BODIPY-based fluorescent redox potential sensors that utilize reversible redox properties of flavin

ChemBioChem

Volumn 9, Issue 6, 2008, Pages 853-856

  Yamada, Yasuyuki ^a   Tomiyama, Yumiko ^a   Morita, Akinori ^a   Ikekita, Masahiko ^a   Aoki, Shin ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Biosensors; Emission spectroscopy; Flavins; Redox chemistry

Indexed keywords

BORA 3A,4A DIAZA S INDACENE; QUERCETIN; RIBOFLAVIN; THIOPHENE; UNCLASSIFIED DRUG; 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; FLUORESCENT DYE; RIBOFLAVIN DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BIOSENSOR; CELL MEMBRANE PERMEABILITY; CELLULAR DISTRIBUTION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; CYTOSOL; ELECTRON TRANSPORT; FLUORESCENCE; HELA CELL; HUMAN; HUMAN CELL; HYDROPHILICITY; IMAGE ANALYSIS; LIGHT ABSORPTION; MITOCHONDRION; NUCLEOLUS; OXIDATION REDUCTION POTENTIAL; PRIORITY JOURNAL; QUANTUM YIELD; STAINING; SYNTHESIS; CHEMISTRY; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

BORON COMPOUNDS; ELECTROCHEMISTRY; FLAVINS; FLUORESCENCE; FLUORESCENT DYES; HELA CELLS; HUMANS; OXIDATION-REDUCTION; PHOTOCHEMISTRY;

EID: 44049090983     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700718     Document Type: Article

References (39)

1. a) Oxidative Stress, Disease, and Cancer (Ed.: K. K Singh), Imperial College Press, London, 2005;
2. b) Redox Regulation of Cell Signaling and Its Clinical Application (Eds.: L. Packer, J. Yodoi), Marcel Dekker, New York, 1999.
3. a) C. M. Grant, Mol. Microbiol. 2001, 39, 533-541;
4. b) J. F. Curtin, M. Donovan, T. G. Cotter, J. Immunol. Methods 2002, 265, 49-72.
5. R. P. Haugland, Handbook of Fluorescent Probes and Research Products, 9th ed., Molecular Probes, Eugene, 2002.
6. a) K. Tanaka, T. Miura, N. Umezawa, Y. Urano, K. Kikuchi, T. Higuchi, T. Nagano, J. Am. Chem. Soc. 2001, 123, 2530-2536;
7. b) K. Setsukinai, Y Urano, K. Kakinuma, H. J. Majima, T. Nagano, J. Biol. Chem. 2003, 278, 3-170-3175;
8. c) H. Maeda, Y. Fukuyasu, S. Yoshida, M. Fukuda, K. Saeki, H. Matsuno, Y. Yamauchi, K. Yoshida, K. Hirata, K. Miyamoto, Angew. Chem. 2004, 116, 2443-2445; Angew. Chem. Int. Ed. 2004, 43, 2389-2391;
9. d) A. E. Albers, V. S. Okreglak, C. J. Chang, J. Am. Chem. Soc. 2006, 128, 9640-9641.
10. a) T. Nagano, T. Yoshimura, Chem. Rev. 2002, 102, 1235-1269;
11. b) Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T Nagano, J. Am. Chem. Soc. 2004, 126, 3357-3367;
12. c) E. Sasaki, H. Kojima, H. Nishimatsu, Y. Urano, K. Kikuchi, Y. Hirata, T. Nagano, J. Am. Chem. Soc. 2005, 127, 3684-3685;
13. d) T. Ueno, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2006, 128, 10640-10641.
14. a) G. T Hanson, R. Aggeler, D. Oglesbee, M. Cannon, R. A. Capaldi, R. Y. Tsien, S. J. Remington, J. Biol. Chem. 2004, 279, 13044-13053;
15. b) C. T. Dooley, T. M. Dore, G. T. Hanson, W. Y. Jackson, S. J. Remington, R. Y. Tsien, J. Biol. Chem. 2004, 279, 22284-22293;
16. c) K Lee, V. Dzubeck, L. Latshaw, J. P. Schneider, J. Am. Chem. Soc. 2004, 126, 13616-13617;
17. d) P. K. Pullela, T. Chiku, M. J. Carvan, III, D. S. Sem, Anal. Biochem. 2006, 352, 265-273;
18. e) E. W. Miller, S. X. Bian, C. J. Chang, J. Am. Chem. Soc. 2007, 129, 3458-3459.
19. E. Silva, A. M. Edwards, Flavins: Photochemistry and Photobioiogy, RSC, Cambridge, 2006.
20. Y. Yamada, S. Aoki, J. Biol. Inorg. Chem. 2006, 11, 1007-1023.
21. a) E. Kimura, T. Koike, M. Shionoya in Structure and Bonding, Vol. 89: Metal Sites in Proteins and Models (Eds.: H. A. O. Hill, J. P. Sadler, A. J. Thompson), Springer, Berlin, 1997, pp. 1-28;
22. b) S. Aoki, E. Kimura, Chem. Rev. 2004, 104, 769-787;
23. c) S. Aoki, E. Kimura in Comprehensive Coordination Chemistry II: Biocoordination Chemistry (Eds.: L. Que, Jr., W. B. Tolman), Elsevier, Oxford, 2004, 8, pp. 601-640.
24. E. L. Loechler, T. C. Hollocher, J. Am. Chem. Soc. 1980, 102, 7312-7321.
25. a) H. Imahori, H. Norieda, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata, S. Fukuzumi, J. Am. Chem. Soc. 2001, 123, 100-110;
26. b) M. P. Debreczeny, W. A. Svec, M. R. Wasielewski, New J. Chem. 1996, 20, 815-828;
27. c) R. Ziessel, L. Bonardi, P. Retailleau, G. Ulrich, J. Org. Chem. 2006, 77, 3093-3102;
28. d) F. Camerel, L. Bonardi, M. Schmutz, R. Ziessel, J. Am. Chem. Soc. 2006, 128, 4548-4549.
29. T. Carell, L. T. Burgdorf, L. M. Kundu, M. Cichon, Curr. Opin. Chem. Biol. 2001, 5, 491-498.
30. 3CN/toluene): C. Trieflinger, K. Rurak, J. Daub, Angew. Chem. 2005, 117, 2328-2331; Angew. Chem. Int. Ed. 2005, 44, 2288-2291.
31. red is due to some interactions, such as π-π stacking between BODIPY and the reduced flavin unit.
32. red ratio value; details will be described elsewhere.
33. red (ca. 13-fold) was obtained by excitation at 440 nm in 100 mm HEPES (pH 7.0) containing 30% DMSO. In this work, we chose a common wavelength (450 nm) to excite 1-4 for comparison.
34. Redox potentials of the DTT-based redox buffer were calculated from the Nernst equation, as described in the Supporting Information. Redox equilibria of 2 in DT7-based redox buffer were obtained in 2 h.
35. 0, value obtained from CV (-0.24 V vs. SHE calculated from -0.44 V vs. Ag/AgCl; Table 1) was attributed to the different electrodes and solvents used in CV.
36. 0, = 30 mV) of 2 and 3 listed in Table 1.
37. 0, values of 3 in CV experiments (data not shown).
38. We could not detect the formation of superoxide anion radicals, which might be generated upon photoirradiation of 2, in aqueous solutions and in living cells, due to lack of appropriate sensors for ROS with a fluorescence emission that can be distinguished from that of 2.
39. ox was slightly (5-10%) quenched (Figure S8), possibly due to photoreduction of the flavin unit. Improvements with respect to this point are now underway.