization were designed and synthesized, (E)-ester aldehydes. The high reactivity of these probes enabled the labeling of lysine residues in peptides, proteins, and even amino groups on the cell surfaces at very low concentrations of the target molecules (~10⁻⁸ M) within a short reaction time (~5 min) to result in "selective" and "non-destructive" labeling of the more accessible amines. The first MicroPET of glycoproteins, ⁶⁸Ga-DOTA-orosomucoid and asialoorosomucoid, successfully visualized the differences in the circulatory residence of glycoproteins, in the presence or absence of sialic acids. In vivo dynamics of the new N-glycoclusters, prepared by the "self-activating" Huisgen cycloaddition reaction, could also be affected significantly by their partial structures at the non-reducing end, i.e., the presence or absence of sialic acids, and/or sialoside linkages to galactose. Azaelectrocyclization chemistry is also applicable to the engineering of the proteins and/or the cell surfaces by the oligosaccharides; lymphocytes chemically engineered by sialo-N-glycan successfully target the tumor implanted in BALB/C nude mice, detected by noninvasive fluorescence imaging.

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Metabolic Labeling of Sialic Acids in Living Animals with Alkynyl Sugars

Cited by 205 publications

References 29 publications

Cell surface glycoprotein profiling of cancer cells based on bioorthogonal chemistry

Cell surface glycoprotein profiling of cancer cells based on bioorthogonal chemistry

Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry

Chemical Approach to a Whole Body Imaging of Sialo-N-Linked Glycans

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