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A Polyaza Macrocycle Ligand Bearing Anthracenyl Fluorophores for Selective Signaling of Zn(II) in Aqueous Solution

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Abstract

Based on a metal-template synthetic strategy, a new polyaza macrocycle bearing two anthracenyl fluorophores ligand, N,N′-bis[(anthracen-10-yl)methylene]-5,6,8,9,14,15,17,18-octahydrodibenzo[f,m][1,3,5,8,10,12]hexaazacyclotetradecine-7,16-diamine (L), was prepared and fully characterized. In the presence of Zn(II), L displayed remarkable chelation-enhanced fluorescence and can selectively respond to the presence of Zn(II) ion compared with other cations in HEPES-buffered aqueous methanol solutions. Results obtained from UV–Vis and fluorescence titrations indicated that L chelates to Zn(II) by forming a complex with a 1:1 molar ratio.

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References

  1. Kaim, W., Schwederski, B.: Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life. Wiley, Chichester (1994)

    Google Scholar 

  2. Czarnik, A.W.: Fluorescent Chemosensors for Ion and Molecule Recognition. American Chemical Society, Washington, DC (1993)

    Book  Google Scholar 

  3. Martínez-Máñez, R., Sancanón, F.: Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 103, 4419–4476 (2003). doi:10.1021/cr010421e

    Article  Google Scholar 

  4. Magri, D.C., Brown, G.J., McClean, G.D., de Silva, A.P.: Communicating chemical congregation: a molecular and logic gate with three chemical inputs as a “lab-on-a-molecule” prototype. J. Am. Chem. Soc. 128, 4950–44951 (2006). doi:10.1021/ja058295+

    Article  CAS  Google Scholar 

  5. Zhao, Y.-P., Zhao, C.-C., Wu, L.-Z., Zhang, L.-P., Tung, C.-H., Pan, Y.-J.: First fluorescent sensor for fluoride based on 2-ureido-4[1H]-pyrimidinone quadruple hydrogen-bonded AADD supramolecular assembly. J. Org. Chem. 71, 2143–2146 (2006). doi:10.1021/jo051932u

    Article  CAS  Google Scholar 

  6. Falchuk, K.H.: The molecular basis for the role of zinc in developmental biology. Mol. Cell. Biochem. 188, 41–48 (1998). doi:10.1023/A:1006808119862

    Article  CAS  Google Scholar 

  7. Maret, W., Jacob, C., Vallee, B.L., Fischer, E.H.: Inhibitory sites in enzymes: zinc removal and reactivation by thionein. Proc. Natl. Acad. Sci. USA 96, 1936–1940 (1999). doi:10.1073/pnas.96.5.1936

    Article  Google Scholar 

  8. Choi, D.W., Koh, J.Y.: Zinc and brain injury. Annu. Rev. Neurosci. 21, 347–375 (1998). doi:10.1146/annurev.neuro.21.1.347

    Article  CAS  Google Scholar 

  9. Zalewski, P.D., Forbes, I.J., Betts, W.H.: 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). Biochem. J. 296, 403–408 (1993)

    CAS  Google Scholar 

  10. Ajayaghosh, A., Carol, P., Sreejith, S.: A ratiometric fluorescence probe for selective visual sensing of Zn2+. J. Am. Chem. Soc. 127, 14962–14963 (2005). doi:10.1021/ja054149s

    Article  CAS  Google Scholar 

  11. Zhang, X.X., Hayes, D., Smith, S.J., Friedle, S., Lippard, S.J.: New strategy for quantifying biological zinc by a modified Zinpyr fluorescence sensor. J. Am. Chem. Soc. 130, 15788–15789 (2008). doi:10.1021/ja807156b

    Article  CAS  Google Scholar 

  12. Zhang, Y., Guo, X., Si, W., Jia, L., Qian, X.: Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. Org. Lett. 10, 473–476 (2008). doi:10.1021/ol702869w

    Article  CAS  Google Scholar 

  13. Xue, L., Liu, C., Jiang, H.: A ratiometric fluorescent sensor with a large Stokes shift for imaging zinc ions in living cells. Chem. Commun. (Camb.) 9, 1061–1063 (2009). doi:10.1039/b814501f

    Article  Google Scholar 

  14. Hung, C.-H., Chang, G.-F., Kumar, A., Lin, G.-F., Luo, L.-Y., Ching, W.-M., Diau, E.W.-G.: m-Benziporphodimethene: a new porphyrin analogue fluorescence zinc(II) sensor. Chem. Commun. (Camb.) 8, 978–980 (2008). doi:10.1039/b714412a

    Article  Google Scholar 

  15. Liu, Z.-P., Zhang, C.-L., Li, Y.-L., Wu, Z.-Y., Qian, F., Yang, X.-L., He, W.-J., Gao, X., Guo, Z.-J.: A Zn2+ fluorescent sensor derived from 2-(pyridin-2-yl)benzoimidazole with ratiometric sensing potential. Org. Lett. 11, 795–798 (2009)

    Article  CAS  Google Scholar 

  16. Qian, F., Zhang, C.-L., Zhang, Y.-M., He, W.-J., Gao, X., Hu, P., Guo, Z.-J.: Visible light excitable Zn2+ fluorescent sensor derived from an intramolecular charge transfer fluorophore and its in vitro and in vivo application. J. Am. Chem. Soc. 131, 1460–1468 (2009). doi:10.1021/ja806489y

    Article  CAS  Google Scholar 

  17. Boyd, S., Cabral, N.M., Ghiggino, K.P., Grannas, M.J., McFadyen, W.D., Tregloan, P.A.: Nickel complexation and photophysics of alkylanthracenyl dioxocyclam macrocycle derivatives. Aust. J. Chem. 53, 651–658 (2000). doi:10.1071/CH00106

    Article  CAS  Google Scholar 

  18. Amendola, V., Fabbrizzi, L., Licchelli, M., Mangano, C., Pallavicini, P., Parodi, L., Poggi, A.: Molecular events switched by transition metals. Coord. Chem. Rev. 190–192, 649–669 (1999). doi:10.1016/S0010-8545(99)00110-1

    Article  Google Scholar 

  19. Funston, A.M., Ghiggino, K.P., Grannas, M.J., McFadyen, W.D., Tregloan, P.A.: Synthesis, structural studies and photochemistry of cobalt(III) complexes of anthracenylcyclam macrocycles. Dalton Trans. 19, 3704–3712 (2003). doi:10.1039/b305773a

    Article  Google Scholar 

  20. Beer, P.D., Sambrook, M.R., Curiel, D.: Anion-templated assembly of interpenetrated and interlocked structures. Chem. Commun. (Camb.) 20, 2105–2117 (2006). doi:10.1039/b516435b

    Article  Google Scholar 

  21. de Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T., Huxley, A.J.M., McCoy, C.P., Rademacher, J.T., Rice, T.E.: Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97, 1515–1566 (1997). doi:10.1021/cr960386p

    Article  Google Scholar 

  22. Shakir, M., Azim, Y., Chishti, H.T.N., Begum, N., Chingsubam, P., Siddiqi, M.Y.: Synthesis, physico-chemical and antimicrobial screening studies on 14-and 16-membered hexaazamacrocyclic complexes bearing pendant amine groups. J. Braz. Chem. Soc. 17, 272–278 (2006). doi:10.1590/S0103-50532006000200009

    Article  CAS  Google Scholar 

  23. Balzani, V., Scandola, F.: Supramolecular Photochemistry. Horwood, New York (1991)

    Google Scholar 

  24. Dai, Z., Proni, G., Mancheno, D., Karimi, S., Berova, N., Canary, J.W.: Detection of zinc ions by differential circularly polarized fluorescence excitation. J. Am. Chem. Soc. 126, 11760–11761 (2004). doi:10.1021/ja047213z

    Article  CAS  Google Scholar 

  25. Royzen, M., Durandin, A., Jr., Young, V.G., Geacintov, N.E., Canary, J.W.: A sensitive probe for the detection of Zn(II) by time-resolved fluorescence. J. Am. Chem. Soc. 128, 3854–3855 (2006). doi:10.1021/ja056631g

    Article  CAS  Google Scholar 

  26. Marquis, D., Desvergne, J.-P., Bouas-Laurent, H.: Photoresponsive supramolecular systems: synthesis and photophysical and photochemical study of bis-(9,10-anthracenediyl)coronands AAOnOn. J. Org. Chem. 60, 7984–7996 (1995). doi:10.1021/jo00129a045

    Article  CAS  Google Scholar 

  27. Woo, H.Y., Liu, B., Kohler, B., Korystov, D., Mikhailovsky, A., Bazan, G.C.: Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J. Am. Chem. Soc. 127, 14721–14729 (2005). doi:10.1021/ja052906g

    Article  CAS  Google Scholar 

  28. Zheng, Y., Orbulescu, J., Ji, X., Andreopoulos, F.M., Pham, S.M., Leblanc, R.M.: Development of fluorescent film sensors for the detection of divalent copper. J. Am. Chem. Soc. 125, 2680–2686 (2003). doi:10.1021/ja0293610

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng, 224051, P.R. China

    Shuhong Cao, Hongbo Li & Jinwen Chen

  2. School of Chemistry and Chemical Engineering, Nantong University, Nantong, 226019, P.R. China

    Tingting Chen

Authors
  1. Shuhong Cao
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  2. Hongbo Li
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  3. Tingting Chen
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  4. Jinwen Chen
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Correspondence to Jinwen Chen.

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Cao, S., Li, H., Chen, T. et al. A Polyaza Macrocycle Ligand Bearing Anthracenyl Fluorophores for Selective Signaling of Zn(II) in Aqueous Solution. J Solution Chem 38, 1520–1527 (2009). https://doi.org/10.1007/s10953-009-9465-5

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  • DOI: https://doi.org/10.1007/s10953-009-9465-5

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