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

Journal of the American Chemical Society

Volumn 131, Issue 44, 2009, Pages 15982-15983

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

19F NMR; A549 CELLS; AEROBIC CONDITION; ANION RADICALS; BIOLOGICAL REDUCTIONS; CHEMICAL EQUATIONS; CYTOCHROME P450 REDUCTASE; ENZYMATIC REDUCTION; FAST SPIN ECHOS; HYPOXIC TREATMENT; KINETIC ANALYSIS; MOLECULAR UNDERSTANDING; MR IMAGING; ONE-ELECTRON REDUCTIONS; REACTION MECHANISM; SELECTIVE ACTIVATION; SELECTIVE REDUCTION; SEMIQUINONES; TERT-BUTYL ALCOHOLS;

ALCOHOLS; CHEMICAL REACTIONS; FLUORINE; MAGNETIC RESONANCE IMAGING; NUCLEAR MAGNETIC RESONANCE; ORGANIC POLYMERS; SELECTIVE CATALYTIC REDUCTION;

MOLECULAR OXYGEN;

FLUORINE; INDOLE DERIVATIVE;

ARTICLE; CELL HYPOXIA; CONTROLLED STUDY; ELECTRON; FLUORINE NUCLEAR MAGNETIC RESONANCE; HUMAN; HUMAN CELL; KINETICS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS;

ANOXIA; CELL LINE; FLUORINE RADIOISOTOPES; HUMANS; INDOLEQUINONES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION;

EID: 70450187446     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904953b     Document Type: Article

References (29)

1. (a) Chen, Y.; Hu, L. Med. Res. Rev. 2009, 29, 29.
2. (b) Colucci, M. A.; Moody, C. J.; Couch, G. D. Org. Biomol. Chem. 2008, 6, 637.
3. Tanabe, K.; Zhang, Z.; Ito, T.; Hatta, H.; Nishimoto, S. Org. Biomol. Chem. 2007, 5, 3745.
4. (a) Kizaka-Kondoh, S.; Inoue, M.; Harada, H.; Hiraoka, M. Cancer Sci. 2003, 94, 1021.
5. (b) Harris, A. L. Nat. Rev. Cancer 2002, 2, 38.
6. (a) Zimmermann, U.; Nöth, U.; Gröhn, P.; Jork, A.; Ulrichs, K.; Lutz, J.; Haase, A. Artif. Cells, Blood Substitutes, Immobilization Biotechnol. 2000, 28, 129.
7. (b) Yu, J.; Kodibagkar, V. D.; Cui, W.; Mason, R. P. Curr. Med. Chem. 2005, 12, 819.
8. (c) Higuchi, M.; Iwata, N.; Matsuba, Y.; Sato, K.; Sasamoto, K.; Saido, T. C. Nat. Neurosci. 2005, 8, 527.
9. (d) Ahrens, E. T.; Flores, R.; Xu, H. Y.; Morel, P. A. Nat. Biotechnol. 2005, 23, 983.
10. (a) Tanaka, K.; Kitamura, N.; Naka, K.; Chujo, Y. Chem. Commun. 2008, 6176.
11. (b) Mizukami, S.; Takikawa, R.; Sugihara, F.; Hori, Y.; Tochio, H.; Waelchli, M.; Shirakawa, M.; Kikuchi, K. J. Am. Chem. Soc. 2008, 130, 794.
12. (c) Cui, W.; Otten, P.; Li, Y.; Koeneman, K. S.; Yu, J.; Mason, R. P. Magn. Reson. Med. 2004, 51, 616.
13. (d) Oishi, M.; Sumitani, S.; Nagasaki, Y. Bioconjugate Chem. 2007, 18, 1379.
14. For recent reports on detecting the effects of reductases, see: (a) Robinson, S. P.; Griffiths, J. R. Philos. Trans. R. Soc. London, Ser. B 2004, 359, 987.
15. (b) Krohn, K. A.; Link, J. M.; Mason, R. P. Int. J. Nucl. Med. 2008, 49, 129S.
16. (c) Salmon, H. W.; Siemann, D. W. Radiother. Oncol. 2004, 73, 359.
17. (a) Tanabe, K.; Hirata, N.; Harada, H.; Hiraoka, M.; Nishimoto, S. ChemBioChem 2008, 9, 426.
18. (b) Zhang, Z.; Tanabe, K.; Hatta, H.; Nishimoto, S. Org. Biomol. Chem. 2005, 3, 1905.
19. (a) Hernick, M.; Flader, C.; Borch, R. F. J. Med. Chem. 2002, 45, 3540.
20. (b) Everett, S. A.; Swann, E.; Naylor, M. A.; Stratford, M. R. L.; Patel, K. B.; Tian, A.; Newman, R. G.; Vojnovic, B.; Moody, C. J.; Wardman, P. Biochem. Pharmacol. 2002, 63, 1629.
21. (c) Swann, E.; Barraja, P.; Oberlander, A. M.; Gardipee, W. T.; Hundnott, A. R.; Beall, H. D.; Moody, C. J. J. Med. Chem. 2001, 44, 3311.
22. (a) Kimura, A.; Narazaki, M.; Kanazawa, Y.; Fujiwara, H. Magn. Reson. Imag. 2004, 22, 855.
23. (b) Kuribayashi, H.; Doi, Y.; Kanazawa, Y. Magn. Reson. Med. 2001, 46, 864.
24. We observed slow reduction of IQ-F during the treatment with NQO1 that catalyzes two-electron reduction independent of the presence of oxygen. Therefore, IQ-F may not be an ideal substrate for NQO1. See Figure S6.
25. Moore, W. J. Physical Chemistry; Prentice-Hall, Inc.: NJ, 1972.
26. Yu, L. J.; Matis, J.; Scudiero, D. A.; Hite, K. M.; Monk, A.; Sausville, E. A.; Waxman, D. J. Drug Metab. Dispos. 2001, 29, 304.
27. To prepare an aqueous solution of IQ-F, we employed a solubilization kit for hydrophobic drugs (PUREBRIGHT).
28. McRobbie, D. W.; Moore, E. A.; Graves, M. J.; Prince, M. R. MRI From Picture to Proton; Cambridge University Press: Cambridge, 2003.
29. An experimental detail was illustrated in Figure S4. See also Experimental Section described in the Supporting Information.