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Site‐Specific In Vivo Bioorthogonal Ligation via Chemical Modulation
Author(s) -
Koo Heebeom,
Lee Jeong Heon,
Bao Kai,
Wu Yunshan,
El Fakhri Georges,
Henary Maged,
Yun Seok Hyun,
Choi Hak Soo
Publication year - 2016
Publication title -
advanced healthcare materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.288
H-Index - 90
eISSN - 2192-2659
pISSN - 2192-2640
DOI - 10.1002/adhm.201600574
Subject(s) - bioorthogonal chemistry , in vivo , ligation , modulation (music) , biophysics , chemistry , materials science , nanotechnology , combinatorial chemistry , click chemistry , microbiology and biotechnology , biology , physics , acoustics
A critical limitation of bioorthogonal click chemistry for in vivo applications has been its low reaction efficiency due to the pharmacokinetic barriers, such as blood distribution, circulation, and elimination in living organisms. To identify key factors that dominate the efficiency of click chemistry, here a rational design of near‐infrared fluorophores containing tetrazine as a click moiety is proposed. Using trans ‐cyclooctene‐modified cells in live mice, it is found that the in vivo click chemistry can be improved by subtle changes in lipophilicity and surface charges of intravenously administered moieties. By controlling pharmacokinetics, biodistribution, and clearance of click moieties, it is proved that the chemical structure dominates the fate of in vivo click ligation.