Bioorthogonal Copper Free Click Chemistry for Labeling and Tracking of Chondrocytes In Vivo

Hwa In Yoon, Ji Young Yhee, Jin Hee Na, Sangmin Lee, Hyukjin Lee, Sun Woong Kang, Hyeyoun Chang, Ju Hee Ryu, Seulki Lee, Ick Chan Kwon, Yong Woo Cho, Kwangmeyung Kim

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)


Establishment of an appropriate cell labeling and tracking method is essential for the development of cell-based therapeutic strategies. Here, we are introducing a new method for cell labeling and tracking by combining metabolic gylcoengineering and bioorthogonal copper-free Click chemistry. First, chondrocytes were treated with tetraacetylated N-azidoacetyl-D-mannosamine (Ac4ManNAz) to generate unnatural azide groups (-N3) on the surface of the cells. Subsequently, the unnatural azide groups on the cell surface were specifically conjugated with near-infrared fluorescent (NIRF) dye-tagged dibenzyl cyclooctyne (DBCO-650) through bioorthogonal copper-free Click chemistry. Importantly, DBCO-650-labeled chondrocytes presented strong NIRF signals with relatively low cytotoxicity and the amounts of azide groups and DBCO-650 could be easily controlled by feeding different amounts of Ac4ManNAz and DBCO-650 to the cell culture system. For the in vivo cell tracking, DBCO-650-labeled chondrocytes (1 × 106 cells) seeded on the 3D scaffold were subcutaneously implanted into mice and the transplanted DBCO-650-labeled chondrocytes could be effectively tracked in the prolonged time period of 4 weeks using NIRF imaging technology. Furthermore, this new cell labeling and tracking technology had minimal effect on cartilage formation in vivo. (Figure Presented).

Original languageEnglish
Pages (from-to)927-936
Number of pages10
JournalBioconjugate Chemistry
Issue number4
Publication statusPublished - 2016 Apr 20

Bibliographical note

Funding Information:
This study was funded by Development of High Medical Technology Project (HI14C2755) of KHIDI, Global Research Laboratory Project (NRF-2013K1A1A2A02050115) of KNRF and the KIST Intramural project of Theranosis, Korea.

Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry


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