title: Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells.
abstract: The tetrazole-based photoclick chemistry has provided a powerful tool to image proteins in live cells. To extend photoclick chemistry to living organisms with improved spatiotemporal control, here we report the design of naphthalene-based tetrazoles that can be efficiently activated by two-photon excitation with a 700 nm femtosecond pulsed laser. A water-soluble, cell-permeable naphthalene-based tetrazole was identified that reacts with acrylamide with the effective two-photon cross-section for the cycloaddition reaction determined to be 3.8 GM. Furthermore, the use of this naphthalene-tetrazole for real-time, spatially controlled imaging of microtubules in live mammalian cells via the fluorogenic, two-photon-triggered photoclick chemistry was demonstrated.
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Yu
authors.forename: Tymish Y
authors.initials: TY
authors.lastname: Ohulchanskyy
authors.forename: Peng
authors.initials: P
authors.lastname: An
authors.forename: Paras N
authors.initials: PN
authors.lastname: Prasad
authors.forename: Qing
authors.initials: Q
authors.lastname: Lin
mesh_terms: D000818:Animals; D016466:CHO Cells; D002470:Cell Survival; D057930:Click Chemistry; D003412:Cricetulus; D005456:Fluorescent Dyes / Q000737:chemistry*; D008856:Microscopy, Fluorescence; D008870:Microtubules / Q000648:ultrastructure*; D008958:Models, Molecular; D009281:Naphthalenes / Q000737:chemistry*; D061848:Optical Imaging; D017785:Photons; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D009281:Naphthalenes; D013777:Tetrazoles; C031721:naphthalene; C045574:1H-tetrazole