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Mechanism-Based Molecular Design of Highly Selective Fluorescence Probes for Nitrative Stress
Abstract
Nitrative stress is implicated in various pathogenic processes, including neurodegenerative disorders, but there is no practical fluorescence probe which can monitor the generation of nitrative stress with high selectivity. To design a suitable fluorescence probe, we have first focused on the fluorescence quenching mechanism of the nitro group, which has been believed to be a unique quencher of fluorescent dyes. We found that nitro group-based fluorescence quenching could be explained in terms of an electron transfer process, from the excited fluorophore to the electron-deficient aromatic nitro moiety. By utilizing this result, we succeeded in developing novel fluorogenic probes, NiSPYs, which can selectively monitor the generation of nitrative stress based on aromatic nitration. NiSPYs showed strong fluorescence enhancement upon the reaction with nitrating agents, including peroxynitrite, but showed little or no fluorescence augmentation in the presence of other reactive oxygen species. NiSPYs should be potentially useful as tools to study the role of nitrative stress in various biological applications.
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Cites
Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils
Eiserich, J. P., Hristova, M., Cross, C. E., Jones, A. D., Freeman, B. A., Halliwell, B., & van der Vliet, A. (1998) · Nature · doi:10.1038/34923 · Cited by 1,496
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Ulrich, G., Ziessel, R., & Harriman, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200702070 · Cited by 3,161
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Chen, X., Tian, X., Shin, I., & Yoon, J. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15037e · Cited by 980
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Wang, C., Chi, W., Qiao, Q., Tan, D., Xu, Z., & Liu, X. (2021) · Chemical Society Reviews · doi:10.1039/d1cs00239b · Cited by 710
Yu, F., Li, P., Wang, B., & Han, K. (2013) · Journal of the American Chemical Society · doi:10.1021/ja401360a · Cited by 621
Yu, F., Li, P., Li, G., Zhao, G., Chu, T., & Han, K. (2011) · Journal of the American Chemical Society · doi:10.1021/ja202582x · Cited by 578
“Turn-on” fluorescent sensing with “reactive” probes
Eun Jun, M., Roy, B., & Han Ahn, K. (2011) · Chemical Communications · doi:10.1039/c1cc00014d · Cited by 434
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Metadata
- Authors
- Ueno, T., Urano, Y., Kojima, H., & Nagano, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-07-28
- Volume
- 128
- Issue
- 33
- Pages
- 10640-10641
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2048567906
- Cited by
- 348
- References
- 2
- FWCI
- 5.33
- Type
- journal article
- Language
- en
- Open access
- closed
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