Fluorescence ON/OFF switching Zn2+ sensor based on pyridine-pyridone scaffold

Sensors and Actuators, B: Chemical

Volumn 181, Issue , 2013, Pages 823-828

  Hagimori, Masayori ^a   Uto, Takuhiro ^b   Mizuyama, Naoko ^c   Temma, Takashi ^d   Yamaguchi, Yasuchika ^b   Tominaga, Yoshinori ^e   Saji, Hideo ^d  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b NAGASAKI INTERNATIONAL UNIVERSITY   (Japan)

^c SAGA UNIVERSITY HOSPITAL   (Japan)

^d KYOTO UNIVERSITY   (Japan)

^e NAGASAKI UNIVERSITY   (Japan)

Author keywords

Fluorescent ON OFF switching; Large Stokes shift; Pyridine pyridone; Small molecule; Water soluble; Zn2+

Indexed keywords

BIOLOGICAL APPLICATIONS; ELECTRON-DONATING GROUP; FLUORESCENT SENSORS; GOOD WATER-SOLUBILITY; PYRIDINE-PYRIDONE; SMALL MOLECULES; STOKES SHIFT; WATER-SOLUBLE;

ELECTRON TRANSITIONS; FLUORESCENCE; PYRIDINE; SENSORS; SWITCHING; ZINC;

FLUOROPHORES;

EID: 84875461721     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2013.02.033     Document Type: Article

References (24)

1. K.H. Falchuk The molecular basis for the role of zinc in developmental biology Molecular and Cellular Biochemistry 188 1998 41 48 (Pubitemid 28493316)
2. D.K. Perry, M.J. Smyth, H.R. Stennicke, G.S. Salvesen, P. Duriez, G.G. Poirier, and Y.A. Hannun Zinc is a potent inhibitor of the apoptotic protease, caspase-3. A novel target for zinc in the inhibition of apoptosis Journal of Biological Chemistry 272 1997 18530 18533 (Pubitemid 27318188)
3. P.D. Zalewski, I.J. Forbes, and W.H. Betts Correlation of apoptosis with change in intracellular labile Zn(II) using zinquin [(2-methyl-8-p- toluenesulphonamido-6-quinolyloxy)acetic acid], a new specific fluorescent probe for Zn(II) Biochemical Journal 296 1993 403 408 (Pubitemid 23350843)
4. W. Maret, and Y. Li Coordination dynamics of zinc in proteins Chemical Reviews 109 2009 4682 4707
5. H. Kitamura, H. Morikawa, H. Kamon, M. Iguchi, S. Hojyo, T. Fukada, S. Yamashita, T. Kaisho, S. Akira, M. Murakami, and T. Hirano Toll-like receptor-mediated regulation of zinc homeostasis influences dendritic cell function Nature Immunology 7 2006 971 977 (Pubitemid 44263911)
6. M. Hershfinkel, K. Kandler, M.E. Knoch, M. Dagan-Rabin, M.A. Aras, C. Abramovitch-Dahan, I. Sekler, and E. Aizenman Intracellular zinc inhibits KCC2 transporter activity Nature Neuroscience 12 2009 725 727
7. C.J. Frederickson, J.Y. Koh, and A.I. Bush The neurobiology of zinc in health and disease Nature Reviews Neuroscience 6 2005 449 462 (Pubitemid 40774861)
8. A.I. Bush Metals and neuroscience Current Opinion in Chemical Biology 4 2000 184 191 (Pubitemid 30189310)
9. M. Paker, F.L. Humoller, and D.J. Mahler Determination of copper and zinc in biological material Clinical Chemistry 13 1967 40 48
10. S.C. Burdette, and S.J. Lippard Meeting of the minds: metalloneurochemistry Proceedings of the National Academy of Sciences of the United States of America 100 2003 3605 3610 (Pubitemid 36418081)
11. E.M. Nolan, and S.J. Lippard Small-molecule fluorescent sensors for investigating zinc metalloneurochemistry Accounts of Chemical Research 42 2009 193 203
12. K.L. Haas, and K.J. Franz Application of metal coordination chemistry to explore and manipulate cell biology Chemical Reviews 109 2009 4921 4960
13. E.L. Que, D.W. Domaille, and C.J. Chang Metals in neurobiology: probing their chemistry and biology with molecular imaging Chemical Reviews 108 2008 1517 1549 (Pubitemid 351796396)
14. K. Kikuchi, K. Komatsu, and T. Nagano Zinc sensing for cellular application Current Opinion in Chemical Biology 8 2004 182 191 (Pubitemid 38452434)
15. 2+ Journal of the American Chemical Society 122 2000 5644 5645 (Pubitemid 30431087)
16. C.J. Chang, J. Jaworski, E.M. Nolan, M. Sheng, and S.J. Lippard A tautomeric zinc sensor for ratiometric fluorescence imaging: application to nitric oxide-induced release of intracellular zinc Proceedings of the National Academy of Sciences of the United States of America 101 2004 1129 1134 (Pubitemid 38182654)
17. T. Hirano, K. Kikuchi, Y. Urano, and T. Nagano Improved fluorescent probes for zinc, ZnAFs, suitable for biological applications Journal of the American Chemical Society 124 2002 6555 6562 (Pubitemid 34602646)
18. C. Lu, Z. Xu, J. Cui, R. Zhang, and X. Qian Ratiometric and highly selective fluorescent sensor for cadmium under physiological pH range: a new strategy to discriminate cadmium from zinc Journal of Organic Chemistry 72 2007 3554 3557 (Pubitemid 46668159)
19. 2+ Journal of Organic Chemistry 73 2008 8212 8218
20. 2+ based on pyridine-pyridone scaffold Talanta 83 2011 1730 1735
21. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Advanced Drug Delivery Reviews 46 2001 3 26 (Pubitemid 33653411)
22. A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, and T.E. Rice Signaling recognition events with fluorescent sensors and switches Chemical Reviews 97 1997 1515 1566 (Pubitemid 127659605)
23. A. Kovalchuk, J.L. Bricks, G. Reck, K. Rurack, B. Schulz, A. Szumna, and H. Weibhoff A charge transfer-type fluorescent molecular sensor that "lights up" in the visible upon hydrogen bond-assisted complexation of anions Chemical Communications 2004 1946 1947 (Pubitemid 39336014)
24. F.-Y. Wu, and Y.-B. Jiang p-Dimethylaminobenzamide as an ICT dual fluorescent neutral receptor for anions under proton coupled electron transfer sensing mechanism Chemical Physics Letters 355 2002 438 444