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5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: A New Efficient Phosphorylated Nitrone for the in Vitro and in Vivo Spin Trapping of Oxygen-Centered Radicals
Abstract
5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO, 2), a new spin trap, has been synthesized via a two-step synthetic route, and its ability to spin trap oxy radicals in biological milieu has been addressed. The in vitro spin trapping of hydroxyl and superoxide radicals was investigated in a phosphate buffer 0.1 M, and the hyperfine coupling constants of the spin adducts were determined. The rates of spin trapping of hydroxyl and superoxide radicals with 2 were found to be close to those reported for 5,5-dimethyl-1-pyrroline N-oxide (DMPO). However, the DEPMPO-superoxide spin adduct was shown to be significantly more persistent (15 times at pH 7) than the DMPO--superoxide spin adduct. Using 2 as a spin trap, the production of superoxide has been clearly characterized during the reperfusion of ischemic isolated rat hearts.
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Cited by
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Vásquez-Vivar, J., Kalyanaraman, B., Martásek, P., Hogg, N., Masters, B. S. S., Karoui, H., Tordo, P., & Pritchard, K. A. (1998) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.95.16.9220 · Cited by 1,484
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Ago, T., Kitazono, T., Ooboshi, H., Iyama, T., Han, Y. H., Takada, J., Wakisaka, M., Ibayashi, S., Utsumi, H., & Iida, M. (2004) · Circulation · doi:10.1161/01.cir.0000105680.92873.70 · Cited by 497
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Metadata
- Authors
- Frejaville, C., Karoui, H., Tuccio, B., Moigne, F. L., Culcasi, M., Pietri, S., Lauricella, R., & Tordo, P.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1995-01
- Volume
- 38
- Issue
- 2
- Pages
- 258-265
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1984693449
- Cited by
- 512
- References
- 0
- FWCI
- 9.83
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: 5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: A New Efficient Phosphorylated Nitrone for the in Vitro and in Vivo Spin Trapping of Oxygen-Centered Radicals. https://app.cochat.ai/papers/10.1021/jm00002a007
- The paper
- Frejaville, C., Karoui, H., Tuccio, B., Moigne, F. L., Culcasi, M., Pietri, S., Lauricella, R., & Tordo, P. (1995). 5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: A New Efficient Phosphorylated Nitrone for the in Vitro and in Vivo Spin Trapping of Oxygen-Centered Radicals. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00002a007
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