The DOI matches its Crossref record; 6 of the 6 references it cites were found in a registry or an index.
Protein S-guanylation by the biological signal 8-nitroguanosine 3′,5′-cyclic monophosphate
Open accessAbstract
The signaling pathway of nitric oxide (NO) depends mainly on guanosine 3',5'-cyclic monophosphate (cGMP). Here we report the formation and chemical biology of a nitrated derivative of cGMP, 8-nitroguanosine 3',5'-cyclic monophosphate (8-nitro-cGMP), in NO-mediated signal transduction. Immunocytochemistry demonstrated marked 8-nitro-cGMP production in various cultured cells in an NO-dependent manner. This finding was confirmed by HPLC plus electrochemical detection and tandem mass spectrometry. 8-Nitro-cGMP activated cGMP-dependent protein kinase and showed unique redox-active properties independent of cGMP activity. Formation of protein Cys-cGMP adducts by 8-nitro-cGMP was identified as a new post-translational modification, which we call protein S-guanylation. 8-Nitro-cGMP seems to regulate the redox-sensor signaling protein Keap1, via S-guanylation of the highly nucleophilic cysteine sulfhydryls of Keap1. This study reveals 8-nitro-cGMP to be a second messenger of NO and sheds light on new areas of the physiology and chemical biology of signal transduction by NO.
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Cites
Protein S-nitrosylation: Purview and parameters
Hess, D. T., Matsumoto, A., Kim, S.-O., Marshall, H. E., & Stamler, J. S. (2005) · Nature Reviews Molecular Cell Biology · doi:10.1038/nrm1569 · Cited by 2,153
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
Wakabayashi, N., Dinkova-Kostova, A. T., Holtzclaw, W. D., Kang, M.-I., Kobayashi, A., Yamamoto, M., Kensler, T. W., & Talalay, P. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0307301101 · Cited by 986 · cited 1×
“We first focused on the thiol-rich, redox-sensor signaling protein Kelch-like ECH-associated protein 1 (Keap1), because it has a number of highly nucleophilic cysteine residue”
BackgroundCyclic guanosine monophosphate as a mediator of vasodilation.
Murad, F. (1986) · Journal of Clinical Investigation · doi:10.1172/jci112536 · Cited by 799
Tong, K. I., Katoh, Y., Kusunoki, H., Itoh, K., Tanaka, T., & Yamamoto, M. (2006) · Molecular and Cellular Biology · doi:10.1128/mcb.26.8.2887-2900.2006 · Cited by 759 · cited 1×
“His-tagged mouse recombinant Keap1 was expressed in Escherichia coli and purified as described elsewher”
MethodSelf-citationNitrated Fatty Acids: Endogenous Anti-inflammatory Signaling Mediators
Cui, T., Schopfer, F. J., Zhang, J., Chen, K., Ichikawa, T., Baker Paul, R. S., Batthyany, C., Chacko, B. K., Feng, X., Patel, R. P., et al. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m603357200 · Cited by 351
Cited by
The Molecular Mechanisms Regulating the KEAP1-NRF2 Pathway
Baird, L., & Yamamoto, M. (2020) · Molecular and Cellular Biology · doi:10.1128/mcb.00099-20 · Cited by 1,542
Self-citationMolecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution
Taguchi, K., Motohashi, H., & Yamamoto, M. (2011) · Genes to Cells · doi:10.1111/j.1365-2443.2010.01473.x · Cited by 1,478
Self-citationReactive cysteine persulfides and S-polythiolation regulate oxidative stress and redox signaling
Ida, T., Sawa, T., Ihara, H., Tsuchiya, Y., Watanabe, Y., Kumagai, Y., Suematsu, M., Motohashi, H., Fujii, S., Matsunaga, T., et al. (2014) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1321232111 · Cited by 934
Self-citationFang, J., Islam, W., & Maeda, H. (2020) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2020.06.005 · Cited by 757
AUTACs: Cargo-Specific Degraders Using Selective Autophagy
Takahashi, D., Moriyama, J., Nakamura, T., Miki, E., Takahashi, E., Sato, A., Akaike, T., Itto-Nakama, K., & Arimoto, H. (2019) · Molecular Cell · doi:10.1016/j.molcel.2019.09.009 · Cited by 675
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Metadata
- Authors
- Sawa, T., Zaki, M. H., Okamoto, T., Akuta, T., Tokutomi, Y., Kim-Mitsuyama, S., Ihara, H., Kobayashi, A., Yamamoto, M., Fujii, S., Arimoto, H., & Akaike, T.
- Venue
- Nature Chemical Biology
- Published
- 2007-09-30
- Volume
- 3
- Issue
- 11
- Pages
- 727-735
- ISSN
- 1552-4450 (ISSN-L)
- 1552-4469
- OpenAlex
- W2155314275
- Cited by
- 272
- References
- 6
- FWCI
- 8.70
- Type
- journal article
- Language
- en
- Open access
- green
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- Sawa, T., Zaki, M. H., Okamoto, T., Akuta, T., Tokutomi, Y., Kim-Mitsuyama, S., Ihara, H., Kobayashi, A., Yamamoto, M., Fujii, S., Arimoto, H., & Akaike, T. (2007). Protein S-guanylation by the biological signal 8-nitroguanosine 3′,5′-cyclic monophosphate. Nature Chemical Biology. https://doi.org/10.1038/nchembio.2007.33
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