A new selective fluorescent chemical sensor for Fe3+ based on rhodamine B and a 1,4,7,10-tetraoxa-13-azacyclopentadecane conjugate and its imaging in living cells

Sensors and Actuators, B: Chemical

Volumn 208, Issue , 2015, Pages 54-66

  Bao, Xiaofeng ^a   Cao, Xiaowei ^a   Nie, Xuemei ^a   Xu, Yuan ^b   Guo, Wanhua ^c   Zhou, Baojing ^a   Zhang, Luyong ^b   Liao, Hong ^b   Pang, Tao ^b  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c THE AFFILIATED DRUM TOWER HOSPITAL OF NANJING UNIVERSITY MEDICAL SCHOOL   (China)

Author keywords

Cell imaging; Fluorescent probe; Iron ions; Rhodamine B

Indexed keywords

CELLS; CYTOLOGY; FLUORESCENCE; FLUORESCENCE MICROSCOPY; METAL IONS; PROBES;

BINDING ABILITIES; BINDING ANALYSIS; CELL IMAGING; FLUORESCENT PROBES; HIGH SELECTIVITY; HUMAN LIVER CELLS; IRON IONS; RHODAMINE B;

IRON COMPOUNDS;

EID: 84911874099     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2014.10.127     Document Type: Article

References (55)

1. J. Chan, S.C. Dodani, and C.J. Chang Reaction-based small-molecule fluorescent probes for chemoselective bioimaging Nat. Chem. 4 2012 973 984
2. 2+ J. Am. Chem. Soc. 127 2005 10107 10111
3. Z. Liu, W. He, and Z. Guo Metal coordination in photoluminescent sensing Chem. Soc. Rev. 42 2013 1568 1600
4. 4+) and imaging in living cells Inorg. Chem. 52 2013 10825 10834
5. L. Yuan, W. Lin, K. Zheng, L. He, and W. Huang Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging Chem. Soc. Rev. 42 2013 622 661
6. G. Papanikolaou, and K. Pantopoulos Iron metabolism and toxicity Toxicol. Appl. Pharmacol. 202 2005 199 211
7. T.A. Rouault, and W.H. Tong Iron-sulfur cluster biogenesis and human disease Trends. Genet. 24 2008 398 407
8. M. Andjelkovic, J. Van Camp, B. De Meulenaer, G. Depaemelaere, C. Socaciu, M. Verloo, and R. Verhe Iron-chelation properties of phenolic acids bearing catechol and galloyl groups Food Chem. 98 2006 23 31
9. K.D. Welch, T.Z. Davis, and S.D. Aust Iron autoxidation and free radical generation: effects of buffers, ligands, and chelators Arch. Biochem. Biophys. 397 2002 360 369
10. T. Ganz Hepcidin a key regulator of iron metabolism and mediator of anemia of inflammation Blood 102 2003 783 788
11. T. Walczyk, and F. von Blanckenburg Natural iron isotope variations in human blood Science 295 2002 2065 2066
12. R.U. Onyenwoke, and J. Wiegel Iron(III) reduction: a novel activity of the human NAD(P)H: oxidoreductase Biochem. Biophys. Res. Commun. 353 2007 389 393
13. E.C. Theil Ferritin protein nanocages use ion channels, catalytic sites, and nucleation channels to manage iron/oxygen chemistry Curr. Opin. Chem. Biol. 15 2011 304 311
14. C.J. Earley, J.R. Connor, J.L. Beard, E.A. Malecki, D.K. Epstein, and R.P. Allen Abnormalities in CSF concentrations of ferritin and transferrin in restless legs syndrome Neurology 54 2000 1698 1700
15. D.A. Weinstein, C.N. Roy, M.D. Fleming, M.F. Loda, J.I. Wolfsdorf, and N.C. Andrews Inappropriate expression of hepcidin is associated with iron refractory anemia: implications for the anemia of chronic disease Blood 100 2002 3776 3781
16. X. Huang Iron overload and its association with cancer risk in humans: evidence for iron as a carcinogenic metal Mutat. Res. Fundam. Mol. Mech. Mutagen. 533 2003 153 171
17. R.L. Nelson, F.G. Davis, V. Persky, and E. Becker Risk of neoplastic and other diseases among people with heterozygosity for hereditary hemochromatosis Cancer 76 1995 875 879
18. T.J. Wu, C.T. Sempos, J.L. Freudenheim, P. Muti, and E. Smith Serum iron, copper and zinc concentrations and risk of cancer mortality in US adults Ann. Epidemiol. 14 2004 195 201
19. J.C. Duvigneau, C. Piskernik, S. Haindl, B. Kloesch, R.T. Hartl, M. Huettemann, I. Lee, T. Ebel, R. Moldzio, M. Gemeiner, H. Redl, and A.V. Kozlov A novel endotoxin-induced pathway: upregulation of heme oxygenase 1, accumulation of free iron, and free iron-mediated mitochondrial dysfunction Lab Invest. 88 2008 70 77
20. G.T. Sucak, Z.A. Yegin, Z.N. Oezkurt, S.Z. Aki, T. Karakan, and G. Akyol The role of liver biopsy in the workup of liver dysfunction late after SCT: is the role of iron overload underestimated? Bone Marrow Transplant. 42 2008 461 467
21. R. Agarwal, N. Vasavada, N.G. Sachs, and S. Chase Oxidative stress and renal injury with intravenous iron in patients with chronic kidney disease Kidney. Int. 65 2004 2279 2289
22. W.H. Hoerl Clinical aspects of iron use in the anemia of kidney disease J. Am. Soc. Nephrol. 18 2007 382 393
23. D. Berg, M. Gerlach, M.B.H. Youdim, K.L. Double, L. Zecca, P. Riederer, and G. Becker Brain iron pathways and their relevance to Parkinson's disease J. Neurochem. 79 2001 225 236
24. D. Kaur, F. Yantiri, S. Rajagopalan, J. Kumar, J.O. Mo, R. Boonplueang, V. Viswanath, R. Jacobs, L. Yang, M.F. Beal, D. DiMonte, I. Volitaskis, L. Ellerby, R.A. Cherny, A.I. Bush, and J.K. Andersen Genetic or pharmacological iron chelation prevents MPTP-induced neurotoxicity in vivo: a novel therapy for Parkinson's disease Neuron 37 2003 899 909
25. J.A. Duce, A. Tsatsanis, M.A. Cater, S.A. James, E. Robb, K. Wikhe, S.L. Leong, K. Perez, T. Johanssen, M.A. Greenough, H.-H. Cho, D. Galatis, R.D. Moir, C.L. Masters, C. McLean, R.E. Tanzi, R. Cappai, K.J. Barnham, G.D. Ciccotosto, J.T. Rogers, and A.I. Bush Iron-export ferroxidase activity of beta-amyloid precursor protein is inhibited by zinc in Alzheimer's disease Cell 142 2010 857 867
26. S. Mandel, T. Amit, O. Bar-Am, and M.B.H. Youdim Iron dysregulation in Alzheimer's disease: multimodal brain permeable iron chelating drugs, possessing neuroprotective-neurorescue and amyloid precursor protein-processing regulatory activities as therapeutic agents Prog. Neurobiol. 82 2007 348 360
27. 2+ in an aqueous medium Org. Lett. 13 2011 1162 1165
28. X. Chen, S.-W. Nam, G.-H. Kim, N. Song, Y. Jeong, I. Shin, S.K. Kim, J. Kim, S. Park, and J. Yoon A near-infrared fluorescent sensor for detection of cyanide in aqueous solution and its application for bioimaging Chem. Commun. 46 2010 8953 8955
29. 2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells J. Am. Chem. Soc. 131 2009 2008 2012
30. K.M.K. Swamy, H.N. Kim, J.H. Soh, Y. Kim, S.-J. Kim, and J. Yoon Manipulation of fluorescent and colorimetric changes of fluorescein derivatives and applications for sensing silver ions Chem. Commun. 10 2009 1234 2123
31. S. Yagi, S. Nakamura, D. Watanabe, and H. Nakazumi Colorimetric sensing of metal ions by bis(spiropyran) podands: towards naked-eye detection of alkaline earth metal ions Dyes Pigment. 80 2009 98 105
32. E. David, J. Lejeune, S. Pellet-Rostaing, R. Schulz, M. Lemaire, J. Chauvin, and A. Deronzier Synthesis of fluorescent rhodamine dyes using an extension of the Heck reaction Tetrahedron. Lett. 49 2008 1860 1864
33. J.X. Liu, Z.J. Diwu, W.Y. Leung, Y.X. Lu, B. Patch, and R.P. Haugland Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths Tetrahedron. Lett. 44 2003 4355 4359
34. C. Wu, Q.-N. Bian, B.-G. Zhang, X. Cai, S.-D. Zhang, H. Zheng, S.-Y. Yang, and Y.-B. Jiang Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom Org. Lett. 14 2012 4198 4201
35. 2+ based on a rhodamine derivative with a ferrocene unit Org. Lett. 9 2007 4729 4732
36. X.-Q. Zhan, Z.-H. Qian, H. Zheng, B.-Y. Su, Z. Lan, and J.-G. Xu Rhodamine thiospirolactone. Highly selective and sensitive reversible sensing of Hg(II) Chem. Commun. 16 2008 1859 1861
37. O.A. Egorova, H. Seo, A. Chatterjee, and K.H. Ahn Reaction-based fluorescent sensing of Au(I)/Au(III) species: mechanistic implications on vinylgold intermediates Org. Lett. 12 2010 401 403
38. 2+ sensor Angew. Chem. Int. Ed. Engl. 48 2009 3996 3998
39. 2+ RSC Adv. 3 2013 24140 24145
40. A. Pal, B. Bag, M. Thirunavoukkarasu, S. Pattanaik, and B.K. Mishra Solvent mediated tuning of selectivity in a rhodamine based probe and bioimaging for Pb(II) detection in plant tissues RSC Adv. 3 2013 18263 18266
41. 2+-selective ratiometric and off-on sensor based on the rhodamine derivative bearing pyrene group Org. Lett. 11 2009 4442 4445
42. 3+ Inorg. Chem. Commun. 20 2012 93 96
43. 3+-sensing Chem. Commun. 49 2013 7797 7799
44. 3+ imaging in living cells J. Org. Chem. 77 2012 1143 1147
45. J. Isaad, and A. El Achari A water soluble fluorescent BODIPY dye with azathia-crown ether functionality for mercury chemosensing in environmental media Analyst 138 2013 3809 3819
46. 2+ Dalton Trans. 41 2012 8767 8769
47. 2+ in water Dalton Trans. 42 2013 1969 1972
48. I.-M. Simionca, A. Arvinte, R. Ardeleanu, and M. Pinteala Siloxane-crown ether polyamide based electrode for electrochemical determination of lead(II) in aqueous solution Electroanalysis 24 2012 1995 2004
49. R. Velu, N. Won, J. Kwag, S. Jung, J. Hur, S. Kim, and N. Park Metal ion-induced dual fluorescent change for aza-crown ether acridinedione-functionalized gold nanorods and quantum dots New. J. Chem. 36 2012 1725 1728
50. 3+ based on rhodamine B and a 4,13-diaza-18-crown 6-ether conjugate RSC Adv. 4 2014 2563 2567
51. C. Yang, L. Liu, T.W. Mu, and Q.X. Guo The performance of the Benesi-Hildebrand method in measuring the binding constants of the cyclodextrin complexation Anal. Sci. 16 2000 537 539
52. 2- in physiological conditions and in live cells Inorg. Chem. 52 2013 743 752
53. P.H. Chan, J.W. Schmidley, R.A. Fishman, and S.M. Longar Brain injury, edema, and vascular permeability changes induced by oxygen-derived free radicals Neurology 34 1984 315 320
54. R. Hultcrantz, J.L. Ericsson, T. Hirth, Virchows, and B. Archiv Levels of malondialdehyde production in rat liver following loading and unloading with iron Virchows. Arch. B: Cell. Pathol. Incl. Mol. Pathol. 45 1984 139 146
55. M. Nakano A possible mechanism of iron neurotoxicity Eur. Neurol. 33 Suppl. 1 1993 44 51