"Reactive" probe for fluoride: "Turn-on" fluorescent sensing in aqueous solution and bioimaging in living cells

Sensors and Actuators, B: Chemical

Volumn 199, Issue , 2014, Pages 54-61

  Cheng, Xiaohong ^a,b   Jia, Huizhen ^a   Feng, Jun ^a   Qin, Jingui ^a   Li, Zhen ^a  

^a WUHAN UNIVERSITY   (China)

^b HUBEI UNIVERSITY OF ARTS AND SCIENCE   (China)

Author keywords

Bioimaging application; Chemical reaction based probe; Fluorescence; Fluoride; High sensitivity

Indexed keywords

CHEMICAL REACTIONS; FLUORESCENCE; IONS; PROBES;

BIO-IMAGING; CLEAVAGE REACTION; DETECTION LIMITS; FLUORESCENT SENSING; FLUORESCENT SIGNALS; FLUORIDE; GREEN FLUORESCENCE; HIGH SENSITIVITY;

FLUORINE COMPOUNDS;

EID: 84898973709     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2014.03.054     Document Type: Article

References (58)

1. D.-S. Kim, Y.-M. Chung, M. Jun, and K.H. Ahn Selective colorimetric sensing of anions in aqueous media through reversible covalent bonding J. Org. Chem. 74 2009 4849 4854
2. P.D. Beer, and P.A. Gale Erkennung und Nachweis von Anionen: gegenwärtiger Stand und Perspektiven Angew. Chem. 113 2001 502 532
3. S.W. Thomas, G.D. Joly, and T.M. Swager Chemical sensors based on amplifying fluorescent conjugated polymers Chem. Rev. 107 2007 1339 1386 (Pubitemid 46736542)
4. J. Yoon, S.K. Kim, N.J. Singh, and K.S. Kim Imidazolium receptors for the recognition of anions Chem. Soc. Rev. 35 2006 355 360 (Pubitemid 43475201)
5. F.P. Schmidtchen, and M. Berger Artificial organic host molecules for anions Chem. Rev. 97 1997 1609 1646 (Pubitemid 127659607)
6. 4 Angew. Chem., Int. Ed. Engl. 33 1994 467 468 (Pubitemid 24987383)
7. J.V. Kumar, and M.E. Moss Fluorides in dental public health programs Dent. Clin. North Am. 52 2008 387 401
8. J.R. Farley, J.E. Wergedal, and D.J. Baylink Fluoride directly stimulates proliferation and alkaline phosphatase activity of bone-forming cells Science 222 1983 330 332 (Pubitemid 13013396)
9. H.S. Horowitz The 2001 CDC recommendations for using fluoride to prevent and control dental caries in the United States J. Public Health Dent. 63 2003 3 8
10. M. Kleerekoper The role of fluoride in the prevention of osteoporosis Endocrinol. Metab. Clin. North Am. 27 1998 441 452 (Pubitemid 28285874)
11. M.H. Arhima, O.P. Gulati, and S.C. Sharma The effect of pycnogenol on fluoride induced rat kidney lysosomal damage in vitro Phytother. Res. 18 2004 244 246 (Pubitemid 38568754)
12. H. Matsui, M. Morimoto, K. Horimoto, and Y. Nishimura Some characteristics of fluoride-induced cell death in rat thymocytes: cytotoxicity of sodium fluoride Toxicol. In Vitro 21 2007 1113 1120 (Pubitemid 47238241)
13. P.P. Singh, M.K. Barjatiya, S. Dhing, R. Bhatnagar, S. Kothari, and V. Dhar Evidence suggesting that high intake of fluoride provokes nephrolithiasis in tribal populations Urol. Res. 29 2001 238 244 (Pubitemid 32822055)
14. M.L. Cittanova, B. Lelongt, and M.C. Verpont Mechanism of hyperchloremic metabolic acidosis Anesthesiology 84 1996 428 435
15. B. Zhu, F. Yuan, R. Li, Y. Li, Q. Wei, Z. Ma, B. Du, and X. Zhang A highly selective colorimetric and ratiometric fluorescent chemodosimeter for imaging fluoride ions in living cells Chem. Commun. 47 2011 7098 7100
16. T.-J. Cheng, T.-M. Chen, C.-H. Chen, and Y.-K. Lai Induction of stress response and differential expression of 70 kDa stress proteins by sodium fluoride in hela and rat brain tumor 9l cells J. Cell. Biochem. 69 1998 221 231 (Pubitemid 28152954)
17. C.A. Angell Changing family and household: contemporary lessons from historical research Annu. Rev. Phys. Chem. 34 1983 593 611
18. C.A. Angell, R.D. Bressel, M. Gemmati, E.J. Sare, and J.C. Tucker Water and its anomalies in perspective: tetrahedral liquids with and without liquid-liquid phase transitions Phys. Chem. Chem. Phys. 2 2000 1559 1566
19. X. Liu, D. Bai, and S. Wang Charge-transfer emission in nonplanar three-coordinate organoboron compounds for fluorescent sensing of fluoride Angew. Chem., Int. Ed. 45 2006 5475 5478 (Pubitemid 44384329)
20. C.B. Black, B. Andrioletti, A.C. Try, C. Ruiperez, and J.L. Sessler Dipyrrolylquinoxalines: efficient sensors for fluoride anion in organic solution J. Am. Chem. Soc. 121 1999 10438 10439
21. S. Yamaguchi, S. Akiyama, and K. Tamao Photophysical properties changes caused by hypercoordination of organosilicon compounds: from trianthrylfluorosilane to trianthryldifluorosilicate J. Am. Chem. Soc. 122 2000 6793 6794 (Pubitemid 30490013)
22. M. Vázquez, L. Fabbrizzi, A. Taglietti, R.M. Pedrido, A.M. González-Noya, and M.R. Bermejo A colorimetric approach to anion sensing: a selective chemosensor of fluoride ions, in which color is generated by anion-enhanced π delocalization Angew. Chem., Int. Ed. 43 2004 1962 1965 (Pubitemid 39257807)
23. X. Jiang, M.C. Vieweger, J.C. Bollinger, B. Dragnea, and D. Lee Reactivity-based fluoride detection: evolving design principles for spring-loaded turn-on fluorescent probes J. Org. Lett. 9 2007 3579 3582
24. T.W. Hudnall, and F.P. GabbaÏ A BODIPY boronium cation for the sensing of uoride ions Chem. Commun. 44 2008 4596 4597
25. R.M. Duke, E.B. Veale, F.M. Pfeffer, P.E. Krugerc, and T. Gunnlaugsson Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1, 8-naphthalimide-based chemosensors Chem. Soc. Rev. 39 2010 3936 3953
26. A. Li, J. Wang, F. Wang, and Y. Jiang Anion complexation and sensing using modified urea and thiourea-based Chem. Soc. Rev. 39 2010 3729 3745
27. Z. Xu, S.K. Kim, and J. Yoon Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006-2009 Chem. Soc. Rev. 39 2010 1457 1466
28. P.A. Gale Anion receptor chemistry: highlights from 2008 and 2009 Chem. Soc. Rev. 39 2010 3746 3771
29. M.E. Moragues, R. Martínez-máñez, and F. Sancenón Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the year 2009 Chem. Soc. Rev. 40 2011 2593 2643
30. X. Cao, W. Lin, Q. Yu, and Wang Ratiometric sensing of fluoride anions based on a BODIPY-Coumarin platform J. Org. Lett. 13 2011 6098 6101
31. Y. Qu, J. Hua, and H. Tian Colorimetric and ratiometric red fluorescent chemosensor for fluoride ion based on diketopyrrolopyrrole Org. Lett. 12 2010 3320 3323
32. Q. Lu, L. Dong, J. Zhang, J. Li, L. Jiang, Y. Huang, S. Qin, C. Hu, and X. Yu Imidazolium-functionalized BINOL as a multifunctional receptor for chromogenic and chiral anion recognition Org. Lett. 11 2009 669 672
33. V. Bhalla, H. Singh, and M. Kumar Facile cyclization of terphenyl to triphenylene: a new chemodosimeter for fluoride ions Org. Lett. 12 2010 628 631
34. Y. Lin, and C. Chen Acridinium salt-based fluoride and acetate chromofluorescent probes: molecular insights into anion selectivity switching Org. Lett. 11 2009 4858 4861
35. Z. Xu, S.K. Kim, S.J. Han, C. Lee, G. Kociok-Kohn, T.D. James, and J. Yoon Ratiometric fluorescence sensing of fluoride ions by an asymmetric bidentate receptor containing a boronic acid and Imidazolium Group Eur. J. Org. Chem. 18 2009 3058 3065
36. P. Bose, and P. Ghosh Visible and near-infrared sensing of fluoride by indole conjugated urea/thiourea ligands Chem. Commun. 46 2010 2962 2964
37. X. He, S. Hu, K. Liu, Y. Guo, J. Xu, and S. Shao Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode Org. Lett. 8 2006 333 336 (Pubitemid 43163995)
38. 3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels J. Am. Chem. Soc. 129 2007 13661 13674 (Pubitemid 350071795)
39. Q. Wang, Y. Xie, Y. Ding, X. Li, and W. Zhu Colorimetric fluoride sensors based on deprotonation of pyrrole-hemiquinone compounds Chem. Commun. 46 2010 3669 3671
40. F. Zheng, F. Zeng, C. Yu, X. Hou, and S. Wu A PEGylated fluorescent turn-on sensor for detecting fluoride ions in totally aqueous media and its imaging in live cells Chem. Eur. J. 19 2013 936 942
41. - based on combination of desilylation reaction and excited-state proton transfer Chem. Commun. 47 2011 3957 3959
42. L. Fu, F. Jiang, D. Fortin, P.D. Harvey, and Y. Liu A reaction-based chromogenic and fluorescent chemodosimeter for fluoride anions Chem. Commun. 47 2011 5503 5505
43. T.W. Hudnall, and F.P. Gabbai Ammonium boranes for the selective complexation of cyanide or fluoride ions in water J. Am. Chem. Soc. 129 2007 11978 11986 (Pubitemid 47512026)
44. D.A. Jose, D.R. Kumar, B. Ganguly, and A. Das Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites Org. Lett. 6 2004 3445 3448 (Pubitemid 39406910)
45. M.H. Lee, D.T. Quang, H.S. Jung, J. Yoon, C.-H. Lee, and J.S. Kim Ion-induced FRET on-off in fluorescent Calix[4]arene J. Org. Chem. 72 2007 4242 4245 (Pubitemid 46846970)
46. H.J. Kim, S.K. Kim, J.Y. Lee, and S.J. Kim Fluoride-sensing calix-luminophores based on regioselective binding J. Org. Chem. 71 2006 6611 6614 (Pubitemid 44252453)
47. X. Peng, Y. Wu, J. Fan, M. Tian, and K. Han Colorimetric and ratiometric fluorescence sensing of fluoride: tuning selectivity in proton transfer J. Org. Chem. 70 2005 10524 10531 (Pubitemid 41759927)
48. S.K. Kim, and J. Yoon A new fluorescent PET chemosensor for fluoride ions Chem. Commun. 38 2002 770 771 (Pubitemid 34309836)
49. - based on inhibition of excited-state intramolecular proton transfer Tetrahedron Lett. 50 2009 983 987
50. T.-H. Kim, and T.M. Swager A Fluorescent self-amplifying wavelength-responsive sensory polymer for fluoride ions Angew. Chem., Int. Ed. 42 2003 4803 4806 (Pubitemid 37314612)
51. X. Cheng, S. Li, G. Xu, C. Li, J. Qin, and Z. Li A reaction-based colorimetric fluoride probe: rapid "Naked-Eye" detection and large absorption shift ChemPlusChem 77 2012 908 913
52. L. Mugherli, O.N. Burchak, F. Chatelain, and M.Y. Balakirev Fluorogenic ester substrates to assess proteolytic activity Bioorg. Med. Chem. Lett. 16 2006 4488 4491 (Pubitemid 44109968)
53. S.Y. Kim, J. Park, M. Koh, S.B. Park, and J.-I. Hong Fluorescent probe for detection of uoride in water and bioimagingin A549 human lung carcinoma cells Chem. Commun. 45 2009 4735 4737
54. P. Sokkalingam, and C.-H. Lee Highly sensitive fluorescence "Turn-On" indicator for fluoride anion with remarkable selectivity in organic and aqueous media J. Org. Chem. 76 2011 3820 3828
55. M. Shortreed, R. Kopelman, M. Kuhn, and B. Hoyland Highly selective colorimetric sensing of cyanide based on formation of dipyrrin adducts Anal. Chem. 68 1996 1414 1418
56. R. Hu, J. Feng, D. Hu, S. Wang, S. Li, Y. Li, and G. Yang A rapid aqueous fluoride ion sensor with dual output modes Angew. Chem., Int. Ed. 49 2010 4915 4918
57. Y. Zhou, J.-Y. Li, K. Chu, K. Liu, C. Yao, and J. Li Fluorescence turn-on detection of hypochlorous acid via HOCl-promoted dihydrofluorescein-ether oxidation and its application in vivo Chem. Commun. 48 2012 4677 4679
58. M. Cametti, and K. Rissanen Recognition and sensing of fluoride anion Chem. Commun. 45 2009 2809 2829