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Carbofluoresceins and Carborhodamines as Scaffolds for High-Contrast Fluorogenic Probes
Open accessAbstract
Fluorogenic molecules are important tools for advanced biochemical and biological experiments. The extant collection of fluorogenic probes is incomplete, however, leaving regions of the electromagnetic spectrum unutilized. Here, we synthesize green-excited fluorescent and fluorogenic analogues of the classic fluorescein and rhodamine 110 fluorophores by replacement of the xanthene oxygen with a quaternary carbon. These anthracenyl "carbofluorescein" and "carborhodamine 110" fluorophores exhibit excellent fluorescent properties and can be masked with enzyme- and photolabile groups to prepare high-contrast fluorogenic molecules useful for live cell imaging experiments and super-resolution microscopy. Our divergent approach to these red-shifted dye scaffolds will enable the preparation of numerous novel fluorogenic probes with high biological utility.
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Cited by
Bright photoactivatable fluorophores for single-molecule imaging
Grimm, J. B., English, B. P., Choi, H., Muthusamy, A. K., Mehl, B. P., Dong, P., Brown, T. A., Lippincott-Schwartz, J., Liu, Z., Lionnet, T., et al. (2016) · Nature Methods · doi:10.1038/nmeth.4034 · Cited by 435
Self-citationHybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging
Wang, L., Du, W., Hu, Z., Uvdal, K., Li, L., & Huang, W. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201901061 · Cited by 348
Switchable Fluorophores for Single-Molecule Localization Microscopy
Li, H., & Vaughan, J. C. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00767 · Cited by 319
Xanthene-Based NIR-II Dyes for In Vivo Dynamic Imaging of Blood Circulation
Liu, D., He, Z., Zhao, Y., Yang, Y., Shi, W., Li, X., & Ma, H. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.1c07711 · Cited by 217
A general approach to the design of high-performance near-infrared (NIR) D-π-A type fluorescent dyes
Luo, X., Li, J., Zhao, J., Gu, L., Qian, X., & Yang, Y. (2019) · Chinese Chemical Letters · doi:10.1016/j.cclet.2019.03.012 · Cited by 119
Metadata
- Authors
- Grimm, J. B., Sung, A. J., Legant, W. R., Hulamm, P., Matlosz, S. M., Betzig, E., & Lavis, L. D.
- Venue
- ACS Chemical Biology
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-04-24
- Volume
- 8
- Issue
- 6
- Pages
- 1303-1310
- ISSN
- 1554-8929 (ISSN-L)
- 1554-8937
- OpenAlex
- W2018343578
- Cited by
- 217
- References
- 0
- FWCI
- 6.42
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Grimm, J. B., Sung, A. J., Legant, W. R., Hulamm, P., Matlosz, S. M., Betzig, E., & Lavis, L. D. (2013). Carbofluoresceins and Carborhodamines as Scaffolds for High-Contrast Fluorogenic Probes. ACS Chemical Biology. https://doi.org/10.1021/cb4000822
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