A sensitive and specific Raman probe based on bisarylbutadiyne for live cell imaging of mitochondria

  • Bioorg Med Chem Lett. 2015 Feb 1;25(3):664-7. doi: 10.1016/j.bmcl.2014.11.080.
Hiroyuki Yamakoshi  1 ,  Almar Palonpon  2 ,  Kosuke Dodo  3 ,  Jun Ando  4 ,  Satoshi Kawata  5 ,  Katsumasa Fujita  6 ,  Mikiko Sodeoka  7
Affiliations
  • 1. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
  • 2. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; Department of Applied Physics, Osaka University, 2-1 Yamadaoka Suita, Osaka 565-0871, Japan.
  • 3. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; CREST, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
  • 4. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; CREST, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Department of Applied Physics, Osaka University, 2-1 Yamadaoka Suita, Osaka 565-0871, Japan.
  • 5. Department of Applied Physics, Osaka University, 2-1 Yamadaoka Suita, Osaka 565-0871, Japan.
  • 6. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; CREST, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Department of Applied Physics, Osaka University, 2-1 Yamadaoka Suita, Osaka 565-0871, Japan.
  • 7. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; CREST, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. Electronic address: [email protected].
PMID: 25522818 DOI: 10.1016/j.bmcl.2014.11.080
Abstract

We previously showed that bisarylbutadiyne (BADY), which has a conjugated diyne structure, exhibits an intense peak in the cellular Raman-silent region. Here, we synthesized a mitochondria-selective Raman probe by linking bisphenylbutadiyne with triphenylphosphonium, a well-known mitochondrial targeting moiety. This probe, named MitoBADY, has a Raman peak 27 times more intense than that of 5-ethynyl-2'-deoxyuridine. Raman microscopy using submicromolar extracellular probe concentrations successfully visualized mitochondria in living cells. A full Raman spectrum is acquired at each pixel of the scanned sample, and we showed that simultaneous Raman imaging of MitoBADY and endogenous cellular biomolecules can be achieved in a single scan. MitoBADY should be useful for the study of mitochondrial dynamics.

Keywords
Imaging; Live cell; Mitochondria; Raman; Triphenylphosphonium.
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