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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
A general method to improve fluorophores for live-cell and single-molecule microscopy
Grimm, J. B., English, B. P., Chen, J., Slaughter, J. P., Zhang, Z., Revyakin, A., Patel, R., Macklin, J. J., Normanno, D., Singer, R. H., et al. (2015) · Nature Methods · doi:10.1038/nmeth.3256 · Cited by 1,501
Self-citationA general method to fine-tune fluorophores for live-cell and in vivo imaging
Grimm, J. B., Muthusamy, A. K., Liang, Y., Brown, T. A., Lemon, W. C., Patel, R., Lu, R., Macklin, J. J., Keller, P. J., Ji, N., et al. (2017) · Nature Methods · doi:10.1038/nmeth.4403 · Cited by 665
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Lavis, L. D., & Raines, R. T. (2014) · ACS Chemical Biology · doi:10.1021/cb500078u · Cited by 536
Self-citationA Critical and Comparative Review of Fluorescent Tools for Live-Cell Imaging
Specht, E. A., Braselmann, E., & Palmer, A. E. (2017) · Annual Review of Physiology · doi:10.1146/annurev-physiol-022516-034055 · Cited by 444
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Volarić, J., Szymanski, W., Simeth, N. A., & Feringa, B. L. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00547a · Cited by 438
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
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Li, H., & Vaughan, J. C. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00767 · Cited by 319
A general method to optimize and functionalize red-shifted rhodamine dyes
Grimm, J. B., Tkachuk, A. N., Xie, L., Choi, H., Mohar, B., Falco, N., Schaefer, K., Patel, R., Zheng, Q., Liu, Z., et al. (2020) · Nature Methods · doi:10.1038/s41592-020-0909-6 · Cited by 298
Self-citationXanthene-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
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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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