Electrocyclization‐Based Labeling Allows Efficient In Vivo Imaging of Cellular Trafficking

Tanaka, Katsunori; Minami, Kaori; Tahara, Tsuyoshi; Fujii, Yûzo; Siwu, Eric R. O.; Nozaki, Satoshi; Onoe, Hirotaka; Yokoi, Satomi; Koyama, Koichi; Watanabe, Yasuyoshi; Fukase, Koichi

doi:10.1002/cmdc.201000027

Cited by 29 publications

(26 citation statements)

References 74 publications

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“…7) (10). For instances, the C6 glioma cells could be efficiently labeled by treating with even 10 -8 M PBS buffer solution of TAMRA-STELLA + or Cy5-STELLA + (1c, d) at either 24 ˚C or 37 ˚C only for two minutes.…”

Section: E Live Cell Surface Labeling and Imaging Through Rapid Azaementioning

confidence: 99%

“…7), and the noninvasive fluorescence imaging was performed in the BALB/c nude mouse (Fig. 8A) (10). The dynamic images provided the marked results that the trafficking of the cells into the spleen and the lymph nodes as the secondary lymphoid organs, was clearly visualized with exceptionally high imaging contrasts compared with those reported previously (4,31); thus, the observation highlights our azaelectrocyclization- based labeling in applying to a whole cell-based in vivo imaging (32).…”

Section: E Live Cell Surface Labeling and Imaging Through Rapid Azaementioning

confidence: 99%

“…Thus, we developed the highly efficient positron emitting metal and fluorescence labeling probes for the N-glycoconjugates by designing the rapid azaelectrocyclization with the amino groups (4,9), and achieved the noninvasive in vivo imaging of the N-glycoproteins (4,9) or the whole living cells (10). Furthermore, the world's largest N-glycoclusters with molecular mass of 50 kDa, which efficiently mimic the multivalency effects in vivo, could be prepared, and their imaging studies successfully visualized the remarkable dependence of the non-reducing end sialic acid and its linkages to galactose on the clearance and the organ-specific accumulation (11).…”

Section: A Introductionmentioning

confidence: 99%

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Development of Azaelectrocyclization-Based Labeling and Application to Noninvasive Imaging and Targeting Using N-Glycan Derivatives—In Pursuit of N-Glycan Functions on Proteins, Dendrimers, and Living Cells—

Tanaka

Fukase

2012

TIGG

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The authors have developed the new positron emitting metal and fluorescence labeling protocol of ε-amino group of lysine through their rapid 6π-azaelectrocyclization. Using the same reaction, the small organic molecules could also be introduced on the amino groups of the living cell surface with simple operations under quite mild conditions, establishing the chemistry-based cell surface engineering with complex-type N-glycans. PET and the noninvasive fluorescence imaging of the N-glycoproteins and the world's largest N-glycoclusters, mimicking the natural glyco-bioenvironment, for the first time visualized the differences in their in vivo dynamics and excretion pathway depending on the presence of the non-reducing end sialic acid as well as their linkages to the galactose residue. The authors also synthetically developed the artificial lymphocytes to target the tumors in living animals by introducing the complex-type N-glycans on the cell surfaces.

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Section: E Live Cell Surface Labeling and Imaging Through Rapid Azaementioning

confidence: 99%

Section: E Live Cell Surface Labeling and Imaging Through Rapid Azaementioning

confidence: 99%

Section: A Introductionmentioning

confidence: 99%

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Development of Azaelectrocyclization-Based Labeling and Application to Noninvasive Imaging and Targeting Using N-Glycan Derivatives—In Pursuit of N-Glycan Functions on Proteins, Dendrimers, and Living Cells—

Tanaka

Fukase

2012

TIGG

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“…In this personal account, we want to describe our recent trials on the in vivo imaging of the sialo-N-glycans; we first describe (1) the new chemistry-based labeling of the amino groups [28][29][30], e.g., lysines or ethanol amines, which is quite useful not only for the labeling of the glycans and/or the glycoconjugates, but also generally for the peptides, proteins, as well as the cell surfaces [31]. Then, PET and the noninvasive fluorescence images of (2) sialo-and asialo-glycoproteins [8,9,[28][29][30], (3) dendrimer-type glycoclusters consisting of 16 molecules of N-glycans [32], and (4) chemically engineered lymphocytes by sialo-N-glycans [33] are discussed.…”

Section: Introductionmentioning

confidence: 99%

“…Then, PET and the noninvasive fluorescence images of (2) sialo-and asialo-glycoproteins [8,9,[28][29][30], (3) dendrimer-type glycoclusters consisting of 16 molecules of N-glycans [32], and (4) chemically engineered lymphocytes by sialo-N-glycans [33] are discussed. These imaging studies clearly visualize the remarkable dependence of in vivo dynamics and organ-specific accumulation on the partial structures of the non-reducing end of the N-glycans.…”

Section: Introductionmentioning

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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