Heteroaromatic donors in donor-acceptor-donor based fluorophores facilitate zinc ion sensing and cell imaging

Photochemical and Photobiological Sciences

Volumn 11, Issue 11, 2012, Pages 1715-1723

  Sreejith, Sivaramapanicker ^a   Divya, Kizhumuri P ^a   Jayamurthy, Purushothaman ^a   Mathew, Jomon ^b   Anupama, V N ^a   Philips, Divya Susan ^a   Anees, Palappuravan ^a   Ajayaghosh, Ayyappanpillai ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FLUORESCENT DYE; ION; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE; ZINC;

ARTICLE; CELL STRAIN MCF 7; CHEMISTRY; FLUORESCENCE MICROSCOPY; HUMAN; PH; QUANTUM THEORY; SPECTROFLUOROMETRY;

AMINES; FLUORESCENT DYES; HUMANS; HYDROGEN-ION CONCENTRATION; IONS; MCF-7 CELLS; MICROSCOPY, FLUORESCENCE; PYRROLES; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; THIOPHENES; ZINC;

EID: 84867636160     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp25110h     Document Type: Article

References (40)

1. C. J. Frederickson Neurobiology of zinc and zinc-containing neurons Int. Rev. Neurobiol. 1989 31 145
2. B. L. Vallee K. H. Falchuk The biochemical basis of zinc physiology Physiol. Rev. 1993 73 79
3. J. M. Berg Y. Shi The galvanization of biology: a growing appreciation for the roles of zinc Science 1996 271 1081
4. S. L. Sensi L. M. T. Canzoniero S. P. Yu H. S. Ying J. Koh G. A. Kerchner D. W. Choi Measurementof intracellular free zinc in living cortical neurons: routes of entry J. Neurosci. 1997 17 9554
5. J. E. Coleman Zinc enzymes Curr. Opin. Chem. Biol. 1998 2 222
6. P. Carol S. Sreejith A. Ajayaghosh Ratiometric and near-infrared molecular probes for the detection and imaging of zinc ions Chem.-Asian J. 2007 2 338
7. E. L. Que D. W. Domaille C. J. Chang Metals in neurobiology: probing their chemistry and biology with molecular imaging Chem. Rev. 2008 108 1517
8. E. M. Nolan S. J. Lippard Small-molecule fluorescent sensors for investigating zinc metalloneurochemistry Acc. Chem. Res. 2009 42 193
9. Z. Dai J. W. Canary Tailoring tripodal ligands for zinc sensing New J. Chem. 2007 31 1708
10. P. Jiang Z. Guo Fluorescent detection of zinc in biological systems: recent development on the design of chemosensors and biosensors Coord. Chem. Rev. 2004 248 205
11. N. C. Lim H. C. Freake C. Brückner Illuminating zinc ions in biological systems Chem.-Eur. J. 2005 11 38
12. D. W. Domaille E. L. Que C. J. Chang Synthetic fluorescent sensors for studying the cell biology of metals Nat. Chem. Biol. 2008 4 168
13. 2+ Chem. Soc. Rev. 2010 39 1996
14. J. R. Lakowickz, Principles of Fluorescence Spectroscopy, Springer, New York, 3rd edn, 2006
15. K. W. Dunn S. Mayor J. N. Meyers F. R. Maxfield Application of ratio fluorescence microscopy in the study of cell physiology FASEB J. 1994 8 573
16. Z. Wang M. A. Palacios G. Zyryanov P. Anzenbacher Harnessing a ratiometric fluorescence output from a sensor array Chem.-Eur. J. 2008 14 8540
17. N. B. Sankaran S. Nishizawa M. Watanabe T. Uchida N. Teramae Designing ratiometric fluorescent sensors for alkali metal ions from simple PET sensors by controlling spacer length J. Mater. Chem. 2005 15 2755
18. E. J. Park M. Brasuel C. Behrend M. A. Phibert R. Kopelman Ratiometric optical PEBBLE nanosensors for real-time magnesium ion concentrations inside viable cells Anal. Chem. 2003 75 3784
19. 2+ indicators with greatly improved fluorescence properties J. Biol. Chem. 1985 260 3440
20. A. Coskun E. Deniz E. U. Akkaya Cation modulation of carbonyldipyrrinone (CDP) fluorescence: emission-ratiometric sensing of calcium J. Mater. Chem. 2005 15 2908
21. L. Xue C. Liu H. Jiang A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells Chem. Commun. 2009 1061
22. S. Maruyama K. Kikuchi T. Hirano Y. Urano T. Nagano A novel, cell-permeable, fluorescent probe for ratiometric imaging of zinc ion J. Am. Chem. Soc. 2002 124 10650
23. 2+ J. Am. Chem. Soc. 2003 125 11458
24. M. Taki J. L. Wolford T. V. O'Halloran Emission ratiometric imaging of intracellular zinc: design of a benzoxazole fluorescent sensor and its application in two-photon microscopy J. Am. Chem. Soc. 2004 126 712
25. 2+ J. Am. Chem. Soc. 2005 127 14962
26. K. Kiyose H. Kojima Y. Urano T. Nagano Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore J. Am. Chem. Soc. 2006 128 6548
27. C. J. Chang J. Jaworski E. M. Nolan M. Sheng S. J. Lippard A tautomeric zinc sensor for ratiometric fluorescence imaging: application to nitric oxide-induced release of intracellular zinc Proc. Natl. Acad. Sci. U. S. A. 2004 101 1129
28. 2+ fluorescent chemosensor with a large red-shift in emission Tetrahedron 2006 62 10117
29. K. Komatsu Y. Urano H. Kojima T. Nagano Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc J. Am. Chem. Soc. 2007 129 13447
30. M. M. Henary Y. Wu C. J. Fahrni Zinc(ii)-selective ratiometric fluorescent sensors based on inhibition of excited-state intramolecular proton transfer Chem.-Eur. J. 2004 10 3015
31. F. Galindo J. Becerril I. Burguete S. V. Luis L. Vigara Synthesis and study of a cyclophane displaying dual fluorescence emission: a novel ratiometric sensor for carboxylic acids in organic medium Tetrahedron Lett. 2004 45 1659
32. H. Cao D. I. Diaz N. DiCesare J. R. Lakowicz M. D. Heagy Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose Org. Lett. 2002 4 1503
33. II) appanded xanthone: excitation ratiometric chemosensor for phosphate anions Angew. Chem., Int. Ed. 2006 45 5518
34. Z. Xu N. J. Singh J. Lim J. Pan H. N. Kim S. Park K. S. Kim J. Yoon Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH J. Am. Chem. Soc. 2009 131 15528
35. 2+-specific turn-on fluorescent probe for ratiometric sensing of pyrophosphate in both water and blood serum Dalton Trans. 2011 40 1984
36. P. Nandhikonda M. D. Heagy Dual fluorescent N-aryl-2,3-naphthalimides: applications in ratiometric DNA detection and white organic light emitting devices Org. Lett. 2010 12 4796
37. J. Ueberfeld D. R. Walt Reversible ratiometric probe for quantitative DNA measurements Anal. Chem. 2004 76 947
38. 2+-specific fluorescent molecular probe for the selective detection of endogenous cyanide in bio-relevant samples Chem. Commun. 2010 46 6069
39. B. Valeur I. Larey Design principles of fluorescent molecular sensors for cation recognition Coord. Chem. Rev. 2000 205 3
40. S. Sreejith K. P. Divya T. K. Manojkumar A. Ajayaghosh Multiple analyte response and molecular logic operations by excited state charge-transfer modulation in a bipyridine integrated fluorophore Chem.-Asian J. 2011 6 430