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- W1955215908 abstract "8-Nitroguanosine is formed by the nitration of guanosine, and has been conventionally classified as a genotoxic material. Recently, 8-nitroguanosine 3',5'-cyclic monophosphate (8-nitro-cGMP) has become of great interest due to its biological role as an intracellular signaling molecule. In an attempt to develop recognition molecules for 8-nitroguanosine, we have determined a 1,3-diazaphenoxazine nucleoside derivative (nitroG-grasp) bearing a thiol group with a urea linker, which efficiently displaces the nitro group through the formation of multiple hydrogen-bonded complexes with 8-nitroguanosine. However, a drawback of this capture molecule was that the displacement efficiency was not sufficient to capture 8-nitroguanosine in water. Taking into account that both the flexibility of the linker and the pKa value of the thiol group are determinants of the reactivity, new nitroG-grasp molecules were designed to have a fixed linker structure with different pKa values. Compared to the previous nitroG-grasp, the new compounds with the (2-aminophenyl)methanethiol or the propylene acetal of 3-amino-1-mercaptopropan-2-one unit have exhibited more than 10-100 times faster reactivity in the aqueous media. These compounds may be potential components to construct new nitroG-grasp molecules to capture 8-nitro-cGMP in the biological systems." @default.
- W1955215908 created "2016-06-24" @default.
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- W1955215908 date "2015-01-01" @default.
- W1955215908 modified "2023-09-23" @default.
- W1955215908 title "New NitroG-Grasp Molecules with Enhanced Capture Reactivity for 8-Nitroguanosine in the Aqueous Media" @default.
- W1955215908 doi "https://doi.org/10.1248/cpb.c15-00550" @default.
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