Synthesis of new derivatives of 8-oxoG-clamp for better understanding the recognition mode and improvement of selective affinity.

Zhichun Li, Osamu Nakagawa, Yohei Koga, Yosuke Taniguchi, Shigeki Sasaki

Graduate School of Pharmaceutical Sciences, Kyushu University, Higashi-ku, Fukuoka 812-8582, Japan.

Bioorganic & medicinal chemistry 2010 Jun 1

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8-Oxoguanosine (8-oxoG) is a representative metabolite derived by the oxidation of guanosine (G) and is regarded as a marker of oxidative stress in the cells. We previously reported the 8-oxoG-clamp as the first fluorescent probe for detection of 8-oxoG. In this study, new 8-oxoG-clamp derivatives having a variety of N-functional groups were synthesized and their recognition properties were investigated. The sp(3) oxygen atom of the carbamate unit was revealed to play a significant role in the hydrogen bonding interactions, and the pyrene group produced higher stability with 8-oxoG compared with the original 8-oxoG-clamp.

Citation

Zhichun Li, Osamu Nakagawa, Yohei Koga, Yosuke Taniguchi, Shigeki Sasaki. Synthesis of new derivatives of 8-oxoG-clamp for better understanding the recognition mode and improvement of selective affinity. Bioorganic & medicinal chemistry. 2010 Jun 1;18(11):3992-8