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Tanaka K.,Osaka University | Tanaka K.,RIKEN | Moriwaki K.,Osaka University | Yokoi S.,Kishida Chemical Co. | And 3 more authors.
Bioorganic and Medicinal Chemistry | Year: 2013

Noninvasive imaging of cancer metastasis through the efficient cell labeling constitutes a major technological breakthrough for cancer research and patient monitoring post-surgery. In the current work, we expanded our cell surface labeling technique on the whole-body fluorescence imaging of tumor metastasis in BALB/c nude mice. Four kinds of human cancer cells (two cancer cell lines, MKN45 and HCT116, and their transfected versions expressing surface glycan-related genes, MKN45-GnT-V and HCT116-GMDS) were labeled by azaelectrocyclization with Hilyte Fluor 750 for 10 min and without affecting cell viability. Fluorescence-labeled cancer cells were injected into the abdominal cavities of BALB/c mice and whole-body scans were performed with an eXplore Optix device. In accordance with previous findings, the fluorescence imaging clearly showed that tumor metastasis was dependent upon the cell surface glycans: A larger polylactosamine structure or the loss of fucosylation on the cancer cell surfaces, respectively, enhanced the metastatic potential of the tumor cells. Our noninvasive technique provides the landmark opportunity for sensitively monitoring the dynamics of the cancer cells depending on their surface structures and/or the host environments, thus impacts on the cancer prognosis and the therapeutic applications. © 2012 Elsevier Ltd. All rights reserved.

Tanaka K.,Osaka University | Siwu E.R.O.,Osaka University | Minami K.,Osaka University | Hasegawa K.,RIKEN | And 7 more authors.
Angewandte Chemie - International Edition | Year: 2010

Body image: Self-activating Huisgen 1,3-dipolar cycloaddition and 6π azaelectrocyclization of lysine-based dendrimers (see picture) enable the in vivo dynamics and organ-specific accumulation of N-glycans to be visualized. The sugar structure and glycosyl bond linkages of N-glycans control the whole-body trafficking of the clusters in nude mice and a cancer model. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Tanaka K.,Osaka University | Minami K.,Osaka University | Tahara T.,RIKEN | Siwu E.R.O.,Osaka University | And 5 more authors.
Journal of Carbohydrate Chemistry | Year: 2010

Combined azaelectrocyclization and Staudinger ligation allowed proteins and living cells to be modified by small molecules (i.e., biotin or N-glycans). Chemically engineered lymphocytes modified by complex-type N-glycan targeted DLD-1 tissues implanted in nude mice at the whole-body level. Copyright © Taylor & Francis Group, LLC.

Tanaka K.,Osaka University | Minami K.,Osaka University | Tahara T.,RIKEN | Fujii Y.,Osaka University | And 7 more authors.
ChemMedChem | Year: 2010

(Chemical Equation Presented) Labeling the living! New synthetic chemistry allows living cells to be labeled for 10 min at extremely low concentrations without deactivating cell functions; lymphocyte trafficking was visualized with high-contrast fluorescence imaging at the whole-body level. © 2010 Wiley-VCH Verlag GmbH& Co. KGaA.

Tanaka K.,Osaka University | Yokoi S.,Kishida Chemical Co. | Morimoto K.,Osaka University | Iwata T.,Osaka University | And 5 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

Versatile method for living cell labeling has been established. Cell surfaces are initially biotinylated by azaelectrocyclization, and then treated with the fluorescence-labeled avidin or the anti-biotin antibody. © 2011 Elsevier Ltd. All rights reserved.

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