Journal of the American Chemical Society 2011-09-14

Design of chemical shift-switching 19F magnetic resonance imaging probe for specific detection of human monoamine oxidase A.

Koya Yamaguchi, Ryosuke Ueki, Hiroshi Nonaka, Fuminori Sugihara, Tetsuya Matsuda, Shinsuke Sando

Index: J. Am. Chem. Soc. 133(36) , 14208-11, (2011)

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Abstract

Monoamine oxidase (MAO) A is a flavoenzyme that catalyzes the oxidation of biologically important monoamines and is thought to be associated with psychiatric disorders. Here, we report a strategy for rationally designing a (19)F magnetic resonance imaging probe for the specific detection of human MAO-A (hMAO-A) activity. Our designed (19)F probe was oxidized expeditiously by hMAO-A to produce 2-fluoro-4-nitrophenol via a spontaneous β-elimination mechanism. Concomitant with the structural change of the probe to the product, the (19)F chemical shift changed by 4.2 ppm, which was enough to visualize the probe and enzymatic product separately. Importantly, our probe achieved excellent discrimination of hMAO-A from its isoform hMAO-B.