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Tanabe, K. et al.

Kazuhito Tanabe, Hiroshi Harada, Michiko Narazaki, Kazuo Tanaka, Kenichi Inafuku, Hirokazu Komatsu, Takeo Ito, Hisatsugu Yamada, Yoshiki Chujo, Tetsuya Matsuda, Masahiro Hiraoka, Sei-ichi Nishimoto,

Monitoring of biological one-electron reduction by (19)F NMR using hypoxia selective activation of an (19)F-labeled indolequinone derivative.

Biological reduction of fluorine-labeled indolequinone derivative (IQ-F) was characterized by (19)F NMR for quantitative molecular understanding. The chemical shift change in (19)F NMR allowed monitoring of the enzymatic reduction of IQ-F. Upon hypoxic treatment of IQ-F with NADPH:cytochrome P450 reductase, IQ-F was activated via catalytic one-electron reduction to release nonafluoro-tert-butyl alcohol (F-OH), while the formation of F-OH was significantly suppressed under aerobic conditions. Similar hypoxia-selective reduction of IQ-F occurred within A549 cells, which expresses NADPH:cytochrome P450 reductase. The kinetic analysis was also performed to propose a reaction mechanism. The molecular oxygen slightly prevents the binding of IQ-F to reductase, while the rate of net reaction was decreased due to oxidation of a semiquinone anion radical intermediate generated by one-electron reduction of IQ-F. The disappearance of IQ-F and appearance of F-OH were imaged by (19)F fast spin echo, thus visualizing the hypoxia-selective reduction of IQ-F by means of MR imaging.[1]

References

Monitoring of biological one-electron reduction by (19)F NMR using hypoxia selective activation of an (19)F-labeled indolequinone derivative. Tanabe, K., Harada, H., Narazaki, M., Tanaka, K., Inafuku, K., Komatsu, H., Ito, T., Yamada, H., Chujo, Y., Matsuda, T., Hiraoka, M., Nishimoto, S. J. Am. Chem. Soc. (2009) [Pubmed]

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