Bioorthogonal Labeling, Bioimaging, and Photocytotoxicity Studies of Phosphorescent Ruthenium(II) Polypyridine Dibenzocyclooctyne Complexes

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

19 Scopus Citations
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Author(s)

  • Alex Man-Hei Yip
  • Kenneth Yin Zhang
  • Hua-Wei Liu
  • Po Lam Wu
  • King Fai Li
  • Kok Wai Cheah

Detail(s)

Original languageEnglish
Pages (from-to)10729-10740
Journal / PublicationChemistry - A European Journal
Volume21
Issue number30
Online published19 Jun 2015
Publication statusPublished - 20 Jul 2015

Abstract

The synthesis, characterization, photophysics, lipophilicity, and cellular properties of new phosphorescent ruthenium(II) polypyridine complexes functionalized with a dibenzocyclooctyne (DIBO) or amine moiety [Ru(N^N)2(L)](PF6)2 are reported (L=4-(13-N-(3,4:7,8-dibenzocyclooctyne-5-oxycarbonyl) amino-4,7,10-trioxa-tridecanyl-aminocarbonyl-oxy-methyl)-4′-methyl-2,2′-bipyridine bpy-DIBO, N^N=2,2′-bipyridine bpy (1a), 1,10-phenanthroline phen (2a); L=4-(13-amino-4,7,10-trioxa-tridecanylaminocarbonyl-oxy-methyl)-4′-methyl-2,2′-bipyridine bpy-NH2, N^N=bpy (1b), phen (2b)). The strain-promoted alkyne-azide cycloaddition (SPAAC) reaction of the DIBO complexes 1a and 2a with benzyl azide were studied. Also, the DIBO complexes 1a and 2a can selectively label N-azidoglycans located on the surface of CHO-K1 and A549 cells that were pretreated with 1,3,4,6-tetra-O-acetyl-N-azidoacetyl-D-mannosamine (Ac4ManNAz). Additionally, the intracellular trafficking and localization of these biomolecules were monitored using laser-scanning confocal microscopy. Interestingly, the biolabeling and cellular uptake efficiency of the DIBO complexes 1a and 2a were cell-line dependent, as revealed by flow cytometry and ICP-MS. Furthermore, the complexes showed good biocompatibility toward the Ac4ManNAz-pretreated cells in the dark, but exhibited photoinduced cytotoxicity due to the generation of singlet oxygen. Tracing of cell-surface glycans: New azide-reactive phosphorescent ruthenium(II) polypyridine dibenzocyclooctyne (DIBO) complexes were designed to selectively label and visualize N-azidoglycans of 1,3,4,6-tetra-O-acetyl-N-azidoacetyl-D-mannosamine (Ac4ManNAz)-pretreated cells (see figure).

Research Area(s)

  • bioorthogonal labeling, cell-surface glycan recycling, imaging agents, photocytotoxicity, ruthenium

Citation Format(s)

Bioorthogonal Labeling, Bioimaging, and Photocytotoxicity Studies of Phosphorescent Ruthenium(II) Polypyridine Dibenzocyclooctyne Complexes. / Tang, Tommy Siu-Ming; Yip, Alex Man-Hei; Zhang, Kenneth Yin; Liu, Hua-Wei; Wu, Po Lam; Li, King Fai; Cheah, Kok Wai; Lo, Kenneth Kam-Wing.

In: Chemistry - A European Journal, Vol. 21, No. 30, 20.07.2015, p. 10729-10740.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review