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.
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Substituting the chalcogen atom in the pyrylium ring from sulfur to selenium shifted the ethynyl stretching mode from 2120-2140 cm−1 for thiopyrylium dyes to 2140-2170 cm−1 for selenopyrylium dyes.
“also shifted the Raman band associated with the ethynyl stretching mode from 2120-2140 cm-1 for the thiopyrylium dyes to 2140-2170 cm-1 for the selenopyrylium dyes 16.”
From Design and evaluation of Raman reporters for the Raman-silent region (2022) · cites this paper as [16]
In the Raman-silent region, only Raman bands from triple bond vibrational modes (e.g., alkyne, cyanide, nitrile) appear.
“as only Raman bands from triple bond (e.g., alkyne, cyanide, nitrile, etc.) vibrational modes appear 15, 16”
From Design and evaluation of Raman reporters for the Raman-silent region (2022) · cites this paper as [16]
The Raman shift displayed by reporter molecules is very sensitive to substituents on the para-substituted aromatic rings on the chromophore.
“Our work corroborated the findings by Yamakoshi et al.16 in which the Raman shift displayed by reporter molecules was very sensitive to substituents on the para-substituted aromatic rings on the chromophore.”
From Design and evaluation of Raman reporters for the Raman-silent region (2022) · cites this paper as [16]
Cites
Taniguchi, Y., Choi, P. J., Li, G.-W., Chen, H., Babu, M., Hearn, J., Emili, A., & Xie, X. S. (2010) · Science · doi:10.1126/science.1188308 · Cited by 1,982 · see citing works
Imaging of EdU, an Alkyne-Tagged Cell Proliferation Probe, by Raman Microscopy
Yamakoshi, H., Dodo, K., Okada, M., Ando, J., Palonpon, A., Fujita, K., Kawata, S., & Sodeoka, M. (2011) · Journal of the American Chemical Society · doi:10.1021/ja108404p · Cited by 356 · see citing works
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Vibrational spectroscopic imaging of living systems: An emerging platform for biology and medicine
Cheng, J.-X., & Xie, X. S. (2015) · Science · doi:10.1126/science.aaa8870 · Cited by 874 · see citing works
Biological imaging of chemical bonds by stimulated Raman scattering microscopy
Hu, F., Shi, L., & Min, W. (2019) · Nature Methods · doi:10.1038/s41592-019-0538-0 · Cited by 392 · see citing works
Stimulated Raman Scattering: From Bulk to Nano
Prince, R. C., Frontiera, R. R., & Potma, E. O. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00545 · Cited by 350 · see citing works
Kong, K. V., Ho, C. J. H., Gong, T., Lau, W. K. O., & Olivo, M. (2014) · Biosensors and Bioelectronics · doi:10.1016/j.bios.2013.12.062 · Cited by 81 · see citing works
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Design and evaluation of Raman reporters for the Raman-silent region
Plakas, K., Rosch, L. E., Clark, M. D., Adbul-Rashed, S., Shaffer, T. M., Harmsen, S., Gambhir, S. S., & Detty, M. R. (2022) · Nanotheranostics · doi:10.7150/ntno.58965 · Cited by 22 · see citing works
“Our work corroborated the findings by Yamakoshi et al.[16] in which the Raman shift displayed by reporter molecules was very sensitive to substituents on the para-substituted aromatic rings on the chromophore.”
BackgroundResultInfluentialLi, X., Zhou, R., Xu, Y., Wei, X., & He, Y. (2017) · Applied Spectroscopy Reviews · doi:10.1080/05704928.2016.1226183 · Cited by 13 · see citing works
- Authors
- Yamakoshi, H., Dodo, K., Palonpon, A., Ando, J., Fujita, K., Kawata, S., & Sodeoka, M.
- Affiliations
- Japan Science and Technology Agency (JP)
- RIKEN Advanced Science Institute (JP)
- Corresponding author
- Sodeoka, Mikiko
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-12-14
- Volume
- 134
- Issue
- 51
- Pages
- 20681-20689
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2039976599
- Cited by
- 461
- References
- 2
- Citations by year
- 2026: 21 · 2025: 40 · 2024: 39 · 2023: 49 · 2022: 47 · 2021: 51 · 2020: 31 · 2019: 32 · 2018: 35 · 2017: 38 · 2016: 21 · 2015: 26 · 2014: 21 · 2013: 10
- FWCI
- 8.34
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Japan Society for the Promotion of Science (23710276, 24710267)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Spectroscopy Techniques in Biomedical and Chemical Research
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Keywords
- live-cell imaging, conjugated diynes, 5-ethynyl-2'-deoxyuridine
- MeSH terms
- Alkynes, Deoxyuridine, HeLa Cells, Humans, Microscopy, Spectrum Analysis, Raman, Ubiquinone, Molecular Imaging
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