title: Second Generation TQ-Ligation for Cell Organelle Imaging.
abstract: Bioorthogonal ligations play a crucial role in labeling diverse types of biomolecules in living systems. Herein, we describe a novel class of ortho-quinolinone quinone methide (oQQM) precursors that show a faster kinetic rate in the "click cycloaddition" with thio-vinyl ether (TV) than the first generation TQ-ligation in both chemical and biological settings. We further demonstrate that the second generation TQ-ligation is also orthogonal to the widely used strain-promoted azide-alkyne cycloaddition (SPAAC) both in vitro and in vivo, revealing that these two types of bioorthogonal ligations could be used as an ideal reaction pair for the simultaneous tracking of multiple elements within a single system. Remarkably, the second generation TQ-ligation and SPAAC are effective for selective and simultaneous imaging of two different cell organelles in live cells.
authors.affiliation: †Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100730, China.|‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: Xiaoyun
authors.initials: X
authors.lastname: Zhang
authors.affiliation: †Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100730, China.|‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Dong
authors.affiliation: †Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100730, China.|‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Li
authors.affiliation: ‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Liu
authors.affiliation: ‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Li
authors.affiliation: ‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.
authors.forename: She
authors.initials: S
authors.lastname: Chen
authors.affiliation: †Graduate School of Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100730, China.|‡National Institute of Biological Sciences (NIBS), Beijing 102206, China.|§Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Lei
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000818:Animals; D001386:Azides / Q000737:chemistry; D002460:Cell Line; D002467:Cell Nucleus / Q000648:ultrastructure; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D066246:ErbB Receptors / Q000032:analysis*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D045563:Indolequinones / Q000737:chemistry*; D007700:Kinetics; D018613:Microscopy, Confocal; D008928:Mitochondria / Q000648:ultrastructure; D061848:Optical Imaging / Q000379:methods; D012710:Serum Albumin, Bovine / Q000032:analysis; D013194:Staining and Labeling; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D045563:Indolequinones; D013438:Sulfhydryl Compounds; D014753:Vinyl Compounds; C068040:quinone methide; D012710:Serum Albumin, Bovine; C100195:vinyl ether; D066246:ErbB Receptors