title: Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells.
abstract: Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure-Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second alkyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged CoQ analogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2'-deoxyuridine (EdU) and a CoQ analogue, with distinct Raman tags was demonstrated.
authors.affiliation: Sodeoka Live Cell Chemistry Project, Exploratory Research for Advanced Technology, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamakoshi
authors.forename: Kosuke
authors.initials: K
authors.lastname: Dodo
authors.forename: Almar
authors.initials: A
authors.lastname: Palonpon
authors.forename: Jun
authors.initials: J
authors.lastname: Ando
authors.forename: Katsumasa
authors.initials: K
authors.lastname: Fujita
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kawata
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
mesh_terms: D000480:Alkynes / Q000032:analysis*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000032:analysis; D006367:HeLa Cells; D006801:Humans; D008853:Microscopy / Q000379:methods; D057054:Molecular Imaging / Q000379:methods; D013059:Spectrum Analysis, Raman; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000032:analysis
chemical_list: D000480:Alkynes; D014451:Ubiquinone; C031086:5-ethynyl-2'-deoxyuridine; D003857:Deoxyuridine