Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions

Aya Shibata; Yukiko Nakano; Mika Ito; Mika Araki; Jie Zhang; Yasuhiko Yoshida; Satoshi Shuto; Bengt Mannervik; Ralf Mogenstern; Yoshihiro Ito; Hiroshi Abe

doi:10.1039/C3AN01339A

Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions†

Aya Shibata,^ah Yukiko Nakano,^ah Mika Ito,^abh Mika Araki,^ach Jie Zhang,^f Yasuhiko Yoshida,^c Satoshi Shuto,^b Bengt Mannervik,^de Ralf Mogenstern,^f Yoshihiro Ito*^ah and Hiroshi Abe*^abgh

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* Corresponding authors

^a Nano Medical Engineering Laboratory, RIKEN, 2-1 Hirosawa, Wako-Shi, Saitama 351-0198, Japan
E-mail: y-ito@riken.jp
Fax: +81-48-462-9300
Tel: +81-48-467-4979

^b Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo-Shi, Hokkaido 060-0812, Japan
E-mail: h-abe@pharm.hokudai.ac.jp

^c Graduate School of Engineering, Toyo University, 2100 Kujirai, Kawagoe-Shi, Saitama 350-8585, Japan

^d Department of Biochemistry, Uppsala University, Biomedical Center, Box 576, SE-75123 Uppsala, Sweden

^e Department of Neurochemistry, Stockholm University, Svante Arrhenius väg 21A, SE-10691 Stockholm, Sweden

^f Institute of Environmental Medicine, Division of Biochemical Toxicology, Karolinska Institutet, SE-17177 Stockholm, Sweden

^g PRESTO, Japan Science and Technology Agency, 4-1-8, Honcho, Kawaguchi-Shi, Saitama 332-0012, Japan

^h Emergent Bioengineering Materials Research Team, RIKEN Center for Emergent Matter Science, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan

Abstract

We have synthesized a series of 4-substituted-2-nitrobenzene-sulfonyl compounds for caged fluorogenic probes and conducted a Hammett plot analysis using the steady-state kinetic parameters. The results revealed that the glutathione transferase (GST) alpha catalyzed reaction was dependent on the σ value in the same way as the non-enzymatic reaction, whereas the dependence of the σ value of the GST mu and pi was not as pronounced as that of GST alpha.

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Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions†

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Fluorogenic probes using 4-substituted-2-nitrobenzenesulfonyl derivatives as caging groups for the analysis of human glutathione transferase catalyzed reactions

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