Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells

Hiroyuki Yamakoshi, Kosuke Dodo, Almar Palonpon, Jun Ando, Katsumasa Fujita, Satoshi Kawata, Mikiko Sodeoka

Research output: Contribution to journalArticlepeer-review

335 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)20681-20689
Number of pages9
JournalJournal of the American Chemical Society
Issue number51
Publication statusPublished - 2012 Dec 26


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