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Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH
Abstract
A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich pi-pi stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I(375)/I(487)) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that 1 is a useful fluorescent sensor for investigations of ATP-relevant biological processes.
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Cited by
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Lee, M. H., Kim, J. S., & Sessler, J. L. (2015) · Chemical Society Reviews · doi:10.1039/c4cs00280f · Cited by 1,642
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Busschaert, N., Caltagirone, C., Van Rossom, W., & Gale, P. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00099 · Cited by 1,249
Artificial Receptors for the Recognition of Phosphorylated Molecules
Hargrove, A. E., Nieto, S., Zhang, T., Sessler, J. L., & Anslyn, E. V. (2011) · Chemical Reviews · doi:10.1021/cr100242s · Cited by 649
Revisiting Fluorescent Calixarenes: From Molecular Sensors to Smart Materials
Kumar, R., Sharma, A., Singh, H., Suating, P., Kim, H. S., Sunwoo, K., Shim, I., Gibb, B. C., & Kim, J. S. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00605 · Cited by 538
Self-citationShi, J., Wu, Y., Tong, B., Zhi, J., & Dong, Y. (2014) · Sensors and Actuators B: Chemical · doi:10.1016/j.snb.2014.03.004 · Cited by 29
Metadata
- Authors
- Xu, Z., Singh, N. J., Lim, J., Pan, J., Kim, H. N., Park, S., Kim, K. S., & Yoon, J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-09-23
- Volume
- 131
- Issue
- 42
- Pages
- 15528-15533
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1989320253
- Cited by
- 590
- References
- 0
- FWCI
- 17.45
- Type
- journal article
- Language
- en
- Open access
- closed
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- Xu, Z., Singh, N. J., Lim, J., Pan, J., Kim, H. N., Park, S., Kim, K. S., & Yoon, J. (2009). Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH. Journal of the American Chemical Society. https://doi.org/10.1021/ja906855a
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