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β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold
Abstract
We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for β-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize β-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.
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Cited by
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Gu, K., Xu, Y., Li, H., Guo, Z., Zhu, S., Zhu, S., Shi, P., James, T. D., Tian, H., & Zhu, W.-H. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b01705 · Cited by 498
Uno, S.-N., Kamiya, M., Yoshihara, T., Sugawara, K., Okabe, K., Tarhan, M. C., Fujita, H., Funatsu, T., Okada, Y., Tobita, S., et al. (2014) · Nature Chemistry · doi:10.1038/nchem.2002 · Cited by 469
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Metadata
- Authors
- Kamiya, M., Asanuma, D., Kuranaga, E., Takeishi, A., Sakabe, M., Miura, M., Nagano, T., & Urano, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-08-03
- Volume
- 133
- Issue
- 33
- Pages
- 12960-12963
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2315452255
- Cited by
- 247
- References
- 0
- FWCI
- 4.65
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kamiya, M., Asanuma, D., Kuranaga, E., Takeishi, A., Sakabe, M., Miura, M., Nagano, T., & Urano, Y. (2011). β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold. Journal of the American Chemical Society. https://doi.org/10.1021/ja204781t
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