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Bioorthogonal Labeling, Bioimaging, and Photocytotoxicity Studies of Phosphorescent Ruthenium(II) Polypyridine Dibenzocyclooctyne Complexes
Author(s) -
Tang Tommy SiuMing,
Yip Alex ManHei,
Zhang Kenneth Yin,
Liu HuaWei,
Wu Po Lam,
Li King Fai,
Cheah Kok Wai,
Lo Kenneth KamWing
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501040
Subject(s) - chemistry , ruthenium , bioorthogonal chemistry , azide , bipyridine , singlet oxygen , phenanthroline , phosphorescence , cycloaddition , amine gas treating , lipophilicity , click chemistry , photochemistry , stereochemistry , combinatorial chemistry , fluorescence , organic chemistry , catalysis , oxygen , crystal structure , physics , quantum mechanics
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)](PF 6 ) 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 ( 1 a ), 1,10‐phenanthroline phen ( 2 a ); L=4‐(13‐amino‐4,7,10‐trioxa‐tridecanylaminocarbonyl‐oxy‐methyl)‐4′‐methyl‐2,2′‐bipyridine bpy‐NH 2 , N^N=bpy ( 1 b ), phen ( 2 b )). The strain‐promoted alkyne–azide cycloaddition (SPAAC) reaction of the DIBO complexes 1 a and 2 a with benzyl azide were studied. Also, the DIBO complexes 1 a and 2 a 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 (Ac 4 ManNAz). 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 1 a and 2 a were cell‐line dependent, as revealed by flow cytometry and ICP‐MS. Furthermore, the complexes showed good biocompatibility toward the Ac 4 ManNAz‐pretreated cells in the dark, but exhibited photoinduced cytotoxicity due to the generation of singlet oxygen.